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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (6) Show 6 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2007-05-22 17:49:55 UTC

Update Date

2022-03-07 02:49:30 UTC

HMDB ID

HMDB0006216

Secondary Accession Numbers

HMDB0003439
HMDB03439
HMDB06216

Metabolite Identification

Common Name

11-cis-Retinol

Description

Cis-11-retinol is produce from vitamin A cycle driven by interphotoreceptor retinoid binding protein(IRBP). cis-11-retinol is released from retinal pigment epithelium(RPE) membranes. (PMID: 10655150 ). Retinoid metabolism of RPE cells freshly isolated by trypsinization showed no 11- cis -retinal and little 11- cis -retinol formation. Nondamaged cells cultured on thermally responsive surfaces detached in sheets upon temperature change. They showed metabolism similar to that of cells freshly isolated by nonenzymatic means. After trypsinization, confluent cultures dissociated into individual cells, but these cells showed poor retinoid metabolism, including no detectable retinyl esters or 11- cis -retinoid isomers. (PMID: 10375454 ).

Structure

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

HMDB0006216
     RDKit          3D
11-cis-Retinol
 51 51  0  0  0  0  0  0  0  0999 V2000
   -3.7590    2.1943   -1.1200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8483    0.9923   -0.2433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7475    0.2860    0.1214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5055    0.8001   -0.4054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2846    0.3753   -0.2363 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8377    1.0508   -0.8714 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7496    2.2313   -1.7332 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1003    0.5612   -0.6601 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2082    1.2211   -1.2820 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4485    0.8828   -1.1630 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9452   -0.2191   -0.3733 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1721   -1.0642    0.5177 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2698   -0.4441   -0.4044 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0184   -1.4809    0.2881 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9779   -0.9261    1.1682 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0135   -0.8741    0.9629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9127   -1.8745    1.1269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4662   -0.4906    2.3595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1595   -1.6886    0.3154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3743   -0.8738    0.0697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1627    0.5883    0.2627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3123    1.9445   -2.1246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1435    2.9504   -0.6236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7783    2.5429   -1.3558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6029    1.7071   -1.0662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1344   -0.4701    0.3940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2430    2.6493   -1.8974 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3723    3.0606   -1.3128 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1890    1.9066   -2.7325 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0618   -0.3032   -0.0466 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0388    2.1140   -1.9402 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2002    1.5194   -1.7354 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6033   -1.8665    0.0570 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6158   -0.4596    1.3047 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9052   -1.6325    1.1982 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8836    0.2328   -1.0292 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4904   -2.2559    0.8270 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6317   -2.0931   -0.4915 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1000    0.0062    0.8871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2459   -1.5925    1.9441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4589   -2.2369    0.2061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4423   -2.8221    1.5403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8462   -1.0195    3.1222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4909   -0.8692    2.5134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4163    0.5899    2.5557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4012   -2.4688    1.0744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7805   -2.2192   -0.5699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6831   -1.0447   -1.0033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2508   -1.1876    0.6693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9609    1.1105   -0.3595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3944    0.9597    1.2953 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
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3272    1.9659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1018    1.9659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 13 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0006216

> <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-IOUUIBBYSA-N

> <FORMULA>
C20H30O

> <MOLECULAR_WEIGHT>
286.4516

> <EXACT_MASS>
286.229665582

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
35.685679783607306

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E,4Z,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>
97.9234

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.58e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
vitamin a

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0006216
     RDKit          3D
11-cis-Retinol
 51 51  0  0  0  0  0  0  0  0999 V2000
   -3.7590    2.1943   -1.1200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8483    0.9923   -0.2433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7475    0.2860    0.1214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5055    0.8001   -0.4054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2846    0.3753   -0.2363 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8377    1.0508   -0.8714 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7496    2.2313   -1.7332 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1003    0.5612   -0.6601 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2082    1.2211   -1.2820 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4485    0.8828   -1.1630 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9452   -0.2191   -0.3733 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1721   -1.0642    0.5177 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2698   -0.4441   -0.4044 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0184   -1.4809    0.2881 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9779   -0.9261    1.1682 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0135   -0.8741    0.9629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9127   -1.8745    1.1269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4662   -0.4906    2.3595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1595   -1.6886    0.3154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3743   -0.8738    0.0697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1627    0.5883    0.2627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3123    1.9445   -2.1246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1435    2.9504   -0.6236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7783    2.5429   -1.3558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6029    1.7071   -1.0662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1344   -0.4701    0.3940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2430    2.6493   -1.8974 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3723    3.0606   -1.3128 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1890    1.9066   -2.7325 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0618   -0.3032   -0.0466 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0388    2.1140   -1.9402 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2002    1.5194   -1.7354 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6033   -1.8665    0.0570 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6158   -0.4596    1.3047 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9052   -1.6325    1.1982 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8836    0.2328   -1.0292 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4904   -2.2559    0.8270 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6317   -2.0931   -0.4915 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1000    0.0062    0.8871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2459   -1.5925    1.9441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4589   -2.2369    0.2061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4423   -2.8221    1.5403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8462   -1.0195    3.1222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4909   -0.8692    2.5134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4163    0.5899    2.5557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4012   -2.4688    1.0744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7805   -2.2192   -0.5699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6831   -1.0447   -1.0033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2508   -1.1876    0.6693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9609    1.1105   -0.3595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3944    0.9597    1.2953 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      10.669   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.611   3.670   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.057   3.670   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4                                                            
CONECT    6    2    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   19                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   13   20   21                                             
CONECT   20   19                                                            
CONECT   21   19                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   42    0
END

COMPND    HMDB0006216
HETATM    1  C1  UNL     1      -3.759   2.194  -1.120  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.848   0.992  -0.243  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.747   0.286   0.121  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.505   0.800  -0.405  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.285   0.375  -0.236  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.838   1.051  -0.871  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.750   2.231  -1.733  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.100   0.561  -0.660  1.00  0.00           C  
HETATM    9  C9  UNL     1       3.208   1.221  -1.282  1.00  0.00           C  
HETATM   10  C10 UNL     1       4.448   0.883  -1.163  1.00  0.00           C  
HETATM   11  C11 UNL     1       4.945  -0.219  -0.373  1.00  0.00           C  
HETATM   12  C12 UNL     1       4.172  -1.064   0.518  1.00  0.00           C  
HETATM   13  C13 UNL     1       6.270  -0.444  -0.404  1.00  0.00           C  
HETATM   14  C14 UNL     1       7.018  -1.481   0.288  1.00  0.00           C  
HETATM   15  O1  UNL     1       7.978  -0.926   1.168  1.00  0.00           O  
HETATM   16  C15 UNL     1      -3.014  -0.874   0.963  1.00  0.00           C  
HETATM   17  C16 UNL     1      -1.913  -1.874   1.127  1.00  0.00           C  
HETATM   18  C17 UNL     1      -3.466  -0.491   2.359  1.00  0.00           C  
HETATM   19  C18 UNL     1      -4.160  -1.689   0.315  1.00  0.00           C  
HETATM   20  C19 UNL     1      -5.374  -0.874   0.070  1.00  0.00           C  
HETATM   21  C20 UNL     1      -5.163   0.588   0.263  1.00  0.00           C  
HETATM   22  H1  UNL     1      -3.312   1.945  -2.125  1.00  0.00           H  
HETATM   23  H2  UNL     1      -3.143   2.950  -0.624  1.00  0.00           H  
HETATM   24  H3  UNL     1      -4.778   2.543  -1.356  1.00  0.00           H  
HETATM   25  H4  UNL     1      -1.603   1.707  -1.066  1.00  0.00           H  
HETATM   26  H5  UNL     1      -0.134  -0.470   0.394  1.00  0.00           H  
HETATM   27  H6  UNL     1      -0.243   2.649  -1.897  1.00  0.00           H  
HETATM   28  H7  UNL     1       1.372   3.061  -1.313  1.00  0.00           H  
HETATM   29  H8  UNL     1       1.189   1.907  -2.733  1.00  0.00           H  
HETATM   30  H9  UNL     1       2.062  -0.303  -0.047  1.00  0.00           H  
HETATM   31  H10 UNL     1       3.039   2.114  -1.940  1.00  0.00           H  
HETATM   32  H11 UNL     1       5.200   1.519  -1.735  1.00  0.00           H  
HETATM   33  H12 UNL     1       3.603  -1.866   0.057  1.00  0.00           H  
HETATM   34  H13 UNL     1       3.616  -0.460   1.305  1.00  0.00           H  
HETATM   35  H14 UNL     1       4.905  -1.632   1.198  1.00  0.00           H  
HETATM   36  H15 UNL     1       6.884   0.233  -1.029  1.00  0.00           H  
HETATM   37  H16 UNL     1       6.490  -2.256   0.827  1.00  0.00           H  
HETATM   38  H17 UNL     1       7.632  -2.093  -0.491  1.00  0.00           H  
HETATM   39  H18 UNL     1       8.100   0.006   0.887  1.00  0.00           H  
HETATM   40  H19 UNL     1      -1.246  -1.593   1.944  1.00  0.00           H  
HETATM   41  H20 UNL     1      -1.459  -2.237   0.206  1.00  0.00           H  
HETATM   42  H21 UNL     1      -2.442  -2.822   1.540  1.00  0.00           H  
HETATM   43  H22 UNL     1      -2.846  -1.020   3.122  1.00  0.00           H  
HETATM   44  H23 UNL     1      -4.491  -0.869   2.513  1.00  0.00           H  
HETATM   45  H24 UNL     1      -3.416   0.590   2.556  1.00  0.00           H  
HETATM   46  H25 UNL     1      -4.401  -2.469   1.074  1.00  0.00           H  
HETATM   47  H26 UNL     1      -3.780  -2.219  -0.570  1.00  0.00           H  
HETATM   48  H27 UNL     1      -5.683  -1.045  -1.003  1.00  0.00           H  
HETATM   49  H28 UNL     1      -6.251  -1.188   0.669  1.00  0.00           H  
HETATM   50  H29 UNL     1      -5.961   1.110  -0.359  1.00  0.00           H  
HETATM   51  H30 UNL     1      -5.394   0.960   1.295  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

HMDB0006216
     RDKit          3D
11-cis-Retinol
 51 51  0  0  0  0  0  0  0  0999 V2000
   -3.7590    2.1943   -1.1200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8483    0.9923   -0.2433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7475    0.2860    0.1214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5055    0.8001   -0.4054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2846    0.3753   -0.2363 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8377    1.0508   -0.8714 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7496    2.2313   -1.7332 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1003    0.5612   -0.6601 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2082    1.2211   -1.2820 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4485    0.8828   -1.1630 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9452   -0.2191   -0.3733 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1721   -1.0642    0.5177 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2698   -0.4441   -0.4044 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0184   -1.4809    0.2881 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9779   -0.9261    1.1682 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0135   -0.8741    0.9629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9127   -1.8745    1.1269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4662   -0.4906    2.3595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1595   -1.6886    0.3154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3743   -0.8738    0.0697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1627    0.5883    0.2627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3123    1.9445   -2.1246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1435    2.9504   -0.6236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7783    2.5429   -1.3558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6029    1.7071   -1.0662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1344   -0.4701    0.3940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2430    2.6493   -1.8974 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3723    3.0606   -1.3128 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1890    1.9066   -2.7325 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0618   -0.3032   -0.0466 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0388    2.1140   -1.9402 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2002    1.5194   -1.7354 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6033   -1.8665    0.0570 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6158   -0.4596    1.3047 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9052   -1.6325    1.1982 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8836    0.2328   -1.0292 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4904   -2.2559    0.8270 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6317   -2.0931   -0.4915 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1000    0.0062    0.8871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2459   -1.5925    1.9441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4589   -2.2369    0.2061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4423   -2.8221    1.5403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8462   -1.0195    3.1222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4909   -0.8692    2.5134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4163    0.5899    2.5557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4012   -2.4688    1.0744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7805   -2.2192   -0.5699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6831   -1.0447   -1.0033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2508   -1.1876    0.6693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9609    1.1105   -0.3595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3944    0.9597    1.2953 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
11-cis-Vitamin a alcohol	HMDB
cis-11-Retinol	HMDB
3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraen-1-ol, (all-e)-isomer	HMDB
all trans Retinol	HMDB
all-trans-Retinol	HMDB
Aquasol a	HMDB
Retinol	HMDB
Vitamin a	HMDB
Vitamin a1	HMDB

Chemical Formula

C₂₀H₃₀O

Average Molecular Weight

286.4516

Monoisotopic Molecular Weight

286.229665582

IUPAC Name

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

Traditional Name

vitamin a

CAS Registry Number

22737-96-8

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-IOUUIBBYSA-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:16302 )
Retinoids (C00899 )
Retinoids (LMPR01090005 )

Ontology

Physiological effect

Health effect

Intervention

Hemodialysis (HMDB: HMDB0006216)

Endocrine system disorder

Thyroidal or parathyroidal disorder

Thyroid cancer (HMDB: HMDB0006216)

Observation

Disposition

Biological location

Cellular substructure

Cell

Fibroblast

Fibroblast (HMDB: HMDB0006216)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0006216)
Saliva (HMDB: HMDB0006216)

Organ

Tissue

Connective tissue

Adipose tissue (HMDB: HMDB0006216)

Epithelium

Epidermis (HMDB: HMDB0006216)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0006216)
Gastrointestinal (HMDB: HMDB0006216)

Source

Endogenous

Endogenous (HMDB: HMDB0006216)

Plant

Animal

Animal (HMDB: HMDB0006216)

Exogenous

Food

Food (HMDB: HMDB0006216)

Animal origin

Poultry

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

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

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

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

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

Equine

Horse (FooDB: FOOD00378)

Herbs and Spices (FooDB: FOOD00866)

Nut

Almond (FooDB: FOOD00148)
Brazil nut (FooDB: FOOD00024)
Cashew nut (FooDB: FOOD00011)
Chestnut (FooDB: FOOD00045)
Hazelnut (FooDB: FOOD00376)
Peanut (FooDB: FOOD00016)
Pecan nut (FooDB: FOOD00044)
Pine nut (FooDB: FOOD00138)
Pistachio (FooDB: FOOD00140)
Walnut (FooDB: FOOD00608)
Acorn (FooDB: FOOD00282)
Beech nut (FooDB: FOOD00299)
Butternut (FooDB: FOOD00316)
Chinese chestnut (FooDB: FOOD00331)
European chestnut (FooDB: FOOD00363)
Hickory nut (FooDB: FOOD00377)
Macadamia nut (FooDB: FOOD00525)
Mixed nuts (FooDB: FOOD00771)
Pili nut (FooDB: FOOD00432)
Colorado pinyon (FooDB: FOOD00433)
Black walnut (FooDB: FOOD00093)
Common walnut (FooDB: FOOD00094)
Japanese chestnut (FooDB: FOOD00385)
Common hazelnut (FooDB: FOOD00062)
Macadamia nut (M. tetraphylla) (FooDB: FOOD00225)
Japanese walnut (FooDB: FOOD00240)
Nuts (FooDB: FOOD00869)

Fruit

Pome

Drupe

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

Tropical fruit

Berry

Bilberry (FooDB: FOOD00193)
Rubus (Blackberry, Raspberry) (FooDB: FOOD00160)
Vaccinium (Blueberry, Cranberry, Huckleberry) (FooDB: FOOD00188)
Blackcurrant (FooDB: FOOD00155)
Redcurrant (FooDB: FOOD00156)
Elderberry (FooDB: FOOD00358)
Gooseberry (FooDB: FOOD00157)
Grape (FooDB: FOOD00369)
Lingonberry (FooDB: FOOD00194)
Loganberry (FooDB: FOOD00400)
Strawberry (FooDB: FOOD00083)
Boysenberry (FooDB: FOOD00542)
American cranberry (FooDB: FOOD00192)
Common grape (FooDB: FOOD00204)
Strawberry guava (FooDB: FOOD00482)
Black mulberry (FooDB: FOOD00117)
Red raspberry (FooDB: FOOD00162)
Muscadine grape (FooDB: FOOD00203)
Salmonberry (FooDB: FOOD00456)
Alaska blueberry (FooDB: FOOD00380)
Sea-buckthornberry (FooDB: FOOD00087)
Black elderberry (FooDB: FOOD00166)
Black crowberry (FooDB: FOOD00075)
Black huckleberry (FooDB: FOOD00084)
Mulberry (FooDB: FOOD00116)
Black chokeberry (FooDB: FOOD00136)
Cloudberry (FooDB: FOOD00161)
Black raspberry (FooDB: FOOD00163)
Rowanberry (FooDB: FOOD00176)
Lowbush blueberry (FooDB: FOOD00189)
Sparkleberry (FooDB: FOOD00190)
Highbush blueberry (FooDB: FOOD00191)
Arctic blackberry (FooDB: FOOD00207)
Bayberry (FooDB: FOOD00209)
Elliott's blueberry (FooDB: FOOD00210)
Canada blueberry (FooDB: FOOD00211)
Bog bilberry (FooDB: FOOD00212)
Buffalo currant (FooDB: FOOD00213)
European cranberry (FooDB: FOOD00217)
Deerberry (FooDB: FOOD00218)
Cascade huckleberry (FooDB: FOOD00220)
Oval-leaf huckleberry (FooDB: FOOD00221)
Evergreen huckleberry (FooDB: FOOD00222)
Red huckleberry (FooDB: FOOD00223)
Summer grape (FooDB: FOOD00227)
Fox grape (FooDB: FOOD00228)
Half-highbush blueberry (FooDB: FOOD00248)
Jostaberry (FooDB: FOOD00257)
Sweet rowanberry (FooDB: FOOD00265)
Skunk currant (FooDB: FOOD00267)
Squashberry (FooDB: FOOD00344)
Ohelo berry (FooDB: FOOD00419)
Chinese bayberry (FooDB: FOOD00852)
Saskatoon berry (FooDB: FOOD00884)
Nanking cherry (FooDB: FOOD00885)

Other fruit

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

Citrus

Grapefruit (FooDB: FOOD00256)
Lemon (FooDB: FOOD00054)
Lime (FooDB: FOOD00053)
Sweet orange (FooDB: FOOD00057)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)
Persian lime (FooDB: FOOD00543)
Pummelo (FooDB: FOOD00055)
Grapefruit/Pummelo hybrid (FooDB: FOOD00255)
Citrus (FooDB: FOOD00859)

Fruits (FooDB: FOOD00871)

Vegetable

Shoot vegetable

Fruit vegetable

Eggplant (FooDB: FOOD00174)
Avocado (FooDB: FOOD00130)
Groundcherry (FooDB: FOOD00371)
Olive (FooDB: FOOD00121)
Pepper (FooDB: FOOD00040)
Garden tomato (FooDB: FOOD00171)
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)
Garden tomato (var.) (FooDB: FOOD00173)
Cherry tomato (FooDB: FOOD00172)
Pepper (C. baccatum) (FooDB: FOOD00231)
Pepper (C. chinense) (FooDB: FOOD00232)
Pepper (Capsicum) (FooDB: FOOD00233)
Pepper (C. frutescens) (FooDB: FOOD00428)
Pepper (C. pubescens) (FooDB: FOOD00849)
Orange bell pepper (FooDB: FOOD00879)

Root vegetable

Cabbage

Leaf vegetable

Lettuce (FooDB: FOOD00095)
Swiss chard (FooDB: FOOD00237)
Garden cress (FooDB: FOOD00099)
Endive (FooDB: FOOD00048)
Spinach (FooDB: FOOD00178)
Common beet (FooDB: FOOD00025)
Garland chrysanthemum (FooDB: FOOD00333)
Jute (FooDB: FOOD00389)
Lambsquarters (FooDB: FOOD00394)
New Zealand spinach (FooDB: FOOD00415)
Swamp cabbage (FooDB: FOOD00091)
Rocket salad (ssp.) (FooDB: FOOD00077)
Yautia (FooDB: FOOD00510)
Romaine lettuce (FooDB: FOOD00888)
Rocket salad (FooDB: FOOD00244)
Chicory leaves (FooDB: FOOD00250)
Corn salad (FooDB: FOOD00340)
Malabar spinach (FooDB: FOOD00404)
Ostrich fern (FooDB: FOOD00556)
Green vegetables (FooDB: FOOD00872)

Mushroom

Tuber

Onion-family vegetable

Leek (FooDB: FOOD00007)
Allium (FooDB: FOOD00005)
Wild leek (FooDB: FOOD00396)
Shallot (FooDB: FOOD00243)
Garden onion (FooDB: FOOD00006)
Garden onion (var.) (FooDB: FOOD00226)
Onion-family vegetables (FooDB: FOOD00855)
Green onion (FooDB: FOOD00963)
Red onion (FooDB: FOOD00962)

Other vegetable

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

Stalk vegetable

Brassica

Brassicas (FooDB: FOOD00857)

Cereal and cereal product

Other bread

Other bread (FooDB: FOOD00269)

Cereal

Cereal product

Dough

Sourdough (FooDB: FOOD00275)

Cereals and cereal products (FooDB: FOOD00858)

Pulse

Bean

Lentil

Lentils (FooDB: FOOD00098)

Pea

Other pulse

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

Pulses (FooDB: FOOD00867)

Soy

Soy bean (FooDB: FOOD00085)

Soy product

Other soy product (FooDB: FOOD00271)

Abalone (FooDB: FOOD00279)
Conch (FooDB: FOOD00611)

Gourd

Chayote (FooDB: FOOD00325)
Cucumber (FooDB: FOOD00065)
Muskmelon (FooDB: FOOD00064)
Cucurbita (FooDB: FOOD00066)
Watermelon (FooDB: FOOD00052)
Bitter gourd (FooDB: FOOD00115)
Calabash (FooDB: FOOD00318)
Towel gourd (FooDB: FOOD00492)
Winter squash (FooDB: FOOD00283)
Butternut squash (FooDB: FOOD00317)
Wax gourd (FooDB: FOOD00499)
Green zucchini (FooDB: FOOD00875)
Yellow zucchini (FooDB: FOOD00876)
Japanese pumpkin (FooDB: FOOD00886)
Sunburst squash (pattypan squash) (FooDB: FOOD00874)
Tinda (FooDB: FOOD00559)
Horned melon (FooDB: FOOD00761)

Tea

Herbal tea

Greenthread tea (FooDB: FOOD00820)

Cocoa and cocoa product

Cocoa

Cocoa bean (FooDB: FOOD00182)

Exogenous (HMDB: HMDB0006216)

Synthetic

Personal care products

Personal care products (HMDB: HMDB0006216)

Process

Role

Industrial application

Personal care product

Personal care product (HMDB: HMDB0006216)

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0006216)

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0006216)

Food and nutrition

Food and nutrition (HMDB: HMDB0006216)

Biological role

Energy source (HMDB: HMDB0006216)

Physical Properties

State

Solid

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0076 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	35.69 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]+	175.783	31661259
DarkChem	[M-H]-	172.893	31661259
DeepCCS	[M+H]+	187.504	30932474
DeepCCS	[M-H]-	185.146	30932474
DeepCCS	[M-2H]-	218.821	30932474
DeepCCS	[M+Na]+	194.048	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
11-cis-Retinol	C\C(=C/CO)\C=C/C=C(\C)/C=C/C1=C(C)CCCC1(C)C	3108.0	Standard polar	33892256
11-cis-Retinol	C\C(=C/CO)\C=C/C=C(\C)/C=C/C1=C(C)CCCC1(C)C	2431.2	Standard non polar	33892256
11-cis-Retinol	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
11-cis-Retinol,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
11-cis-Retinol,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 - 11-cis-Retinol GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-1190000000-346a3e44c44d46353e80	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 11-cis-Retinol GC-MS (1 TMS) - 70eV, Positive	splash10-0006-7139000000-7242603c3f7f12c824cd	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 11-cis-Retinol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 11-cis-Retinol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-052r-2950000000-c24ec8ff8d0ba6c1f23f	2018-05-25	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - 11-cis-Retinol Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-000i-0290000000-25c523b646154b291da8	2018-05-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 11-cis-Retinol Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-05gj-3900000000-a63c286f931608f650a3	2018-05-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 11-cis-Retinol Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-05mo-9700000000-e627db30469c74bb037f	2018-05-25	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-cis-Retinol 10V, Positive-QTOF	splash10-00kr-1490000000-7205fba02aeb80622df8	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-cis-Retinol 20V, Positive-QTOF	splash10-00m0-3920000000-951836eaf171751b137c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-cis-Retinol 40V, Positive-QTOF	splash10-0lei-9810000000-b9b76a3e956e61a7d39e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-cis-Retinol 10V, Negative-QTOF	splash10-000i-0090000000-575d71f5f53354f828c2	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-cis-Retinol 20V, Negative-QTOF	splash10-0a4r-0090000000-c71c47589510cf7c1a0b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-cis-Retinol 40V, Negative-QTOF	splash10-00ku-3690000000-26f7587a1f34c10cd8f7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-cis-Retinol 10V, Negative-QTOF	splash10-0a4i-0090000000-fe93459d3069e264b77f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-cis-Retinol 20V, Negative-QTOF	splash10-05mx-0190000000-f81760535f6050971f92	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-cis-Retinol 40V, Negative-QTOF	splash10-00li-0960000000-4dbc516b202b90a6c265	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-cis-Retinol 10V, Positive-QTOF	splash10-015i-1890000000-fb68e645ac6c84dc722c	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-cis-Retinol 20V, Positive-QTOF	splash10-05a9-2910000000-aa07b89a9cfe132b8725	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-cis-Retinol 40V, Positive-QTOF	splash10-06dl-5900000000-6de72efc591b252620c9	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)	2018-05-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

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

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023840

KNApSAcK ID

Not Available

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5280382

PDB ID

Not Available

ChEBI ID

16302

Food Biomarker Ontology

Not Available

VMH ID

RETINOL_CIS_11

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Brown, Paul K.; Wald, George. The neo-b isomer of vitamin A and retinine. Journal of Biological Chemistry (1956), 222 865-77.

Material Safety Data Sheet (MSDS)

Not Available

General References

Edwards RB, Adler AJ: IRBP enhances removal of 11- cis -retinaldehyde from isolated RPE membranes. Exp Eye Res. 2000 Feb;70(2):235-45. [PubMed:10655150 ]
von Recum HA, Okano T, Kim SW, Bernstein PS: Maintenance of retinoid metabolism in human retinal pigment epithelium cell culture. Exp Eye Res. 1999 Jul;69(1):97-107. [PubMed:10375454 ]

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

Palmityl-CoA + 11-cis-Retinol → Coenzyme A + 11-cis-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. Retinoid isomerohydrolase

General function:: Secondary metabolites biosynthesis, transport and catabolism
Specific function:: Plays important roles in the production of 11-cis retinal and in visual pigment regeneration. The soluble form binds vitamin A (all-trans-retinol), making it available for LRAT processing to all-trans-retinyl ester. The membrane form, palmitoylated by LRAT, binds all-trans-retinyl esters, making them available for IMH (isomerohydrolase) processing to all-cis-retinol. The soluble form is regenerated by transferring its palmitoyl groups onto 11-cis-retinol, a reaction catalyzed by LRAT. The enzymatic activity is linearly dependent of the expression levels and membrane association.
Gene Name:: RPE65
Uniprot ID:: Q16518
Molecular weight:: 60947.08

Reactions

An all-trans-retinyl ester + Water → 11-cis-Retinol + a fatty acid	details
Retinyl ester + Water → 11-cis-Retinol + Fatty acid	details

Enzyme Details

4. 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

Palmitoylphosphatidylcholine + 11-cis-Retinol → 11-cis-Retinyl palmitate + 2-Acyl-sn-glycero-3-phosphocholine	details

Enzyme Details

5. Acyl-CoA wax alcohol acyltransferase 1

General function:: Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:: Acyltransferase that predominantly esterify long chain (wax) alcohols with acyl-CoA-derived fatty acids to produce wax esters. Wax esters are enriched in sebum, suggesting that it plays a central role in lipid metabolism in skin. Has a preference for arachidyl alcohol as well as decyl alcohol, demonstrating its relatively poor activity using saturated long chain alcohols (C16, C18, and C20).
Gene Name:: AWAT1
Uniprot ID:: Q58HT5
Molecular weight:: 37758.815

Enzyme Details

6. Acyl-CoA wax alcohol acyltransferase 2

General function:: Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:: Acyltransferase that predominantly esterify long chain (wax) alcohols with acyl-CoA-derived fatty acids to produce wax esters. Wax esters are enriched in sebum, suggesting that it plays a central role in lipid metabolism in skin. Has no activity using decyl alcohol and significantly prefers the C16 and C18 alcohols. May also have 2-acylglycerol O-acyltransferase (MGAT) and acyl-CoA:retinol acyltransferase (ARAT) activities, to catalyze the synthesis of diacylglycerols and retinyl esters; however this activity is unclear in vivo.
Gene Name:: AWAT2
Uniprot ID:: Q6E213
Molecular weight:: 38093.25

Showing metabocard for 11-cis-Retinol (HMDB0006216)

MOL for HMDB0006216 (11-cis-Retinol)

3D MOL for HMDB0006216 (11-cis-Retinol)

3D SDF for HMDB0006216 (11-cis-Retinol)

3D-SDF for HMDB0006216 (11-cis-Retinol)

PDB for HMDB0006216 (11-cis-Retinol)

3D PDB for HMDB0006216 (11-cis-Retinol)

SMILES for HMDB0006216 (11-cis-Retinol)

INCHI for HMDB0006216 (11-cis-Retinol)

Structure for HMDB0006216 (11-cis-Retinol)

3D Structure for HMDB0006216 (11-cis-Retinol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions

Reactions

Reactions