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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-05-22 15:12:17 UTC

Update Date

2022-03-07 02:49:17 UTC

HMDB ID

HMDB0002890

Secondary Accession Numbers

HMDB02890

Metabolite Identification

Common Name

3-cis-Hydroxy-b,e-Caroten-3'-one

Description

cis-3-hydroxy-b,e-Caroten-3'-one is a carotenoid found in human fluids. Carotenoids are isoprenoid molecules that are widespread in nature and are typically seen as pigments in fruits, flowers, birds and crustacea. Animals are unable to synthesise carotenoids de novo, and rely upon the diet as a source of these compounds. Over recent years there has been considerable interest in dietary carotenoids with respect to their potential in alleviating age-related diseases in humans. This attention has been mirrored by significant advances in cloning most of the carotenoid genes and in the genetic manipulation of crop plants with the intention of increasing levels in the diet. Studies have shown an inverse relationship between the consumption of certain fruits and vegetables and the risk of epithelial cancer. Since carotenoids are among the micronutrients found in cancer preventive foods, detailed qualitative and quantitative determination of these compounds, particularly in fruits and vegetables and in human plasma, have recently become increasingly important. (PMID: 1416048 , 15003396 ).

Structure

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


  Mrv1652304202019482D          

 41 42  0  0  0  0            999 V2000
    4.2065   -7.9889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4921   -8.4014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7776   -7.9889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7776   -7.1639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4921   -6.7514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2065   -7.1639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6190   -8.7034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0316   -7.9889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4921   -5.9265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0631   -8.4014    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9210   -6.7514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9210   -5.9265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6355   -5.5140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3500   -5.9265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6355   -4.6890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0644   -5.5140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   17.7815   -5.9265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0670   -5.5140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5276   -5.9265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0670   -7.9889    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  2  0  0  0  0
  6  1  1  0  0  0  0
  7  1  1  0  0  0  0
  8  1  1  0  0  0  0
  9  5  1  0  0  0  0
 10  3  1  0  0  0  0
 11  6  1  0  0  0  0
 12 11  2  0  0  0  0
 13 12  1  0  0  0  0
 14 13  2  0  0  0  0
 15 13  1  0  0  0  0
 16 14  1  0  0  0  0
 17 16  2  0  0  0  0
 18 17  1  0  0  0  0
 19 18  2  0  0  0  0
 20 18  1  0  0  0  0
 21 19  1  0  0  0  0
 22 21  2  0  0  0  0
 23 22  1  0  0  0  0
 24 23  2  0  0  0  0
 25 24  1  0  0  0  0
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 27 25  2  0  0  0  0
 28 27  1  0  0  0  0
 29 28  2  0  0  0  0
 30 29  1  0  0  0  0
 31 30  2  0  0  0  0
 32 31  1  0  0  0  0
 33 29  1  0  0  0  0
 34 32  1  0  0  0  0
 35 32  1  0  0  0  0
 36 35  2  0  0  0  0
 37 34  1  0  0  0  0
 38 36  1  0  0  0  0
 39 38  2  0  0  0  0
 39 34  1  0  0  0  0
 40 34  1  0  0  0  0
 41 35  1  0  0  0  0
M  END

HMDB0002890
     RDKit          3D
3-cis-Hydroxy-b,e-Caroten-3'-one
 95 96  0  0  0  0  0  0  0  0999 V2000
   11.0339    2.3064    3.3612 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7710    1.6779    2.2038 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0284    2.0035    2.0532 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0
  2  3  2  0
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 40 92  1  0
 41 93  1  0
 41 94  1  0
 41 95  1  0
M  END


  Mrv1652304202019482D          

 41 42  0  0  0  0            999 V2000
    4.2065   -7.9889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4921   -8.4014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7776   -7.9889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7776   -7.1639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4921   -6.7514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2065   -7.1639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6190   -8.7034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0316   -7.9889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4921   -5.9265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0631   -8.4014    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9210   -6.7514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9210   -5.9265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6355   -5.5140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3500   -5.9265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6355   -4.6890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0644   -5.5140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7789   -5.9265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4934   -5.5140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2078   -5.9265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4934   -4.6890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9223   -5.5140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6368   -5.9265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6368   -6.7515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3512   -7.1639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0657   -6.7515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3512   -7.9889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7802   -7.1640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4946   -6.7515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2091   -7.1640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9236   -6.7515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6380   -7.1640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3525   -6.7515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2091   -7.9889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3525   -5.9265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0670   -7.1640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7815   -6.7515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9401   -5.2120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7815   -5.9265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0670   -5.5140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5276   -5.9265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0670   -7.9889    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  2  0  0  0  0
  6  1  1  0  0  0  0
  7  1  1  0  0  0  0
  8  1  1  0  0  0  0
  9  5  1  0  0  0  0
 10  3  1  0  0  0  0
 11  6  1  0  0  0  0
 12 11  2  0  0  0  0
 13 12  1  0  0  0  0
 14 13  2  0  0  0  0
 15 13  1  0  0  0  0
 16 14  1  0  0  0  0
 17 16  2  0  0  0  0
 18 17  1  0  0  0  0
 19 18  2  0  0  0  0
 20 18  1  0  0  0  0
 21 19  1  0  0  0  0
 22 21  2  0  0  0  0
 23 22  1  0  0  0  0
 24 23  2  0  0  0  0
 25 24  1  0  0  0  0
 26 24  1  0  0  0  0
 27 25  2  0  0  0  0
 28 27  1  0  0  0  0
 29 28  2  0  0  0  0
 30 29  1  0  0  0  0
 31 30  2  0  0  0  0
 32 31  1  0  0  0  0
 33 29  1  0  0  0  0
 34 32  1  0  0  0  0
 35 32  1  0  0  0  0
 36 35  2  0  0  0  0
 37 34  1  0  0  0  0
 38 36  1  0  0  0  0
 39 38  2  0  0  0  0
 39 34  1  0  0  0  0
 40 34  1  0  0  0  0
 41 35  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0002890

> <DATABASE_NAME>
hmdb

> <SMILES>
C\C(\C=C\C=C(/C)\C=C\C1C(C)=CC=CC1(C)C)=C\C=C/C=C(\C)/C=C/C=C(\C)/C=C/C1=C(C)CC(O)CC1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C40H54O/c1-30(18-13-20-32(3)23-25-37-34(5)22-15-27-39(37,7)8)16-11-12-17-31(2)19-14-21-33(4)24-26-38-35(6)28-36(41)29-40(38,9)10/h11-27,36-37,41H,28-29H2,1-10H3/b12-11-,18-13+,19-14+,25-23+,26-24+,30-16-,31-17+,32-20+,33-21+

> <INCHI_KEY>
HBHHQQIZEXNSHZ-KYFZIPCGSA-N

> <FORMULA>
C40H54O

> <MOLECULAR_WEIGHT>
550.8562

> <EXACT_MASS>
550.41746635

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
95

> <JCHEM_AVERAGE_POLARIZABILITY>
71.05222916185575

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3,5,5-trimethyl-4-[(1E,3E,5E,7E,9Z,11Z,13E,15E,17E)-3,7,12,16-tetramethyl-18-(2,6,6-trimethylcyclohexa-2,4-dien-1-yl)octadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]cyclohex-3-en-1-ol

> <ALOGPS_LOGP>
8.96

> <JCHEM_LOGP>
9.419098740999999

> <ALOGPS_LOGS>
-5.84

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.907213404525137

> <JCHEM_PKA_STRONGEST_BASIC>
-1.089784856860705

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
194.66450000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.88e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,5,5-trimethyl-4-[(1E,3E,5E,7E,9Z,11Z,13E,15E,17E)-3,7,12,16-tetramethyl-18-(2,6,6-trimethylcyclohexa-2,4-dien-1-yl)octadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]cyclohex-3-en-1-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0002890
     RDKit          3D
3-cis-Hydroxy-b,e-Caroten-3'-one
 95 96  0  0  0  0  0  0  0  0999 V2000
   11.0339    2.3064    3.3612 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7710    1.6779    2.2038 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0284    2.0035    2.0532 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7977    1.4452    0.9766 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2454    0.6022    0.1415 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8709    0.1770    0.2322 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2213    0.3386   -1.1514 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8136   -1.3745    0.4456 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.8379    1.4836    0.7434 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4903   -3.8866    0.6443 H   0  0  0  0  0  0  0  0  0  0  0  0
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 39 32  1  0
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 41 95  1  0
M  END

HEADER    PROTEIN                                 20-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-20         0                                  
HETATM    1  C   UNK     0       7.852 -14.913   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.519 -15.683   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.185 -14.913   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.185 -13.373   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.519 -12.603   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.852 -13.373   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.622 -16.246   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.392 -14.913   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.519 -11.063   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       3.851 -15.683   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       9.186 -12.603   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.186 -11.063   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.520 -10.293   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.853 -11.063   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.520  -8.753   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.187 -10.293   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.521 -11.063   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      15.854 -10.293   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      17.188 -11.063   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      15.854  -8.753   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      18.522 -10.293   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      19.855 -11.063   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      19.855 -12.603   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      21.189 -13.373   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      22.523 -12.603   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      21.189 -14.913   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      23.856 -13.373   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      25.190 -12.603   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      26.524 -13.373   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      27.857 -12.603   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      29.191 -13.373   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      30.525 -12.603   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      26.524 -14.913   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      30.525 -11.063   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      31.858 -13.373   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      33.192 -12.603   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      29.755  -9.729   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      33.192 -11.063   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      31.858 -10.293   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      28.985 -11.063   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      31.858 -14.913   0.000  0.00  0.00           C+0
CONECT    1    2    6    7    8                                             
CONECT    2    1    3                                                       
CONECT    3    2    4   10                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    9                                                  
CONECT    6    5    1   11                                                  
CONECT    7    1                                                            
CONECT    8    1                                                            
CONECT    9    5                                                            
CONECT   10    3                                                            
CONECT   11    6   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13   16                                                       
CONECT   15   13                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18   21                                                       
CONECT   20   18                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24   27                                                       
CONECT   26   24                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   33                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   34   35                                                  
CONECT   33   29                                                            
CONECT   34   32   37   39   40                                             
CONECT   35   32   36   41                                                  
CONECT   36   35   38                                                       
CONECT   37   34                                                            
CONECT   38   36   39                                                       
CONECT   39   38   34                                                       
CONECT   40   34                                                            
CONECT   41   35                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   84    0
END

COMPND    HMDB0002890
HETATM    1  C1  UNL     1      11.034   2.306   3.361  1.00  0.00           C  
HETATM    2  C2  UNL     1      11.771   1.678   2.204  1.00  0.00           C  
HETATM    3  C3  UNL     1      13.028   2.004   2.053  1.00  0.00           C  
HETATM    4  C4  UNL     1      13.798   1.445   0.977  1.00  0.00           C  
HETATM    5  C5  UNL     1      13.245   0.602   0.142  1.00  0.00           C  
HETATM    6  C6  UNL     1      11.871   0.177   0.232  1.00  0.00           C  
HETATM    7  C7  UNL     1      11.221   0.339  -1.151  1.00  0.00           C  
HETATM    8  C8  UNL     1      11.814  -1.375   0.446  1.00  0.00           C  
HETATM    9  C9  UNL     1      11.072   0.774   1.297  1.00  0.00           C  
HETATM   10  C10 UNL     1       9.838   1.484   0.743  1.00  0.00           C  
HETATM   11  C11 UNL     1       8.655   0.949   0.933  1.00  0.00           C  
HETATM   12  C12 UNL     1       7.397   1.582   0.426  1.00  0.00           C  
HETATM   13  C13 UNL     1       7.434   2.844  -0.311  1.00  0.00           C  
HETATM   14  C14 UNL     1       6.261   0.974   0.642  1.00  0.00           C  
HETATM   15  C15 UNL     1       4.977   1.429   0.235  1.00  0.00           C  
HETATM   16  C16 UNL     1       3.859   0.737   0.463  1.00  0.00           C  
HETATM   17  C17 UNL     1       2.598   1.261   0.023  1.00  0.00           C  
HETATM   18  C18 UNL     1       2.532   2.590  -0.666  1.00  0.00           C  
HETATM   19  C19 UNL     1       1.502   0.531   0.238  1.00  0.00           C  
HETATM   20  C20 UNL     1       1.529  -0.752   0.885  1.00  0.00           C  
HETATM   21  C21 UNL     1       0.438  -1.484   1.063  1.00  0.00           C  
HETATM   22  C22 UNL     1      -0.856  -1.044   0.623  1.00  0.00           C  
HETATM   23  C23 UNL     1      -1.973  -1.776   0.726  1.00  0.00           C  
HETATM   24  C24 UNL     1      -1.854  -3.122   1.329  1.00  0.00           C  
HETATM   25  C25 UNL     1      -3.235  -1.185   0.314  1.00  0.00           C  
HETATM   26  C26 UNL     1      -4.361  -1.863   0.303  1.00  0.00           C  
HETATM   27  C27 UNL     1      -5.602  -1.228  -0.105  1.00  0.00           C  
HETATM   28  C28 UNL     1      -6.766  -1.848  -0.197  1.00  0.00           C  
HETATM   29  C29 UNL     1      -6.938  -3.280   0.100  1.00  0.00           C  
HETATM   30  C30 UNL     1      -7.952  -1.053  -0.556  1.00  0.00           C  
HETATM   31  C31 UNL     1      -9.105  -1.620  -0.690  1.00  0.00           C  
HETATM   32  C32 UNL     1     -10.375  -0.926  -1.047  1.00  0.00           C  
HETATM   33  C33 UNL     1     -11.458  -1.639  -1.174  1.00  0.00           C  
HETATM   34  C34 UNL     1     -11.400  -3.109  -0.966  1.00  0.00           C  
HETATM   35  C35 UNL     1     -12.792  -1.070  -1.526  1.00  0.00           C  
HETATM   36  C36 UNL     1     -12.851   0.368  -1.031  1.00  0.00           C  
HETATM   37  O1  UNL     1     -12.943   0.370   0.365  1.00  0.00           O  
HETATM   38  C37 UNL     1     -11.662   1.124  -1.519  1.00  0.00           C  
HETATM   39  C38 UNL     1     -10.331   0.523  -1.204  1.00  0.00           C  
HETATM   40  C39 UNL     1      -9.786   1.183   0.074  1.00  0.00           C  
HETATM   41  C40 UNL     1      -9.406   0.947  -2.348  1.00  0.00           C  
HETATM   42  H1  UNL     1      10.912   1.626   4.204  1.00  0.00           H  
HETATM   43  H2  UNL     1      11.570   3.207   3.716  1.00  0.00           H  
HETATM   44  H3  UNL     1      10.023   2.627   3.001  1.00  0.00           H  
HETATM   45  H4  UNL     1      13.548   2.704   2.727  1.00  0.00           H  
HETATM   46  H5  UNL     1      14.854   1.732   0.861  1.00  0.00           H  
HETATM   47  H6  UNL     1      13.909   0.225  -0.651  1.00  0.00           H  
HETATM   48  H7  UNL     1      10.847   1.365  -1.305  1.00  0.00           H  
HETATM   49  H8  UNL     1      12.033   0.176  -1.885  1.00  0.00           H  
HETATM   50  H9  UNL     1      10.475  -0.459  -1.308  1.00  0.00           H  
HETATM   51  H10 UNL     1      12.595  -1.789  -0.185  1.00  0.00           H  
HETATM   52  H11 UNL     1      11.903  -1.562   1.520  1.00  0.00           H  
HETATM   53  H12 UNL     1      10.808  -1.683   0.106  1.00  0.00           H  
HETATM   54  H13 UNL     1      10.687  -0.064   1.964  1.00  0.00           H  
HETATM   55  H14 UNL     1       9.926   2.407   0.208  1.00  0.00           H  
HETATM   56  H15 UNL     1       8.610   0.020   1.476  1.00  0.00           H  
HETATM   57  H16 UNL     1       6.531   3.169  -0.807  1.00  0.00           H  
HETATM   58  H17 UNL     1       7.676   3.656   0.444  1.00  0.00           H  
HETATM   59  H18 UNL     1       8.338   2.883  -0.993  1.00  0.00           H  
HETATM   60  H19 UNL     1       6.295   0.012   1.201  1.00  0.00           H  
HETATM   61  H20 UNL     1       4.864   2.368  -0.285  1.00  0.00           H  
HETATM   62  H21 UNL     1       4.029  -0.194   0.979  1.00  0.00           H  
HETATM   63  H22 UNL     1       3.121   2.468  -1.600  1.00  0.00           H  
HETATM   64  H23 UNL     1       1.505   2.901  -0.852  1.00  0.00           H  
HETATM   65  H24 UNL     1       3.093   3.302  -0.024  1.00  0.00           H  
HETATM   66  H25 UNL     1       0.588   0.984  -0.109  1.00  0.00           H  
HETATM   67  H26 UNL     1       2.440  -1.172   1.253  1.00  0.00           H  
HETATM   68  H27 UNL     1       0.550  -2.437   1.554  1.00  0.00           H  
HETATM   69  H28 UNL     1      -0.988  -0.072   0.171  1.00  0.00           H  
HETATM   70  H29 UNL     1      -1.490  -3.887   0.644  1.00  0.00           H  
HETATM   71  H30 UNL     1      -2.838  -3.464   1.737  1.00  0.00           H  
HETATM   72  H31 UNL     1      -1.215  -3.047   2.251  1.00  0.00           H  
HETATM   73  H32 UNL     1      -3.270  -0.120  -0.004  1.00  0.00           H  
HETATM   74  H33 UNL     1      -4.299  -2.895   0.605  1.00  0.00           H  
HETATM   75  H34 UNL     1      -5.578  -0.153  -0.358  1.00  0.00           H  
HETATM   76  H35 UNL     1      -5.945  -3.758   0.161  1.00  0.00           H  
HETATM   77  H36 UNL     1      -7.541  -3.836  -0.658  1.00  0.00           H  
HETATM   78  H37 UNL     1      -7.417  -3.401   1.118  1.00  0.00           H  
HETATM   79  H38 UNL     1      -7.812  -0.014  -0.696  1.00  0.00           H  
HETATM   80  H39 UNL     1      -9.185  -2.701  -0.536  1.00  0.00           H  
HETATM   81  H40 UNL     1     -12.404  -3.531  -1.134  1.00  0.00           H  
HETATM   82  H41 UNL     1     -11.024  -3.384   0.051  1.00  0.00           H  
HETATM   83  H42 UNL     1     -10.684  -3.506  -1.723  1.00  0.00           H  
HETATM   84  H43 UNL     1     -13.590  -1.641  -1.042  1.00  0.00           H  
HETATM   85  H44 UNL     1     -12.902  -1.140  -2.615  1.00  0.00           H  
HETATM   86  H45 UNL     1     -13.765   0.822  -1.424  1.00  0.00           H  
HETATM   87  H46 UNL     1     -13.836   0.624   0.661  1.00  0.00           H  
HETATM   88  H47 UNL     1     -11.749   1.362  -2.591  1.00  0.00           H  
HETATM   89  H48 UNL     1     -11.685   2.120  -1.003  1.00  0.00           H  
HETATM   90  H49 UNL     1      -9.032   1.904  -0.211  1.00  0.00           H  
HETATM   91  H50 UNL     1     -10.646   1.770   0.505  1.00  0.00           H  
HETATM   92  H51 UNL     1      -9.479   0.428   0.795  1.00  0.00           H  
HETATM   93  H52 UNL     1      -8.729   1.712  -1.967  1.00  0.00           H  
HETATM   94  H53 UNL     1      -9.987   1.429  -3.181  1.00  0.00           H  
HETATM   95  H54 UNL     1      -8.874   0.061  -2.696  1.00  0.00           H  
CONECT    1    2   42   43   44
CONECT    2    3    3    9
CONECT    3    4   45
CONECT    4    5    5   46
CONECT    5    6   47
CONECT    6    7    8    9
CONECT    7   48   49   50
CONECT    8   51   52   53
CONECT    9   10   54
CONECT   10   11   11   55
CONECT   11   12   56
CONECT   12   13   14   14
CONECT   13   57   58   59
CONECT   14   15   60
CONECT   15   16   16   61
CONECT   16   17   62
CONECT   17   18   19   19
CONECT   18   63   64   65
CONECT   19   20   66
CONECT   20   21   21   67
CONECT   21   22   68
CONECT   22   23   23   69
CONECT   23   24   25
CONECT   24   70   71   72
CONECT   25   26   26   73
CONECT   26   27   74
CONECT   27   28   28   75
CONECT   28   29   30
CONECT   29   76   77   78
CONECT   30   31   31   79
CONECT   31   32   80
CONECT   32   33   33   39
CONECT   33   34   35
CONECT   34   81   82   83
CONECT   35   36   84   85
CONECT   36   37   38   86
CONECT   37   87
CONECT   38   39   88   89
CONECT   39   40   41
CONECT   40   90   91   92
CONECT   41   93   94   95
END

HMDB0002890
     RDKit          3D
3-cis-Hydroxy-b,e-Caroten-3'-one
 95 96  0  0  0  0  0  0  0  0999 V2000
   11.0339    2.3064    3.3612 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7710    1.6779    2.2038 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0284    2.0035    2.0532 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7977    1.4452    0.9766 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2454    0.6022    0.1415 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8709    0.1770    0.2322 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2213    0.3386   -1.1514 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8136   -1.3745    0.4456 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0723    0.7738    1.2969 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8379    1.4836    0.7434 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6550    0.9492    0.9333 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3973    1.5822    0.4255 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4335    2.8437   -0.3108 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2610    0.9737    0.6415 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9767    1.4290    0.2352 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8590    0.7372    0.4630 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5981    1.2605    0.0233 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5319    2.5896   -0.6663 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5017    0.5307    0.2379 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5286   -0.7515    0.8853 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4378   -1.4836    1.0631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8561   -1.0444    0.6229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9727   -1.7759    0.7264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8537   -3.1216    1.3294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2350   -1.1850    0.3144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3612   -1.8632    0.3025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6025   -1.2282   -0.1049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7656   -1.8479   -0.1965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9376   -3.2798    0.1003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9522   -1.0531   -0.5556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1048   -1.6196   -0.6902 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3751   -0.9265   -1.0466 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4579   -1.6386   -1.1738 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3997   -3.1087   -0.9660 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.7915   -1.0696   -1.5257 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.8508    0.3680   -1.0314 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.9425    0.3703    0.3650 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6618    1.1236   -1.5192 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3310    0.5231   -1.2038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7865    1.1830    0.0745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4057    0.9466   -2.3484 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9119    1.6257    4.2039 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.5697    3.2072    3.7164 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0234    2.6266    3.0013 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.5481    2.7042    2.7268 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.8537    1.7320    0.8608 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.9094    0.2248   -0.6507 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8471    1.3653   -1.3049 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.0335    0.1760   -1.8850 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4747   -0.4585   -1.3079 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.5954   -1.7891   -0.1852 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.9035   -1.5622    1.5199 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8084   -1.6834    0.1064 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6874   -0.0638    1.9641 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9264    2.4067    0.2080 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6095    0.0202    1.4761 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5313    3.1687   -0.8068 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6762    3.6558    0.4440 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3380    2.8825   -0.9933 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2946    0.0118    1.2006 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8636    2.3681   -0.2848 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0292   -0.1937    0.9793 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1208    2.4675   -1.6003 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5054    2.9012   -0.8519 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0928    3.3019   -0.0236 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5880    0.9844   -0.1089 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4400   -1.1717    1.2532 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5503   -2.4371    1.5545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9883   -0.0718    0.1709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4903   -3.8866    0.6443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8375   -3.4644    1.7369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2149   -3.0469    2.2512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2699   -0.1196   -0.0042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2992   -2.8946    0.6048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5777   -0.1535   -0.3581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9445   -3.7581    0.1608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5409   -3.8360   -0.6583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4168   -3.4009    1.1175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8119   -0.0142   -0.6961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1849   -2.7015   -0.5360 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.4040   -3.5308   -1.1338 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0235   -3.3839    0.0514 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6844   -3.5061   -1.7230 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.5900   -1.6405   -1.0417 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.9017   -1.1404   -2.6146 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.7653    0.8223   -1.4244 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.8361    0.6237    0.6611 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.7486    1.3619   -2.5907 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6848    2.1200   -1.0032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0321    1.9041   -0.2113 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6461    1.7699    0.5054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4790    0.4278    0.7952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7288    1.7124   -1.9665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9865    1.4286   -3.1805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8736    0.0611   -2.6958 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
cis-3-Hydroxy-b,e-caroten-3'-one	HMDB

Chemical Formula

C₄₀H₅₄O

Average Molecular Weight

550.8562

Monoisotopic Molecular Weight

550.41746635

IUPAC Name

3,5,5-trimethyl-4-[(1E,3E,5E,7E,9Z,11Z,13E,15E,17E)-3,7,12,16-tetramethyl-18-(2,6,6-trimethylcyclohexa-2,4-dien-1-yl)octadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]cyclohex-3-en-1-ol

Traditional Name

3,5,5-trimethyl-4-[(1E,3E,5E,7E,9Z,11Z,13E,15E,17E)-3,7,12,16-tetramethyl-18-(2,6,6-trimethylcyclohexa-2,4-dien-1-yl)octadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]cyclohex-3-en-1-ol

CAS Registry Number

143167-27-5

SMILES

C\C(\C=C\C=C(/C)\C=C\C1C(C)=CC=CC1(C)C)=C\C=C/C=C(\C)/C=C/C=C(\C)/C=C/C1=C(C)CC(O)CC1(C)C

InChI Identifier

InChI=1S/C40H54O/c1-30(18-13-20-32(3)23-25-37-34(5)22-15-27-39(37,7)8)16-11-12-17-31(2)19-14-21-33(4)24-26-38-35(6)28-36(41)29-40(38,9)10/h11-27,36-37,41H,28-29H2,1-10H3/b12-11-,18-13+,19-14+,25-23+,26-24+,30-16-,31-17+,32-20+,33-21+

InChI Key

HBHHQQIZEXNSHZ-KYFZIPCGSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as xanthophylls. These are carotenoids containing an oxygenated carotene backbone. Carotenes are characterized by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain. Carotenes belonging form a subgroup of the carotenoids family. Xanthophylls arise by oxygenation of the carotene backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Tetraterpenoids

Direct Parent

Xanthophylls

Alternative Parents

Substituents

Xanthophyll
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0002890)
Membrane (HMDB: HMDB0002890)

Source

Exogenous

Exogenous (HMDB: HMDB0002890)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Endogenous

Endogenous (HMDB: HMDB0002890)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00079 g/L	ALOGPS
logP	8.96	ALOGPS
logP	9.42	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	18.91	ChemAxon
pKa (Strongest Basic)	-1.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	194.66 m³·mol⁻¹	ChemAxon
Polarizability	71.05 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	240.689	31661259
DarkChem	[M-H]-	237.254	31661259
DeepCCS	[M+H]+	257.06	30932474
DeepCCS	[M-H]-	255.235	30932474
DeepCCS	[M-2H]-	288.479	30932474
DeepCCS	[M+Na]+	262.666	30932474
AllCCS	[M+H]+	252.5	32859911
AllCCS	[M+H-H2O]+	250.7	32859911
AllCCS	[M+NH4]+	254.2	32859911
AllCCS	[M+Na]+	254.7	32859911
AllCCS	[M-H]-	224.1	32859911
AllCCS	[M+Na-2H]-	226.9	32859911
AllCCS	[M+HCOO]-	230.1	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.	4.53 minutes	32390414
Predicted by Siyang on May 30, 2022	45.7781 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.67 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	5869.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	1315.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	495.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	829.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	543.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	1796.0 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	1194.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	136.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	3928.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	1337.3 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	2327.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	1595.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	938.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	585.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	1135.7 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	10.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-cis-Hydroxy-b,e-Caroten-3'-one	C\C(\C=C\C=C(/C)\C=C\C1C(C)=CC=CC1(C)C)=C\C=C/C=C(\C)/C=C/C=C(\C)/C=C/C1=C(C)CC(O)CC1(C)C	5474.8	Standard polar	33892256
3-cis-Hydroxy-b,e-Caroten-3'-one	C\C(\C=C\C=C(/C)\C=C\C1C(C)=CC=CC1(C)C)=C\C=C/C=C(\C)/C=C/C=C(\C)/C=C/C1=C(C)CC(O)CC1(C)C	4482.1	Standard non polar	33892256
3-cis-Hydroxy-b,e-Caroten-3'-one	C\C(\C=C\C=C(/C)\C=C\C1C(C)=CC=CC1(C)C)=C\C=C/C=C(\C)/C=C/C=C(\C)/C=C/C1=C(C)CC(O)CC1(C)C	4119.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-cis-Hydroxy-b,e-Caroten-3'-one,1TMS,isomer #1	CC1=CC=CC(C)(C)C1/C=C/C(C)=C/C=C/C(C)=C\C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CC(O[Si](C)(C)C)CC1(C)C	4628.9	Semi standard non polar	33892256
3-cis-Hydroxy-b,e-Caroten-3'-one,1TBDMS,isomer #1	CC1=CC=CC(C)(C)C1/C=C/C(C)=C/C=C/C(C)=C\C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CC(O[Si](C)(C)C(C)(C)C)CC1(C)C	4829.1	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 - 3-cis-Hydroxy-b,e-Caroten-3'-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-0000190000-9a4f1b59190873e4c3f2	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-cis-Hydroxy-b,e-Caroten-3'-one GC-MS (1 TMS) - 70eV, Positive	splash10-0a4i-4100029000-2267338460caac887526	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-cis-Hydroxy-b,e-Caroten-3'-one GC-MS ("3-cis-Hydroxy-b,e-Caroten-3'-one,1TMS,#1" TMS) - 70eV, Positive	Not Available	2021-10-14	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-cis-Hydroxy-b,e-Caroten-3'-one GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-10-15	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 - 3-cis-Hydroxy-b,e-Caroten-3'-one 10V, Positive-QTOF	splash10-0f89-0524190000-1e02685f864d4398d7f4	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-cis-Hydroxy-b,e-Caroten-3'-one 20V, Positive-QTOF	splash10-0002-0849100000-6f9630a2e1b4f4a7d8a2	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-cis-Hydroxy-b,e-Caroten-3'-one 40V, Positive-QTOF	splash10-000b-0559100000-0c9fb166a1407029df16	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-cis-Hydroxy-b,e-Caroten-3'-one 10V, Negative-QTOF	splash10-0002-0000090000-41b1c053e1e4d235aee0	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-cis-Hydroxy-b,e-Caroten-3'-one 20V, Negative-QTOF	splash10-0002-0000090000-4398e765e8ece96df97b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-cis-Hydroxy-b,e-Caroten-3'-one 40V, Negative-QTOF	splash10-001i-0525190000-be086b830e4986cd5674	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-cis-Hydroxy-b,e-Caroten-3'-one 10V, Negative-QTOF	splash10-0002-0002090000-d245c75cd19588a03e96	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-cis-Hydroxy-b,e-Caroten-3'-one 20V, Negative-QTOF	splash10-0002-0335190000-999fb2b02ad985c493ff	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-cis-Hydroxy-b,e-Caroten-3'-one 40V, Negative-QTOF	splash10-0532-0739110000-9042f2060acceb7d73fd	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-cis-Hydroxy-b,e-Caroten-3'-one 10V, Positive-QTOF	splash10-0ufu-0456960000-9fe311e67e18bacfd40d	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-cis-Hydroxy-b,e-Caroten-3'-one 20V, Positive-QTOF	splash10-059i-0579420000-17a05d03fb902a9282dd	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-cis-Hydroxy-b,e-Caroten-3'-one 40V, Positive-QTOF	splash10-03di-0789100000-c5cb71a2c7841303f1f2	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB112208

KNApSAcK ID

Not Available

Chemspider ID

35013048

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53477759

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Khachik F, Beecher GR, Goli MB, Lusby WR, Smith JC Jr: Separation and identification of carotenoids and their oxidation products in the extracts of human plasma. Anal Chem. 1992 Sep 15;64(18):2111-22. [PubMed:1416048 ]
Fraser PD, Bramley PM: The biosynthesis and nutritional uses of carotenoids. Prog Lipid Res. 2004 May;43(3):228-65. [PubMed:15003396 ]

Showing metabocard for 3-cis-Hydroxy-b,e-Caroten-3'-one (HMDB0002890)

MOL for HMDB0002890 (3-cis-Hydroxy-b,e-Caroten-3'-one)

3D MOL for HMDB0002890 (3-cis-Hydroxy-b,e-Caroten-3'-one)

3D SDF for HMDB0002890 (3-cis-Hydroxy-b,e-Caroten-3'-one)

3D-SDF for HMDB0002890 (3-cis-Hydroxy-b,e-Caroten-3'-one)

PDB for HMDB0002890 (3-cis-Hydroxy-b,e-Caroten-3'-one)

3D PDB for HMDB0002890 (3-cis-Hydroxy-b,e-Caroten-3'-one)

SMILES for HMDB0002890 (3-cis-Hydroxy-b,e-Caroten-3'-one)

INCHI for HMDB0002890 (3-cis-Hydroxy-b,e-Caroten-3'-one)

Structure for HMDB0002890 (3-cis-Hydroxy-b,e-Caroten-3'-one)

3D Structure for HMDB0002890 (3-cis-Hydroxy-b,e-Caroten-3'-one)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra