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Showing metabocard for (4Z,7Z,10Z,13Z)-15-{3-[(2Z)-pent-2-en-1-yl]oxiran-2-yl}pentadeca-4,7,10,13-tetraenoyl-CoA (HMDB0301641)

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Record Information
Version5.0
StatusPredicted
Creation Date2021-09-22 01:43:57 UTC
Update Date2021-10-01 16:55:10 UTC
HMDB IDHMDB0301641
Secondary Accession NumbersNone
Metabolite Identification
Common Name(4Z,7Z,10Z,13Z)-15-{3-[(2Z)-pent-2-en-1-yl]oxiran-2-yl}pentadeca-4,7,10,13-tetraenoyl-CoA
Description(4z,7z,10z,13z)-15-{3-[(2z)-pent-2-en-1-yl]oxiran-2-yl}pentadeca-4,7,10,13-tetraenoyl-coa is an acyl-CoA or acyl-coenzyme A. More specifically, it is a (4Z_7Z_10Z_13Z)-15-{3-[(2Z)-pent-2-en-1-yl]oxiran-2-yl}pentadeca-4_7_10_13-tetraenoic acid thioester of coenzyme A. (4z,7z,10z,13z)-15-{3-[(2z)-pent-2-en-1-yl]oxiran-2-yl}pentadeca-4,7,10,13-tetraenoyl-coa is an acyl-CoA with 22 fatty acid group as the acyl moiety attached to coenzyme A. Coenzyme A was discovered in 1946 by Fritz Lipmann (Journal of Biological Chemistry (1946) 162 (3): 743–744) and its structure was determined in the early 1950s at the Lister Institute in London. Coenzyme A is a complex, thiol-containing molecule that is naturally synthesized from pantothenate (vitamin B5), which is found in various foods such as meat, vegetables, cereal grains, legumes, eggs, and milk. More specifically, coenzyme A (CoASH or CoA) consists of a beta-mercaptoethylamine group linked to the vitamin pantothenic acid (B5) through an amide linkage and 3'-phosphorylated ADP. Coenzyme A is synthesized in a five-step process that requires four molecules of ATP, pantothenate and cysteine. It is believed that there are more than 1100 types of acyl-CoA’s in the human body, which also corresponds to the number of acylcarnitines in the human body. Acyl-CoAs exists in all living species, ranging from bacteria to plants to humans. The general role of acyl-CoA’s is to assist in transferring fatty acids from the cytoplasm to mitochondria. This process facilitates the production of fatty acids in cells, which are essential in cell membrane structure. Acyl-CoA's are also susceptible to beta oxidation, forming, ultimately, acetyl-CoA. Acetyl-CoA can enter the citric acid cycle, eventually forming several equivalents of ATP. In this way, fats are converted to ATP -- or biochemical energy. Acyl-CoAs can be classified into 9 different categories depending on the size of their acyl-group: 1) short-chain acyl-CoAs; 2) medium-chain acyl-CoAs; 3) long-chain acyl-CoAs; and 4) very long-chain acyl-CoAs; 5) hydroxy acyl-CoAs; 6) branched chain acyl-CoAs; 7) unsaturated acyl-CoAs; 8) dicarboxylic acyl-CoAs and 9) miscellaneous acyl-CoAs. Short-chain acyl-CoAs have acyl-groups with two to four carbons (C2-C4), medium-chain acyl-CoAs have acyl-groups with five to eleven carbons (C5-C11), long-chain acyl-CoAs have acyl-groups with twelve to twenty carbons (C12-C20) while very long-chain acyl-CoAs have acyl groups with more than 20 carbons. (4z,7z,10z,13z)-15-{3-[(2z)-pent-2-en-1-yl]oxiran-2-yl}pentadeca-4,7,10,13-tetraenoyl-coa is therefore classified as a very long chain acyl-CoA. The oxidative degradation of fatty acids is a two-step process, catalyzed by acyl-CoA synthetase/synthase. Fatty acids are first converted to their acyl phosphate, the precursor to acyl-CoA. The latter conversion is mediated by acyl-CoA synthase. Three types of acyl-CoA synthases are employed, depending on the chain length of the fatty acid. (4z,7z,10z,13z)-15-{3-[(2z)-pent-2-en-1-yl]oxiran-2-yl}pentadeca-4,7,10,13-tetraenoyl-coa, being a very long chain acyl-CoA is a substrate for very long chain acyl-CoA synthase. The second step of fatty acid degradation is beta oxidation. Beta oxidation occurs in mitochondria and, in the case of very long chain acyl-CoAs, the peroxisome. After its formation in the cytosol, (4Z,7Z,10Z,13Z)-15-{3-[(2Z)-pent-2-en-1-yl]oxiran-2-yl}pentadeca-4,7,10,13-tetraenoyl-CoA is transported into the mitochondria, the locus of beta oxidation. Transport of (4Z,7Z,10Z,13Z)-15-{3-[(2Z)-pent-2-en-1-yl]oxiran-2-yl}pentadeca-4,7,10,13-tetraenoyl-CoA into the mitochondria requires carnitine palmitoyltransferase 1 (CPT1), which converts (4Z,7Z,10Z,13Z)-15-{3-[(2Z)-pent-2-en-1-yl]oxiran-2-yl}pentadeca-4,7,10,13-tetraenoyl-CoA into (4Z_7Z_10Z_13Z)-15-{3-[(2Z)-pent-2-en-1-yl]oxiran-2-yl}pentadeca-4_7_10_13-tetraenoylcarnitine, which gets transported into the mitochondrial matrix. Once in the matrix, (4Z_7Z_10Z_13Z)-15-{3-[(2Z)-pent-2-en-1-yl]oxiran-2-yl}pentadeca-4_7_10_13-tetraenoylcarnitine is converted back to (4Z,7Z,10Z,13Z)-15-{3-[(2Z)-pent-2-en-1-yl]oxiran-2-yl}pentadeca-4,7,10,13-tetraenoyl-CoA by CPT2, whereupon beta-oxidation can begin. Beta oxidation of (4Z,7Z,10Z,13Z)-15-{3-[(2Z)-pent-2-en-1-yl]oxiran-2-yl}pentadeca-4,7,10,13-tetraenoyl-CoA occurs in four steps. First, since (4Z,7Z,10Z,13Z)-15-{3-[(2Z)-pent-2-en-1-yl]oxiran-2-yl}pentadeca-4,7,10,13-tetraenoyl-CoA is a very long chain acyl-CoA it is the substrate for a very long chain acyl-CoA dehydrogenase, which catalyzes dehydrogenation of (4Z,7Z,10Z,13Z)-15-{3-[(2Z)-pent-2-en-1-yl]oxiran-2-yl}pentadeca-4,7,10,13-tetraenoyl-CoA, creating a double bond between the alpha and beta carbons. FAD is the hydrogen acceptor, yielding FADH2. Second, Enoyl-CoA hydrase catalyzes the addition of water across the newly formed double bond to make an alcohol. Third, 3-hydroxyacyl-CoA dehydrogenase oxidizes the alcohol group to a ketone and NADH is produced from NAD+. Finally, Thiolase cleaves between the alpha carbon and ketone to release one molecule of acetyl-CoA and a new acyl-CoA which is now 2 carbons shorter. This four-step process repeats until (4Z,7Z,10Z,13Z)-15-{3-[(2Z)-pent-2-en-1-yl]oxiran-2-yl}pentadeca-4,7,10,13-tetraenoyl-CoA has had all its carbons removed from the chain, leaving only acetyl-CoA. Beta oxidation, as well as alpha-oxidation, also occurs in the peroxisome. The peroxisome handles beta oxidation of fatty acids that have more than 20 carbons in their chain because the peroxisome contains very-long-chain Acyl-CoA synthetases and dehydrogenases. The heart primarily metabolizes fat for energy and Acyl-CoA metabolism has been identified as a critical molecule in early-stage heart muscle pump failure. Cellular acyl-CoA content also correlates with insulin resistance, suggesting that it can mediate lipotoxicity in non-adipose tissues. Acyl-CoA: diacylglycerol acyltransferase (DGAT) plays an important role in energy metabolism on account of key enzyme in triglyceride biosynthesis. The study of acyl-CoAs is an active area of research and it is likely that many novel acyl-CoAs will be discovered in the coming years. It is also likely that many novel roles in health and disease will be uncovered for these molecules.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0301641 ((4Z,7Z,10Z,13Z)-15-{3-[(2Z)-pent-2-en-1-yl]oxiran-2-yl}pentadeca-4,7,10,13-tetraenoyl-CoA)


  Mrv1652304102105592D          

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M  END
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3D MOL for HMDB0301641 ((4Z,7Z,10Z,13Z)-15-{3-[(2Z)-pent-2-en-1-yl]oxiran-2-yl}pentadeca-4,7,10,13-tetraenoyl-CoA)

HMDB0301641
     RDKit          3D
(4Z,7Z,10Z,13Z)-15-{3-[(2Z)-pent-2-en-1-yl]oxiran-2-yl}pentadeca-4,7,10,13-te...
138141  0  0  0  0  0  0  0  0999 V2000
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M  END
Download

3D SDF for HMDB0301641 ((4Z,7Z,10Z,13Z)-15-{3-[(2Z)-pent-2-en-1-yl]oxiran-2-yl}pentadeca-4,7,10,13-tetraenoyl-CoA)


  Mrv1652304102105592D          

 72 75  0  0  0  0            999 V2000
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   16.6671    8.0601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3816    7.6476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   18.8105    7.6476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5250    8.0601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2395    7.6476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   21.6684    7.6476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
HMDB0301641

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC=CCC1OC1CC=CCC=CCC=CCC=CCCC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N

> <INCHI_IDENTIFIER>
InChI=1S/C43H66N7O18P3S/c1-4-5-16-19-30-31(65-30)20-17-14-12-10-8-6-7-9-11-13-15-18-21-34(52)72-25-24-45-33(51)22-23-46-41(55)38(54)43(2,3)27-64-71(61,62)68-70(59,60)63-26-32-37(67-69(56,57)58)36(53)42(66-32)50-29-49-35-39(44)47-28-48-40(35)50/h5,7-10,13-17,28-32,36-38,42,53-54H,4,6,11-12,18-27H2,1-3H3,(H,45,51)(H,46,55)(H,59,60)(H,61,62)(H2,44,47,48)(H2,56,57,58)

> <INCHI_KEY>
CCGDDLGKOSNYHP-UHFFFAOYSA-N

> <FORMULA>
C43H66N7O18P3S

> <MOLECULAR_WEIGHT>
1094.01

> <EXACT_MASS>
1093.339790481

> <JCHEM_ACCEPTOR_COUNT>
18

> <JCHEM_ATOM_COUNT>
138

> <JCHEM_AVERAGE_POLARIZABILITY>
109.4229011392314

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({[hydroxy({3-hydroxy-2,2-dimethyl-3-[(2-{[2-({15-[3-(pent-2-en-1-yl)oxiran-2-yl]pentadeca-4,7,10,13-tetraenoyl}sulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]propoxy})phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid

> <ALOGPS_LOGP>
3.24

> <JCHEM_LOGP>
0.15619452385203933

> <ALOGPS_LOGS>
-3.55

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
1.900120734776186

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.820978781339821

> <JCHEM_PKA_STRONGEST_BASIC>
4.006053268556904

> <JCHEM_POLAR_SURFACE_AREA>
376.15999999999997

> <JCHEM_REFRACTIVITY>
269.3578

> <JCHEM_ROTATABLE_BOND_COUNT>
34

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.10e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[5-(6-aminopurin-9-yl)-4-hydroxy-2-({[hydroxy([hydroxy(3-hydroxy-2,2-dimethyl-3-[(2-{[2-({15-[3-(pent-2-en-1-yl)oxiran-2-yl]pentadeca-4,7,10,13-tetraenoyl}sulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]propoxy)phosphoryl]oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxyphosphonic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0301641 ((4Z,7Z,10Z,13Z)-15-{3-[(2Z)-pent-2-en-1-yl]oxiran-2-yl}pentadeca-4,7,10,13-tetraenoyl-CoA)

HMDB0301641
     RDKit          3D
(4Z,7Z,10Z,13Z)-15-{3-[(2Z)-pent-2-en-1-yl]oxiran-2-yl}pentadeca-4,7,10,13-te...
138141  0  0  0  0  0  0  0  0999 V2000
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   18.5088   -0.2197    2.4041 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.3117    0.3187    2.3983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8662   -0.9858    2.6732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0197    1.3081    3.5902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3990    2.0453    3.4522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8680    2.9178    2.7919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6591    2.0357   -0.2946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6332    3.2244    1.0287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2287    2.0327    0.8698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1736    0.3816   -0.0252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0482    0.2421    1.5578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3284    1.1421   -1.8353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5803   -0.3678    3.6340 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2736   -0.3748    0.0836 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4031   -1.2333    1.6401 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.2414   -1.9230    0.0832 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.9368    0.3793    2.8708 H   0  0  0  0  0  0  0  0  0  0  0  0
  -14.7946   -2.4937    0.6093 H   0  0  0  0  0  0  0  0  0  0  0  0
  -19.7302   -2.5550    1.1560 H   0  0  0  0  0  0  0  0  0  0  0  0
  -20.8029   -1.1411    1.0400 H   0  0  0  0  0  0  0  0  0  0  0  0
  -18.4060    2.2446    3.1584 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.9968    1.7227    1.2177 H   0  0  0  0  0  0  0  0  0  0  0  0
  -14.6046    2.3581   -0.1491 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.7256   -0.3066   -0.9243 H   0  0  0  0  0  0  0  0  0  0  0  0
  -14.7031    0.8995   -2.6688 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.4406   -1.1575   -2.8828 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  3
 11 12  1  0
 12 13  1  0
 13 14  2  3
 14 15  1  0
 15 16  1  0
 16 17  2  3
 17 18  1  0
 18 19  1  0
 19 20  2  3
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  2  0
 29 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  2  0
 34 36  1  0
 36 37  1  0
 36 38  1  0
 38 39  1  0
 38 40  1  0
 38 41  1  0
 41 42  1  0
 42 43  1  0
 43 44  2  0
 43 45  1  0
 43 46  1  0
 46 47  1  0
 47 48  2  0
 47 49  1  0
 47 50  1  0
 50 51  1  0
 51 52  1  0
 52 53  1  0
 53 54  1  0
 54 55  1  0
 55 56  1  0
 56 57  2  0
 57 58  1  0
 58 59  2  0
 59 60  1  0
 59 61  1  0
 61 62  2  0
 62 63  1  0
 63 64  2  0
 54 65  1  0
 65 66  1  0
 65 67  1  0
 67 68  1  0
 68 69  1  0
 69 70  2  0
 69 71  1  0
 69 72  1  0
  8  6  1  0
 67 52  1  0
 64 55  1  0
 64 58  1  0
  1 73  1  0
  1 74  1  0
  1 75  1  0
  2 76  1  0
  2 77  1  0
  3 78  1  0
  4 79  1  0
  5 80  1  0
  5 81  1  0
  6 82  1  0
  8 83  1  0
  9 84  1  0
  9 85  1  0
 10 86  1  0
 11 87  1  0
 12 88  1  0
 12 89  1  0
 13 90  1  0
 14 91  1  0
 15 92  1  0
 15 93  1  0
 16 94  1  0
 17 95  1  0
 18 96  1  0
 18 97  1  0
 19 98  1  0
 20 99  1  0
 21100  1  0
 21101  1  0
 22102  1  0
 22103  1  0
 26104  1  0
 26105  1  0
 27106  1  0
 27107  1  0
 28108  1  0
 31109  1  0
 31110  1  0
 32111  1  0
 32112  1  0
 33113  1  0
 36114  1  0
 37115  1  0
 39116  1  0
 39117  1  0
 39118  1  0
 40119  1  0
 40120  1  0
 40121  1  0
 41122  1  0
 41123  1  0
 45124  1  0
 49125  1  0
 51126  1  0
 51127  1  0
 52128  1  0
 54129  1  0
 56130  1  0
 60131  1  0
 60132  1  0
 62133  1  0
 65134  1  0
 66135  1  0
 67136  1  0
 71137  1  0
 72138  1  0
M  END
Download

PDB for HMDB0301641 ((4Z,7Z,10Z,13Z)-15-{3-[(2Z)-pent-2-en-1-yl]oxiran-2-yl}pentadeca-4,7,10,13-tetraenoyl-CoA)

HEADER    PROTEIN                                 10-APR-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-APR-21         0                                  
HETATM    1  O   UNK     0      20.443  16.586   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      20.443  15.046   0.000  0.00  0.00           C+0
HETATM    3  S   UNK     0      19.109  14.276   0.000  0.00  0.00           S+0
HETATM    4  C   UNK     0      17.775  15.046   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      16.441  14.276   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      15.108  15.046   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      13.774  14.276   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      13.774  12.736   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      12.440  15.046   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.107  14.276   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       9.773  15.046   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       8.439  14.276   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       8.439  12.736   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       7.106  15.046   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       7.106  16.586   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       5.772  14.276   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.002  15.609   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.542  12.942   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.438  13.506   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       3.105  14.276   0.000  0.00  0.00           O+0
HETATM   21  P   UNK     0       1.771  13.506   0.000  0.00  0.00           P+0
HETATM   22  O   UNK     0       1.001  14.839   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       2.541  12.172   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       0.437  12.736   0.000  0.00  0.00           O+0
HETATM   25  P   UNK     0      -0.896  13.506   0.000  0.00  0.00           P+0
HETATM   26  O   UNK     0      -0.126  14.839   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -1.666  12.172   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -2.230  14.276   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -3.564  13.506   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -4.897  14.276   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -5.058  15.807   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -6.565  16.127   0.000  0.00  0.00           C+0
HETATM   33  N   UNK     0      -7.191  17.534   0.000  0.00  0.00           N+0
HETATM   34  C   UNK     0      -8.697  17.854   0.000  0.00  0.00           C+0
HETATM   35  N   UNK     0      -8.858  19.386   0.000  0.00  0.00           N+0
HETATM   36  C   UNK     0      -7.452  20.012   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -6.976  21.477   0.000  0.00  0.00           C+0
HETATM   38  N   UNK     0      -5.469  21.797   0.000  0.00  0.00           N+0
HETATM   39  C   UNK     0      -4.439  20.653   0.000  0.00  0.00           C+0
HETATM   40  N   UNK     0      -4.915  19.188   0.000  0.00  0.00           N+0
HETATM   41  C   UNK     0      -6.421  18.868   0.000  0.00  0.00           C+0
HETATM   42  N   UNK     0      -8.006  22.621   0.000  0.00  0.00           N+0
HETATM   43  C   UNK     0      -7.335  14.794   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      -8.866  14.633   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0      -6.304  13.649   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0      -6.624  12.143   0.000  0.00  0.00           O+0
HETATM   47  P   UNK     0      -8.089  11.667   0.000  0.00  0.00           P+0
HETATM   48  O   UNK     0      -8.565  13.132   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0      -9.554  11.191   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0      -7.613  10.202   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0      21.776  14.276   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      23.110  15.046   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      24.444  14.276   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      25.777  15.046   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      27.111  14.276   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      28.445  15.046   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      29.778  14.276   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      31.112  15.046   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0      32.446  14.276   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0      33.779  15.046   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0      35.113  14.276   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0      36.447  15.046   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0      37.780  14.276   0.000  0.00  0.00           C+0
HETATM   64  C   UNK     0      39.114  15.046   0.000  0.00  0.00           C+0
HETATM   65  C   UNK     0      40.448  14.276   0.000  0.00  0.00           C+0
HETATM   66  O   UNK     0      41.988  14.276   0.000  0.00  0.00           O+0
HETATM   67  C   UNK     0      41.218  12.942   0.000  0.00  0.00           C+0
HETATM   68  C   UNK     0      41.218  11.402   0.000  0.00  0.00           C+0
HETATM   69  C   UNK     0      42.551  10.632   0.000  0.00  0.00           C+0
HETATM   70  C   UNK     0      42.551   9.092   0.000  0.00  0.00           C+0
HETATM   71  C   UNK     0      43.885   8.322   0.000  0.00  0.00           C+0
HETATM   72  C   UNK     0      45.219   9.092   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   51                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18   19                                             
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   16   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23   24                                             
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   21   25                                                       
CONECT   25   24   26   27   28                                             
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   25   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   45                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   43                                                  
CONECT   33   32   34   41                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37   41                                                  
CONECT   37   36   38   42                                                  
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   36   33                                                  
CONECT   42   37                                                            
CONECT   43   32   44   45                                                  
CONECT   44   43                                                            
CONECT   45   43   30   46                                                  
CONECT   46   45   47                                                       
CONECT   47   46   48   49   50                                             
CONECT   48   47                                                            
CONECT   49   47                                                            
CONECT   50   47                                                            
CONECT   51    2   52                                                       
CONECT   52   51   53                                                       
CONECT   53   52   54                                                       
CONECT   54   53   55                                                       
CONECT   55   54   56                                                       
CONECT   56   55   57                                                       
CONECT   57   56   58                                                       
CONECT   58   57   59                                                       
CONECT   59   58   60                                                       
CONECT   60   59   61                                                       
CONECT   61   60   62                                                       
CONECT   62   61   63                                                       
CONECT   63   62   64                                                       
CONECT   64   63   65                                                       
CONECT   65   64   66   67                                                  
CONECT   66   65   67                                                       
CONECT   67   66   65   68                                                  
CONECT   68   67   69                                                       
CONECT   69   68   70                                                       
CONECT   70   69   71                                                       
CONECT   71   70   72                                                       
CONECT   72   71                                                            
MASTER        0    0    0    0    0    0    0    0   72    0  150    0
END
Download

3D PDB for HMDB0301641 ((4Z,7Z,10Z,13Z)-15-{3-[(2Z)-pent-2-en-1-yl]oxiran-2-yl}pentadeca-4,7,10,13-tetraenoyl-CoA)

COMPND    HMDB0301641
HETATM    1  C1  UNL     1      21.311  -2.264   2.760  1.00  0.00           C  
HETATM    2  C2  UNL     1      20.759  -1.089   1.949  1.00  0.00           C  
HETATM    3  C3  UNL     1      19.750  -0.374   2.740  1.00  0.00           C  
HETATM    4  C4  UNL     1      18.509  -0.220   2.404  1.00  0.00           C  
HETATM    5  C5  UNL     1      17.907  -0.740   1.168  1.00  0.00           C  
HETATM    6  C6  UNL     1      17.377   0.478   0.403  1.00  0.00           C  
HETATM    7  O1  UNL     1      16.363   1.153   1.288  1.00  0.00           O  
HETATM    8  C7  UNL     1      15.976   0.492   0.057  1.00  0.00           C  
HETATM    9  C8  UNL     1      15.501   1.388  -1.028  1.00  0.00           C  
HETATM   10  C9  UNL     1      14.059   1.320  -1.265  1.00  0.00           C  
HETATM   11  C10 UNL     1      13.234   0.561  -0.592  1.00  0.00           C  
HETATM   12  C11 UNL     1      11.765   0.546  -0.895  1.00  0.00           C  
HETATM   13  C12 UNL     1      11.456   1.464  -1.990  1.00  0.00           C  
HETATM   14  C13 UNL     1      10.904   1.108  -3.125  1.00  0.00           C  
HETATM   15  C14 UNL     1      10.493  -0.240  -3.520  1.00  0.00           C  
HETATM   16  C15 UNL     1       9.090  -0.509  -3.789  1.00  0.00           C  
HETATM   17  C16 UNL     1       8.026   0.190  -3.704  1.00  0.00           C  
HETATM   18  C17 UNL     1       7.887   1.581  -3.271  1.00  0.00           C  
HETATM   19  C18 UNL     1       6.935   1.568  -2.089  1.00  0.00           C  
HETATM   20  C19 UNL     1       6.377   0.474  -1.633  1.00  0.00           C  
HETATM   21  C20 UNL     1       5.459   0.550  -0.471  1.00  0.00           C  
HETATM   22  C21 UNL     1       4.086   0.055  -0.959  1.00  0.00           C  
HETATM   23  C22 UNL     1       3.101   0.095   0.124  1.00  0.00           C  
HETATM   24  O2  UNL     1       3.490   0.233   1.271  1.00  0.00           O  
HETATM   25  S1  UNL     1       1.369  -0.039  -0.155  1.00  0.00           S  
HETATM   26  C23 UNL     1       0.922  -0.236  -1.890  1.00  0.00           C  
HETATM   27  C24 UNL     1       1.287  -1.627  -2.341  1.00  0.00           C  
HETATM   28  N1  UNL     1       0.546  -2.577  -1.525  1.00  0.00           N  
HETATM   29  C25 UNL     1      -0.883  -2.561  -1.552  1.00  0.00           C  
HETATM   30  O3  UNL     1      -1.523  -1.758  -2.260  1.00  0.00           O  
HETATM   31  C26 UNL     1      -1.593  -3.527  -0.712  1.00  0.00           C  
HETATM   32  C27 UNL     1      -2.965  -3.188  -0.265  1.00  0.00           C  
HETATM   33  N2  UNL     1      -3.169  -2.162   0.673  1.00  0.00           N  
HETATM   34  C28 UNL     1      -2.925  -0.802   0.743  1.00  0.00           C  
HETATM   35  O4  UNL     1      -2.398  -0.126  -0.156  1.00  0.00           O  
HETATM   36  C29 UNL     1      -3.291   0.012   1.968  1.00  0.00           C  
HETATM   37  O5  UNL     1      -3.932  -0.753   2.912  1.00  0.00           O  
HETATM   38  C30 UNL     1      -4.100   1.225   1.621  1.00  0.00           C  
HETATM   39  C31 UNL     1      -4.391   1.939   2.941  1.00  0.00           C  
HETATM   40  C32 UNL     1      -3.325   2.196   0.749  1.00  0.00           C  
HETATM   41  C33 UNL     1      -5.387   0.876   0.940  1.00  0.00           C  
HETATM   42  O6  UNL     1      -6.083   2.062   0.650  1.00  0.00           O  
HETATM   43  P1  UNL     1      -7.544   1.795  -0.121  1.00  0.00           P  
HETATM   44  O7  UNL     1      -8.325   3.099  -0.069  1.00  0.00           O  
HETATM   45  O8  UNL     1      -7.273   1.382  -1.739  1.00  0.00           O  
HETATM   46  O9  UNL     1      -8.368   0.563   0.654  1.00  0.00           O  
HETATM   47  P2  UNL     1      -9.288   1.129   1.952  1.00  0.00           P  
HETATM   48  O10 UNL     1      -9.104   2.590   2.215  1.00  0.00           O  
HETATM   49  O11 UNL     1      -8.851   0.188   3.305  1.00  0.00           O  
HETATM   50  O12 UNL     1     -10.916   0.754   1.617  1.00  0.00           O  
HETATM   51  C34 UNL     1     -10.901  -0.479   0.974  1.00  0.00           C  
HETATM   52  C35 UNL     1     -12.315  -0.942   0.623  1.00  0.00           C  
HETATM   53  O13 UNL     1     -13.003  -1.033   1.799  1.00  0.00           O  
HETATM   54  C36 UNL     1     -13.963  -0.061   1.850  1.00  0.00           C  
HETATM   55  N3  UNL     1     -15.267  -0.638   1.581  1.00  0.00           N  
HETATM   56  C37 UNL     1     -15.538  -1.810   0.983  1.00  0.00           C  
HETATM   57  N4  UNL     1     -16.859  -2.025   0.909  1.00  0.00           N  
HETATM   58  C38 UNL     1     -17.474  -0.982   1.466  1.00  0.00           C  
HETATM   59  C39 UNL     1     -18.802  -0.678   1.660  1.00  0.00           C  
HETATM   60  N5  UNL     1     -19.859  -1.526   1.254  1.00  0.00           N  
HETATM   61  N6  UNL     1     -19.082   0.498   2.276  1.00  0.00           N  
HETATM   62  C40 UNL     1     -18.102   1.328   2.677  1.00  0.00           C  
HETATM   63  N7  UNL     1     -16.804   1.037   2.489  1.00  0.00           N  
HETATM   64  C41 UNL     1     -16.483  -0.119   1.884  1.00  0.00           C  
HETATM   65  C42 UNL     1     -13.668   0.950   0.782  1.00  0.00           C  
HETATM   66  O14 UNL     1     -14.835   1.510   0.269  1.00  0.00           O  
HETATM   67  C43 UNL     1     -12.943   0.116  -0.247  1.00  0.00           C  
HETATM   68  O15 UNL     1     -11.994   0.861  -0.944  1.00  0.00           O  
HETATM   69  P3  UNL     1     -12.450   0.846  -2.581  1.00  0.00           P  
HETATM   70  O16 UNL     1     -11.408   1.536  -3.435  1.00  0.00           O  
HETATM   71  O17 UNL     1     -13.975   1.538  -2.790  1.00  0.00           O  
HETATM   72  O18 UNL     1     -12.549  -0.755  -3.111  1.00  0.00           O  
HETATM   73  H1  UNL     1      21.573  -1.898   3.782  1.00  0.00           H  
HETATM   74  H2  UNL     1      22.222  -2.689   2.317  1.00  0.00           H  
HETATM   75  H3  UNL     1      20.534  -3.042   2.897  1.00  0.00           H  
HETATM   76  H4  UNL     1      20.497  -1.385   0.944  1.00  0.00           H  
HETATM   77  H5  UNL     1      21.670  -0.413   1.822  1.00  0.00           H  
HETATM   78  H6  UNL     1      20.093   0.066   3.700  1.00  0.00           H  
HETATM   79  H7  UNL     1      17.834   0.345   3.088  1.00  0.00           H  
HETATM   80  H8  UNL     1      18.627  -1.219   0.503  1.00  0.00           H  
HETATM   81  H9  UNL     1      17.052  -1.433   1.386  1.00  0.00           H  
HETATM   82  H10 UNL     1      18.091   1.225   0.072  1.00  0.00           H  
HETATM   83  H11 UNL     1      15.411  -0.431   0.272  1.00  0.00           H  
HETATM   84  H12 UNL     1      15.747   2.466  -0.767  1.00  0.00           H  
HETATM   85  H13 UNL     1      16.094   1.176  -1.954  1.00  0.00           H  
HETATM   86  H14 UNL     1      13.671   1.971  -2.078  1.00  0.00           H  
HETATM   87  H15 UNL     1      13.548  -0.076   0.203  1.00  0.00           H  
HETATM   88  H16 UNL     1      11.437  -0.480  -0.986  1.00  0.00           H  
HETATM   89  H17 UNL     1      11.271   0.966   0.024  1.00  0.00           H  
HETATM   90  H18 UNL     1      11.705   2.540  -1.859  1.00  0.00           H  
HETATM   91  H19 UNL     1      10.763   1.918  -3.898  1.00  0.00           H  
HETATM   92  H20 UNL     1      10.839  -1.024  -2.791  1.00  0.00           H  
HETATM   93  H21 UNL     1      11.133  -0.506  -4.443  1.00  0.00           H  
HETATM   94  H22 UNL     1       8.911  -1.584  -4.156  1.00  0.00           H  
HETATM   95  H23 UNL     1       7.069  -0.348  -4.016  1.00  0.00           H  
HETATM   96  H24 UNL     1       8.785   2.042  -2.892  1.00  0.00           H  
HETATM   97  H25 UNL     1       7.419   2.147  -4.113  1.00  0.00           H  
HETATM   98  H26 UNL     1       6.705   2.529  -1.595  1.00  0.00           H  
HETATM   99  H27 UNL     1       6.573  -0.478  -2.081  1.00  0.00           H  
HETATM  100  H28 UNL     1       5.820  -0.112   0.352  1.00  0.00           H  
HETATM  101  H29 UNL     1       5.406   1.570  -0.071  1.00  0.00           H  
HETATM  102  H30 UNL     1       3.778   0.756  -1.757  1.00  0.00           H  
HETATM  103  H31 UNL     1       4.305  -0.973  -1.331  1.00  0.00           H  
HETATM  104  H32 UNL     1      -0.132  -0.003  -2.076  1.00  0.00           H  
HETATM  105  H33 UNL     1       1.477   0.533  -2.526  1.00  0.00           H  
HETATM  106  H34 UNL     1       2.367  -1.819  -2.252  1.00  0.00           H  
HETATM  107  H35 UNL     1       1.036  -1.776  -3.430  1.00  0.00           H  
HETATM  108  H36 UNL     1       1.076  -3.252  -0.936  1.00  0.00           H  
HETATM  109  H37 UNL     1      -0.936  -3.835   0.166  1.00  0.00           H  
HETATM  110  H38 UNL     1      -1.618  -4.495  -1.317  1.00  0.00           H  
HETATM  111  H39 UNL     1      -3.504  -2.842  -1.224  1.00  0.00           H  
HETATM  112  H40 UNL     1      -3.558  -4.121  -0.014  1.00  0.00           H  
HETATM  113  H41 UNL     1      -3.651  -2.536   1.604  1.00  0.00           H  
HETATM  114  H42 UNL     1      -2.312   0.319   2.398  1.00  0.00           H  
HETATM  115  H43 UNL     1      -4.866  -0.986   2.673  1.00  0.00           H  
HETATM  116  H44 UNL     1      -5.020   1.308   3.590  1.00  0.00           H  
HETATM  117  H45 UNL     1      -3.399   2.045   3.452  1.00  0.00           H  
HETATM  118  H46 UNL     1      -4.868   2.918   2.792  1.00  0.00           H  
HETATM  119  H47 UNL     1      -3.659   2.036  -0.295  1.00  0.00           H  
HETATM  120  H48 UNL     1      -3.633   3.224   1.029  1.00  0.00           H  
HETATM  121  H49 UNL     1      -2.229   2.033   0.870  1.00  0.00           H  
HETATM  122  H50 UNL     1      -5.174   0.382  -0.025  1.00  0.00           H  
HETATM  123  H51 UNL     1      -6.048   0.242   1.558  1.00  0.00           H  
HETATM  124  H52 UNL     1      -6.328   1.142  -1.835  1.00  0.00           H  
HETATM  125  H53 UNL     1      -9.580  -0.368   3.634  1.00  0.00           H  
HETATM  126  H54 UNL     1     -10.274  -0.375   0.084  1.00  0.00           H  
HETATM  127  H55 UNL     1     -10.403  -1.233   1.640  1.00  0.00           H  
HETATM  128  H56 UNL     1     -12.241  -1.923   0.083  1.00  0.00           H  
HETATM  129  H57 UNL     1     -13.937   0.379   2.871  1.00  0.00           H  
HETATM  130  H58 UNL     1     -14.795  -2.494   0.609  1.00  0.00           H  
HETATM  131  H59 UNL     1     -19.730  -2.555   1.156  1.00  0.00           H  
HETATM  132  H60 UNL     1     -20.803  -1.141   1.040  1.00  0.00           H  
HETATM  133  H61 UNL     1     -18.406   2.245   3.158  1.00  0.00           H  
HETATM  134  H62 UNL     1     -12.997   1.723   1.218  1.00  0.00           H  
HETATM  135  H63 UNL     1     -14.605   2.358  -0.149  1.00  0.00           H  
HETATM  136  H64 UNL     1     -13.726  -0.307  -0.924  1.00  0.00           H  
HETATM  137  H65 UNL     1     -14.703   0.899  -2.669  1.00  0.00           H  
HETATM  138  H66 UNL     1     -13.441  -1.157  -2.883  1.00  0.00           H  
CONECT    1    2   73   74   75
CONECT    2    3   76   77
CONECT    3    4    4   78
CONECT    4    5   79
CONECT    5    6   80   81
CONECT    6    7    8   82
CONECT    7    8
CONECT    8    9   83
CONECT    9   10   84   85
CONECT   10   11   11   86
CONECT   11   12   87
CONECT   12   13   88   89
CONECT   13   14   14   90
CONECT   14   15   91
CONECT   15   16   92   93
CONECT   16   17   17   94
CONECT   17   18   95
CONECT   18   19   96   97
CONECT   19   20   20   98
CONECT   20   21   99
CONECT   21   22  100  101
CONECT   22   23  102  103
CONECT   23   24   24   25
CONECT   25   26
CONECT   26   27  104  105
CONECT   27   28  106  107
CONECT   28   29  108
CONECT   29   30   30   31
CONECT   31   32  109  110
CONECT   32   33  111  112
CONECT   33   34  113
CONECT   34   35   35   36
CONECT   36   37   38  114
CONECT   37  115
CONECT   38   39   40   41
CONECT   39  116  117  118
CONECT   40  119  120  121
CONECT   41   42  122  123
CONECT   42   43
CONECT   43   44   44   45   46
CONECT   45  124
CONECT   46   47
CONECT   47   48   48   49   50
CONECT   49  125
CONECT   50   51
CONECT   51   52  126  127
CONECT   52   53   67  128
CONECT   53   54
CONECT   54   55   65  129
CONECT   55   56   64
CONECT   56   57   57  130
CONECT   57   58
CONECT   58   59   59   64
CONECT   59   60   61
CONECT   60  131  132
CONECT   61   62   62
CONECT   62   63  133
CONECT   63   64   64
CONECT   65   66   67  134
CONECT   66  135
CONECT   67   68  136
CONECT   68   69
CONECT   69   70   70   71   72
CONECT   71  137
CONECT   72  138
END
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SMILES for HMDB0301641 ((4Z,7Z,10Z,13Z)-15-{3-[(2Z)-pent-2-en-1-yl]oxiran-2-yl}pentadeca-4,7,10,13-tetraenoyl-CoA)

CCC=CCC1OC1CC=CCC=CCC=CCC=CCCC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N
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INCHI for HMDB0301641 ((4Z,7Z,10Z,13Z)-15-{3-[(2Z)-pent-2-en-1-yl]oxiran-2-yl}pentadeca-4,7,10,13-tetraenoyl-CoA)

InChI=1S/C43H66N7O18P3S/c1-4-5-16-19-30-31(65-30)20-17-14-12-10-8-6-7-9-11-13-15-18-21-34(52)72-25-24-45-33(51)22-23-46-41(55)38(54)43(2,3)27-64-71(61,62)68-70(59,60)63-26-32-37(67-69(56,57)58)36(53)42(66-32)50-29-49-35-39(44)47-28-48-40(35)50/h5,7-10,13-17,28-32,36-38,42,53-54H,4,6,11-12,18-27H2,1-3H3,(H,45,51)(H,46,55)(H,59,60)(H,61,62)(H2,44,47,48)(H2,56,57,58)
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View in JSmolView Stereo Labels
Synonyms
ValueSource
4-({[({[5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-2-hydroxy-3,3-dimethyl-N-(2-{[2-({15-[3-(pent-2-en-1-yl)oxiran-2-yl]pentadeca-4,7,10,13-tetraenoyl}sulfanyl)ethyl]-C-hydroxycarbonimidoyl}ethyl)butanimidateHMDB
4-({[({[5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-2-hydroxy-3,3-dimethyl-N-(2-{[2-({15-[3-(pent-2-en-1-yl)oxiran-2-yl]pentadeca-4,7,10,13-tetraenoyl}sulphanyl)ethyl]-C-hydroxycarbonimidoyl}ethyl)butanimidateHMDB
4-({[({[5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-2-hydroxy-3,3-dimethyl-N-(2-{[2-({15-[3-(pent-2-en-1-yl)oxiran-2-yl]pentadeca-4,7,10,13-tetraenoyl}sulphanyl)ethyl]-C-hydroxycarbonimidoyl}ethyl)butanimidic acidHMDB
Chemical FormulaC43H66N7O18P3S
Average Molecular Weight1094.01
Monoisotopic Molecular Weight1093.339790481
IUPAC Name{[5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({[hydroxy({3-hydroxy-2,2-dimethyl-3-[(2-{[2-({15-[3-(pent-2-en-1-yl)oxiran-2-yl]pentadeca-4,7,10,13-tetraenoyl}sulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]propoxy})phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid
Traditional Name[5-(6-aminopurin-9-yl)-4-hydroxy-2-({[hydroxy([hydroxy(3-hydroxy-2,2-dimethyl-3-[(2-{[2-({15-[3-(pent-2-en-1-yl)oxiran-2-yl]pentadeca-4,7,10,13-tetraenoyl}sulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]propoxy)phosphoryl]oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxyphosphonic acid
CAS Registry NumberNot Available
SMILES
CCC=CCC1OC1CC=CCC=CCC=CCC=CCCC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N
InChI Identifier
InChI=1S/C43H66N7O18P3S/c1-4-5-16-19-30-31(65-30)20-17-14-12-10-8-6-7-9-11-13-15-18-21-34(52)72-25-24-45-33(51)22-23-46-41(55)38(54)43(2,3)27-64-71(61,62)68-70(59,60)63-26-32-37(67-69(56,57)58)36(53)42(66-32)50-29-49-35-39(44)47-28-48-40(35)50/h5,7-10,13-17,28-32,36-38,42,53-54H,4,6,11-12,18-27H2,1-3H3,(H,45,51)(H,46,55)(H,59,60)(H,61,62)(H2,44,47,48)(H2,56,57,58)
InChI KeyCCGDDLGKOSNYHP-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as long-chain fatty acyl coas. These are acyl CoAs where the group acylated to the coenzyme A moiety is a long aliphatic chain of 13 to 21 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl thioesters
Direct ParentLong-chain fatty acyl CoAs
Alternative Parents
Substituents
  • Coenzyme a or derivatives
  • Purine ribonucleoside diphosphate
  • Purine ribonucleoside bisphosphate
  • Purine ribonucleoside 3',5'-bisphosphate
  • Ribonucleoside 3'-phosphate
  • Pentose-5-phosphate
  • Pentose phosphate
  • N-glycosyl compound
  • Glycosyl compound
  • Beta amino acid or derivatives
  • Pentose monosaccharide
  • Organic pyrophosphate
  • Monosaccharide phosphate
  • 6-aminopurine
  • Purine
  • Imidazopyrimidine
  • Monoalkyl phosphate
  • Aminopyrimidine
  • Imidolactam
  • Alkyl phosphate
  • Pyrimidine
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • N-substituted imidazole
  • N-acyl-amine
  • Monosaccharide
  • Fatty amide
  • Heteroaromatic compound
  • Tetrahydrofuran
  • Imidazole
  • Azole
  • Carbothioic s-ester
  • Thiocarboxylic acid ester
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Amino acid or derivatives
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Sulfenyl compound
  • Thiocarboxylic acid or derivatives
  • Ether
  • Oxirane
  • Dialkyl ether
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
DispositionNot Available
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP3.24ALOGPS
logP0.16ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)0.82ChemAxon
pKa (Strongest Basic)4.01ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area376.16 ŲChemAxon
Rotatable Bond Count34ChemAxon
Refractivity269.36 m³·mol⁻¹ChemAxon
Polarizability109.42 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
AllCCS[M+H]+301.23532859911
AllCCS[M+H-H2O]+301.72432859911
AllCCS[M+Na]+300.60132859911
AllCCS[M+NH4]+300.74732859911
AllCCS[M-H]-321.93132859911
AllCCS[M+Na-2H]-328.02632859911
AllCCS[M+HCOO]-334.60732859911
DeepCCS[M+H]+271.47730932474
DeepCCS[M-H]-268.2530932474
DeepCCS[M-2H]-304.39230932474
DeepCCS[M+Na]+279.48330932474

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Predicted by Siyang on May 30, 202218.3823 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20225.04 minutes32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid3552.6 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid136.6 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid213.5 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid181.5 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid223.2 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid775.0 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid649.5 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)689.7 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid1450.4 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid804.9 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1268.0 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid552.7 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid409.0 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate384.8 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA116.5 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water10.0 seconds40023050

Predicted Kovats Retention Indices

Not Available
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
MSMass Spectrum (Electron Ionization)Not Available2022-08-06Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (4Z,7Z,10Z,13Z)-15-{3-[(2Z)-pent-2-en-1-yl]oxiran-2-yl}pentadeca-4,7,10,13-tetraenoyl-CoA 10V, Positive-QTOFsplash10-0006-9000000000-2dadce16b74684d18bd82021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (4Z,7Z,10Z,13Z)-15-{3-[(2Z)-pent-2-en-1-yl]oxiran-2-yl}pentadeca-4,7,10,13-tetraenoyl-CoA 20V, Positive-QTOFsplash10-005i-9300000103-d63825485ae996f5fb892021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (4Z,7Z,10Z,13Z)-15-{3-[(2Z)-pent-2-en-1-yl]oxiran-2-yl}pentadeca-4,7,10,13-tetraenoyl-CoA 40V, Positive-QTOFsplash10-000i-0000490000-2d09b00ea1740a1f3d162021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (4Z,7Z,10Z,13Z)-15-{3-[(2Z)-pent-2-en-1-yl]oxiran-2-yl}pentadeca-4,7,10,13-tetraenoyl-CoA 10V, Negative-QTOFsplash10-0006-9000000000-1600ee74362d22662d3a2021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (4Z,7Z,10Z,13Z)-15-{3-[(2Z)-pent-2-en-1-yl]oxiran-2-yl}pentadeca-4,7,10,13-tetraenoyl-CoA 20V, Negative-QTOFsplash10-0096-9000100101-f24f6fd74aec929a86812021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (4Z,7Z,10Z,13Z)-15-{3-[(2Z)-pent-2-en-1-yl]oxiran-2-yl}pentadeca-4,7,10,13-tetraenoyl-CoA 40V, Negative-QTOFsplash10-004r-9102400402-d2fa422d70cd0dfcd17b2021-10-21Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Abe T, Fujino T, Fukuyama R, Minoshima S, Shimizu N, Toh H, Suzuki H, Yamamoto T: Human long-chain acyl-CoA synthetase: structure and chromosomal location. J Biochem. 1992 Jan;111(1):123-8. [PubMed:1607358 ]
  2. Wishart DS, Li C, Marcu A, Badran H, Pon A, Budinski Z, Patron J, Lipton D, Cao X, Oler E, Li K, Paccoud M, Hong C, Guo AC, Chan C, Wei W, Ramirez-Gaona M: PathBank: a comprehensive pathway database for model organisms. Nucleic Acids Res. 2020 Jan 8;48(D1):D470-D478. doi: 10.1093/nar/gkz861. [PubMed:31602464 ]