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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 00:35:25 UTC

Update Date

2021-09-26 22:57:21 UTC

HMDB ID

HMDB0247586

Secondary Accession Numbers

None

Metabolite Identification

Common Name

9-cis retinol

Description

9-cis retinol 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. Based on a literature review very few articles have been published on 9-cis retinol. This compound has been identified in human blood as reported by (PMID: 31557052 ). 9-cis retinol is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 9-cis retinol is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0247586
     RDKit          3D
9-cis retinol
 51 51  0  0  0  0  0  0  0  0999 V2000
    1.6560    1.4241    1.2879 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9534    0.6287    0.2762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4924    0.4390    0.3339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2505    1.0125    1.2064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7365    0.7689    1.2220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4394    1.4218    2.1357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7373    2.3534    3.0925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9190    1.2858    2.2710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1553   -0.2313    2.0646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8272   -0.4181    0.5972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3610   -0.2033    0.3079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2617    0.2140   -1.1614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7203   -1.5829    0.4537 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6119   -0.0093   -0.6849 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0340   -0.0459   -0.9044 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4766   -0.7688   -1.9785 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7283   -0.9510   -2.3819 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1843   -1.9314   -3.8743 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9265   -1.1392   -2.7880 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1316   -0.5186   -2.0221 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8808   -1.5746   -1.5806 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7282    1.2095    1.3987 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1831    1.2709    2.2907 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5590    2.5226    1.0805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9038   -0.2126   -0.4153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8021    1.6790    1.9350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4988    2.6977    3.8539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9114    1.8441    3.6157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3944    3.2676    2.5579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4441    1.8130    1.4554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2299    1.5288    3.2797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4766   -0.7359    2.7554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2128   -0.4934    2.2444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4004    0.3498    0.0226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1157   -1.4557    0.2556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3114    0.2975   -1.6141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6745   -0.4834   -1.7730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8478    1.2370   -1.1545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4762   -1.9716   -0.5544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8908   -1.6083    1.1572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5007   -2.3124    0.8312 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0107   -0.6033   -1.4308 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7129    0.4605   -0.2585 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5543   -1.2282   -2.4660 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8216   -1.4110   -4.5349 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2070   -1.5426   -3.8675 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4155   -2.8260   -3.3452 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3173   -1.7009   -3.6392 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7271    0.0772   -1.1956 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6478    0.0794   -2.7960 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5240   -1.9229   -0.7268 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  3
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
  2 14  2  3
 14 15  1  0
 15 16  2  3
 16 17  1  0
 17 18  1  0
 17 19  2  3
 19 20  1  0
 20 21  1  0
 11  5  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  4 26  1  0
  7 27  1  0
  7 28  1  0
  7 29  1  0
  8 30  1  0
  8 31  1  0
  9 32  1  0
  9 33  1  0
 10 34  1  0
 10 35  1  0
 12 36  1  0
 12 37  1  0
 12 38  1  0
 13 39  1  0
 13 40  1  0
 13 41  1  0
 14 42  1  0
 15 43  1  0
 16 44  1  0
 18 45  1  0
 18 46  1  0
 18 47  1  0
 19 48  1  0
 20 49  1  0
 20 50  1  0
 21 51  1  0
M  END

  Mrv1533005011519012D          

 21 21  0  0  0  0            999 V2000
    5.7158    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    2.0625    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  4  0  0  0
  4  5  1  0  0  0  0
  6  2  1  4  0  0  0
  6  7  2  0  0  0  0
  8  7  1  4  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 11  9  1  4  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>
HMDB0247586

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=CCO)C=CC=C(C)C=CC1=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

> <INCHI_KEY>
FPIPGXGPPPQFEQ-UHFFFAOYSA-N

> <FORMULA>
C20H30O

> <MOLECULAR_WEIGHT>
286.459

> <EXACT_MASS>
286.229665586

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
36.57176913367702

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
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>
α-sol

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0247586
     RDKit          3D
9-cis retinol
 51 51  0  0  0  0  0  0  0  0999 V2000
    1.6560    1.4241    1.2879 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9534    0.6287    0.2762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4924    0.4390    0.3339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2505    1.0125    1.2064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7365    0.7689    1.2220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4394    1.4218    2.1357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7373    2.3534    3.0925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9190    1.2858    2.2710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1553   -0.2313    2.0646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8272   -0.4181    0.5972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3610   -0.2033    0.3079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2617    0.2140   -1.1614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7203   -1.5829    0.4537 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6119   -0.0093   -0.6849 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0340   -0.0459   -0.9044 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4766   -0.7688   -1.9785 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7283   -0.9510   -2.3819 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1843   -1.9314   -3.8743 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9265   -1.1392   -2.7880 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1316   -0.5186   -2.0221 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8808   -1.5746   -1.5806 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7282    1.2095    1.3987 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1831    1.2709    2.2907 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5590    2.5226    1.0805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9038   -0.2126   -0.4153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8021    1.6790    1.9350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4988    2.6977    3.8539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9114    1.8441    3.6157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3944    3.2676    2.5579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4441    1.8130    1.4554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2299    1.5288    3.2797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4766   -0.7359    2.7554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2128   -0.4934    2.2444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4004    0.3498    0.0226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1157   -1.4557    0.2556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3114    0.2975   -1.6141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6745   -0.4834   -1.7730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8478    1.2370   -1.1545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4762   -1.9716   -0.5544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8908   -1.6083    1.1572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5007   -2.3124    0.8312 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0107   -0.6033   -1.4308 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7129    0.4605   -0.2585 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5543   -1.2282   -2.4660 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8216   -1.4110   -4.5349 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2070   -1.5426   -3.8675 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4155   -2.8260   -3.3452 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3173   -1.7009   -3.6392 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7271    0.0772   -1.1956 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6478    0.0794   -2.7960 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5240   -1.9229   -0.7268 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  3
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
  2 14  2  3
 14 15  1  0
 15 16  2  3
 16 17  1  0
 17 18  1  0
 17 19  2  3
 19 20  1  0
 20 21  1  0
 11  5  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  4 26  1  0
  7 27  1  0
  7 28  1  0
  7 29  1  0
  8 30  1  0
  8 31  1  0
  9 32  1  0
  9 33  1  0
 10 34  1  0
 10 35  1  0
 12 36  1  0
 12 37  1  0
 12 38  1  0
 13 39  1  0
 13 40  1  0
 13 41  1  0
 14 42  1  0
 15 43  1  0
 16 44  1  0
 18 45  1  0
 18 46  1  0
 18 47  1  0
 19 48  1  0
 20 49  1  0
 20 50  1  0
 21 51  1  0
M  END

HEADER    PROTEIN                                 01-MAY-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   01-MAY-15         0                                  
HETATM    1  C   UNK     0      10.669   6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.003   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.337   4.620   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      14.670   3.850   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    HMDB0247586
HETATM    1  C1  UNL     1       1.656   1.424   1.288  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.953   0.629   0.276  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.492   0.439   0.334  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.250   1.012   1.206  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.736   0.769   1.222  1.00  0.00           C  
HETATM    6  C6  UNL     1      -3.439   1.422   2.136  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.737   2.353   3.093  1.00  0.00           C  
HETATM    8  C8  UNL     1      -4.919   1.286   2.271  1.00  0.00           C  
HETATM    9  C9  UNL     1      -5.155  -0.231   2.065  1.00  0.00           C  
HETATM   10  C10 UNL     1      -4.827  -0.418   0.597  1.00  0.00           C  
HETATM   11  C11 UNL     1      -3.361  -0.203   0.308  1.00  0.00           C  
HETATM   12  C12 UNL     1      -3.262   0.214  -1.161  1.00  0.00           C  
HETATM   13  C13 UNL     1      -2.720  -1.583   0.454  1.00  0.00           C  
HETATM   14  C14 UNL     1       1.612  -0.009  -0.685  1.00  0.00           C  
HETATM   15  C15 UNL     1       3.034  -0.046  -0.904  1.00  0.00           C  
HETATM   16  C16 UNL     1       3.477  -0.769  -1.979  1.00  0.00           C  
HETATM   17  C17 UNL     1       4.728  -0.951  -2.382  1.00  0.00           C  
HETATM   18  C18 UNL     1       4.184  -1.931  -3.874  1.00  0.00           C  
HETATM   19  C19 UNL     1       5.926  -1.139  -2.788  1.00  0.00           C  
HETATM   20  C20 UNL     1       7.132  -0.519  -2.022  1.00  0.00           C  
HETATM   21  O1  UNL     1       7.881  -1.575  -1.581  1.00  0.00           O  
HETATM   22  H1  UNL     1       2.728   1.209   1.399  1.00  0.00           H  
HETATM   23  H2  UNL     1       1.183   1.271   2.291  1.00  0.00           H  
HETATM   24  H3  UNL     1       1.559   2.523   1.081  1.00  0.00           H  
HETATM   25  H4  UNL     1      -0.904  -0.213  -0.415  1.00  0.00           H  
HETATM   26  H5  UNL     1      -0.802   1.679   1.935  1.00  0.00           H  
HETATM   27  H6  UNL     1      -3.499   2.698   3.854  1.00  0.00           H  
HETATM   28  H7  UNL     1      -1.911   1.844   3.616  1.00  0.00           H  
HETATM   29  H8  UNL     1      -2.394   3.268   2.558  1.00  0.00           H  
HETATM   30  H9  UNL     1      -5.444   1.813   1.455  1.00  0.00           H  
HETATM   31  H10 UNL     1      -5.230   1.529   3.280  1.00  0.00           H  
HETATM   32  H11 UNL     1      -4.477  -0.736   2.755  1.00  0.00           H  
HETATM   33  H12 UNL     1      -6.213  -0.493   2.244  1.00  0.00           H  
HETATM   34  H13 UNL     1      -5.400   0.350   0.023  1.00  0.00           H  
HETATM   35  H14 UNL     1      -5.116  -1.456   0.256  1.00  0.00           H  
HETATM   36  H15 UNL     1      -4.311   0.297  -1.614  1.00  0.00           H  
HETATM   37  H16 UNL     1      -2.674  -0.483  -1.773  1.00  0.00           H  
HETATM   38  H17 UNL     1      -2.848   1.237  -1.154  1.00  0.00           H  
HETATM   39  H18 UNL     1      -2.476  -1.972  -0.554  1.00  0.00           H  
HETATM   40  H19 UNL     1      -1.891  -1.608   1.157  1.00  0.00           H  
HETATM   41  H20 UNL     1      -3.501  -2.312   0.831  1.00  0.00           H  
HETATM   42  H21 UNL     1       1.011  -0.603  -1.431  1.00  0.00           H  
HETATM   43  H22 UNL     1       3.713   0.461  -0.258  1.00  0.00           H  
HETATM   44  H23 UNL     1       2.554  -1.228  -2.466  1.00  0.00           H  
HETATM   45  H24 UNL     1       4.822  -1.411  -4.535  1.00  0.00           H  
HETATM   46  H25 UNL     1       3.207  -1.543  -3.867  1.00  0.00           H  
HETATM   47  H26 UNL     1       4.416  -2.826  -3.345  1.00  0.00           H  
HETATM   48  H27 UNL     1       6.317  -1.701  -3.639  1.00  0.00           H  
HETATM   49  H28 UNL     1       6.727   0.077  -1.196  1.00  0.00           H  
HETATM   50  H29 UNL     1       7.648   0.079  -2.796  1.00  0.00           H  
HETATM   51  H30 UNL     1       7.524  -1.923  -0.727  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3   14   14
CONECT    3    4    4   25
CONECT    4    5   26
CONECT    5    6    6   11
CONECT    6    7    8
CONECT    7   27   28   29
CONECT    8    9   30   31
CONECT    9   10   32   33
CONECT   10   11   34   35
CONECT   11   12   13
CONECT   12   36   37   38
CONECT   13   39   40   41
CONECT   14   15   42
CONECT   15   16   16   43
CONECT   16   17   44
CONECT   17   18   19   19
CONECT   18   45   46   47
CONECT   19   20   48
CONECT   20   21   49   50
CONECT   21   51
END

HMDB0247586
     RDKit          3D
9-cis retinol
 51 51  0  0  0  0  0  0  0  0999 V2000
    1.6560    1.4241    1.2879 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9534    0.6287    0.2762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4924    0.4390    0.3339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2505    1.0125    1.2064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7365    0.7689    1.2220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4394    1.4218    2.1357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7373    2.3534    3.0925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9190    1.2858    2.2710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1553   -0.2313    2.0646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8272   -0.4181    0.5972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3610   -0.2033    0.3079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2617    0.2140   -1.1614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7203   -1.5829    0.4537 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6119   -0.0093   -0.6849 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0340   -0.0459   -0.9044 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4766   -0.7688   -1.9785 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7283   -0.9510   -2.3819 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1843   -1.9314   -3.8743 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9265   -1.1392   -2.7880 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1316   -0.5186   -2.0221 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8808   -1.5746   -1.5806 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7282    1.2095    1.3987 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1831    1.2709    2.2907 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5590    2.5226    1.0805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9038   -0.2126   -0.4153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8021    1.6790    1.9350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4988    2.6977    3.8539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9114    1.8441    3.6157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3944    3.2676    2.5579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4441    1.8130    1.4554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2299    1.5288    3.2797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4766   -0.7359    2.7554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2128   -0.4934    2.2444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4004    0.3498    0.0226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1157   -1.4557    0.2556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3114    0.2975   -1.6141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6745   -0.4834   -1.7730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8478    1.2370   -1.1545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4762   -1.9716   -0.5544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8908   -1.6083    1.1572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5007   -2.3124    0.8312 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0107   -0.6033   -1.4308 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7129    0.4605   -0.2585 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5543   -1.2282   -2.4660 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8216   -1.4110   -4.5349 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2070   -1.5426   -3.8675 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4155   -2.8260   -3.3452 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3173   -1.7009   -3.6392 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7271    0.0772   -1.1956 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6478    0.0794   -2.7960 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5240   -1.9229   -0.7268 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  3
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
  2 14  2  3
 14 15  1  0
 15 16  2  3
 16 17  1  0
 17 18  1  0
 17 19  2  3
 19 20  1  0
 20 21  1  0
 11  5  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  4 26  1  0
  7 27  1  0
  7 28  1  0
  7 29  1  0
  8 30  1  0
  8 31  1  0
  9 32  1  0
  9 33  1  0
 10 34  1  0
 10 35  1  0
 12 36  1  0
 12 37  1  0
 12 38  1  0
 13 39  1  0
 13 40  1  0
 13 41  1  0
 14 42  1  0
 15 43  1  0
 16 44  1  0
 18 45  1  0
 18 46  1  0
 18 47  1  0
 19 48  1  0
 20 49  1  0
 20 50  1  0
 21 51  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₂₀H₃₀O

Average Molecular Weight

286.459

Monoisotopic Molecular Weight

286.229665586

IUPAC Name

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

Not Available

SMILES

CC(=CCO)C=CC=C(C)C=CC1=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

InChI Key

FPIPGXGPPPQFEQ-UHFFFAOYSA-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

retinoid (CHEBI:50211 )
primary alcohol (CHEBI:50211 )
a retinol (CPD-882 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

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
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	36.57 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
DeepCCS	[M+H]+	175.859	30932474
DeepCCS	[M-H]-	173.501	30932474
DeepCCS	[M-2H]-	206.387	30932474
DeepCCS	[M+Na]+	181.952	30932474
AllCCS	[M+H]+	174.3	32859911
AllCCS	[M+H-H2O]+	171.1	32859911
AllCCS	[M+NH4]+	177.3	32859911
AllCCS	[M+Na]+	178.2	32859911
AllCCS	[M-H]-	179.7	32859911
AllCCS	[M+Na-2H]-	180.4	32859911
AllCCS	[M+HCOO]-	181.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
9-cis retinol	CC(=CCO)C=CC=C(C)C=CC1=C(C)CCCC1(C)C	3108.0	Standard polar	33892256
9-cis retinol	CC(=CCO)C=CC=C(C)C=CC1=C(C)CCCC1(C)C	2431.2	Standard non polar	33892256
9-cis retinol	CC(=CCO)C=CC=C(C)C=CC1=C(C)CCCC1(C)C	2417.0	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 - 9-cis retinol GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-1190000000-346a3e44c44d46353e80	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 9-cis retinol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 9-cis retinol GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 9-cis retinol GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-cis retinol 10V, Positive-QTOF	splash10-00kr-0490000000-97ed49d705440e4d32e7	2015-05-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-cis retinol 20V, Positive-QTOF	splash10-00ks-3930000000-274e54c63df28cdefc8d	2015-05-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-cis retinol 40V, Positive-QTOF	splash10-0fri-9820000000-88842ca9675eca774a22	2015-05-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-cis retinol 10V, Negative-QTOF	splash10-000i-0090000000-d0ff1cdc72141d0daa0e	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-cis retinol 20V, Negative-QTOF	splash10-0a4r-0090000000-c0a067ff8ed271b80945	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-cis retinol 40V, Negative-QTOF	splash10-00ku-4590000000-5098f6e6dbf290bc209d	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-cis retinol 10V, Positive-QTOF	splash10-015i-1890000000-fb68e645ac6c84dc722c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-cis retinol 20V, Positive-QTOF	splash10-05a9-2910000000-aa07b89a9cfe132b8725	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-cis retinol 40V, Positive-QTOF	splash10-06dl-5900000000-6de72efc591b252620c9	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-cis retinol 10V, Negative-QTOF	splash10-0a4i-0090000000-fe93459d3069e264b77f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-cis retinol 20V, Negative-QTOF	splash10-05mx-0190000000-f81760535f6050971f92	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-cis retinol 40V, Negative-QTOF	splash10-00li-0960000000-4dbc516b202b90a6c265	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

1042

KEGG Compound ID

Not Available

BioCyc ID

Retinols

BiGG ID

Not Available

Wikipedia Link

Retinol

METLIN ID

Not Available

PubChem Compound

1071

PDB ID

Not Available

ChEBI ID

50211

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for 9-cis retinol (HMDB0247586)

MOL for HMDB0247586 (9-cis retinol)

3D MOL for HMDB0247586 (9-cis retinol)

3D SDF for HMDB0247586 (9-cis retinol)

3D-SDF for HMDB0247586 (9-cis retinol)

PDB for HMDB0247586 (9-cis retinol)

3D PDB for HMDB0247586 (9-cis retinol)

SMILES for HMDB0247586 (9-cis retinol)

INCHI for HMDB0247586 (9-cis retinol)

Structure for HMDB0247586 (9-cis retinol)

3D Structure for HMDB0247586 (9-cis retinol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra