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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-22 14:17:40 UTC

Update Date

2022-03-07 02:49:13 UTC

HMDB ID

HMDB0002186

Secondary Accession Numbers

HMDB02186

Metabolite Identification

Common Name

Hypogeic acid

Description

Hypogeic acid is a fatty acids found in human milk Approximately 50% of the dietary calories in human milk are supplied to new-borns as fat. More than 98% of this milk fat is in the form of triglycerides, which contain fatty acid glycerol esters. Fatty acid composition in human milk changes in colostrum, transitional milk and mature milk. Knowledge of fatty acid composition of human milk is of importance for the manufacture of infant formulas, determination of the influence of diet in fatty acid composition of human milk and changes in composition with lactation. (CAN 136:246580, AN 2002:67899).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0002186
     RDKit          3D
Hypogeic acid
 48 47  0  0  0  0  0  0  0  0999 V2000
   -6.5379    1.1337   -1.2796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2669    0.7473   -0.5496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4819   -0.2843   -1.3066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2242   -0.6567   -0.5732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4992   -1.2268    0.7840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2095   -1.6078    1.5176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3373   -0.4182    1.7013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0585   -0.7907    2.4517 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6611   -1.7795    1.6707 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8753   -1.5759    1.2136 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6165   -0.3551    1.4391 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9756    0.3300    0.1144 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8236   -0.5744   -0.7434 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1427    0.1502   -2.0262 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8902    1.4272   -1.8312 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1890    1.2709   -1.1671 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6894    0.1975   -0.7743 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9403    2.4274   -0.9515 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9199    2.0651   -0.8270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3410    1.3218   -2.3477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3308    0.3699   -1.1930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7023    1.6859   -0.3732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6035    0.3446    0.4501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1338   -1.1592   -1.4595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2085    0.1464   -2.2831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6463   -1.3698   -1.1777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5946    0.2548   -0.4596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0549   -0.5293    1.4366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1394   -2.1217    0.6474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7242   -2.4509    0.9934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5500   -2.0188    2.5001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9620   -0.1158    0.6779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8169    0.4284    2.1914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4184   -1.2438    3.4308 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4231    0.1596    2.6607 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1680   -2.7535    1.4575 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3926   -2.3694    0.6140 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6324   -0.6310    1.8743 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2318    0.4174    2.0728 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0459    0.6563   -0.3863 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5967    1.2062    0.3901 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7058   -0.8742   -0.1680 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2913   -1.5074   -1.0263 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1724    0.4051   -2.5146 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6943   -0.5524   -2.7049 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0921    1.8415   -2.8490 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2307    2.1463   -1.3031 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2809    2.5705   -0.0138 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  0
  6 31  1  0
  7 32  1  0
  7 33  1  0
  8 34  1  0
  8 35  1  0
  9 36  1  0
 10 37  1  0
 11 38  1  0
 11 39  1  0
 12 40  1  0
 12 41  1  0
 13 42  1  0
 13 43  1  0
 14 44  1  0
 14 45  1  0
 15 46  1  0
 15 47  1  0
 18 48  1  0
M  END

LMFA01030055
  Mrv1652303312018252D          

 18 17  0  0  0  0            999 V2000
   11.4304    5.6601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1448    5.2476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8594    5.6601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5739    5.2476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2884    5.6601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0030    5.2476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7175    5.6601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4320    5.2476    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7175    6.4851    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6054    5.6601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8908    5.2476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1763    5.6601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4619    5.2476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7474    5.6601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0329    5.2476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3184    5.6601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6039    5.2476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8895    5.6601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  7  9  2  0  0  0  0
  1 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0002186

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCCCC\C=C/CCCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h9-10H,2-8,11-15H2,1H3,(H,17,18)/b10-9-

> <INCHI_KEY>
PJHOFUXBXJNUAC-KTKRTIGZSA-N

> <FORMULA>
C16H30O2

> <MOLECULAR_WEIGHT>
254.4082

> <EXACT_MASS>
254.224580204

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
32.870219879579025

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(7Z)-hexadec-7-enoic acid

> <ALOGPS_LOGP>
6.74

> <JCHEM_LOGP>
5.894661121

> <ALOGPS_LOGS>
-5.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.885823668538633

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
78.20019999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.37e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-hexadecenoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0002186
     RDKit          3D
Hypogeic acid
 48 47  0  0  0  0  0  0  0  0999 V2000
   -6.5379    1.1337   -1.2796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2669    0.7473   -0.5496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4819   -0.2843   -1.3066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2242   -0.6567   -0.5732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4992   -1.2268    0.7840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2095   -1.6078    1.5176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3373   -0.4182    1.7013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0585   -0.7907    2.4517 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6611   -1.7795    1.6707 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8753   -1.5759    1.2136 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6165   -0.3551    1.4391 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9756    0.3300    0.1144 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8236   -0.5744   -0.7434 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1427    0.1502   -2.0262 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8902    1.4272   -1.8312 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1890    1.2709   -1.1671 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6894    0.1975   -0.7743 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9403    2.4274   -0.9515 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9199    2.0651   -0.8270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3410    1.3218   -2.3477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3308    0.3699   -1.1930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7023    1.6859   -0.3732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6035    0.3446    0.4501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1338   -1.1592   -1.4595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2085    0.1464   -2.2831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6463   -1.3698   -1.1777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5946    0.2548   -0.4596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0549   -0.5293    1.4366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1394   -2.1217    0.6474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7242   -2.4509    0.9934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5500   -2.0188    2.5001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9620   -0.1158    0.6779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8169    0.4284    2.1914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4184   -1.2438    3.4308 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4231    0.1596    2.6607 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1680   -2.7535    1.4575 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3926   -2.3694    0.6140 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6324   -0.6310    1.8743 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2318    0.4174    2.0728 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0459    0.6563   -0.3863 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5967    1.2062    0.3901 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7058   -0.8742   -0.1680 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2913   -1.5074   -1.0263 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1724    0.4051   -2.5146 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6943   -0.5524   -2.7049 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0921    1.8415   -2.8490 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2307    2.1463   -1.3031 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2809    2.5705   -0.0138 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  0
  6 31  1  0
  7 32  1  0
  7 33  1  0
  8 34  1  0
  8 35  1  0
  9 36  1  0
 10 37  1  0
 11 38  1  0
 11 39  1  0
 12 40  1  0
 12 41  1  0
 13 42  1  0
 13 43  1  0
 14 44  1  0
 14 45  1  0
 15 46  1  0
 15 47  1  0
 18 48  1  0
M  END

HEADER    PROTEIN                                 31-MAR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: LMFA01030055                                      
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   31-MAR-20         0                                  
HETATM    1  C   UNK     0      21.337  10.566   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      22.670   9.796   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      24.004  10.566   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      25.338   9.796   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      26.672  10.566   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      28.006   9.796   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      29.339  10.566   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      30.673   9.796   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      29.339  12.106   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      19.797  10.566   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      18.463   9.796   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      17.129  10.566   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      15.796   9.796   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.462  10.566   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.128   9.796   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.794  10.566   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.461   9.796   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.127  10.566   0.000  0.00  0.00           C+0
CONECT    1    2   10                                                       
CONECT    2    1    3                                                       
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                                                            
CONECT   10    1   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   34    0
END

COMPND    HMDB0002186
HETATM    1  C1  UNL     1      -6.538   1.134  -1.280  1.00  0.00           C  
HETATM    2  C2  UNL     1      -5.267   0.747  -0.550  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.482  -0.284  -1.307  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.224  -0.657  -0.573  1.00  0.00           C  
HETATM    5  C5  UNL     1      -3.499  -1.227   0.784  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.210  -1.608   1.518  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.337  -0.418   1.701  1.00  0.00           C  
HETATM    8  C8  UNL     1      -0.059  -0.791   2.452  1.00  0.00           C  
HETATM    9  C9  UNL     1       0.661  -1.779   1.671  1.00  0.00           C  
HETATM   10  C10 UNL     1       1.875  -1.576   1.214  1.00  0.00           C  
HETATM   11  C11 UNL     1       2.616  -0.355   1.439  1.00  0.00           C  
HETATM   12  C12 UNL     1       2.976   0.330   0.114  1.00  0.00           C  
HETATM   13  C13 UNL     1       3.824  -0.574  -0.743  1.00  0.00           C  
HETATM   14  C14 UNL     1       4.143   0.150  -2.026  1.00  0.00           C  
HETATM   15  C15 UNL     1       4.890   1.427  -1.831  1.00  0.00           C  
HETATM   16  C16 UNL     1       6.189   1.271  -1.167  1.00  0.00           C  
HETATM   17  O1  UNL     1       6.689   0.198  -0.774  1.00  0.00           O  
HETATM   18  O2  UNL     1       6.940   2.427  -0.952  1.00  0.00           O  
HETATM   19  H1  UNL     1      -6.920   2.065  -0.827  1.00  0.00           H  
HETATM   20  H2  UNL     1      -6.341   1.322  -2.348  1.00  0.00           H  
HETATM   21  H3  UNL     1      -7.331   0.370  -1.193  1.00  0.00           H  
HETATM   22  H4  UNL     1      -4.702   1.686  -0.373  1.00  0.00           H  
HETATM   23  H5  UNL     1      -5.604   0.345   0.450  1.00  0.00           H  
HETATM   24  H6  UNL     1      -5.134  -1.159  -1.460  1.00  0.00           H  
HETATM   25  H7  UNL     1      -4.208   0.146  -2.283  1.00  0.00           H  
HETATM   26  H8  UNL     1      -2.646  -1.370  -1.178  1.00  0.00           H  
HETATM   27  H9  UNL     1      -2.595   0.255  -0.460  1.00  0.00           H  
HETATM   28  H10 UNL     1      -4.055  -0.529   1.437  1.00  0.00           H  
HETATM   29  H11 UNL     1      -4.139  -2.122   0.647  1.00  0.00           H  
HETATM   30  H12 UNL     1      -1.724  -2.451   0.993  1.00  0.00           H  
HETATM   31  H13 UNL     1      -2.550  -2.019   2.500  1.00  0.00           H  
HETATM   32  H14 UNL     1      -0.962  -0.116   0.678  1.00  0.00           H  
HETATM   33  H15 UNL     1      -1.817   0.428   2.191  1.00  0.00           H  
HETATM   34  H16 UNL     1      -0.418  -1.244   3.431  1.00  0.00           H  
HETATM   35  H17 UNL     1       0.423   0.160   2.661  1.00  0.00           H  
HETATM   36  H18 UNL     1       0.168  -2.754   1.458  1.00  0.00           H  
HETATM   37  H19 UNL     1       2.393  -2.369   0.614  1.00  0.00           H  
HETATM   38  H20 UNL     1       3.632  -0.631   1.874  1.00  0.00           H  
HETATM   39  H21 UNL     1       2.232   0.417   2.073  1.00  0.00           H  
HETATM   40  H22 UNL     1       2.046   0.656  -0.386  1.00  0.00           H  
HETATM   41  H23 UNL     1       3.597   1.206   0.390  1.00  0.00           H  
HETATM   42  H24 UNL     1       4.706  -0.874  -0.168  1.00  0.00           H  
HETATM   43  H25 UNL     1       3.291  -1.507  -1.026  1.00  0.00           H  
HETATM   44  H26 UNL     1       3.172   0.405  -2.515  1.00  0.00           H  
HETATM   45  H27 UNL     1       4.694  -0.552  -2.705  1.00  0.00           H  
HETATM   46  H28 UNL     1       5.092   1.841  -2.849  1.00  0.00           H  
HETATM   47  H29 UNL     1       4.231   2.146  -1.303  1.00  0.00           H  
HETATM   48  H30 UNL     1       7.281   2.570  -0.014  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3   22   23
CONECT    3    4   24   25
CONECT    4    5   26   27
CONECT    5    6   28   29
CONECT    6    7   30   31
CONECT    7    8   32   33
CONECT    8    9   34   35
CONECT    9   10   10   36
CONECT   10   11   37
CONECT   11   12   38   39
CONECT   12   13   40   41
CONECT   13   14   42   43
CONECT   14   15   44   45
CONECT   15   16   46   47
CONECT   16   17   17   18
CONECT   18   48
END

HMDB0002186
     RDKit          3D
Hypogeic acid
 48 47  0  0  0  0  0  0  0  0999 V2000
   -6.5379    1.1337   -1.2796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2669    0.7473   -0.5496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4819   -0.2843   -1.3066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2242   -0.6567   -0.5732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4992   -1.2268    0.7840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2095   -1.6078    1.5176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3373   -0.4182    1.7013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0585   -0.7907    2.4517 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6611   -1.7795    1.6707 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8753   -1.5759    1.2136 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6165   -0.3551    1.4391 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9756    0.3300    0.1144 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8236   -0.5744   -0.7434 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1427    0.1502   -2.0262 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8902    1.4272   -1.8312 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1890    1.2709   -1.1671 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6894    0.1975   -0.7743 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9403    2.4274   -0.9515 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9199    2.0651   -0.8270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3410    1.3218   -2.3477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3308    0.3699   -1.1930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7023    1.6859   -0.3732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6035    0.3446    0.4501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1338   -1.1592   -1.4595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2085    0.1464   -2.2831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6463   -1.3698   -1.1777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5946    0.2548   -0.4596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0549   -0.5293    1.4366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1394   -2.1217    0.6474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7242   -2.4509    0.9934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5500   -2.0188    2.5001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9620   -0.1158    0.6779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8169    0.4284    2.1914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4184   -1.2438    3.4308 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4231    0.1596    2.6607 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1680   -2.7535    1.4575 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3926   -2.3694    0.6140 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6324   -0.6310    1.8743 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2318    0.4174    2.0728 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0459    0.6563   -0.3863 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5967    1.2062    0.3901 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7058   -0.8742   -0.1680 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2913   -1.5074   -1.0263 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1724    0.4051   -2.5146 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6943   -0.5524   -2.7049 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0921    1.8415   -2.8490 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2307    2.1463   -1.3031 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2809    2.5705   -0.0138 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  0
  6 31  1  0
  7 32  1  0
  7 33  1  0
  8 34  1  0
  8 35  1  0
  9 36  1  0
 10 37  1  0
 11 38  1  0
 11 39  1  0
 12 40  1  0
 12 41  1  0
 13 42  1  0
 13 43  1  0
 14 44  1  0
 14 45  1  0
 15 46  1  0
 15 47  1  0
 18 48  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(Z)-7-Hexadecenoic acid	ChEBI
16:1 cis7	ChEBI
7-Hexadecenoic acid	ChEBI
C16:1(N=9)	ChEBI
(Z)-7-Hexadecenoate	Generator
7-Hexadecenoate	Generator
Hypogeate	Generator
7Z-Palmitoleate	HMDB
Hypogeic acid	ChEBI

Chemical Formula

C₁₆H₃₀O₂

Average Molecular Weight

254.4082

Monoisotopic Molecular Weight

254.224580204

IUPAC Name

(7Z)-hexadec-7-enoic acid

Traditional Name

7-hexadecenoic acid

CAS Registry Number

2416-19-5

SMILES

CCCCCCCC\C=C/CCCCCC(O)=O

InChI Identifier

InChI=1S/C16H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h9-10H,2-8,11-15H2,1H3,(H,17,18)/b10-9-

InChI Key

PJHOFUXBXJNUAC-KTKRTIGZSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Long-chain fatty acids

Alternative Parents

Substituents

Long-chain fatty acid
Unsaturated fatty acid
Straight chain fatty acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

hexadecenoic acid (CHEBI:35465 )
Unsaturated fatty acids (LMFA01030766 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 27329611)

Cellular substructure

Extracellular (HMDB: HMDB0002186)
Membrane (HMDB: HMDB0002186)

Source

Exogenous

Exogenous (HMDB: HMDB0002186)

Food

Soy

Soy bean (FooDB: FOOD00085)

Endogenous

Endogenous (HMDB: HMDB0002186)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	374.80 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	0.13 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	6.640 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00044 g/L	ALOGPS
logP	6.74	ALOGPS
logP	5.89	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	4.89	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	78.2 m³·mol⁻¹	ChemAxon
Polarizability	32.87 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	168.278	31661259
DarkChem	[M-H]-	168.847	31661259
DeepCCS	[M+H]+	173.475	30932474
DeepCCS	[M-H]-	169.455	30932474
DeepCCS	[M-2H]-	206.942	30932474
DeepCCS	[M+Na]+	182.711	30932474
AllCCS	[M+H]+	170.1	32859911
AllCCS	[M+H-H2O]+	166.9	32859911
AllCCS	[M+NH4]+	173.1	32859911
AllCCS	[M+Na]+	173.9	32859911
AllCCS	[M-H]-	171.5	32859911
AllCCS	[M+Na-2H]-	172.9	32859911
AllCCS	[M+HCOO]-	174.5	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	10.29 minutes	32390414
Predicted by Siyang on May 30, 2022	22.3337 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.94 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	34.2 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2925.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	615.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	242.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	370.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	566.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	977.0 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	777.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	95.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	2083.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	613.9 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1781.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	759.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	479.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	646.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	588.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Hypogeic acid	CCCCCCCC\C=C/CCCCCC(O)=O	2908.4	Standard polar	33892256
Hypogeic acid	CCCCCCCC\C=C/CCCCCC(O)=O	1902.5	Standard non polar	33892256
Hypogeic acid	CCCCCCCC\C=C/CCCCCC(O)=O	1953.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Hypogeic acid,1TMS,isomer #1	CCCCCCCC/C=C\CCCCCC(=O)O[Si](C)(C)C	2020.1	Semi standard non polar	33892256
Hypogeic acid,1TBDMS,isomer #1	CCCCCCCC/C=C\CCCCCC(=O)O[Si](C)(C)C(C)(C)C	2267.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Hypogeic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f6x-9510000000-bdce75d8af5ee132cf28	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hypogeic acid GC-MS (1 TMS) - 70eV, Positive	splash10-0fmr-9320000000-551ab7e6f36944ae8af5	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hypogeic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hypogeic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hypogeic acid 10V, Positive-QTOF	splash10-0a4r-0190000000-2b0ab958644904fa3131	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hypogeic acid 20V, Positive-QTOF	splash10-0a4i-6980000000-9e4893e4f28f372d46f8	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hypogeic acid 40V, Positive-QTOF	splash10-052f-9700000000-07b34dfe9673051c7dd9	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hypogeic acid 10V, Negative-QTOF	splash10-0udi-0090000000-f95c32d87a7c925eb0b6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hypogeic acid 20V, Negative-QTOF	splash10-0zfr-1090000000-0e53950395e4681a05e7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hypogeic acid 40V, Negative-QTOF	splash10-0a4i-9220000000-069cdf9a767dd948a604	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hypogeic acid 10V, Positive-QTOF	splash10-0a4r-5490000000-7120b44fb5857824f928	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hypogeic acid 20V, Positive-QTOF	splash10-05ur-9300000000-7dad5182251945868410	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hypogeic acid 40V, Positive-QTOF	splash10-0apl-9000000000-0dbf555eda66430abcc2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hypogeic acid 10V, Negative-QTOF	splash10-0udi-0090000000-59ee0bcbfc44b6d6a52a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hypogeic acid 20V, Negative-QTOF	splash10-0udr-1090000000-e0dcc20ec70f6b8a1c71	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hypogeic acid 40V, Negative-QTOF	splash10-0006-9310000000-e0f040eaac68ddf1f77b	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	50.6 +/- 15.8 uM	Adult (>18 years old)	Not Specified	Normal	27329611	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	67.3 +/- 75.2 uM	Adult (>18 years old)	Not Specified	Isovaleric acidemia	27329611	details

Associated Disorders and Diseases

Disease References

Isovaleric acidemia
Dercksen M, Kulik W, Mienie LJ, Reinecke CJ, Wanders RJ, Duran M: Polyunsaturated fatty acid status in treated isovaleric acidemia patients. Eur J Clin Nutr. 2016 Oct;70(10):1123-1126. doi: 10.1038/ejcn.2016.100. Epub 2016 Jun 22. [PubMed:27329611 ]

Associated OMIM IDs

243500 (Isovaleric acidemia)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB004011

KNApSAcK ID

Not Available

Chemspider ID

4476987

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5318393

PDB ID

Not Available

ChEBI ID

35465

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1439911

References

Synthesis Reference

Fukuba, Hiroyasu; Yamazawa, Nobue; Mitsuzawa, Tokuko. Higher-fatty acid dehydrogenase in plant seeds. IV. Dehydrogenation position in fatty acid molecules. Nippon Nogei Kagaku Kaishi (1957), 31 132-6.

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Hypogeic acid (HMDB0002186)

MOL for HMDB0002186 (Hypogeic acid)

3D MOL for HMDB0002186 (Hypogeic acid)

3D SDF for HMDB0002186 (Hypogeic acid)

3D-SDF for HMDB0002186 (Hypogeic acid)

PDB for HMDB0002186 (Hypogeic acid)

3D PDB for HMDB0002186 (Hypogeic acid)

SMILES for HMDB0002186 (Hypogeic acid)

INCHI for HMDB0002186 (Hypogeic acid)

Structure for HMDB0002186 (Hypogeic acid)

3D Structure for HMDB0002186 (Hypogeic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra