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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2007-05-22 18:00:08 UTC

Update Date

2022-03-07 02:49:30 UTC

HMDB ID

HMDB0006221

Secondary Accession Numbers

HMDB06221

Metabolite Identification

Common Name

13-cis Retinol

Description

13-cis Retinol is a retinoid inapplicable to the visual processes, and therefore it could be an important catabolic metabolite and its biosynthesis could be part of a process involved in regulating 11-cis-retinol concentrations within the retinal pigment epithelium of 11-cis-retinol dehydrogenase. 13-cis Retinol accumulates as a consequence of reduced 11-cis-retinol oxidation capacity. Reduced 11-cis-retinol oxidation occurs in 11-cis-Retinol dehydrogenase deficiency. Mutations in the 11-cis-retinol dehydrogenase gene in humans have been associated with fundus albipunctatus (delayed dark adaptation and punctata are typical symptoms of this human hereditary ocular disease). (PMID: 10825191 ).

Structure

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

HMDB0006221
     RDKit          3D
13-cis Retinol
 51 51  0  0  0  0  0  0  0  0999 V2000
   -2.9829   -3.0798    0.4598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6085   -1.7117    0.4984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7935   -0.6307    0.3401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3894   -0.9464    0.1463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3895   -0.1220   -0.0483 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9848   -0.5543   -0.2291 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4448   -1.9570   -0.2246 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9033    0.4148   -0.4179 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2919    0.0102   -0.6017 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2538    0.9389   -0.7954 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6251    0.5737   -0.9789 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9364   -0.9237   -0.9429 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5781    1.4230   -1.1670 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4401    2.8583   -1.2252 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2456    3.4637   -1.0812 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4574    0.6567    0.4031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3014    0.9000   -0.8640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6369    1.8845    0.6475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5161    0.5918    1.5416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5957   -0.3283    1.0862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0503   -1.6644    0.6754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5091   -3.2947   -0.5019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2723   -3.1555    1.3315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7685   -3.8182    0.6778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0748   -2.0062    0.1581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5750    0.9309   -0.0978 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1830   -2.1434    0.6063 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6751   -2.7101   -0.1558 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0649   -2.1821   -1.1484 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6581    1.4585   -0.4382 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6211   -1.0115   -0.5933 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8998    1.9442   -0.7981 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2890   -1.3830   -1.7075 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5932   -1.2419    0.0627 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0037   -1.0987   -1.0971 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6159    0.9852   -1.2970 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9257    3.2964   -2.1574 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0918    3.2590   -0.3649 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0905    3.9738   -0.2567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1731    1.5245   -0.6067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6696    1.3537   -1.6550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6358   -0.0903   -1.2167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4198    2.6521    1.0308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9280    1.8053    1.4614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3156    2.3189   -0.2939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9397    1.5960    1.6730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0263    0.1658    2.4135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2837   -0.4873    1.9650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2401    0.0510    0.2789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3023   -2.4510    1.4541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5604   -2.0389   -0.2399 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


  Mrv1652304202020002D          

 21 21  0  0  0  0            999 V2000
    0.0000    0.8250    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
   -0.7145   -0.4125    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   -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
    1.4289    0.8250    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
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.4125    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
    5.0012    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    1.5395    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 19  1  0  0  0  0
  1 20  1  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5 21  1  0  0  0  0
  1  6  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
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 16  1  0  0  0  0
 10 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
 13 17  1  0  0  0  0
 14 18  1  0  0  0  0
 18 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0006221

> <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-HWCYFHEPSA-N

> <FORMULA>
C20H30O

> <MOLECULAR_WEIGHT>
286.4516

> <EXACT_MASS>
286.229665582

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
36.278495170360316

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2Z,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>
97.9234

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.58e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
13-cis retinol

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0006221
     RDKit          3D
13-cis Retinol
 51 51  0  0  0  0  0  0  0  0999 V2000
   -2.9829   -3.0798    0.4598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6085   -1.7117    0.4984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7935   -0.6307    0.3401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3894   -0.9464    0.1463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3895   -0.1220   -0.0483 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9848   -0.5543   -0.2291 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4448   -1.9570   -0.2246 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9033    0.4148   -0.4179 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2919    0.0102   -0.6017 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2538    0.9389   -0.7954 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6251    0.5737   -0.9789 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9364   -0.9237   -0.9429 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5781    1.4230   -1.1670 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4401    2.8583   -1.2252 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2456    3.4637   -1.0812 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4574    0.6567    0.4031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3014    0.9000   -0.8640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6369    1.8845    0.6475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5161    0.5918    1.5416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5957   -0.3283    1.0862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0503   -1.6644    0.6754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5091   -3.2947   -0.5019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2723   -3.1555    1.3315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7685   -3.8182    0.6778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0748   -2.0062    0.1581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5750    0.9309   -0.0978 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1830   -2.1434    0.6063 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6751   -2.7101   -0.1558 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0649   -2.1821   -1.1484 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6581    1.4585   -0.4382 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6211   -1.0115   -0.5933 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8998    1.9442   -0.7981 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2890   -1.3830   -1.7075 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5932   -1.2419    0.0627 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0037   -1.0987   -1.0971 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6159    0.9852   -1.2970 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9257    3.2964   -2.1574 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0918    3.2590   -0.3649 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0905    3.9738   -0.2567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1731    1.5245   -0.6067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6696    1.3537   -1.6550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6358   -0.0903   -1.2167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4198    2.6521    1.0308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9280    1.8053    1.4614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3156    2.3189   -0.2939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9397    1.5960    1.6730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0263    0.1658    2.4135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2837   -0.4873    1.9650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2401    0.0510    0.2789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3023   -2.4510    1.4541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5604   -2.0389   -0.2399 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                                 20-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-20         0                                  
HETATM    1  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668   0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.336   0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.003   0.770   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      13.337  -1.540   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       5.335   3.080   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.669   3.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.770   2.874   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.770   2.874   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.667  -1.540   0.000  0.00  0.00           C+0
CONECT    1   19   20    2    6                                             
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4   21    6                                                  
CONECT    6    1    5    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   16                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   17                                                  
CONECT   14   13   18                                                       
CONECT   15   18                                                            
CONECT   16    9                                                            
CONECT   17   13                                                            
CONECT   18   14   15                                                       
CONECT   19    1                                                            
CONECT   20    1                                                            
CONECT   21    5                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   42    0
END

COMPND    HMDB0006221
HETATM    1  C1  UNL     1      -2.983  -3.080   0.460  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.608  -1.712   0.498  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.794  -0.631   0.340  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.389  -0.946   0.146  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.389  -0.122  -0.048  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.985  -0.554  -0.229  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.445  -1.957  -0.225  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.903   0.415  -0.418  1.00  0.00           C  
HETATM    9  C9  UNL     1       3.292   0.010  -0.602  1.00  0.00           C  
HETATM   10  C10 UNL     1       4.254   0.939  -0.795  1.00  0.00           C  
HETATM   11  C11 UNL     1       5.625   0.574  -0.979  1.00  0.00           C  
HETATM   12  C12 UNL     1       5.936  -0.924  -0.943  1.00  0.00           C  
HETATM   13  C13 UNL     1       6.578   1.423  -1.167  1.00  0.00           C  
HETATM   14  C14 UNL     1       6.440   2.858  -1.225  1.00  0.00           C  
HETATM   15  O1  UNL     1       5.246   3.464  -1.081  1.00  0.00           O  
HETATM   16  C15 UNL     1      -3.457   0.657   0.403  1.00  0.00           C  
HETATM   17  C16 UNL     1      -4.301   0.900  -0.864  1.00  0.00           C  
HETATM   18  C17 UNL     1      -2.637   1.884   0.648  1.00  0.00           C  
HETATM   19  C18 UNL     1      -4.516   0.592   1.542  1.00  0.00           C  
HETATM   20  C19 UNL     1      -5.596  -0.328   1.086  1.00  0.00           C  
HETATM   21  C20 UNL     1      -5.050  -1.664   0.675  1.00  0.00           C  
HETATM   22  H1  UNL     1      -2.509  -3.295  -0.502  1.00  0.00           H  
HETATM   23  H2  UNL     1      -2.272  -3.155   1.332  1.00  0.00           H  
HETATM   24  H3  UNL     1      -3.768  -3.818   0.678  1.00  0.00           H  
HETATM   25  H4  UNL     1      -1.075  -2.006   0.158  1.00  0.00           H  
HETATM   26  H5  UNL     1      -0.575   0.931  -0.098  1.00  0.00           H  
HETATM   27  H6  UNL     1       2.183  -2.143   0.606  1.00  0.00           H  
HETATM   28  H7  UNL     1       0.675  -2.710  -0.156  1.00  0.00           H  
HETATM   29  H8  UNL     1       2.065  -2.182  -1.148  1.00  0.00           H  
HETATM   30  H9  UNL     1       1.658   1.458  -0.438  1.00  0.00           H  
HETATM   31  H10 UNL     1       3.621  -1.011  -0.593  1.00  0.00           H  
HETATM   32  H11 UNL     1       3.900   1.944  -0.798  1.00  0.00           H  
HETATM   33  H12 UNL     1       5.289  -1.383  -1.708  1.00  0.00           H  
HETATM   34  H13 UNL     1       5.593  -1.242   0.063  1.00  0.00           H  
HETATM   35  H14 UNL     1       7.004  -1.099  -1.097  1.00  0.00           H  
HETATM   36  H15 UNL     1       7.616   0.985  -1.297  1.00  0.00           H  
HETATM   37  H16 UNL     1       6.926   3.296  -2.157  1.00  0.00           H  
HETATM   38  H17 UNL     1       7.092   3.259  -0.365  1.00  0.00           H  
HETATM   39  H18 UNL     1       5.091   3.974  -0.257  1.00  0.00           H  
HETATM   40  H19 UNL     1      -5.173   1.525  -0.607  1.00  0.00           H  
HETATM   41  H20 UNL     1      -3.670   1.354  -1.655  1.00  0.00           H  
HETATM   42  H21 UNL     1      -4.636  -0.090  -1.217  1.00  0.00           H  
HETATM   43  H22 UNL     1      -3.420   2.652   1.031  1.00  0.00           H  
HETATM   44  H23 UNL     1      -1.928   1.805   1.461  1.00  0.00           H  
HETATM   45  H24 UNL     1      -2.316   2.319  -0.294  1.00  0.00           H  
HETATM   46  H25 UNL     1      -4.940   1.596   1.673  1.00  0.00           H  
HETATM   47  H26 UNL     1      -4.026   0.166   2.414  1.00  0.00           H  
HETATM   48  H27 UNL     1      -6.284  -0.487   1.965  1.00  0.00           H  
HETATM   49  H28 UNL     1      -6.240   0.051   0.279  1.00  0.00           H  
HETATM   50  H29 UNL     1      -5.302  -2.451   1.454  1.00  0.00           H  
HETATM   51  H30 UNL     1      -5.560  -2.039  -0.240  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

HMDB0006221
     RDKit          3D
13-cis Retinol
 51 51  0  0  0  0  0  0  0  0999 V2000
   -2.9829   -3.0798    0.4598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6085   -1.7117    0.4984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7935   -0.6307    0.3401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3894   -0.9464    0.1463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3895   -0.1220   -0.0483 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9848   -0.5543   -0.2291 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4448   -1.9570   -0.2246 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9033    0.4148   -0.4179 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2919    0.0102   -0.6017 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2538    0.9389   -0.7954 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6251    0.5737   -0.9789 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9364   -0.9237   -0.9429 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5781    1.4230   -1.1670 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4401    2.8583   -1.2252 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2456    3.4637   -1.0812 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4574    0.6567    0.4031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3014    0.9000   -0.8640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6369    1.8845    0.6475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5161    0.5918    1.5416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5957   -0.3283    1.0862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0503   -1.6644    0.6754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5091   -3.2947   -0.5019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2723   -3.1555    1.3315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7685   -3.8182    0.6778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0748   -2.0062    0.1581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5750    0.9309   -0.0978 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1830   -2.1434    0.6063 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6751   -2.7101   -0.1558 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0649   -2.1821   -1.1484 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6581    1.4585   -0.4382 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6211   -1.0115   -0.5933 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8998    1.9442   -0.7981 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2890   -1.3830   -1.7075 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5932   -1.2419    0.0627 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0037   -1.0987   -1.0971 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6159    0.9852   -1.2970 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9257    3.2964   -2.1574 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0918    3.2590   -0.3649 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0905    3.9738   -0.2567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1731    1.5245   -0.6067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6696    1.3537   -1.6550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6358   -0.0903   -1.2167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4198    2.6521    1.0308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9280    1.8053    1.4614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3156    2.3189   -0.2939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9397    1.5960    1.6730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0263    0.1658    2.4135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2837   -0.4873    1.9650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2401    0.0510    0.2789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3023   -2.4510    1.4541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5604   -2.0389   -0.2399 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
(13cis)-Retinol	ChEBI
(2Z,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-ol	ChEBI
RETINOL	ChEBI
Neovitamin a	Kegg
(11-cis,13-cis)-Retinol acetate	HMDB
11,13-Di-cis-vitamin a acetate	HMDB
11-cis-13-cis-Retinol acetate	HMDB
11-cis-13-cis-Retinyl acetate	HMDB

Chemical Formula

C₂₀H₃₀O

Average Molecular Weight

286.4516

Monoisotopic Molecular Weight

286.229665582

IUPAC Name

(2Z,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

13-cis retinol

CAS Registry Number

2052-63-3

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-HWCYFHEPSA-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:45479 )
Retinoids (LMPR01090011 )

Ontology

Not Available

Feces (PMID: 29808030)

Cellular substructure

Source

Endogenous

Endogenous (HMDB: HMDB0006221)

Exogenous

Exogenous (HMDB: HMDB0006221)

Food

Animal origin

Poultry

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

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

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

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

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

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0076 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	36.28 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]+	176.089	31661259
DarkChem	[M-H]-	173.499	31661259
DeepCCS	[M+H]+	184.485	30932474
DeepCCS	[M-H]-	182.127	30932474
DeepCCS	[M-2H]-	215.758	30932474
DeepCCS	[M+Na]+	190.984	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
13-cis Retinol	C\C(=C\CO)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C	3108.0	Standard polar	33892256
13-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
13-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
13-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
13-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 - 13-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 - 13-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 - 13-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 - 13-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 - 13-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 - 13-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 - 13-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 - 13-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 - 13-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 - 13-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 - 13-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 - 13-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 - 13-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 - 13-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 - 13-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 - 13-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 - 13-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 - 13-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

Feces

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details

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

FDB112229

KNApSAcK ID

Not Available

Chemspider ID

8079655

KEGG Compound ID

C19962

BioCyc ID

Not Available

BiGG ID

2455099

Wikipedia Link

Vitamin A

METLIN ID

Not Available

PubChem Compound

9904001

PDB ID

Not Available

ChEBI ID

45479

Food Biomarker Ontology

Not Available

VMH ID

RETINOL_CIS_13

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Albert, Klaus; Schlotterbeck, Goetz; Braumann, Ulrich; Haendel, Heidrun; Spraul, Manfred; Krack, Gerhard. Structure determination of vitamin A acetate isomers through coupled HPLC and 1H NMR spectroscopy. Angewandte Chemie, International Edition in English (1995), 34(9), 1014-16.

Material Safety Data Sheet (MSDS)

Not Available

General References

Driessen CA, Winkens HJ, Hoffmann K, Kuhlmann LD, Janssen BP, Van Vugt AH, Van Hooser JP, Wieringa BE, Deutman AF, Palczewski K, Ruether K, Janssen JJ: Disruption of the 11-cis-retinol dehydrogenase gene leads to accumulation of cis-retinols and cis-retinyl esters. Mol Cell Biol. 2000 Jun;20(12):4275-87. [PubMed:10825191 ]

Showing metabocard for 13-cis Retinol (HMDB0006221)

MOL for HMDB0006221 (13-cis Retinol)

3D MOL for HMDB0006221 (13-cis Retinol)

3D SDF for HMDB0006221 (13-cis Retinol)

3D-SDF for HMDB0006221 (13-cis Retinol)

PDB for HMDB0006221 (13-cis Retinol)

3D PDB for HMDB0006221 (13-cis Retinol)

SMILES for HMDB0006221 (13-cis Retinol)

INCHI for HMDB0006221 (13-cis Retinol)

Structure for HMDB0006221 (13-cis Retinol)

3D Structure for HMDB0006221 (13-cis Retinol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra