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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (20) Show 20 proteins XML

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

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 Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	8.15 minutes	32390414
Predicted by Siyang on May 30, 2022	24.9271 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.82 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3355.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	757.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	283.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	464.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	346.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	962.8 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	878.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	86.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	2131.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	723.7 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	1602.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	845.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	554.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	484.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	741.3 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.6 seconds	40023050

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

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	1.951 +/- 0.520 uM	Adult (>18 years old)	Both	Normal	6624705	details
Blood	Detected and Quantified	1.445 +/- 0.384 uM	Adult (>18 years old)	Female	Normal	10427874	details
Blood	Detected and Quantified	2.18 uM	Adult (>18 years old)	Female	Normal	19371448	details
Blood	Detected and Quantified	1.993 uM	Adult (>18 years old)	Female	Normal	20332276	details
Blood	Detected and Quantified	1.63 uM	Adult (>18 years old)	Female	Normal	9109609	details
Blood	Detected and Quantified	1.42 uM	Adult (>18 years old)	Female	Normal	9109609	details
Blood	Detected and Quantified	6.249 +/- 1.850 uM	Adult (>18 years old)	Both	Normal	6624705	details
Blood	Detected and Quantified	6.113 +/- 2.594 uM	Adult (>18 years old)	Both	Normal	11454500	details
Blood	Detected and Quantified	5.732 +/- 2.217 uM	Adult (>18 years old)	Both	Normal	11454500	details
Blood	Detected and Quantified	1.910 +/- 0.430 uM	Adult (>18 years old)	Female	Normal	1512628	details
Blood	Detected and Quantified	1.950 +/- 0.470 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	1.880 +/- 0.480 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 +/- 0.430 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	1.860 +/- 0.450 uM	Adult (>18 years old)	Both	Normal	17378949	details
Blood	Detected and Quantified	2.18 uM	Adult (>18 years old)	Male	Normal	9109609	details
Blood	Detected and Quantified	0.530-2.100 uM	Adult (>18 years old)	Not Specified	Normal	2944375	details
Blood	Detected and Quantified	6.553 +/- 2.315 uM	Adult (>18 years old)	Male	Normal	11454500	details
Blood	Detected and Quantified	5.666 +/- 2.0387 uM	Adult (>18 years old)	Male	Normal	11454500	details
Blood	Detected and Quantified	2.400 +/- 0.900 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	2.0800 +/- 0.620 uM	Adult (>18 years old)	Male	Normal	8424386	details
Blood	Detected and Quantified	1.980 +/- 0.540 uM	Adult (>18 years old)	Male	Normal	8424386	details
Blood	Detected and Quantified	2.47 uM	Adult (>18 years old)	Male	Normal	19371448	details
Blood	Detected and Quantified	1.84 +/- 0.46 uM	Adult (>18 years old)	Male	Normal	Geigy Scientific ...	details
Blood	Detected and Quantified	1.99 uM	Adult (>18 years old)	Male	Normal	9109609	details
Blood	Detected and Quantified	5.861 +/- 2.726 uM	Adult (>18 years old)	Female	Normal	11454500	details
Blood	Detected and Quantified	5.781 +/- 2.356 uM	Adult (>18 years old)	Female	Normal	11454500	details
Blood	Detected and Quantified	2.700 +/- 1.100 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	1.970 +/- 0.650 uM	Adult (>18 years old)	Female	Normal	8424386	details
Blood	Detected and Quantified	1.950 +/- 0.610 uM	Adult (>18 years old)	Female	Normal	8424386	details
Blood	Detected and Quantified	1-2 uM	Adult (>18 years old)	Both	Normal	CALIPER Paediatri...	details
Blood	Detected and Quantified	2.470 +/- 0.770 uM	Adult (>18 years old)	Male	Normal	15051849	details
Blood	Detected and Quantified	2.310 +/- 0.960 uM	Adult (>18 years old)	Male	Normal	15051849	details
Blood	Detected and Quantified	2.390 +/- 0.800 uM	Adult (>18 years old)	Female	Normal	15051849	details
Blood	Detected and Quantified	1.770 +/- 0.740 uM	Adult (>18 years old)	Female	Normal	15051849	details
Blood	Detected and Quantified	2.720 +/- 0.790 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	2.220 +/- 0.590 uM	Adult (>18 years old)	Both	Normal	15051849	details
Blood	Detected and Quantified	2.0600 +/- 0.620 uM	Adult (>18 years old)	Both	Normal	15051849	details
Blood	Detected and Quantified	1.840 +/- 0.530 uM	Adult (>18 years old)	Both	Normal	17378949	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	Children (1-13 years old)	Both	Normal	CALIPER Paediatri...	details
Blood	Detected and Quantified	0-2 uM	Infant (0-1 year old)	Both	Normal	CALIPER Paediatri...	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	2.3 (1.2-3.5) uM	Adult (>18 years old)	Female	Normal	19235557	details
Blood	Detected and Quantified	1.76 +/- 0.44 uM	Adult (>18 years old)	Female	Normal	Geigy Scientific ...	details
Blood	Detected and Quantified	0.78 +/- 0.33 uM	Children (1-13 years old)	Both	Normal	Geigy Scientific ...	details
Blood	Detected and Quantified	2.0736 +/- 0.485 uM	Adult (>18 years old)	Male	Normal	1878353	details
Blood	Detected and Quantified	1.850 +/- 0.530 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	1.820 +/- 0.510 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	1.800 +/- 0.500 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	1.790 +/- 0.530 uM	Adult (>18 years old)	Both	Normal	17378949	details
Blood	Detected and Quantified	1.740 +/- 0.540 uM	Adult (>18 years old)	Both	Normal	17378949	details
Blood	Detected and Quantified	2.3 uM	Adult (>18 years old)	Both	Normal	15735096	details
Blood	Detected and Quantified	2.200 +/- 0.634 uM	Adult (>18 years old)	Both	Normal	16755268	details
Blood	Detected and Quantified	2.182 +/- 0.499 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	0.580 +/- 0.360 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	0.831 +/- 0.499 uM	Adult (>18 years old)	Male	Normal	1878353	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 and Quantified	2.50 +/- 0.86 uM	Adult (>18 years old)	Both	Hemodialysis	16221095	details
Blood	Detected and Quantified	2.0 (1.2-2.5) uM	Adult (>18 years old)	Female	Endometrial cancer	19235557	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Bladder cancer	22685041	details
Blood	Detected and Quantified	1.466 +/- 0.349 uM	Adult (>18 years old)	Female	Pregnancy	16925883	details
Blood	Detected and Quantified	0.45 uM	Adult (>18 years old)	Male	Abetalipoproteinemia	2944375	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)

Download (PDF)

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 Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

Enzymes

Reactions

Reactions

Reactions

Reactions

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