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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 20:32:43 UTC

Update Date

2021-09-26 23:15:57 UTC

HMDB ID

HMDB0258798

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Temarotene

Description

1,1,4,4-tetramethyl-6-(1-phenylprop-1-en-2-yl)-1,2,3,4-tetrahydronaphthalene belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids. Based on a literature review very few articles have been published on 1,1,4,4-tetramethyl-6-(1-phenylprop-1-en-2-yl)-1,2,3,4-tetrahydronaphthalene. This compound has been identified in human blood as reported by (PMID: 31557052 ). Temarotene is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Temarotene 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

HMDB0258798
     RDKit          3D
Temarotene
 51 53  0  0  0  0  0  0  0  0999 V2000
    2.0267   -3.7929   -0.8591 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0127   -2.3857   -0.2702 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1490   -1.8806    0.0374 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5021   -0.6011    0.6167 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3762    0.2688    0.0056 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7816    1.4617    0.5621 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2631    1.7809    1.8126 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3870    0.9514    2.4708 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0087   -0.2284    1.8813 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6839   -1.7790   -0.2611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4578   -2.5774   -0.3897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7193   -2.0208   -0.4323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9183   -0.6612   -0.3508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7929    0.1122   -0.2254 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5008   -0.4290   -0.1810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9226    1.5838   -0.1170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9945    2.0114    1.3584 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3681    2.2226   -0.6532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1156    2.1341   -0.8197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1010    1.1490   -1.3391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2752   -0.0660   -0.4100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2319   -1.0047   -1.1583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8371    0.3345    0.9109 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0788   -4.1785   -0.9029 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4924   -4.4975   -0.2003 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5672   -3.8082   -1.8596 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0341   -2.5417   -0.1778 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7722   -0.0069   -0.9828 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4753    2.1441    0.0680 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5532    2.7099    2.2903 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9795    1.2066    3.4586 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3245   -0.9327    2.3351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3175   -3.6487   -0.4550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5419   -2.7225   -0.5333 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3478    0.2690   -0.1211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3255    1.2120    2.0192 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0332    2.2970    1.7386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5897    2.9457    1.4232 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1809    3.3020   -0.8994 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7971    1.6739   -1.4879 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0845    2.2437    0.1962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6185    2.9133   -0.1876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7349    2.7154   -1.7078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0863    1.6318   -1.4566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7013    0.7217   -2.2895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1588   -0.4015   -1.3149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4862   -1.8916   -0.5450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7261   -1.2582   -2.1098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3919   -0.1817    1.7788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8104    1.4479    1.0030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9249    0.0524    0.9044 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  3
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  2 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 16 18  1  0
 16 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
  9  4  1  0
 15 10  1  0
 21 13  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  5 28  1  0
  6 29  1  0
  7 30  1  0
  8 31  1  0
  9 32  1  0
 11 33  1  0
 12 34  1  0
 15 35  1  0
 17 36  1  0
 17 37  1  0
 17 38  1  0
 18 39  1  0
 18 40  1  0
 18 41  1  0
 19 42  1  0
 19 43  1  0
 20 44  1  0
 20 45  1  0
 22 46  1  0
 22 47  1  0
 22 48  1  0
 23 49  1  0
 23 50  1  0
 23 51  1  0
M  END


  Mrv1652309112122332D          

 23 25  0  0  0  0            999 V2000
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    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
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -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
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    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   -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
   -0.7145   -0.4125    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
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8163   -2.3784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0416   -2.3784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0416    0.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8163    0.7284    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  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  4  9  1  0  0  0  0
  2 10  1  0  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  0  0  0  0
 14 15  2  0  0  0  0
 10 15  1  0  0  0  0
 13 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
 12 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 16 22  1  0  0  0  0
 16 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0258798

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=CC1=CC=CC=C1)C1=CC2=C(C=C1)C(C)(C)CCC2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C23H28/c1-17(15-18-9-7-6-8-10-18)19-11-12-20-21(16-19)23(4,5)14-13-22(20,2)3/h6-12,15-16H,13-14H2,1-5H3

> <INCHI_KEY>
MUJQTAMVZYFLCR-UHFFFAOYSA-N

> <FORMULA>
C23H28

> <MOLECULAR_WEIGHT>
304.477

> <EXACT_MASS>
304.219100902

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
37.284096122759024

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1,1,4,4-tetramethyl-6-(1-phenylprop-1-en-2-yl)-1,2,3,4-tetrahydronaphthalene

> <ALOGPS_LOGP>
7.72

> <JCHEM_LOGP>
7.238868095000001

> <ALOGPS_LOGS>
-6.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
101.3244

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.86e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,1,4,4-tetramethyl-6-(1-phenylprop-1-en-2-yl)-2,3-dihydronaphthalene

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0258798
     RDKit          3D
Temarotene
 51 53  0  0  0  0  0  0  0  0999 V2000
    2.0267   -3.7929   -0.8591 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0127   -2.3857   -0.2702 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1490   -1.8806    0.0374 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5021   -0.6011    0.6167 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3762    0.2688    0.0056 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7816    1.4617    0.5621 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2631    1.7809    1.8126 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3870    0.9514    2.4708 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0087   -0.2284    1.8813 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6839   -1.7790   -0.2611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4578   -2.5774   -0.3897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7193   -2.0208   -0.4323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9183   -0.6612   -0.3508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7929    0.1122   -0.2254 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5008   -0.4290   -0.1810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9226    1.5838   -0.1170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9945    2.0114    1.3584 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3681    2.2226   -0.6532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1156    2.1341   -0.8197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1010    1.1490   -1.3391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2752   -0.0660   -0.4100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2319   -1.0047   -1.1583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8371    0.3345    0.9109 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0788   -4.1785   -0.9029 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4924   -4.4975   -0.2003 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5672   -3.8082   -1.8596 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0341   -2.5417   -0.1778 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7722   -0.0069   -0.9828 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4753    2.1441    0.0680 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5532    2.7099    2.2903 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9795    1.2066    3.4586 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3245   -0.9327    2.3351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3175   -3.6487   -0.4550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5419   -2.7225   -0.5333 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3478    0.2690   -0.1211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3255    1.2120    2.0192 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0332    2.2970    1.7386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5897    2.9457    1.4232 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1809    3.3020   -0.8994 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7971    1.6739   -1.4879 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0845    2.2437    0.1962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6185    2.9133   -0.1876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7349    2.7154   -1.7078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0863    1.6318   -1.4566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7013    0.7217   -2.2895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1588   -0.4015   -1.3149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4862   -1.8916   -0.5450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7261   -1.2582   -2.1098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3919   -0.1817    1.7788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8104    1.4479    1.0030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9249    0.0524    0.9044 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  3
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  2 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 16 18  1  0
 16 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
  9  4  1  0
 15 10  1  0
 21 13  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  5 28  1  0
  6 29  1  0
  7 30  1  0
  8 31  1  0
  9 32  1  0
 11 33  1  0
 12 34  1  0
 15 35  1  0
 17 36  1  0
 17 37  1  0
 17 38  1  0
 18 39  1  0
 18 40  1  0
 18 41  1  0
 19 42  1  0
 19 43  1  0
 20 44  1  0
 20 45  1  0
 22 46  1  0
 22 47  1  0
 22 48  1  0
 23 49  1  0
 23 50  1  0
 23 51  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      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667   0.000   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       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.390  -4.440   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.944  -4.440   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.944   1.360   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.390   1.360   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   10                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    4                                                       
CONECT   10    2   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   19                                                  
CONECT   13   12   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14   10                                                       
CONECT   16   13   17   22   23                                             
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   12   20   21                                             
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   16                                                            
CONECT   23   16                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

COMPND    HMDB0258798
HETATM    1  C1  UNL     1       2.027  -3.793  -0.859  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.013  -2.386  -0.270  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.149  -1.881   0.037  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.502  -0.601   0.617  1.00  0.00           C  
HETATM    5  C5  UNL     1       4.376   0.269   0.006  1.00  0.00           C  
HETATM    6  C6  UNL     1       4.782   1.462   0.562  1.00  0.00           C  
HETATM    7  C7  UNL     1       4.263   1.781   1.813  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.387   0.951   2.471  1.00  0.00           C  
HETATM    9  C9  UNL     1       3.009  -0.228   1.881  1.00  0.00           C  
HETATM   10  C10 UNL     1       0.684  -1.779  -0.261  1.00  0.00           C  
HETATM   11  C11 UNL     1      -0.458  -2.577  -0.390  1.00  0.00           C  
HETATM   12  C12 UNL     1      -1.719  -2.021  -0.432  1.00  0.00           C  
HETATM   13  C13 UNL     1      -1.918  -0.661  -0.351  1.00  0.00           C  
HETATM   14  C14 UNL     1      -0.793   0.112  -0.225  1.00  0.00           C  
HETATM   15  C15 UNL     1       0.501  -0.429  -0.181  1.00  0.00           C  
HETATM   16  C16 UNL     1      -0.923   1.584  -0.117  1.00  0.00           C  
HETATM   17  C17 UNL     1      -0.995   2.011   1.358  1.00  0.00           C  
HETATM   18  C18 UNL     1       0.368   2.223  -0.653  1.00  0.00           C  
HETATM   19  C19 UNL     1      -2.116   2.134  -0.820  1.00  0.00           C  
HETATM   20  C20 UNL     1      -3.101   1.149  -1.339  1.00  0.00           C  
HETATM   21  C21 UNL     1      -3.275  -0.066  -0.410  1.00  0.00           C  
HETATM   22  C22 UNL     1      -4.232  -1.005  -1.158  1.00  0.00           C  
HETATM   23  C23 UNL     1      -3.837   0.334   0.911  1.00  0.00           C  
HETATM   24  H1  UNL     1       3.079  -4.179  -0.903  1.00  0.00           H  
HETATM   25  H2  UNL     1       1.492  -4.497  -0.200  1.00  0.00           H  
HETATM   26  H3  UNL     1       1.567  -3.808  -1.860  1.00  0.00           H  
HETATM   27  H4  UNL     1       4.034  -2.542  -0.178  1.00  0.00           H  
HETATM   28  H5  UNL     1       4.772  -0.007  -0.983  1.00  0.00           H  
HETATM   29  H6  UNL     1       5.475   2.144   0.068  1.00  0.00           H  
HETATM   30  H7  UNL     1       4.553   2.710   2.290  1.00  0.00           H  
HETATM   31  H8  UNL     1       2.979   1.207   3.459  1.00  0.00           H  
HETATM   32  H9  UNL     1       2.325  -0.933   2.335  1.00  0.00           H  
HETATM   33  H10 UNL     1      -0.318  -3.649  -0.455  1.00  0.00           H  
HETATM   34  H11 UNL     1      -2.542  -2.723  -0.533  1.00  0.00           H  
HETATM   35  H12 UNL     1       1.348   0.269  -0.121  1.00  0.00           H  
HETATM   36  H13 UNL     1      -1.326   1.212   2.019  1.00  0.00           H  
HETATM   37  H14 UNL     1       0.033   2.297   1.739  1.00  0.00           H  
HETATM   38  H15 UNL     1      -1.590   2.946   1.423  1.00  0.00           H  
HETATM   39  H16 UNL     1       0.181   3.302  -0.899  1.00  0.00           H  
HETATM   40  H17 UNL     1       0.797   1.674  -1.488  1.00  0.00           H  
HETATM   41  H18 UNL     1       1.084   2.244   0.196  1.00  0.00           H  
HETATM   42  H19 UNL     1      -2.618   2.913  -0.188  1.00  0.00           H  
HETATM   43  H20 UNL     1      -1.735   2.715  -1.708  1.00  0.00           H  
HETATM   44  H21 UNL     1      -4.086   1.632  -1.457  1.00  0.00           H  
HETATM   45  H22 UNL     1      -2.701   0.722  -2.289  1.00  0.00           H  
HETATM   46  H23 UNL     1      -5.159  -0.402  -1.315  1.00  0.00           H  
HETATM   47  H24 UNL     1      -4.486  -1.892  -0.545  1.00  0.00           H  
HETATM   48  H25 UNL     1      -3.726  -1.258  -2.110  1.00  0.00           H  
HETATM   49  H26 UNL     1      -3.392  -0.182   1.779  1.00  0.00           H  
HETATM   50  H27 UNL     1      -3.810   1.448   1.003  1.00  0.00           H  
HETATM   51  H28 UNL     1      -4.925   0.052   0.904  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3    3   10
CONECT    3    4   27
CONECT    4    5    5    9
CONECT    5    6   28
CONECT    6    7    7   29
CONECT    7    8   30
CONECT    8    9    9   31
CONECT    9   32
CONECT   10   11   11   15
CONECT   11   12   33
CONECT   12   13   13   34
CONECT   13   14   21
CONECT   14   15   15   16
CONECT   15   35
CONECT   16   17   18   19
CONECT   17   36   37   38
CONECT   18   39   40   41
CONECT   19   20   42   43
CONECT   20   21   44   45
CONECT   21   22   23
CONECT   22   46   47   48
CONECT   23   49   50   51
END

HMDB0258798
     RDKit          3D
Temarotene
 51 53  0  0  0  0  0  0  0  0999 V2000
    2.0267   -3.7929   -0.8591 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0127   -2.3857   -0.2702 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1490   -1.8806    0.0374 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5021   -0.6011    0.6167 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3762    0.2688    0.0056 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7816    1.4617    0.5621 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2631    1.7809    1.8126 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3870    0.9514    2.4708 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0087   -0.2284    1.8813 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6839   -1.7790   -0.2611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4578   -2.5774   -0.3897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7193   -2.0208   -0.4323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9183   -0.6612   -0.3508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7929    0.1122   -0.2254 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5008   -0.4290   -0.1810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9226    1.5838   -0.1170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9945    2.0114    1.3584 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3681    2.2226   -0.6532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1156    2.1341   -0.8197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1010    1.1490   -1.3391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2752   -0.0660   -0.4100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2319   -1.0047   -1.1583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8371    0.3345    0.9109 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0788   -4.1785   -0.9029 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4924   -4.4975   -0.2003 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5672   -3.8082   -1.8596 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0341   -2.5417   -0.1778 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7722   -0.0069   -0.9828 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4753    2.1441    0.0680 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5532    2.7099    2.2903 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9795    1.2066    3.4586 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3245   -0.9327    2.3351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3175   -3.6487   -0.4550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5419   -2.7225   -0.5333 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3478    0.2690   -0.1211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3255    1.2120    2.0192 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0332    2.2970    1.7386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5897    2.9457    1.4232 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1809    3.3020   -0.8994 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7971    1.6739   -1.4879 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0845    2.2437    0.1962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6185    2.9133   -0.1876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7349    2.7154   -1.7078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0863    1.6318   -1.4566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7013    0.7217   -2.2895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1588   -0.4015   -1.3149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4862   -1.8916   -0.5450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7261   -1.2582   -2.1098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3919   -0.1817    1.7788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8104    1.4479    1.0030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9249    0.0524    0.9044 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  3
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  2 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 16 18  1  0
 16 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
  9  4  1  0
 15 10  1  0
 21 13  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  5 28  1  0
  6 29  1  0
  7 30  1  0
  8 31  1  0
  9 32  1  0
 11 33  1  0
 12 34  1  0
 15 35  1  0
 17 36  1  0
 17 37  1  0
 17 38  1  0
 18 39  1  0
 18 40  1  0
 18 41  1  0
 19 42  1  0
 19 43  1  0
 20 44  1  0
 20 45  1  0
 22 46  1  0
 22 47  1  0
 22 48  1  0
 23 49  1  0
 23 50  1  0
 23 51  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,2,3,4-Tetrahydro-1,1,4,4-tetramethyl-6-(1-methyl)-2-(phenylethenyl)naphthalene	MeSH
Temarotene, (e)-isomer	MeSH

Chemical Formula

C₂₃H₂₈

Average Molecular Weight

304.477

Monoisotopic Molecular Weight

304.219100902

IUPAC Name

1,1,4,4-tetramethyl-6-(1-phenylprop-1-en-2-yl)-1,2,3,4-tetrahydronaphthalene

Traditional Name

1,1,4,4-tetramethyl-6-(1-phenylprop-1-en-2-yl)-2,3-dihydronaphthalene

CAS Registry Number

Not Available

SMILES

CC(=CC1=CC=CC=C1)C1=CC2=C(C=C1)C(C)(C)CCC2(C)C

InChI Identifier

InChI=1S/C23H28/c1-17(15-18-9-7-6-8-10-18)19-11-12-20-21(16-19)23(4,5)14-13-22(20,2)3/h6-12,15-16H,13-14H2,1-5H3

InChI Key

MUJQTAMVZYFLCR-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Stilbenes

Sub Class

Not Available

Direct Parent

Stilbenes

Alternative Parents

Substituents

Stilbene
Tetralin
Styrene
Benzenoid
Monocyclic benzene moiety
Aromatic hydrocarbon
Branched unsaturated hydrocarbon
Polycyclic hydrocarbon
Cyclic olefin
Unsaturated hydrocarbon
Olefin
Hydrocarbon
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (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	7.72	ALOGPS
logP	7.24	ChemAxon
logS	-6.7	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	101.32 m³·mol⁻¹	ChemAxon
Polarizability	37.28 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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]+	177.503	30932474
DeepCCS	[M-H]-	175.145	30932474
DeepCCS	[M-2H]-	209.049	30932474
DeepCCS	[M+Na]+	184.277	30932474
AllCCS	[M+H]+	177.1	32859911
AllCCS	[M+H-H2O]+	173.9	32859911
AllCCS	[M+NH4]+	180.1	32859911
AllCCS	[M+Na]+	180.9	32859911
AllCCS	[M-H]-	185.0	32859911
AllCCS	[M+Na-2H]-	184.2	32859911
AllCCS	[M+HCOO]-	183.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Temarotene	CC(=CC1=CC=CC=C1)C1=CC2=C(C=C1)C(C)(C)CCC2(C)C	3045.1	Standard polar	33892256
Temarotene	CC(=CC1=CC=CC=C1)C1=CC2=C(C=C1)C(C)(C)CCC2(C)C	2370.9	Standard non polar	33892256
Temarotene	CC(=CC1=CC=CC=C1)C1=CC2=C(C=C1)C(C)(C)CCC2(C)C	2403.3	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 - Temarotene GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-0090000000-206d32a8cb6dec60f510	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Temarotene GC-MS (Non-derivatized) - 70eV, Positive	Not Available	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

71138

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 Temarotene (HMDB0258798)

MOL for HMDB0258798 (Temarotene)

3D MOL for HMDB0258798 (Temarotene)

3D SDF for HMDB0258798 (Temarotene)

3D-SDF for HMDB0258798 (Temarotene)

PDB for HMDB0258798 (Temarotene)

3D PDB for HMDB0258798 (Temarotene)

SMILES for HMDB0258798 (Temarotene)

INCHI for HMDB0258798 (Temarotene)

Structure for HMDB0258798 (Temarotene)

3D Structure for HMDB0258798 (Temarotene)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra