Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 00:35:28 UTC

Update Date

2021-09-26 22:57:21 UTC

HMDB ID

HMDB0247587

Secondary Accession Numbers

None

Metabolite Identification

Common Name

9-cis Retinol Acetate

Description

3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-yl acetate 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 3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-yl acetate. This compound has been identified in human blood as reported by (PMID: 31557052 ). 9-cis retinol acetate is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 9-cis Retinol Acetate 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

HMDB0247587
     RDKit          3D
9-cis Retinol Acetate
 56 56  0  0  0  0  0  0  0  0999 V2000
    9.4138    0.7162    1.0163 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1114    1.3458    1.0682 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7766    2.1577    0.1548 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0963    1.1785    2.0385 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9034    1.9090    1.7341 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9113    1.8656    2.7626 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7290    1.3969    2.7464 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7292    1.4175    3.8979 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0694    1.1296    1.4201 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8613    0.6287    1.4388 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1355    0.3736    0.2192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1284   -0.1019    0.2701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7582   -0.3792    1.5274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8271   -0.1682   -0.9950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9932   -0.4753   -1.3435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2887   -0.8166   -1.7285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5404   -0.7562   -3.0658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4121   -0.3340   -3.9202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8187   -1.0587   -3.7052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0332   -0.9074   -2.8184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6767   -0.5243   -1.4358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4601   -1.2675   -0.9152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6243   -2.7554   -0.9693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2909   -0.8529    0.5368 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5505   -0.1579    1.6682 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1878    1.5154    1.1828 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5977    0.3060   -0.0268 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2915    3.0021    1.5704 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5578    1.6543    0.7219 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2347    2.3553    3.7278 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2477    1.8858    4.7692 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9701    2.1355    3.5806 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3919    0.3981    4.0163 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6142    1.3919    0.5476 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3784    0.3237    2.3573 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6092    0.5702   -0.7613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2632    0.5493    1.9013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4703   -1.2339    1.4284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0495   -0.6854    2.3532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1463    0.1291   -1.9075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2926   -0.7058    0.0213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3099    0.7923   -3.9024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4285   -0.7825   -3.6508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5671   -0.6796   -4.9976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9863   -0.3718   -4.5478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8567   -2.0913   -4.1824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7796   -0.1911   -3.1947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5901   -1.8670   -2.7705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4637    0.5824   -1.3797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5125   -0.7140   -0.7284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1609   -3.1877   -0.1228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6597   -3.2700   -1.0090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1603   -3.0157   -1.8908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2988   -0.8784    1.0341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7044   -1.6234    1.0480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8163    0.1427    0.6689 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  3
  7  8  1  0
  7  9  1  0
  9 10  2  3
 10 11  1  0
 11 12  2  3
 12 13  1  0
 12 14  1  0
 14 15  2  3
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 22 16  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  0
  8 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
 10 35  1  0
 11 36  1  0
 13 37  1  0
 13 38  1  0
 13 39  1  0
 14 40  1  0
 15 41  1  0
 18 42  1  0
 18 43  1  0
 18 44  1  0
 19 45  1  0
 19 46  1  0
 20 47  1  0
 20 48  1  0
 21 49  1  0
 21 50  1  0
 23 51  1  0
 23 52  1  0
 23 53  1  0
 24 54  1  0
 24 55  1  0
 24 56  1  0
M  END


  Mrv1533004251509562D          

 24 24  0  0  0  0            999 V2000
    9.2881    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    3.3000    0.0000 O   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
    7.1447    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
    5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    0.0000 C   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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  4  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  9  7  1  4  0  0  0
  9 10  2  0  0  0  0
 11 10  1  4  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 14 12  1  4  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 16 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0247587

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C22H32O2/c1-17(9-7-10-18(2)14-16-24-20(4)23)12-13-21-19(3)11-8-15-22(21,5)6/h7,9-10,12-14H,8,11,15-16H2,1-6H3

> <INCHI_KEY>
QGNJRVVDBSJHIZ-UHFFFAOYSA-N

> <FORMULA>
C22H32O2

> <MOLECULAR_WEIGHT>
328.496

> <EXACT_MASS>
328.24023027

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
40.03174569408697

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <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-yl acetate

> <ALOGPS_LOGP>
6.56

> <JCHEM_LOGP>
5.135218583333335

> <ALOGPS_LOGS>
-5.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.004456796498005

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
107.07489999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.38e-03 g/l

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

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0247587
     RDKit          3D
9-cis Retinol Acetate
 56 56  0  0  0  0  0  0  0  0999 V2000
    9.4138    0.7162    1.0163 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1114    1.3458    1.0682 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7766    2.1577    0.1548 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0963    1.1785    2.0385 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9034    1.9090    1.7341 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9113    1.8656    2.7626 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7290    1.3969    2.7464 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7292    1.4175    3.8979 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0694    1.1296    1.4201 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8613    0.6287    1.4388 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1355    0.3736    0.2192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1284   -0.1019    0.2701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7582   -0.3792    1.5274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8271   -0.1682   -0.9950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9932   -0.4753   -1.3435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2887   -0.8166   -1.7285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5404   -0.7562   -3.0658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4121   -0.3340   -3.9202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8187   -1.0587   -3.7052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0332   -0.9074   -2.8184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6767   -0.5243   -1.4358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4601   -1.2675   -0.9152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6243   -2.7554   -0.9693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2909   -0.8529    0.5368 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5505   -0.1579    1.6682 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1878    1.5154    1.1828 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5977    0.3060   -0.0268 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2915    3.0021    1.5704 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5578    1.6543    0.7219 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2347    2.3553    3.7278 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2477    1.8858    4.7692 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9701    2.1355    3.5806 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3919    0.3981    4.0163 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6142    1.3919    0.5476 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3784    0.3237    2.3573 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6092    0.5702   -0.7613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2632    0.5493    1.9013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4703   -1.2339    1.4284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0495   -0.6854    2.3532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1463    0.1291   -1.9075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2926   -0.7058    0.0213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3099    0.7923   -3.9024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4285   -0.7825   -3.6508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5671   -0.6796   -4.9976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9863   -0.3718   -4.5478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8567   -2.0913   -4.1824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7796   -0.1911   -3.1947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5901   -1.8670   -2.7705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4637    0.5824   -1.3797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5125   -0.7140   -0.7284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1609   -3.1877   -0.1228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6597   -3.2700   -1.0090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1603   -3.0157   -1.8908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2988   -0.8784    1.0341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7044   -1.6234    1.0480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8163    0.1427    0.6689 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  3
  7  8  1  0
  7  9  1  0
  9 10  2  3
 10 11  1  0
 11 12  2  3
 12 13  1  0
 12 14  1  0
 14 15  2  3
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 22 16  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  0
  8 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
 10 35  1  0
 11 36  1  0
 13 37  1  0
 13 38  1  0
 13 39  1  0
 14 40  1  0
 15 41  1  0
 18 42  1  0
 18 43  1  0
 18 44  1  0
 19 45  1  0
 19 46  1  0
 20 47  1  0
 20 48  1  0
 21 49  1  0
 21 50  1  0
 23 51  1  0
 23 52  1  0
 23 53  1  0
 24 54  1  0
 24 55  1  0
 24 56  1  0
M  END

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0      17.338   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      16.004   4.620   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      16.004   6.160   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      14.670   3.850   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      13.337   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.003   3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.669   6.160   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.611   3.670   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.057   3.670   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   22                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   16   23   24                                             
CONECT   23   22                                                            
CONECT   24   22                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   48    0
END

COMPND    HMDB0247587
HETATM    1  C1  UNL     1       9.414   0.716   1.016  1.00  0.00           C  
HETATM    2  C2  UNL     1       8.111   1.346   1.068  1.00  0.00           C  
HETATM    3  O1  UNL     1       7.777   2.158   0.155  1.00  0.00           O  
HETATM    4  O2  UNL     1       7.096   1.178   2.038  1.00  0.00           O  
HETATM    5  C3  UNL     1       5.903   1.909   1.734  1.00  0.00           C  
HETATM    6  C4  UNL     1       4.911   1.866   2.763  1.00  0.00           C  
HETATM    7  C5  UNL     1       3.729   1.397   2.746  1.00  0.00           C  
HETATM    8  C6  UNL     1       2.729   1.417   3.898  1.00  0.00           C  
HETATM    9  C7  UNL     1       3.069   1.130   1.420  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.861   0.629   1.439  1.00  0.00           C  
HETATM   11  C9  UNL     1       1.135   0.374   0.219  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.128  -0.102   0.270  1.00  0.00           C  
HETATM   13  C11 UNL     1      -0.758  -0.379   1.527  1.00  0.00           C  
HETATM   14  C12 UNL     1      -0.827  -0.168  -0.995  1.00  0.00           C  
HETATM   15  C13 UNL     1      -1.993  -0.475  -1.343  1.00  0.00           C  
HETATM   16  C14 UNL     1      -3.289  -0.817  -1.728  1.00  0.00           C  
HETATM   17  C15 UNL     1      -3.540  -0.756  -3.066  1.00  0.00           C  
HETATM   18  C16 UNL     1      -2.412  -0.334  -3.920  1.00  0.00           C  
HETATM   19  C17 UNL     1      -4.819  -1.059  -3.705  1.00  0.00           C  
HETATM   20  C18 UNL     1      -6.033  -0.907  -2.818  1.00  0.00           C  
HETATM   21  C19 UNL     1      -5.677  -0.524  -1.436  1.00  0.00           C  
HETATM   22  C20 UNL     1      -4.460  -1.268  -0.915  1.00  0.00           C  
HETATM   23  C21 UNL     1      -4.624  -2.755  -0.969  1.00  0.00           C  
HETATM   24  C22 UNL     1      -4.291  -0.853   0.537  1.00  0.00           C  
HETATM   25  H1  UNL     1       9.551  -0.158   1.668  1.00  0.00           H  
HETATM   26  H2  UNL     1      10.188   1.515   1.183  1.00  0.00           H  
HETATM   27  H3  UNL     1       9.598   0.306  -0.027  1.00  0.00           H  
HETATM   28  H4  UNL     1       6.291   3.002   1.570  1.00  0.00           H  
HETATM   29  H5  UNL     1       5.558   1.654   0.722  1.00  0.00           H  
HETATM   30  H6  UNL     1       5.235   2.355   3.728  1.00  0.00           H  
HETATM   31  H7  UNL     1       3.248   1.886   4.769  1.00  0.00           H  
HETATM   32  H8  UNL     1       1.970   2.135   3.581  1.00  0.00           H  
HETATM   33  H9  UNL     1       2.392   0.398   4.016  1.00  0.00           H  
HETATM   34  H10 UNL     1       3.614   1.392   0.548  1.00  0.00           H  
HETATM   35  H11 UNL     1       1.378   0.324   2.357  1.00  0.00           H  
HETATM   36  H12 UNL     1       1.609   0.570  -0.761  1.00  0.00           H  
HETATM   37  H13 UNL     1      -1.263   0.549   1.901  1.00  0.00           H  
HETATM   38  H14 UNL     1      -1.470  -1.234   1.428  1.00  0.00           H  
HETATM   39  H15 UNL     1      -0.049  -0.685   2.353  1.00  0.00           H  
HETATM   40  H16 UNL     1      -0.146   0.129  -1.907  1.00  0.00           H  
HETATM   41  H17 UNL     1      -2.293  -0.706   0.021  1.00  0.00           H  
HETATM   42  H18 UNL     1      -2.310   0.792  -3.902  1.00  0.00           H  
HETATM   43  H19 UNL     1      -1.429  -0.783  -3.651  1.00  0.00           H  
HETATM   44  H20 UNL     1      -2.567  -0.680  -4.998  1.00  0.00           H  
HETATM   45  H21 UNL     1      -4.986  -0.372  -4.548  1.00  0.00           H  
HETATM   46  H22 UNL     1      -4.857  -2.091  -4.182  1.00  0.00           H  
HETATM   47  H23 UNL     1      -6.780  -0.191  -3.195  1.00  0.00           H  
HETATM   48  H24 UNL     1      -6.590  -1.867  -2.770  1.00  0.00           H  
HETATM   49  H25 UNL     1      -5.464   0.582  -1.380  1.00  0.00           H  
HETATM   50  H26 UNL     1      -6.512  -0.714  -0.728  1.00  0.00           H  
HETATM   51  H27 UNL     1      -5.161  -3.188  -0.123  1.00  0.00           H  
HETATM   52  H28 UNL     1      -3.660  -3.270  -1.009  1.00  0.00           H  
HETATM   53  H29 UNL     1      -5.160  -3.016  -1.891  1.00  0.00           H  
HETATM   54  H30 UNL     1      -5.299  -0.878   1.034  1.00  0.00           H  
HETATM   55  H31 UNL     1      -3.704  -1.623   1.048  1.00  0.00           H  
HETATM   56  H32 UNL     1      -3.816   0.143   0.669  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3    3    4
CONECT    4    5
CONECT    5    6   28   29
CONECT    6    7    7   30
CONECT    7    8    9
CONECT    8   31   32   33
CONECT    9   10   10   34
CONECT   10   11   35
CONECT   11   12   12   36
CONECT   12   13   14
CONECT   13   37   38   39
CONECT   14   15   15   40
CONECT   15   16   41
CONECT   16   17   17   22
CONECT   17   18   19
CONECT   18   42   43   44
CONECT   19   20   45   46
CONECT   20   21   47   48
CONECT   21   22   49   50
CONECT   22   23   24
CONECT   23   51   52   53
CONECT   24   54   55   56
END

HMDB0247587
     RDKit          3D
9-cis Retinol Acetate
 56 56  0  0  0  0  0  0  0  0999 V2000
    9.4138    0.7162    1.0163 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1114    1.3458    1.0682 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7766    2.1577    0.1548 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0963    1.1785    2.0385 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9034    1.9090    1.7341 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9113    1.8656    2.7626 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7290    1.3969    2.7464 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7292    1.4175    3.8979 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0694    1.1296    1.4201 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8613    0.6287    1.4388 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1355    0.3736    0.2192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1284   -0.1019    0.2701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7582   -0.3792    1.5274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8271   -0.1682   -0.9950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9932   -0.4753   -1.3435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2887   -0.8166   -1.7285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5404   -0.7562   -3.0658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4121   -0.3340   -3.9202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8187   -1.0587   -3.7052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0332   -0.9074   -2.8184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6767   -0.5243   -1.4358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4601   -1.2675   -0.9152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6243   -2.7554   -0.9693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2909   -0.8529    0.5368 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5505   -0.1579    1.6682 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1878    1.5154    1.1828 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5977    0.3060   -0.0268 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2915    3.0021    1.5704 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5578    1.6543    0.7219 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2347    2.3553    3.7278 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2477    1.8858    4.7692 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9701    2.1355    3.5806 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3919    0.3981    4.0163 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6142    1.3919    0.5476 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3784    0.3237    2.3573 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6092    0.5702   -0.7613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2632    0.5493    1.9013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4703   -1.2339    1.4284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0495   -0.6854    2.3532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1463    0.1291   -1.9075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2926   -0.7058    0.0213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3099    0.7923   -3.9024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4285   -0.7825   -3.6508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5671   -0.6796   -4.9976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9863   -0.3718   -4.5478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8567   -2.0913   -4.1824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7796   -0.1911   -3.1947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5901   -1.8670   -2.7705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4637    0.5824   -1.3797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5125   -0.7140   -0.7284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1609   -3.1877   -0.1228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6597   -3.2700   -1.0090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1603   -3.0157   -1.8908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2988   -0.8784    1.0341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7044   -1.6234    1.0480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8163    0.1427    0.6689 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  3
  7  8  1  0
  7  9  1  0
  9 10  2  3
 10 11  1  0
 11 12  2  3
 12 13  1  0
 12 14  1  0
 14 15  2  3
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 22 16  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  0
  8 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
 10 35  1  0
 11 36  1  0
 13 37  1  0
 13 38  1  0
 13 39  1  0
 14 40  1  0
 15 41  1  0
 18 42  1  0
 18 43  1  0
 18 44  1  0
 19 45  1  0
 19 46  1  0
 20 47  1  0
 20 48  1  0
 21 49  1  0
 21 50  1  0
 23 51  1  0
 23 52  1  0
 23 53  1  0
 24 54  1  0
 24 55  1  0
 24 56  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3,7-Dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-yl acetic acid	Generator
9-cis Retinol acetic acid	Generator, HMDB
Dif vitamin a masivo	MeSH, HMDB
Vitamin-a-saar	MeSH, HMDB
all-trans-Retinyl acetate	MeSH, HMDB
Retinol acetate	MeSH, HMDB
9-cis-Retinyl acetate	MeSH, HMDB
Vitamin a dispersa	MeSH, HMDB
Dagravit a forte	MeSH, HMDB
RetiNit	MeSH, HMDB
Retinol acetate, (9,13-cis)-isomer	MeSH, HMDB
Retinyl acetate	MeSH
Vitamin a acetate	MeSH, HMDB
RETINYL acetic acid	Generator

Chemical Formula

C₂₂H₃₂O₂

Average Molecular Weight

328.496

Monoisotopic Molecular Weight

328.24023027

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CC(=O)OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C

InChI Identifier

InChI=1S/C22H32O2/c1-17(9-7-10-18(2)14-16-24-20(4)23)12-13-21-19(3)11-8-15-22(21,5)6/h7,9-10,12-14H,8,11,15-16H2,1-6H3

InChI Key

QGNJRVVDBSJHIZ-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 ester
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

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	6.56	ALOGPS
logP	5.14	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	107.07 m³·mol⁻¹	ChemAxon
Polarizability	40.03 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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]+	183.695	30932474
DeepCCS	[M-H]-	181.337	30932474
DeepCCS	[M-2H]-	214.833	30932474
DeepCCS	[M+Na]+	190.06	30932474
AllCCS	[M+H]+	186.5	32859911
AllCCS	[M+H-H2O]+	183.6	32859911
AllCCS	[M+NH4]+	189.2	32859911
AllCCS	[M+Na]+	190.0	32859911
AllCCS	[M-H]-	190.0	32859911
AllCCS	[M+Na-2H]-	190.9	32859911
AllCCS	[M+HCOO]-	192.0	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	29.2339 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.12 minutes	32390414

Predicted Kovats Retention Indices

Not Available

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 9-cis Retinol Acetate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0296-5093000000-8a2656ef2c077328e38f	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 9-cis Retinol Acetate 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 Acetate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	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 Acetate 10V, Positive-QTOF	splash10-014j-0981000000-a7412f9b0e05f4062d0b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-cis Retinol Acetate 20V, Positive-QTOF	splash10-014s-1920000000-ab62a6b9b4a492105a56	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-cis Retinol Acetate 40V, Positive-QTOF	splash10-01bc-3900000000-7697ca2ae21235413e69	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-cis Retinol Acetate 10V, Negative-QTOF	splash10-0a4i-9001000000-89d40b95496b5ff7b4c9	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-cis Retinol Acetate 20V, Negative-QTOF	splash10-0a4i-9000000000-c01bbbf5bed889264ddb	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-cis Retinol Acetate 40V, Negative-QTOF	splash10-0a4i-9000000000-8f334a5ed9affcdc8cee	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

4881

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5057

PDB ID

Not Available

ChEBI ID

94695

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 Acetate (HMDB0247587)

MOL for HMDB0247587 (9-cis Retinol Acetate)

3D MOL for HMDB0247587 (9-cis Retinol Acetate)

3D SDF for HMDB0247587 (9-cis Retinol Acetate)

3D-SDF for HMDB0247587 (9-cis Retinol Acetate)

PDB for HMDB0247587 (9-cis Retinol Acetate)

3D PDB for HMDB0247587 (9-cis Retinol Acetate)

SMILES for HMDB0247587 (9-cis Retinol Acetate)

INCHI for HMDB0247587 (9-cis Retinol Acetate)

Structure for HMDB0247587 (9-cis Retinol Acetate)

3D Structure for HMDB0247587 (9-cis Retinol Acetate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

GC-MS Spectra

MS/MS Spectra