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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-03-07 02:49:00 UTC

HMDB ID

HMDB0000305

Secondary Accession Numbers

HMDB00305

Metabolite Identification

Common Name

Vitamin A

Description

Vitamin A (retinol) is a yellow fat-soluble, antioxidant vitamin important in vision and bone growth. It belongs to the family of chemical compounds known as retinoids. Retinol is ingested in a precursor form; animal sources (milk and eggs) contain retinyl esters, whereas plants (carrots, spinach) contain pro-vitamin A carotenoids. Hydrolysis of retinyl esters results in retinol while pro-vitamin A carotenoids can be cleaved to produce retinal. Retinal, also known as retinaldehyde, can be reversibly reduced to produce retinol or it can be irreversibly oxidized to produce retinoic acid. Retinol and derivatives of retinol that play an essential role in metabolic functioning of the retina, the growth of and differentiation of epithelial tissue, the growth of bone, reproduction, and the immune response. Dietary vitamin A is derived from a variety of carotenoids found in plants. It is enriched in the liver, egg yolks, and the fat component of dairy products.

Structure

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

HMDB0000305
     RDKit          3D
Vitamin A
 51 51  0  0  0  0  0  0  0  0999 V2000
   -3.5592   -2.4974   -1.4233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0570   -1.3113   -0.6449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1723   -0.4485   -0.1382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7452   -0.7661   -0.4112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7322   -0.0504   -0.0129 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6669   -0.4566   -0.3383 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8931   -1.6940   -1.1105 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6175    0.3254    0.0995 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0379    0.0090   -0.1723 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9904    0.8100    0.2792 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4142    0.6094    0.0796 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9883   -0.5182   -0.6572 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2060    1.5209    0.6091 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6689    1.4803    0.5078 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1510    0.4010   -0.1926 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5390    0.7400    0.6536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8691    0.5617    2.0163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0348    2.0075   -0.0265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0162    0.8503    0.8135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7324    0.3804   -0.3989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5365   -1.1460   -0.4915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0159   -3.2035   -0.7892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4416   -3.0174   -1.8362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9618   -2.1692   -2.2983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4802   -1.6644   -0.9942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9094    0.8444    0.5503 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4514   -1.6473   -2.1291 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2875   -2.4991   -0.5850 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9012   -2.0813   -1.1248 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3685    1.2108    0.6648 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3215   -0.8552   -0.7311 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6223    1.6783    0.8416 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1401   -1.1610   -1.0389 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5265   -0.2428   -1.5914 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5732   -1.1840    0.0173 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7539    2.3796    1.1702 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1084    1.5121    1.5393 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0054    2.3894   -0.0718 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0346    0.1503    0.2093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7007    0.3620    2.7645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3159    1.4618    2.3190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2342   -0.3357    2.0753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9400    2.5887   -0.3605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4396    2.6450    0.6487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4871    1.7458   -0.9554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3657    0.2390    1.6814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3213    1.9195    0.9836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8385    0.5286   -0.2925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3455    0.7999   -1.3325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9261   -1.6428    0.4038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0110   -1.5587   -1.3883 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  1  0
  3 16  1  0
 16 17  1  0
 16 18  1  0
 16 19  1  0
 19 20  1  0
 20 21  1  0
 21  2  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  5 26  1  0
  7 27  1  0
  7 28  1  0
  7 29  1  0
  8 30  1  0
  9 31  1  0
 10 32  1  0
 12 33  1  0
 12 34  1  0
 12 35  1  0
 13 36  1  0
 14 37  1  0
 14 38  1  0
 15 39  1  0
 17 40  1  0
 17 41  1  0
 17 42  1  0
 18 43  1  0
 18 44  1  0
 18 45  1  0
 19 46  1  0
 19 47  1  0
 20 48  1  0
 20 49  1  0
 21 50  1  0
 21 51  1  0
M  END

  Mrv1652303192021392D          

 21 21  0  0  0  0            999 V2000
10000.386410003.1200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.101110002.7076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.815610003.1200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.530110002.7076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.244410003.1200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.959910002.7076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.673010003.1200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.388410002.7076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.105810003.1200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.819010002.7076    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10004.673010003.9447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.815610003.9447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.954610001.1073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.484710002.0267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.959410003.9447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.958010003.1204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.243410002.7078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.243410001.8826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.958010001.4702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.672710001.8826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.672710002.7078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3 12  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7 11  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 16 17  1  0  0  0  0
 16 21  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  1 21  1  0  0  0  0
 20 13  1  0  0  0  0
 20 14  1  0  0  0  0
 16 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000305

> <DATABASE_NAME>
hmdb

> <SMILES>
C\C(=C/CO)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,21H,7,10,14-15H2,1-5H3/b9-6+,12-11+,16-8+,17-13+

> <INCHI_KEY>
FPIPGXGPPPQFEQ-OVSJKPMPSA-N

> <FORMULA>
C20H30O

> <MOLECULAR_WEIGHT>
286.4516

> <EXACT_MASS>
286.229665582

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
36.5403584594368

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-ol

> <ALOGPS_LOGP>
6.38

> <JCHEM_LOGP>
4.694093173000001

> <ALOGPS_LOGS>
-4.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.435769749539965

> <JCHEM_PKA_STRONGEST_BASIC>
-2.1707943115512176

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
97.92339999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.58e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
α-sol

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0000305
     RDKit          3D
Vitamin A
 51 51  0  0  0  0  0  0  0  0999 V2000
   -3.5592   -2.4974   -1.4233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0570   -1.3113   -0.6449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1723   -0.4485   -0.1382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7452   -0.7661   -0.4112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7322   -0.0504   -0.0129 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6669   -0.4566   -0.3383 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8931   -1.6940   -1.1105 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6175    0.3254    0.0995 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0379    0.0090   -0.1723 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9904    0.8100    0.2792 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4142    0.6094    0.0796 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9883   -0.5182   -0.6572 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2060    1.5209    0.6091 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6689    1.4803    0.5078 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1510    0.4010   -0.1926 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5390    0.7400    0.6536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8691    0.5617    2.0163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0348    2.0075   -0.0265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0162    0.8503    0.8135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7324    0.3804   -0.3989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5365   -1.1460   -0.4915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0159   -3.2035   -0.7892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4416   -3.0174   -1.8362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9618   -2.1692   -2.2983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4802   -1.6644   -0.9942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9094    0.8444    0.5503 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4514   -1.6473   -2.1291 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2875   -2.4991   -0.5850 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9012   -2.0813   -1.1248 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3685    1.2108    0.6648 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3215   -0.8552   -0.7311 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6223    1.6783    0.8416 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1401   -1.1610   -1.0389 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5265   -0.2428   -1.5914 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5732   -1.1840    0.0173 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7539    2.3796    1.1702 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1084    1.5121    1.5393 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0054    2.3894   -0.0718 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0346    0.1503    0.2093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7007    0.3620    2.7645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3159    1.4618    2.3190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2342   -0.3357    2.0753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9400    2.5887   -0.3605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4396    2.6450    0.6487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4871    1.7458   -0.9554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3657    0.2390    1.6814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3213    1.9195    0.9836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8385    0.5286   -0.2925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3455    0.7999   -1.3325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9261   -1.6428    0.4038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0110   -1.5587   -1.3883 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  1  0
  3 16  1  0
 16 17  1  0
 16 18  1  0
 16 19  1  0
 19 20  1  0
 20 21  1  0
 21  2  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  5 26  1  0
  7 27  1  0
  7 28  1  0
  7 29  1  0
  8 30  1  0
  9 31  1  0
 10 32  1  0
 12 33  1  0
 12 34  1  0
 12 35  1  0
 13 36  1  0
 14 37  1  0
 14 38  1  0
 15 39  1  0
 17 40  1  0
 17 41  1  0
 17 42  1  0
 18 43  1  0
 18 44  1  0
 18 45  1  0
 19 46  1  0
 19 47  1  0
 20 48  1  0
 20 49  1  0
 21 50  1  0
 21 51  1  0
M  END

HEADER    PROTEIN                                 19-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-MAR-20         0                                  
HETATM    1  C   UNK     0    8667.3888672.491   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8668.7228671.721   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8670.0568672.491   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8671.3908671.721   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8672.7238672.491   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8674.0588671.721   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8675.3908672.491   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8676.7258671.721   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8678.0648672.491   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0    8679.3958671.721   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0    8675.3908674.030   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8670.0568674.030   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8666.5828668.734   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8667.5718670.450   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8664.7248674.030   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8664.7228672.491   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8663.3888671.721   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8663.3888670.181   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8664.7228669.411   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8666.0568670.181   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8666.0568671.721   0.000  0.00  0.00           C+0
CONECT    1    2   21                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   12                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   11                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    7                                                            
CONECT   12    3                                                            
CONECT   13   20                                                            
CONECT   14   20                                                            
CONECT   15   16                                                            
CONECT   16   17   21   15                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   13   14                                             
CONECT   21   16   20    1                                                  
MASTER        0    0    0    0    0    0    0    0   21    0   42    0
END

COMPND    HMDB0000305
HETATM    1  C1  UNL     1      -3.559  -2.497  -1.423  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.057  -1.311  -0.645  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.172  -0.448  -0.138  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.745  -0.766  -0.411  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.732  -0.050  -0.013  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.667  -0.457  -0.338  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.893  -1.694  -1.111  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.618   0.325   0.100  1.00  0.00           C  
HETATM    9  C9  UNL     1       3.038   0.009  -0.172  1.00  0.00           C  
HETATM   10  C10 UNL     1       3.990   0.810   0.279  1.00  0.00           C  
HETATM   11  C11 UNL     1       5.414   0.609   0.080  1.00  0.00           C  
HETATM   12  C12 UNL     1       5.988  -0.518  -0.657  1.00  0.00           C  
HETATM   13  C13 UNL     1       6.206   1.521   0.609  1.00  0.00           C  
HETATM   14  C14 UNL     1       7.669   1.480   0.508  1.00  0.00           C  
HETATM   15  O1  UNL     1       8.151   0.401  -0.193  1.00  0.00           O  
HETATM   16  C15 UNL     1      -3.539   0.740   0.654  1.00  0.00           C  
HETATM   17  C16 UNL     1      -2.869   0.562   2.016  1.00  0.00           C  
HETATM   18  C17 UNL     1      -3.035   2.007  -0.026  1.00  0.00           C  
HETATM   19  C18 UNL     1      -5.016   0.850   0.813  1.00  0.00           C  
HETATM   20  C19 UNL     1      -5.732   0.380  -0.399  1.00  0.00           C  
HETATM   21  C20 UNL     1      -5.537  -1.146  -0.492  1.00  0.00           C  
HETATM   22  H1  UNL     1      -3.016  -3.204  -0.789  1.00  0.00           H  
HETATM   23  H2  UNL     1      -4.442  -3.017  -1.836  1.00  0.00           H  
HETATM   24  H3  UNL     1      -2.962  -2.169  -2.298  1.00  0.00           H  
HETATM   25  H4  UNL     1      -1.480  -1.664  -0.994  1.00  0.00           H  
HETATM   26  H5  UNL     1      -0.909   0.844   0.550  1.00  0.00           H  
HETATM   27  H6  UNL     1       0.451  -1.647  -2.129  1.00  0.00           H  
HETATM   28  H7  UNL     1       0.287  -2.499  -0.585  1.00  0.00           H  
HETATM   29  H8  UNL     1       1.901  -2.081  -1.125  1.00  0.00           H  
HETATM   30  H9  UNL     1       1.369   1.211   0.665  1.00  0.00           H  
HETATM   31  H10 UNL     1       3.321  -0.855  -0.731  1.00  0.00           H  
HETATM   32  H11 UNL     1       3.622   1.678   0.842  1.00  0.00           H  
HETATM   33  H12 UNL     1       5.140  -1.161  -1.039  1.00  0.00           H  
HETATM   34  H13 UNL     1       6.527  -0.243  -1.591  1.00  0.00           H  
HETATM   35  H14 UNL     1       6.573  -1.184   0.017  1.00  0.00           H  
HETATM   36  H15 UNL     1       5.754   2.380   1.170  1.00  0.00           H  
HETATM   37  H16 UNL     1       8.108   1.512   1.539  1.00  0.00           H  
HETATM   38  H17 UNL     1       8.005   2.389  -0.072  1.00  0.00           H  
HETATM   39  H18 UNL     1       9.035   0.150   0.209  1.00  0.00           H  
HETATM   40  H19 UNL     1      -3.701   0.362   2.764  1.00  0.00           H  
HETATM   41  H20 UNL     1      -2.316   1.462   2.319  1.00  0.00           H  
HETATM   42  H21 UNL     1      -2.234  -0.336   2.075  1.00  0.00           H  
HETATM   43  H22 UNL     1      -3.940   2.589  -0.360  1.00  0.00           H  
HETATM   44  H23 UNL     1      -2.440   2.645   0.649  1.00  0.00           H  
HETATM   45  H24 UNL     1      -2.487   1.746  -0.955  1.00  0.00           H  
HETATM   46  H25 UNL     1      -5.366   0.239   1.681  1.00  0.00           H  
HETATM   47  H26 UNL     1      -5.321   1.919   0.984  1.00  0.00           H  
HETATM   48  H27 UNL     1      -6.839   0.529  -0.293  1.00  0.00           H  
HETATM   49  H28 UNL     1      -5.346   0.800  -1.332  1.00  0.00           H  
HETATM   50  H29 UNL     1      -5.926  -1.643   0.404  1.00  0.00           H  
HETATM   51  H30 UNL     1      -6.011  -1.559  -1.388  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3    3   21
CONECT    3    4   16
CONECT    4    5    5   25
CONECT    5    6   26
CONECT    6    7    8    8
CONECT    7   27   28   29
CONECT    8    9   30
CONECT    9   10   10   31
CONECT   10   11   32
CONECT   11   12   13   13
CONECT   12   33   34   35
CONECT   13   14   36
CONECT   14   15   37   38
CONECT   15   39
CONECT   16   17   18   19
CONECT   17   40   41   42
CONECT   18   43   44   45
CONECT   19   20   46   47
CONECT   20   21   48   49
CONECT   21   50   51
END

HMDB0000305
     RDKit          3D
Vitamin A
 51 51  0  0  0  0  0  0  0  0999 V2000
   -3.5592   -2.4974   -1.4233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0570   -1.3113   -0.6449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1723   -0.4485   -0.1382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7452   -0.7661   -0.4112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7322   -0.0504   -0.0129 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6669   -0.4566   -0.3383 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8931   -1.6940   -1.1105 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6175    0.3254    0.0995 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0379    0.0090   -0.1723 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9904    0.8100    0.2792 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4142    0.6094    0.0796 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9883   -0.5182   -0.6572 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2060    1.5209    0.6091 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6689    1.4803    0.5078 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1510    0.4010   -0.1926 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5390    0.7400    0.6536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8691    0.5617    2.0163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0348    2.0075   -0.0265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0162    0.8503    0.8135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7324    0.3804   -0.3989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5365   -1.1460   -0.4915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0159   -3.2035   -0.7892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4416   -3.0174   -1.8362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9618   -2.1692   -2.2983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4802   -1.6644   -0.9942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9094    0.8444    0.5503 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4514   -1.6473   -2.1291 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2875   -2.4991   -0.5850 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9012   -2.0813   -1.1248 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3685    1.2108    0.6648 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3215   -0.8552   -0.7311 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6223    1.6783    0.8416 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1401   -1.1610   -1.0389 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5265   -0.2428   -1.5914 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5732   -1.1840    0.0173 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7539    2.3796    1.1702 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1084    1.5121    1.5393 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0054    2.3894   -0.0718 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0346    0.1503    0.2093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7007    0.3620    2.7645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3159    1.4618    2.3190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2342   -0.3357    2.0753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9400    2.5887   -0.3605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4396    2.6450    0.6487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4871    1.7458   -0.9554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3657    0.2390    1.6814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3213    1.9195    0.9836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8385    0.5286   -0.2925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3455    0.7999   -1.3325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9261   -1.6428    0.4038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0110   -1.5587   -1.3883 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  1  0
  3 16  1  0
 16 17  1  0
 16 18  1  0
 16 19  1  0
 19 20  1  0
 20 21  1  0
 21  2  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  5 26  1  0
  7 27  1  0
  7 28  1  0
  7 29  1  0
  8 30  1  0
  9 31  1  0
 10 32  1  0
 12 33  1  0
 12 34  1  0
 12 35  1  0
 13 36  1  0
 14 37  1  0
 14 38  1  0
 15 39  1  0
 17 40  1  0
 17 41  1  0
 17 42  1  0
 18 43  1  0
 18 44  1  0
 18 45  1  0
 19 46  1  0
 19 47  1  0
 20 48  1  0
 20 49  1  0
 21 50  1  0
 21 51  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-ol	ChEBI
(all-e)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraen-1-ol	ChEBI
all-trans Retinol	ChEBI
all-trans-Retinyl alcohol	ChEBI
all-trans-Vitamin a	ChEBI
all-trans-Vitamin a alcohol	ChEBI
Alphalin	ChEBI
Aquasol a	ChEBI
Chocola a	ChEBI
Retinol	ChEBI
Retinol (vit a)	ChEBI
Retinolum	ChEBI
trans-Retinol	ChEBI
Vitamin a alcohol	ChEBI
Vitamin a1	ChEBI
Vitamin a1 alcohol	ChEBI
11-cis-Retinol	MeSH
3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraen-1-ol, (all-e)-isomer	MeSH
all trans Retinol	MeSH
all-trans-Retinol	MeSH
b-Retinol	HMDB
beta-Retinol	HMDB
Vitamin a	ChEBI

Chemical Formula

C₂₀H₃₀O

Average Molecular Weight

286.4516

Monoisotopic Molecular Weight

286.229665582

IUPAC Name

(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-ol

Traditional Name

α-sol

CAS Registry Number

68-26-8

SMILES

C\C(=C/CO)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C

InChI Identifier

InChI=1S/C20H30O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,21H,7,10,14-15H2,1-5H3/b9-6+,12-11+,16-8+,17-13+

InChI Key

FPIPGXGPPPQFEQ-OVSJKPMPSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as retinoids. These are oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Retinoids

Direct Parent

Retinoids

Alternative Parents

Substituents

Retinoid skeleton
Diterpenoid
Fatty alcohol
Fatty acyl
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

retinol (CHEBI:17336 )
Retinoids (C00473 )
Fat-soluble vitamins (C00473 )
Retinoids (LMPR01090000 )

Ontology

Not Available

Adipose tissue (HMDB: HMDB0000305)

Epithelium

Epidermis (HMDB: HMDB0000305)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 16221095)
Saliva (HMDB: HMDB0000305)

Cell

Fibroblasts (HMDB: HMDB0000305)
Neuron (HMDB: HMDB0000305)

Organ

Excreta

Biofluid or Excreta

Feces (PMID: 27543620)

Cellular substructure

Stratum Corneum (HMDB: HMDB0000305)

Source

Exogenous

Exogenous (HMDB: HMDB0000305)

Food

Animal origin

Poultry

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

Lagomorph

Venison

Deer (FooDB: FOOD00524)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Bovine

Swine

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

Equine

Horse (FooDB: FOOD00378)

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Vegetable

Cabbage

Onion-family vegetable

Root vegetable

Shoot vegetable

Leaf vegetable

Common beet (FooDB: FOOD00025)
Endive (FooDB: FOOD00048)
Rocket salad (ssp.) (FooDB: FOOD00077)
Lettuce (FooDB: FOOD00095)
Garden cress (FooDB: FOOD00099)
Spinach (FooDB: FOOD00178)
Swiss chard (FooDB: FOOD00237)
Garland chrysanthemum (FooDB: FOOD00333)
Jute (FooDB: FOOD00389)
Lambsquarters (FooDB: FOOD00394)
Malabar spinach (FooDB: FOOD00404)
New Zealand spinach (FooDB: FOOD00415)
Yautia (FooDB: FOOD00510)
Iceberg lettuce (FooDB: FOOD00973)
Pea shoots (FooDB: FOOD00975)
Water spinach (FooDB: FOOD00977)
Swamp cabbage (FooDB: FOOD00091)
Romaine lettuce (FooDB: FOOD00888)
Corn salad (FooDB: FOOD00340)
Ostrich fern (FooDB: FOOD00556)

Tuber

Fruit vegetable

Olive (FooDB: FOOD00121)
Avocado (FooDB: FOOD00130)
Garden tomato (FooDB: FOOD00171)
Garden tomato (var.) (FooDB: FOOD00173)
Eggplant (FooDB: FOOD00174)
Jalapeno pepper (FooDB: FOOD00955)
Groundcherry (FooDB: FOOD00371)
Pepper (FooDB: FOOD00040)
Mexican groundcherry (FooDB: FOOD00491)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Red bell pepper (FooDB: FOOD00880)
Italian sweet red pepper (FooDB: FOOD00881)
Orange bell pepper (FooDB: FOOD00879)

Stalk vegetable

Other vegetable

Giant butterbur (FooDB: FOOD00314)
Nopal (FooDB: FOOD00416)
Okra (FooDB: FOOD00420)
Sesbania flower (FooDB: FOOD00469)
Agave (FooDB: FOOD00563)
Narrowleaf cattail (FooDB: FOOD00564)
Heart of palm (FooDB: FOOD00718)
Tree fern (FooDB: FOOD00797)
Horseradish tree (FooDB: FOOD00379)
Sacred lotus (FooDB: FOOD00402)
Chinese water chestnut (FooDB: FOOD00332)
Carob (FooDB: FOOD00321)

Mushroom

Vegetable product

Other vegetable product (FooDB: FOOD00671)

Fruit

Tropical fruit

Citrus

Lime (FooDB: FOOD00053)
Lemon (FooDB: FOOD00054)
Pummelo (FooDB: FOOD00055)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)
Grapefruit/Pummelo hybrid (FooDB: FOOD00255)
Grapefruit (FooDB: FOOD00256)
Persian lime (FooDB: FOOD00543)
Sweet orange (FooDB: FOOD00057)

Pome

Other fruit

Fig (FooDB: FOOD00081)
Date (FooDB: FOOD00135)
Jujube (FooDB: FOOD00388)

Drupe

Apricot (FooDB: FOOD00144)
Peach (FooDB: FOOD00149)
Nectarine (FooDB: FOOD00229)
Peach (var.) (FooDB: FOOD00230)
Prunus (Cherry, Plum) (FooDB: FOOD00143)
European plum (FooDB: FOOD00147)
Sour cherry (FooDB: FOOD00146)
Sweet cherry (FooDB: FOOD00145)
Common chokecherry (FooDB: FOOD00562)

Berry

Blackcurrant (FooDB: FOOD00155)
Redcurrant (FooDB: FOOD00156)
American cranberry (FooDB: FOOD00192)
Muscadine grape (FooDB: FOOD00203)
European cranberry (FooDB: FOOD00217)
Grape (FooDB: FOOD00369)
Loganberry (FooDB: FOOD00400)
Ohelo berry (FooDB: FOOD00419)
Strawberry guava (FooDB: FOOD00482)
Green plum (FooDB: FOOD00979)
Black raisin (FooDB: FOOD00968)
Goji (FooDB: FOOD00982)
Monk fruit (FooDB: FOOD00983)
Bilberry (FooDB: FOOD00193)
Rubus (Blackberry, Raspberry) (FooDB: FOOD00160)
Vaccinium (Blueberry, Cranberry, Huckleberry) (FooDB: FOOD00188)
Elderberry (FooDB: FOOD00358)
Gooseberry (FooDB: FOOD00157)
Lingonberry (FooDB: FOOD00194)
Strawberry (FooDB: FOOD00083)
Boysenberry (FooDB: FOOD00542)
Common grape (FooDB: FOOD00204)
Black mulberry (FooDB: FOOD00117)
Red raspberry (FooDB: FOOD00162)
Salmonberry (FooDB: FOOD00456)
Alaska blueberry (FooDB: FOOD00380)
Sea-buckthornberry (FooDB: FOOD00087)
Cloudberry (FooDB: FOOD00161)
Squashberry (FooDB: FOOD00344)
Saskatoon berry (FooDB: FOOD00884)

Herb and spice mixture

Curry powder (FooDB: FOOD00678)

Nut

Cashew nut (FooDB: FOOD00011)
Peanut (FooDB: FOOD00016)
Brazil nut (FooDB: FOOD00024)
Pecan nut (FooDB: FOOD00044)
Chestnut (FooDB: FOOD00045)
Common hazelnut (FooDB: FOOD00062)
Black walnut (FooDB: FOOD00093)
Common walnut (FooDB: FOOD00094)
Pine nut (FooDB: FOOD00138)
Pistachio (FooDB: FOOD00140)
Almond (FooDB: FOOD00148)
Macadamia nut (M. tetraphylla) (FooDB: FOOD00225)
Acorn (FooDB: FOOD00282)
Beech nut (FooDB: FOOD00299)
Butternut (FooDB: FOOD00316)
Chinese chestnut (FooDB: FOOD00331)
European chestnut (FooDB: FOOD00363)
Hazelnut (FooDB: FOOD00376)
Hickory nut (FooDB: FOOD00377)
Japanese chestnut (FooDB: FOOD00385)
Pili nut (FooDB: FOOD00432)
Colorado pinyon (FooDB: FOOD00433)
Macadamia nut (FooDB: FOOD00525)
Walnut (FooDB: FOOD00608)
Mixed nuts (FooDB: FOOD00771)

Cereal and cereal product

Cereal

Cereal product

Other bread

Other bread (FooDB: FOOD00269)
Potato bread (FooDB: FOOD00811)

Leavened bread

Bread products

Other bread product (FooDB: FOOD00805)

Flat bread

Sweet bread

Raisin bread (FooDB: FOOD00817)

Pulse

Pea

Lentil

Lentils (FooDB: FOOD00098)

Other pulse

Lupine (FooDB: FOOD00104)
White lupine (FooDB: FOOD00403)

Bean

Green lentil (FooDB: FOOD00970)

Gourd

Watermelon (FooDB: FOOD00052)
Muskmelon (FooDB: FOOD00064)
Cucumber (FooDB: FOOD00065)
Bitter gourd (FooDB: FOOD00115)
Winter squash (FooDB: FOOD00283)
Butternut squash (FooDB: FOOD00317)
Calabash (FooDB: FOOD00318)
Chayote (FooDB: FOOD00325)
Wax gourd (FooDB: FOOD00499)
Horned melon (FooDB: FOOD00761)
Green zucchini (FooDB: FOOD00875)
Yellow zucchini (FooDB: FOOD00876)
Acorn squash (FooDB: FOOD00972)
Cantaloupe melon (FooDB: FOOD00984)
Cucurbita (FooDB: FOOD00066)
Towel gourd (FooDB: FOOD00492)
Japanese pumpkin (FooDB: FOOD00886)
Sunburst squash (pattypan squash) (FooDB: FOOD00874)

Soy

Soy bean (FooDB: FOOD00085)

Soy product

Tea

Herbal tea

Hibiscus tea (FooDB: FOOD00723)

Beverage

Fermented beverage

Distilled beverage

Vodka (FooDB: FOOD00622)
Spirit (FooDB: FOOD00276)
Gin (FooDB: FOOD00625)
Liquor (FooDB: FOOD00616)
Rum (FooDB: FOOD00629)
Whisky (FooDB: FOOD00623)

Other beverage

Fortified wines

Water

Water (FooDB: FOOD00664)

Nutritional beverage

Nutritional drink (FooDB: FOOD00754)
Energy drink (FooDB: FOOD00703)

Alcoholic beverage

Cocktail (FooDB: FOOD00739)
Other alcoholic beverage (FooDB: FOOD00278)

Aquatic origin

Crustacean

Fish

Atlantic herring (FooDB: FOOD00292)
Atlantic pollock (FooDB: FOOD00295)
Atlantic wolffish (FooDB: FOOD00296)
Striped bass (FooDB: FOOD00298)
Northern bluefin tuna (FooDB: FOOD00305)
Bluefish (FooDB: FOOD00306)
Burbot (FooDB: FOOD00313)
American butterfish (FooDB: FOOD00315)
Common carp (FooDB: FOOD00322)
Channel catfish (FooDB: FOOD00324)
Cisco (FooDB: FOOD00334)
Pacific cod (FooDB: FOOD00337)
Atlantic cod (FooDB: FOOD00338)
Atlantic croaker (FooDB: FOOD00345)
Cusk (FooDB: FOOD00346)
Freshwater drum (FooDB: FOOD00352)
Freshwater eel (FooDB: FOOD00357)
European anchovy (FooDB: FOOD00362)
Turbot (FooDB: FOOD00364)
Florida pompano (FooDB: FOOD00366)
Greenland halibut/turbot (FooDB: FOOD00370)
Grouper (FooDB: FOOD00372)
Hippoglossus (Common halibut) (FooDB: FOOD00375)
Pacific jack mackerel (FooDB: FOOD00383)
King mackerel (FooDB: FOOD00392)
Common ling (FooDB: FOOD00397)
Lingcod (FooDB: FOOD00398)
Milkfish (FooDB: FOOD00408)
Monkfish (FooDB: FOOD00409)
Striped mullet (FooDB: FOOD00412)
Ocean pout (FooDB: FOOD00417)
Pacific herring (FooDB: FOOD00424)
Pacific rockfish (FooDB: FOOD00426)
Northern pike (FooDB: FOOD00431)
Rainbow smelt (FooDB: FOOD00443)
Rainbow trout (FooDB: FOOD00444)
Orange roughy (FooDB: FOOD00448)
Sablefish (FooDB: FOOD00449)
Pink salmon (FooDB: FOOD00450)
Chum salmon (FooDB: FOOD00451)
Coho salmon (FooDB: FOOD00452)
Sockeye salmon (FooDB: FOOD00453)
Chinook salmon (FooDB: FOOD00454)
Atlantic salmon (FooDB: FOOD00455)
Spanish mackerel (FooDB: FOOD00460)
Scup (FooDB: FOOD00463)
Sea trout (FooDB: FOOD00468)
American shad (FooDB: FOOD00470)
Shark (FooDB: FOOD00471)
Sheefish (FooDB: FOOD00472)
Sheepshead (FooDB: FOOD00474)
Skipjack tuna (FooDB: FOOD00476)
Snapper (FooDB: FOOD00477)
Greater sturgeon (FooDB: FOOD00483)
White sucker (FooDB: FOOD00484)
Pumpkinseed sunfish (FooDB: FOOD00486)
Swordfish (FooDB: FOOD00487)
Tilefish (FooDB: FOOD00490)
Whitefish (FooDB: FOOD00503)
Whiting (FooDB: FOOD00504)
Yellowfin tuna (FooDB: FOOD00511)
Yellowtail amberjack (FooDB: FOOD00512)
Pollock (FooDB: FOOD00513)
Gadus (Common cod) (FooDB: FOOD00515)
Atlantic halibut (FooDB: FOOD00516)
Pacific halibut (FooDB: FOOD00517)
Percoidei (Bass and others) (FooDB: FOOD00526)
Flatfish (FooDB: FOOD00535)
Spot croaker (FooDB: FOOD00557)
Anchovy (FooDB: FOOD00566)
Carp bream (FooDB: FOOD00568)
Sturgeon (FooDB: FOOD00570)
Anguilliformes (FooDB: FOOD00577)
Gadiformes (FooDB: FOOD00580)
Lemon sole (FooDB: FOOD00583)
Norway pout (FooDB: FOOD00590)
Pacific ocean perch (FooDB: FOOD00598)
True sole (FooDB: FOOD00604)
Catfish (FooDB: FOOD00605)
Cichlidae (Tilapia) (FooDB: FOOD00699)
Japanese sea bass (FooDB: FOOD00974)
Alaska blackfish (FooDB: FOOD00302)
Devilfish (FooDB: FOOD00349)
Broad whitefish (FooDB: FOOD00502)
Blue whiting (FooDB: FOOD00567)
Clupeinae (Herring, Sardine, Sprat) (FooDB: FOOD00520)
Charr (FooDB: FOOD00571)
Common dab (FooDB: FOOD00574)
Spiny dogfish (FooDB: FOOD00575)
Garfish (FooDB: FOOD00579)
Haddock (FooDB: FOOD00374)
Lake trout (FooDB: FOOD00582)
Lumpsucker (FooDB: FOOD00585)
Scombridae (Bonito, Mackerel, Tuna) (FooDB: FOOD00586)
Norway haddock (FooDB: FOOD00588)
Perciformes (FooDB: FOOD00527)
Pikeperch (FooDB: FOOD00595)
Pleuronectidae (Dab, Halibut, Plaice) (FooDB: FOOD00596)
Salmonidae (Salmon, Trout) (FooDB: FOOD00493)
Thunnus (FooDB: FOOD00607)
Atlantic menhaden (FooDB: FOOD00560)
Dolphin fish (FooDB: FOOD00351)
Atlantic mackerel (FooDB: FOOD00293)
Painted comber (FooDB: FOOD00294)
Walleye (FooDB: FOOD00496)
Alaska pollock (FooDB: FOOD00497)
Pacific sardine (FooDB: FOOD00461)
Albacore tuna (FooDB: FOOD00514)
Smelt (FooDB: FOOD00519)
Pacific salmon (FooDB: FOOD00518)
Fishes (FooDB: FOOD00865)

Mollusk

Blue mussel (FooDB: FOOD00304)
Common octopus (FooDB: FOOD00339)
Cuttlefish (FooDB: FOOD00347)
Eastern oyster (FooDB: FOOD00356)
Pacific oyster (FooDB: FOOD00425)
Scallop (FooDB: FOOD00462)
Whelk (FooDB: FOOD00500)
Squid (FooDB: FOOD00532)
Marine mussel (FooDB: FOOD00587)
Snail (FooDB: FOOD00603)
True oyster (FooDB: FOOD00592)
Abalone (FooDB: FOOD00279)
Bivalvia (Clam, Mussel, Oyster) (FooDB: FOOD00531)
Conch (FooDB: FOOD00611)
North Pacific giant octopus (FooDB: FOOD00418)
Leather chiton (FooDB: FOOD00395)

Seaweed

Roe

Roe (FooDB: FOOD00698)

Bivalvia

Clam (FooDB: FOOD00952)

Other aquatic food

Amphibian

True frog (FooDB: FOOD00578)

Fish product

Other fish product (FooDB: FOOD00665)

Pinniped

Cetacean

Cetacea (Dolphin, Porpoise, Whale) (FooDB: FOOD00609)
Beluga whale (FooDB: FOOD00300)
Bowhead whale (FooDB: FOOD00308)

Egg

Eggs (FooDB: FOOD00619)

Confectionery

Other confectionery

Honey (FooDB: FOOD00626)
Marzipan (FooDB: FOOD00644)
Nougat (FooDB: FOOD00634)
Toffee (FooDB: FOOD00635)
Meringue (FooDB: FOOD00680)
Icing (FooDB: FOOD00700)

Chocolate spread (FooDB: FOOD00676)
Dulce de leche (FooDB: FOOD00714)

Milk dessert

Sweet custard (FooDB: FOOD00716)
Junket (FooDB: FOOD00726)

Milk and milk product

Other milk product

Fermented milk

Fermented milk product

Unfermented milk

Milk (Other mammals) (FooDB: FOOD00690)
Milk (Human) (FooDB: FOOD00666)
Milk (Cow) (FooDB: FOOD00618)
Cow milk, pasteurized, vitamin A + D added, 0% fat (FooDB: FOOD00889)
Cow milk, pasteurized, vitamin A + D added, 1% fat (FooDB: FOOD00890)
Cow milk, pasteurized, vitamin A + D added, 2% fat (FooDB: FOOD00891)
Cow milk, pasteurized, vitamin D added, 3.25% fat (FooDB: FOOD00892)

Milk and milk products (FooDB: FOOD00863)

Fat and oil

Animal fat

Vegetable fat

Margarine-like spread (FooDB: FOOD00844)
Margarine (FooDB: FOOD00843)
Shortening (FooDB: FOOD00783)

Fish oil (FooDB: FOOD00990)
Fats and oils (FooDB: FOOD00864)

Cocoa and cocoa product

Vinegar (FooDB: FOOD00628)
Salt (FooDB: FOOD00647)
Adobo (FooDB: FOOD00758)

Sugar

Sugar (FooDB: FOOD00651)

Dressing

Salad dressing (FooDB: FOOD00645)

Condiment

Sauce

Sauce (FooDB: FOOD00646)

Wrapper

Baby food

Baby food (FooDB: FOOD00668)

Dish

Ground meat

Sausage (FooDB: FOOD00652)
Meatball (FooDB: FOOD00653)
Pate (FooDB: FOOD00655)
Meatloaf (FooDB: FOOD00737)
Cold cut (FooDB: FOOD00770)

Gefilte fish (FooDB: FOOD00833)

Tex-mex cuisine

Chili (FooDB: FOOD00707)
Burrito (FooDB: FOOD00704)
Nachos (FooDB: FOOD00710)
Taco (FooDB: FOOD00708)

Levantine cuisine

Hummus (FooDB: FOOD00845)

Sandwich

Berber cuisine

Couscous (FooDB: FOOD00740)

Mexican cuisine

Asian cuisine

Egg roll (FooDB: FOOD00717)
Rice cake (FooDB: FOOD00796)

Latin american cuisine

Tamale (FooDB: FOOD00795)
Empanada (FooDB: FOOD00830)
Pupusa (FooDB: FOOD00829)
Arepa (FooDB: FOOD00831)

Unclassified food or beverage

Unclassified food or beverage (FooDB: FOOD00672)

Coffee and coffee product

Coffee

Coffee product

Coffee mocha (FooDB: FOOD00743)

Snack

Endogenous

Endogenous (HMDB: HMDB0000305)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Retinol Metabolism (HMDB: HMDB0000305)

Disease pathway

Vitamin A Deficiency (PathBank: SMP0120500)

Role

Biological role

Human metabolite (HMDB: HMDB0000305)

Industrial application

Pharmaceutical industry

Biomarker

Hemodialysis (MarkerDB: MDB00000141)
Endometrial cancer (MarkerDB: MDB00000141)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	61 - 63 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	5.68	BIOBYTE (1995)

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0076 g/L	ALOGPS
logP	6.38	ALOGPS
logP	4.69	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	16.44	ChemAxon
pKa (Strongest Basic)	-2.2	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	5	ChemAxon
Refractivity	97.92 m³·mol⁻¹	ChemAxon
Polarizability	36.54 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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]+	177.597	31661259
DarkChem	[M-H]-	174.049	31661259
DarkChem	[M+H]+	177.597	31661259
DarkChem	[M-H]-	174.049	31661259
AllCCS	[M+H]+	174.329	32859911
AllCCS	[M-H]-	179.664	32859911
DeepCCS	[M+H]+	185.871	30932474
DeepCCS	[M-H]-	183.513	30932474
DeepCCS	[M-2H]-	217.156	30932474
DeepCCS	[M+Na]+	192.383	30932474
AllCCS	[M+H]+	174.3	32859911
AllCCS	[M+H-H2O]+	171.1	32859911
AllCCS	[M+NH4]+	177.3	32859911
AllCCS	[M+Na]+	178.2	32859911
AllCCS	[M-H]-	179.7	32859911
AllCCS	[M+Na-2H]-	180.4	32859911
AllCCS	[M+HCOO]-	181.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Vitamin A	C\C(=C/CO)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C	3108.0	Standard polar	33892256
Vitamin A	C\C(=C/CO)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C	2431.2	Standard non polar	33892256
Vitamin A	C\C(=C/CO)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C	2417.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Vitamin A,1TMS,isomer #1	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/CO[Si](C)(C)C)C(C)(C)CCC1	2597.7	Semi standard non polar	33892256
Vitamin A,1TBDMS,isomer #1	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/CO[Si](C)(C)C(C)(C)C)C(C)(C)CCC1	2794.8	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 - Vitamin A GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-1190000000-7c2230ee88e04e8f3741	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vitamin A GC-MS (1 TMS) - 70eV, Positive	splash10-0006-7139000000-7242603c3f7f12c824cd	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vitamin A GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vitamin A GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vitamin A GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-052r-2950000000-c24ec8ff8d0ba6c1f23f	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vitamin A Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-000i-0290000000-25c523b646154b291da8	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vitamin A Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-05gj-3900000000-a63c286f931608f650a3	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vitamin A Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-05mo-9700000000-e627db30469c74bb037f	2012-07-24	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vitamin A 10V, Positive-QTOF	splash10-00kr-0490000000-97ed49d705440e4d32e7	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vitamin A 20V, Positive-QTOF	splash10-00ks-3930000000-7c5bfbd8b838b97dc2aa	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vitamin A 40V, Positive-QTOF	splash10-0fri-9820000000-6a49bab0c891ffe1e5b2	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vitamin A 10V, Negative-QTOF	splash10-000i-0090000000-d0ff1cdc72141d0daa0e	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vitamin A 20V, Negative-QTOF	splash10-0a4r-0090000000-c0a067ff8ed271b80945	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vitamin A 40V, Negative-QTOF	splash10-00ku-4590000000-cfc35aba420e707075f7	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vitamin A 10V, Negative-QTOF	splash10-0a4i-0090000000-fe93459d3069e264b77f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vitamin A 20V, Negative-QTOF	splash10-05mx-0190000000-f81760535f6050971f92	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vitamin A 40V, Negative-QTOF	splash10-00li-0960000000-4dbc516b202b90a6c265	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vitamin A 10V, Positive-QTOF	splash10-015i-1890000000-fb68e645ac6c84dc722c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vitamin A 20V, Positive-QTOF	splash10-05a9-2910000000-aa07b89a9cfe132b8725	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vitamin A 40V, Positive-QTOF	splash10-06dl-5900000000-6de72efc591b252620c9	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane (predicted from logP)

Biospecimen Locations

Blood
Feces
Saliva

Tissue Locations

Adipose Tissue
Epidermis
Fibroblasts
Intestine
Kidney
Liver
Neuron
Placenta
Spleen
Testis

Pathways

Name	SMPDB/PathBank	KEGG
Retinol Metabolism
Vitamin A Deficiency		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.78 +/- 0.33 uM	Children (1-13 years old)	Both	Normal	Geigy Scientific ...	details
Blood	Detected and Quantified	1.84 +/- 0.46 uM	Adult (>18 years old)	Male	Normal	Geigy Scientific ...	details
Blood	Detected and Quantified	1.76 +/- 0.44 uM	Adult (>18 years old)	Female	Normal	Geigy Scientific ...	details
Blood	Detected and Quantified	1.02 (0.34-2.1) uM	Adolescent (13-18 years old)	Both	Normal	7657478	details
Blood	Detected and Quantified	0.530-2.100 uM	Adult (>18 years old)	Not Specified	Normal	2944375	details
Blood	Detected and Quantified	0-2 uM	Infant (0-1 year old)	Both	Normal	CALIPER Paediatri...	details
Blood	Detected and Quantified	1-2 uM	Children (1-13 years old)	Both	Normal	CALIPER Paediatri...	details
Blood	Detected and Quantified	1-2 uM	Adolescent (13-18 years old)	Both	Normal	CALIPER Paediatri...	details
Blood	Detected and Quantified	1-2 uM	Adult (>18 years old)	Both	Normal	CALIPER Paediatri...	details
Blood	Detected and Quantified	2.3 (1.2-3.5) uM	Adult (>18 years old)	Female	Normal	19235557	details
Blood	Detected and Quantified	2.0600 +/- 0.620 uM	Adult (>18 years old)	Both	Normal	15051849	details
Blood	Detected and Quantified	2.220 +/- 0.590 uM	Adult (>18 years old)	Both	Normal	15051849	details
Blood	Detected and Quantified	2.580 +/- 0.710 uM	Adult (>18 years old)	Both	Normal	15051849	details
Blood	Detected and Quantified	2.720 +/- 0.790 uM	Adult (>18 years old)	Both	Normal	15051849	details
Blood	Detected and Quantified	1.770 +/- 0.740 uM	Adult (>18 years old)	Female	Normal	15051849	details
Blood	Detected and Quantified	2.390 +/- 0.800 uM	Adult (>18 years old)	Female	Normal	15051849	details
Blood	Detected and Quantified	2.310 +/- 0.960 uM	Adult (>18 years old)	Male	Normal	15051849	details
Blood	Detected and Quantified	2.470 +/- 0.770 uM	Adult (>18 years old)	Male	Normal	15051849	details
Blood	Detected and Quantified	0.831 +/- 0.499 uM	Adult (>18 years old)	Male	Normal	1878353	details
Blood	Detected and Quantified	2.0736 +/- 0.485 uM	Adult (>18 years old)	Male	Normal	1878353	details
Blood	Detected and Quantified	2.220 +/- 0.496 uM	Adult (>18 years old)	Male	Normal	1878353	details
Blood	Detected and Quantified	0.580 +/- 0.360 uM	Adult (>18 years old)	Male	Normal	1878353	details
Blood	Detected and Quantified	2.0841 +/- 0.499 uM	Adult (>18 years old)	Male	Normal	1878353	details
Blood	Detected and Quantified	2.182 +/- 0.499 uM	Adult (>18 years old)	Male	Normal	1878353	details
Blood	Detected and Quantified	2.200 +/- 0.634 uM	Adult (>18 years old)	Both	Normal	16755268	details
Blood	Detected and Quantified	2.3 uM	Adult (>18 years old)	Both	Normal	15735096	details
Blood	Detected and Quantified	1.740 +/- 0.540 uM	Adult (>18 years old)	Both	Normal	17378949	details
Blood	Detected and Quantified	1.790 +/- 0.530 uM	Adult (>18 years old)	Both	Normal	17378949	details
Blood	Detected and Quantified	1.790 +/- 0.540 uM	Adult (>18 years old)	Both	Normal	17378949	details
Blood	Detected and Quantified	1.800 +/- 0.500 uM	Adult (>18 years old)	Both	Normal	17378949	details
Blood	Detected and Quantified	1.810 +/- 0.550 uM	Adult (>18 years old)	Both	Normal	17378949	details
Blood	Detected and Quantified	1.820 +/- 0.510 uM	Adult (>18 years old)	Both	Normal	17378949	details
Blood	Detected and Quantified	1.820 +/- 0.560 uM	Adult (>18 years old)	Both	Normal	17378949	details
Blood	Detected and Quantified	1.840 +/- 0.530 uM	Adult (>18 years old)	Both	Normal	17378949	details
Blood	Detected and Quantified	1.850 +/- 0.530 uM	Adult (>18 years old)	Both	Normal	17378949	details
Blood	Detected and Quantified	1.860 +/- 0.450 uM	Adult (>18 years old)	Both	Normal	17378949	details
Blood	Detected and Quantified	1.870 +/- 0.510 uM	Adult (>18 years old)	Both	Normal	17378949	details
Blood	Detected and Quantified	1.880 +/- 0.430 uM	Adult (>18 years old)	Both	Normal	17378949	details
Blood	Detected and Quantified	1.880 +/- 0.470 uM	Adult (>18 years old)	Both	Normal	17378949	details
Blood	Detected and Quantified	1.880 +/- 0.480 uM	Adult (>18 years old)	Both	Normal	17378949	details
Blood	Detected and Quantified	1.890 +/- 0.420 uM	Adult (>18 years old)	Both	Normal	17378949	details
Blood	Detected and Quantified	1.950 +/- 0.470 uM	Adult (>18 years old)	Both	Normal	17378949	details
Blood	Detected and Quantified	1.951 +/- 0.520 uM	Adult (>18 years old)	Both	Normal	6624705	details
Blood	Detected and Quantified	5.732 +/- 2.217 uM	Adult (>18 years old)	Both	Normal	11454500	details
Blood	Detected and Quantified	6.113 +/- 2.594 uM	Adult (>18 years old)	Both	Normal	11454500	details
Blood	Detected and Quantified	6.249 +/- 1.850 uM	Adult (>18 years old)	Both	Normal	6624705	details
Blood	Detected and Quantified	1.42 uM	Adult (>18 years old)	Female	Normal	9109609	details
Blood	Detected and Quantified	1.63 uM	Adult (>18 years old)	Female	Normal	9109609	details
Blood	Detected and Quantified	1.993 uM	Adult (>18 years old)	Female	Normal	20332276	details
Blood	Detected and Quantified	2.18 uM	Adult (>18 years old)	Female	Normal	19371448	details
Blood	Detected and Quantified	1.445 +/- 0.384 uM	Adult (>18 years old)	Female	Normal	10427874	details
Blood	Detected and Quantified	1.910 +/- 0.430 uM	Adult (>18 years old)	Female	Normal	1512628	details
Blood	Detected and Quantified	1.950 +/- 0.610 uM	Adult (>18 years old)	Female	Normal	8424386	details
Blood	Detected and Quantified	1.970 +/- 0.650 uM	Adult (>18 years old)	Female	Normal	8424386	details
Blood	Detected and Quantified	2.391 +/- 0.782 uM	Adult (>18 years old)	Female	Normal	18813024	details
Blood	Detected and Quantified	2.700 +/- 1.100 uM	Adult (>18 years old)	Female	Normal	8424386	details
Blood	Detected and Quantified	5.781 +/- 2.356 uM	Adult (>18 years old)	Female	Normal	11454500	details
Blood	Detected and Quantified	5.861 +/- 2.726 uM	Adult (>18 years old)	Female	Normal	11454500	details
Blood	Detected and Quantified	1.99 uM	Adult (>18 years old)	Male	Normal	9109609	details
Blood	Detected and Quantified	2.18 uM	Adult (>18 years old)	Male	Normal	9109609	details
Blood	Detected and Quantified	2.47 uM	Adult (>18 years old)	Male	Normal	19371448	details
Blood	Detected and Quantified	1.980 +/- 0.540 uM	Adult (>18 years old)	Male	Normal	8424386	details
Blood	Detected and Quantified	2.0800 +/- 0.620 uM	Adult (>18 years old)	Male	Normal	8424386	details
Blood	Detected and Quantified	2.130 +/- 0.380 uM	Adult (>18 years old)	Male	Normal	1512628	details
Blood	Detected and Quantified	2.400 +/- 0.900 uM	Adult (>18 years old)	Male	Normal	8424386	details
Blood	Detected and Quantified	5.666 +/- 2.0387 uM	Adult (>18 years old)	Male	Normal	11454500	details
Blood	Detected and Quantified	6.553 +/- 2.315 uM	Adult (>18 years old)	Male	Normal	11454500	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Saliva	Detected and Quantified	0.015 +/- 0.010 uM	Adult (>18 years old)	Both	Normal	Zerihun T. Dame, ...	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Bladder cancer	22685041	details
Blood	Detected and Quantified	2.50 +/- 0.86 uM	Adult (>18 years old)	Both	Hemodialysis	16221095	details
Blood	Detected and Quantified	0.45 uM	Adult (>18 years old)	Male	Abetalipoproteinemia	2944375	details
Blood	Detected and Quantified	2.0 (1.2-2.5) uM	Adult (>18 years old)	Female	Endometrial cancer	19235557	details
Blood	Detected and Quantified	1.466 +/- 0.349 uM	Adult (>18 years old)	Female	Pregnancy	16925883	details

Associated Disorders and Diseases

Disease References

Hemodialysis
Cabral PC, Diniz Ada S, de Arruda IK: Vitamin A and zinc status in patients on maintenance haemodialysis. Nephrology (Carlton). 2005 Oct;10(5):459-63. [PubMed:16221095 ]
Endometrial cancer
Jeong NH, Song ES, Lee JM, Lee KB, Kim MK, Yun YM, Lee JK, Son SK, Lee JP, Kim JH, Hur SY, Kwon YI: Preoperative levels of plasma micronutrients are related to endometrial cancer risk. Acta Obstet Gynecol Scand. 2009;88(4):434-9. doi: 10.1080/00016340902767187. [PubMed:19235557 ]
Pregnancy
Mikkelsen TB, Osler M, Olsen SF: Validity of protein, retinol, folic acid and n-3 fatty acid intakes estimated from the food-frequency questionnaire used in the Danish National Birth Cohort. Public Health Nutr. 2006 Sep;9(6):771-8. [PubMed:16925883 ]
Abetalipoproteinemia
Lazaro RP, Dentinger MP, Rodichok LD, Barron KD, Satya-Murti S: Muscle pathology in Bassen-Kornzweig syndrome and vitamin E deficiency. Am J Clin Pathol. 1986 Sep;86(3):378-87. [PubMed:2944375 ]

Associated OMIM IDs

608089 (Endometrial cancer)
200100 (Abetalipoproteinemia)

External Links

DrugBank ID

DB00162

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023841

KNApSAcK ID

C00031437

Chemspider ID

Not Available

KEGG Compound ID

C17276

BioCyc ID

CPD-13524

BiGG ID

Not Available

Wikipedia Link

Vitamin_A

METLIN ID

Not Available

PubChem Compound

445354

PDB ID

Not Available

ChEBI ID

17336

Food Biomarker Ontology

Not Available

VMH ID

RETINOL

MarkerDB ID

MDB00000141

Good Scents ID

rw1131351

References

Synthesis Reference

Isler, O.; Ronco, A.; Guex, W.; Hindley, N. C.; Huber, W.; Dialer, K.; Kofler, M. Esters and ethers of synthetic vitamin A. Helvetica Chimica Acta (1949), 32 489-505.

Material Safety Data Sheet (MSDS)

Not Available

General References

Norum KR, Blomhoff R: McCollum Award Lecture, 1992: vitamin A absorption, transport, cellular uptake, and storage. Am J Clin Nutr. 1992 Oct;56(4):735-44. [PubMed:1414975 ]
Graham-Maar RC, Schall JI, Stettler N, Zemel BS, Stallings VA: Elevated vitamin A intake and serum retinol in preadolescent children with cystic fibrosis. Am J Clin Nutr. 2006 Jul;84(1):174-82. [PubMed:16825693 ]
Sorenson AW, Delhumeau C, Bernstein MS, Costanza MC, Morabia A: Impact of 'Mad Cow Disease' publicity on trends in meat and total vitamin A consumption in Geneva between 1993 and 2000. Eur J Clin Nutr. 2003 Jan;57(1):177-85. [PubMed:12548314 ]
Alberts D, Ranger-Moore J, Einspahr J, Saboda K, Bozzo P, Liu Y, Xu XC, Lotan R, Warneke J, Salasche S, Stratton S, Levine N, Goldman R, Islas M, Duckett L, Thompson D, Bartels P, Foote J: Safety and efficacy of dose-intensive oral vitamin A in subjects with sun-damaged skin. Clin Cancer Res. 2004 Mar 15;10(6):1875-80. [PubMed:15041701 ]
Wieringa FT, Dijkhuizen MA, West CE, Thurnham DI, Muhilal, Van der Meer JW: Redistribution of vitamin A after iron supplementation in Indonesian infants. Am J Clin Nutr. 2003 Mar;77(3):651-7. [PubMed:12600856 ]
Egeland GM, Berti P, Soueida R, Arbour LT, Receveur O, Kuhnlein HV: Age differences in vitamin A intake among Canadian Inuit. Can J Public Health. 2004 Nov-Dec;95(6):465-9. [PubMed:15622799 ]
Ribaya-Mercado JD, Solon FS, Fermin LS, Perfecto CS, Solon JA, Dolnikowski GG, Russell RM: Dietary vitamin A intakes of Filipino elders with adequate or low liver vitamin A concentrations as assessed by the deuterated-retinol-dilution method: implications for dietary requirements. Am J Clin Nutr. 2004 Apr;79(4):633-41. [PubMed:15051608 ]
Kieu NT, Yurie K, Hung NT, Yamamoto S, Chuyen NV: Simultaneous analysis of retinol, beta-carotene and tocopherol levels in serum of Vietnamese populations with different incomes. Asia Pac J Clin Nutr. 2002;11(2):92-7. [PubMed:12074187 ]
Torma H, Vahlquist A: Vitamin A esterification in human epidermis: a relation to keratinocyte differentiation. J Invest Dermatol. 1990 Jan;94(1):132-8. [PubMed:2295828 ]
Allen LH, Haskell M: Estimating the potential for vitamin A toxicity in women and young children. J Nutr. 2002 Sep;132(9 Suppl):2907S-2919S. [PubMed:12221269 ]
Ribaya-Mercado JD, Solomons NW, Medrano Y, Bulux J, Dolnikowski GG, Russell RM, Wallace CB: Use of the deuterated-retinol-dilution technique to monitor the vitamin A status of Nicaraguan schoolchildren 1 y after initiation of the Nicaraguan national program of sugar fortification with vitamin A. Am J Clin Nutr. 2004 Nov;80(5):1291-8. [PubMed:15531678 ]
Marquez M, Yepez CE, Sutil-Naranjo R, Rincon M: [Basic aspects and measurement of the antioxidant vitamins A and E]. Invest Clin. 2002 Sep;43(3):191-204. [PubMed:12229281 ]
Mills JP, Penniston KL, Tanumihardjo SA: Extra-hepatic vitamin A concentrations in captive Rhesus (Macaca mulatta) and Marmoset (Callithrix jacchus) monkeys fed excess vitamin A. Int J Vitam Nutr Res. 2005 Mar;75(2):126-32. [PubMed:15929633 ]
Penniston KL, Tanumihardjo SA: The acute and chronic toxic effects of vitamin A. Am J Clin Nutr. 2006 Feb;83(2):191-201. [PubMed:16469975 ]
Jumpsen JA, Brown NE, Thomson AB, Paul Man SF, Goh YK, Ma D, Clandinin MT: Fatty acids in blood and intestine following docosahexaenoic acid supplementation in adults with cystic fibrosis. J Cyst Fibros. 2006 May;5(2):77-84. Epub 2006 Feb 28. [PubMed:16507353 ]

Only showing the first 10 proteins. There are 20 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Diacylglycerol O-acyltransferase 1

General function:: Involved in diacylglycerol O-acyltransferase activity
Specific function:: Catalyzes the terminal and only committed step in triacylglycerol synthesis by using diacylglycerol and fatty acyl CoA as substrates. In contrast to DGAT2 it is not essential for survival. May be involved in VLDL (very low density lipoprotein) assembly. In liver, plays a role in esterifying exogenous fatty acids to glycerol. Functions as the major acyl-CoA retinol acyltransferase (ARAT) in the skin, where it acts to maintain retinoid homeostasis and prevent retinoid toxicity leading to skin and hair disorders.
Gene Name:: DGAT1
Uniprot ID:: O75907
Molecular weight:: 55277.735

Reactions

Acyl-CoA + Vitamin A → Coenzyme A + Retinyl ester	details
Acyl-CoA + Vitamin A → Coenzyme A + Retinyl ester	details
Palmityl-CoA + Vitamin A → Coenzyme A + Retinyl palmitate	details

Enzyme Details

2. 11-cis retinol dehydrogenase

General function:: Involved in oxidoreductase activity
Specific function:: Stereospecific 11-cis retinol dehydrogenase, which catalyzes the final step in the biosynthesis of 11-cis retinaldehyde, the universal chromophore of visual pigments. Also able to oxidize 9-cis-retinol and 13-cis-retinol, but not all-trans-retinol. Active in the presence of NAD as cofactor but not in the presence of NADP.
Gene Name:: RDH5
Uniprot ID:: Q92781
Molecular weight:: 34978.425

Enzyme Details

3. Alcohol dehydrogenase 4

General function:: Involved in zinc ion binding
Specific function:: Not Available
Gene Name:: ADH4
Uniprot ID:: P08319
Molecular weight:: 40221.335

Reactions

Vitamin A + NAD → Retinal + NADH + Hydrogen Ion	details

Enzyme Details

4. Alcohol dehydrogenase class-3

General function:: Involved in zinc ion binding
Specific function:: Class-III ADH is remarkably ineffective in oxidizing ethanol, but it readily catalyzes the oxidation of long-chain primary alcohols and the oxidation of S-(hydroxymethyl) glutathione.
Gene Name:: ADH5
Uniprot ID:: P11766
Molecular weight:: 39723.945

Reactions

Vitamin A + NAD → Retinal + NADH + Hydrogen Ion	details

Enzyme Details

5. Alcohol dehydrogenase 1B

General function:: Involved in zinc ion binding
Specific function:: Not Available
Gene Name:: ADH1B
Uniprot ID:: P00325
Molecular weight:: 39835.17

Reactions

Vitamin A + NAD → Retinal + NADH + Hydrogen Ion	details

Enzyme Details

6. Alcohol dehydrogenase class 4 mu/sigma chain

General function:: Involved in zinc ion binding
Specific function:: Could function in retinol oxidation for the synthesis of retinoic acid, a hormone important for cellular differentiation. Medium-chain (octanol) and aromatic (m-nitrobenzaldehyde) compounds are the best substrates. Ethanol is not a good substrate but at the high ethanol concentrations reached in the digestive tract, it plays a role in the ethanol oxidation and contributes to the first pass ethanol metabolism.
Gene Name:: ADH7
Uniprot ID:: P40394
Molecular weight:: 41480.985

Reactions

Vitamin A + NAD → Retinal + NADH + Hydrogen Ion	details

Enzyme Details

7. Alcohol dehydrogenase 1A

General function:: Involved in zinc ion binding
Specific function:: Not Available
Gene Name:: ADH1A
Uniprot ID:: P07327
Molecular weight:: 39858.37

Reactions

Vitamin A + NAD → Retinal + NADH + Hydrogen Ion	details

Enzyme Details

8. Alcohol dehydrogenase 6

General function:: Involved in zinc ion binding
Specific function:: Not Available
Gene Name:: ADH6
Uniprot ID:: P28332
Molecular weight:: 39072.275

Reactions

Vitamin A + NAD → Retinal + NADH + Hydrogen Ion	details

Enzyme Details

9. Alcohol dehydrogenase 1C

General function:: Involved in zinc ion binding
Specific function:: Not Available
Gene Name:: ADH1C
Uniprot ID:: P00326
Molecular weight:: 39867.27

Reactions

Vitamin A + NAD → Retinal + NADH + Hydrogen Ion	details

Enzyme Details

10. Lecithin retinol acyltransferase

General function:: Involved in phosphatidylcholine-retinol O-acyltransfera
Specific function:: Transfers the acyl group from the sn-1 position of phosphatidylcholine to all-trans retinol, producing all-trans retinyl esters. Retinyl esters are storage forms of vitamin A. LRAT plays a critical role in vision. It provides the all-trans retinyl ester substrates for the isomerohydrolase which processes the esters into 11-cis-retinol in the retinal pigment epithelium; due to a membrane-associated alcohol dehydrogenase, 11 cis-retinol is oxidized and converted into 11-cis-retinaldehyde which is the chromophore for rhodopsin and the cone photopigments.
Gene Name:: LRAT
Uniprot ID:: O95237
Molecular weight:: 25702.635

Reactions

Phosphatidylcholine + Vitamin A → 2-Acyl-sn-glycero-3-phosphocholine + Retinyl ester	details

Only showing the first 10 proteins. There are 20 proteins in total.

Show all enzymes and transporters

Showing metabocard for Vitamin A (HMDB0000305)

MOL for HMDB0000305 (Vitamin A)

3D MOL for HMDB0000305 (Vitamin A)

3D SDF for HMDB0000305 (Vitamin A)

3D-SDF for HMDB0000305 (Vitamin A)

PDB for HMDB0000305 (Vitamin A)

3D PDB for HMDB0000305 (Vitamin A)

SMILES for HMDB0000305 (Vitamin A)

INCHI for HMDB0000305 (Vitamin A)

Structure for HMDB0000305 (Vitamin A)

3D Structure for HMDB0000305 (Vitamin A)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions

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