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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 22:54:06 UTC

Update Date

2021-09-26 22:54:34 UTC

HMDB ID

HMDB0245853

Secondary Accession Numbers

None

Metabolite Identification

Common Name

3,4-Didehydroretinol Acetate

Description

3-Dehydro Retinol Acetate-[d3] 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-Dehydro Retinol Acetate-[d3]. This compound has been identified in human blood as reported by (PMID: 31557052 ). 3,4-didehydroretinol acetate is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 3,4-Didehydroretinol 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

HMDB0245853
     RDKit          3D
3,4-Didehydroretinol Acetate
 54 54  0  0  0  0  0  0  0  0999 V2000
    8.2100    0.5724   -0.1763 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8705    1.1574   -0.4850 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8374    0.6540    0.0021 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7157    2.2639   -1.3099 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4244    2.8178   -1.5999 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5450    1.8720   -2.2465 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3880    1.4479   -1.7890 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8934    1.9525   -0.4933 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6455    0.4838   -2.5968 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5161   -0.1014   -2.4397 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5418   -0.0168   -1.3810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6058   -0.6784   -1.3178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0225   -1.6108   -2.3699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5152   -0.5024   -0.1797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6387   -1.1582   -0.1351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6371   -1.0914    0.9179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7298   -1.8392    0.7900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9207   -2.7249   -0.4106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7853   -1.8406    1.7958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6209   -1.0768    2.8358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4808   -0.2091    3.1071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3993   -0.2057    2.0701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2680    1.2169    1.5771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0818   -0.5699    2.7627 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9852    1.1746   -0.6621 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3850    0.4459    0.8958 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2173   -0.4402   -0.6685 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6951    3.5849   -2.4270 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0393    3.3855   -0.7705 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8633    1.4530   -3.2271 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7810    1.0661    0.2001 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6346    2.5824    0.0538 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9907    2.5441   -0.6315 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1925    0.2139   -3.5423 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2544   -0.8018   -3.2924 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7173    0.6393   -0.5427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1990   -2.5997   -1.8440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0079   -1.2284   -2.7545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3317   -1.8273   -3.1682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1751    0.1879    0.5739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8571   -1.8317   -0.9826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0959   -3.4747   -0.4326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9152   -2.0662   -1.2987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8607   -3.2675   -0.3369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6727   -2.4593    1.6735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4138   -1.0830    3.5830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0685   -0.5127    4.1033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9018    0.8207    3.3051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1325    1.8418    1.9464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3698    1.6686    2.0003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3057    1.2147    0.4617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4444    0.3158    2.9307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5657   -1.4134    2.2770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3204   -0.9465    3.8010 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  2  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
 20 46  1  0
 21 47  1  0
 21 48  1  0
 23 49  1  0
 23 50  1  0
 23 51  1  0
 24 52  1  0
 24 53  1  0
 24 54  1  0
M  END


  Mrv1652309112100542D          

 24 24  0  0  0  0            999 V2000
   -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
    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
    0.7145   -0.4125    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
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    4.5375    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
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  2  7  1  0  0  0  0
  4  8  1  0  0  0  0
  4  9  1  0  0  0  0
 10  3  1  4  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  4  0  0  0
 14 15  2  0  0  0  0
 15 16  1  4  0  0  0
 16 17  2  0  0  0  0
 17 18  1  4  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 16 23  1  0  0  0  0
 12 24  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0245853

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)OCC=C(C)C=CC=C(C)C=CC1=C(C)C=CCC1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C22H30O2/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/h7-14H,15-16H2,1-6H3

> <INCHI_KEY>
FKPNTWPSTBQDNM-UHFFFAOYSA-N

> <FORMULA>
C22H30O2

> <MOLECULAR_WEIGHT>
326.48

> <EXACT_MASS>
326.224580206

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
40.157377466715516

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,7-dimethyl-9-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)nona-2,4,6,8-tetraen-1-yl acetate

> <ALOGPS_LOGP>
6.30

> <JCHEM_LOGP>
4.773296926666668

> <ALOGPS_LOGS>
-4.95

> <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>
108.19149999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.67e-03 g/l

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

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0245853
     RDKit          3D
3,4-Didehydroretinol Acetate
 54 54  0  0  0  0  0  0  0  0999 V2000
    8.2100    0.5724   -0.1763 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8705    1.1574   -0.4850 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8374    0.6540    0.0021 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7157    2.2639   -1.3099 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4244    2.8178   -1.5999 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5450    1.8720   -2.2465 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3880    1.4479   -1.7890 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8934    1.9525   -0.4933 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6455    0.4838   -2.5968 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5161   -0.1014   -2.4397 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5418   -0.0168   -1.3810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6058   -0.6784   -1.3178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0225   -1.6108   -2.3699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5152   -0.5024   -0.1797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6387   -1.1582   -0.1351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6371   -1.0914    0.9179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7298   -1.8392    0.7900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9207   -2.7249   -0.4106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7853   -1.8406    1.7958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6209   -1.0768    2.8358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4808   -0.2091    3.1071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3993   -0.2057    2.0701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2680    1.2169    1.5771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0818   -0.5699    2.7627 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9852    1.1746   -0.6621 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3850    0.4459    0.8958 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2173   -0.4402   -0.6685 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6951    3.5849   -2.4270 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0393    3.3855   -0.7705 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8633    1.4530   -3.2271 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7810    1.0661    0.2001 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6346    2.5824    0.0538 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9907    2.5441   -0.6315 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1925    0.2139   -3.5423 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2544   -0.8018   -3.2924 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7173    0.6393   -0.5427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1990   -2.5997   -1.8440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0079   -1.2284   -2.7545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3317   -1.8273   -3.1682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1751    0.1879    0.5739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8571   -1.8317   -0.9826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0959   -3.4747   -0.4326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9152   -2.0662   -1.2987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8607   -3.2675   -0.3369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6727   -2.4593    1.6735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4138   -1.0830    3.5830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0685   -0.5127    4.1033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9018    0.8207    3.3051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1325    1.8418    1.9464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3698    1.6686    2.0003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3057    1.2147    0.4617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4444    0.3158    2.9307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5657   -1.4134    2.2770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3204   -0.9465    3.8010 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  2  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
 20 46  1  0
 21 47  1  0
 21 48  1  0
 23 49  1  0
 23 50  1  0
 23 51  1  0
 24 52  1  0
 24 53  1  0
 24 54  1  0
M  END

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.611   3.670   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.057   3.670   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.001   6.930   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.001   8.470   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -5.335   9.240   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -5.335  10.780   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -6.668  11.550   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -8.002  10.780   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -9.336  11.550   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0     -10.669  10.780   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -9.336  13.090   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -6.668   8.470   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4   10                                                  
CONECT    4    3    5    8    9                                             
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    2                                                       
CONECT    8    4                                                            
CONECT    9    4                                                            
CONECT   10    3   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   24                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   23                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   16                                                            
CONECT   24   12                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   48    0
END

COMPND    HMDB0245853
HETATM    1  C1  UNL     1       8.210   0.572  -0.176  1.00  0.00           C  
HETATM    2  C2  UNL     1       6.870   1.157  -0.485  1.00  0.00           C  
HETATM    3  O1  UNL     1       5.837   0.654   0.002  1.00  0.00           O  
HETATM    4  O2  UNL     1       6.716   2.264  -1.310  1.00  0.00           O  
HETATM    5  C3  UNL     1       5.424   2.818  -1.600  1.00  0.00           C  
HETATM    6  C4  UNL     1       4.545   1.872  -2.247  1.00  0.00           C  
HETATM    7  C5  UNL     1       3.388   1.448  -1.789  1.00  0.00           C  
HETATM    8  C6  UNL     1       2.893   1.953  -0.493  1.00  0.00           C  
HETATM    9  C7  UNL     1       2.646   0.484  -2.597  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.516  -0.101  -2.440  1.00  0.00           C  
HETATM   11  C9  UNL     1       0.542  -0.017  -1.381  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.606  -0.678  -1.318  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.023  -1.611  -2.370  1.00  0.00           C  
HETATM   14  C12 UNL     1      -1.515  -0.502  -0.180  1.00  0.00           C  
HETATM   15  C13 UNL     1      -2.639  -1.158  -0.135  1.00  0.00           C  
HETATM   16  C14 UNL     1      -3.637  -1.091   0.918  1.00  0.00           C  
HETATM   17  C15 UNL     1      -4.730  -1.839   0.790  1.00  0.00           C  
HETATM   18  C16 UNL     1      -4.921  -2.725  -0.411  1.00  0.00           C  
HETATM   19  C17 UNL     1      -5.785  -1.841   1.796  1.00  0.00           C  
HETATM   20  C18 UNL     1      -5.621  -1.077   2.836  1.00  0.00           C  
HETATM   21  C19 UNL     1      -4.481  -0.209   3.107  1.00  0.00           C  
HETATM   22  C20 UNL     1      -3.399  -0.206   2.070  1.00  0.00           C  
HETATM   23  C21 UNL     1      -3.268   1.217   1.577  1.00  0.00           C  
HETATM   24  C22 UNL     1      -2.082  -0.570   2.763  1.00  0.00           C  
HETATM   25  H1  UNL     1       8.985   1.175  -0.662  1.00  0.00           H  
HETATM   26  H2  UNL     1       8.385   0.446   0.896  1.00  0.00           H  
HETATM   27  H3  UNL     1       8.217  -0.440  -0.669  1.00  0.00           H  
HETATM   28  H4  UNL     1       5.695   3.585  -2.427  1.00  0.00           H  
HETATM   29  H5  UNL     1       5.039   3.386  -0.770  1.00  0.00           H  
HETATM   30  H6  UNL     1       4.863   1.453  -3.227  1.00  0.00           H  
HETATM   31  H7  UNL     1       2.781   1.066   0.200  1.00  0.00           H  
HETATM   32  H8  UNL     1       3.635   2.582   0.054  1.00  0.00           H  
HETATM   33  H9  UNL     1       1.991   2.544  -0.631  1.00  0.00           H  
HETATM   34  H10 UNL     1       3.193   0.214  -3.542  1.00  0.00           H  
HETATM   35  H11 UNL     1       1.254  -0.802  -3.292  1.00  0.00           H  
HETATM   36  H12 UNL     1       0.717   0.639  -0.543  1.00  0.00           H  
HETATM   37  H13 UNL     1      -1.199  -2.600  -1.844  1.00  0.00           H  
HETATM   38  H14 UNL     1      -2.008  -1.228  -2.755  1.00  0.00           H  
HETATM   39  H15 UNL     1      -0.332  -1.827  -3.168  1.00  0.00           H  
HETATM   40  H16 UNL     1      -1.175   0.188   0.574  1.00  0.00           H  
HETATM   41  H17 UNL     1      -2.857  -1.832  -0.983  1.00  0.00           H  
HETATM   42  H18 UNL     1      -4.096  -3.475  -0.433  1.00  0.00           H  
HETATM   43  H19 UNL     1      -4.915  -2.066  -1.299  1.00  0.00           H  
HETATM   44  H20 UNL     1      -5.861  -3.267  -0.337  1.00  0.00           H  
HETATM   45  H21 UNL     1      -6.673  -2.459   1.674  1.00  0.00           H  
HETATM   46  H22 UNL     1      -6.414  -1.083   3.583  1.00  0.00           H  
HETATM   47  H23 UNL     1      -4.069  -0.513   4.103  1.00  0.00           H  
HETATM   48  H24 UNL     1      -4.902   0.821   3.305  1.00  0.00           H  
HETATM   49  H25 UNL     1      -4.132   1.842   1.946  1.00  0.00           H  
HETATM   50  H26 UNL     1      -2.370   1.669   2.000  1.00  0.00           H  
HETATM   51  H27 UNL     1      -3.306   1.215   0.462  1.00  0.00           H  
HETATM   52  H28 UNL     1      -1.444   0.316   2.931  1.00  0.00           H  
HETATM   53  H29 UNL     1      -1.566  -1.413   2.277  1.00  0.00           H  
HETATM   54  H30 UNL     1      -2.320  -0.946   3.801  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   20   45
CONECT   20   21   46
CONECT   21   22   47   48
CONECT   22   23   24
CONECT   23   49   50   51
CONECT   24   52   53   54
END

HMDB0245853
     RDKit          3D
3,4-Didehydroretinol Acetate
 54 54  0  0  0  0  0  0  0  0999 V2000
    8.2100    0.5724   -0.1763 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8705    1.1574   -0.4850 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8374    0.6540    0.0021 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7157    2.2639   -1.3099 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4244    2.8178   -1.5999 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5450    1.8720   -2.2465 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3880    1.4479   -1.7890 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8934    1.9525   -0.4933 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6455    0.4838   -2.5968 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5161   -0.1014   -2.4397 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5418   -0.0168   -1.3810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6058   -0.6784   -1.3178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0225   -1.6108   -2.3699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5152   -0.5024   -0.1797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6387   -1.1582   -0.1351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6371   -1.0914    0.9179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7298   -1.8392    0.7900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9207   -2.7249   -0.4106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7853   -1.8406    1.7958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6209   -1.0768    2.8358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4808   -0.2091    3.1071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3993   -0.2057    2.0701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2680    1.2169    1.5771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0818   -0.5699    2.7627 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9852    1.1746   -0.6621 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3850    0.4459    0.8958 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2173   -0.4402   -0.6685 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6951    3.5849   -2.4270 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0393    3.3855   -0.7705 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8633    1.4530   -3.2271 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7810    1.0661    0.2001 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6346    2.5824    0.0538 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9907    2.5441   -0.6315 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1925    0.2139   -3.5423 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2544   -0.8018   -3.2924 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7173    0.6393   -0.5427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1990   -2.5997   -1.8440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0079   -1.2284   -2.7545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3317   -1.8273   -3.1682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1751    0.1879    0.5739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8571   -1.8317   -0.9826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0959   -3.4747   -0.4326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9152   -2.0662   -1.2987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8607   -3.2675   -0.3369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6727   -2.4593    1.6735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4138   -1.0830    3.5830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0685   -0.5127    4.1033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9018    0.8207    3.3051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1325    1.8418    1.9464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3698    1.6686    2.0003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3057    1.2147    0.4617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4444    0.3158    2.9307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5657   -1.4134    2.2770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3204   -0.9465    3.8010 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  2  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
 20 46  1  0
 21 47  1  0
 21 48  1  0
 23 49  1  0
 23 50  1  0
 23 51  1  0
 24 52  1  0
 24 53  1  0
 24 54  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-Dehydro retinol acetic acid-[D3]	Generator
3,4-Didehydroretinol acetic acid	Generator

Chemical Formula

C₂₂H₃₀O₂

Average Molecular Weight

326.48

Monoisotopic Molecular Weight

326.224580206

IUPAC Name

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

Traditional Name

3,7-dimethyl-9-(2,6,6-trimethylcyclohexa-1,3-dien-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)C=CCC1(C)C

InChI Identifier

InChI=1S/C22H30O2/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/h7-14H,15-16H2,1-6H3

InChI Key

FKPNTWPSTBQDNM-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

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	6.3	ALOGPS
logP	4.77	ChemAxon
logS	-5	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	108.19 m³·mol⁻¹	ChemAxon
Polarizability	40.16 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]+	181.275	30932474
DeepCCS	[M-H]-	178.917	30932474
DeepCCS	[M-2H]-	212.594	30932474
DeepCCS	[M+Na]+	187.82	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3,4-Didehydroretinol Acetate	CC(=O)OCC=C(C)C=CC=C(C)C=CC1=C(C)C=CCC1(C)C	3077.8	Standard polar	33892256
3,4-Didehydroretinol Acetate	CC(=O)OCC=C(C)C=CC=C(C)C=CC1=C(C)C=CCC1(C)C	2460.9	Standard non polar	33892256
3,4-Didehydroretinol Acetate	CC(=O)OCC=C(C)C=CC=C(C)C=CC1=C(C)C=CCC1(C)C	2559.7	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 - 3,4-Didehydroretinol Acetate GC-MS (Non-derivatized) - 70eV, Positive	splash10-00kf-6192000000-8f28843e657183a1fef2	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Didehydroretinol 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 - 3,4-Didehydroretinol Acetate 10V, Positive-QTOF	splash10-014i-0690000000-1e8424f2513348686a04	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Didehydroretinol Acetate 20V, Positive-QTOF	splash10-01b9-1940000000-dad68c4a90b9ba4643ff	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Didehydroretinol Acetate 40V, Positive-QTOF	splash10-014l-2900000000-21ef5112e6b5d1517cff	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Didehydroretinol Acetate 10V, Negative-QTOF	splash10-0a4i-9012000000-111810ba9771b1c7ece0	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Didehydroretinol Acetate 20V, Negative-QTOF	splash10-0a4i-9000000000-c01bbbf5bed889264ddb	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Didehydroretinol Acetate 40V, Negative-QTOF	splash10-0a4i-9000000000-6d9782d61b4b05396a06	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

167863

PDB ID

Not Available

ChEBI ID

Not Available

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 3,4-Didehydroretinol Acetate (HMDB0245853)

MOL for HMDB0245853 (3,4-Didehydroretinol Acetate)

3D MOL for HMDB0245853 (3,4-Didehydroretinol Acetate)

3D SDF for HMDB0245853 (3,4-Didehydroretinol Acetate)

3D-SDF for HMDB0245853 (3,4-Didehydroretinol Acetate)

PDB for HMDB0245853 (3,4-Didehydroretinol Acetate)

3D PDB for HMDB0245853 (3,4-Didehydroretinol Acetate)

SMILES for HMDB0245853 (3,4-Didehydroretinol Acetate)

INCHI for HMDB0245853 (3,4-Didehydroretinol Acetate)

Structure for HMDB0245853 (3,4-Didehydroretinol Acetate)

3D Structure for HMDB0245853 (3,4-Didehydroretinol Acetate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra