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enzymes (5) Show 5 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:37 UTC

HMDB ID

HMDB0014452

Secondary Accession Numbers

HMDB14452

Metabolite Identification

Common Name

Bexarotene

Description

Bexarotene is only found in individuals that have used or taken this drug. It is an antineoplastic agent indicated by the FDA for Cutaneous T cell lymphoma. It has been used off-label for lung cancer, breast cancer, and Kaposi's sarcoma (Wikipedia ). Bexarotene selectively binds with and activates retinoid X receptor subtypes. There are three subtypes in total: RXR_α, RXR_β, RXR_γ. The exact mechanism of action of bexarotene in the treatment of CTCL is unknown but the drug has activity in all clinical stages of CTCL.

Structure

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

307
  Mrv0541 02231214352D          

 26 28  0  0  0  0            999 V2000
    5.9770   -2.7941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5481   -2.7886    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.9411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    2.5911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.3536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    2.1786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    1.3536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    2.1786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    0.2266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    0.2266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    3.3056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    3.3056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8165    0.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8165    2.6197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5640    1.3364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5640    2.1958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2769    0.9212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2769    2.6111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2737    0.0962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9929    1.3309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5577   -0.3136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9866   -0.3191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5545   -1.1386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9834   -1.1441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2673   -1.5538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2641   -2.3788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 26  1  0  0  0  0
  2 26  2  0  0  0  0
  3  5  1  0  0  0  0
  3  7  1  0  0  0  0
  3  9  1  0  0  0  0
  3 10  1  0  0  0  0
  4  6  1  0  0  0  0
  4  8  1  0  0  0  0
  4 11  1  0  0  0  0
  4 12  1  0  0  0  0
  5  6  1  0  0  0  0
  7  8  2  0  0  0  0
  7 13  1  0  0  0  0
  8 14  1  0  0  0  0
 13 15  2  0  0  0  0
 14 16  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 16 18  1  0  0  0  0
 17 19  1  0  0  0  0
 17 20  2  0  0  0  0
 19 21  2  0  0  0  0
 19 22  1  0  0  0  0
 21 23  1  0  0  0  0
 22 24  2  0  0  0  0
 23 25  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
M  END

HMDB0014452
     RDKit          3D
Bexarotene
 54 56  0  0  0  0  0  0  0  0999 V2000
    2.1531    0.3565    2.7642 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0423    0.0777    1.4698 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2545    0.0241    0.6726 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2447    0.2803   -0.6799 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4031    0.2167   -1.4403 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6139   -0.1091   -0.8554 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8464   -0.1865   -1.6117 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9171   -0.4825   -1.0525 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8305    0.0708   -2.9636 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6357   -0.3660    0.4898 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4675   -0.2969    1.2284 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6941   -0.1286    0.9243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3416    0.7146    1.3327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6275    0.5541    0.8770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9239   -0.4577   -0.0052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9250   -1.3082   -0.4277 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3861   -1.1248    0.0536 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4370   -2.0888   -0.3856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2820   -0.7139   -0.5573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2725   -0.4957   -2.0718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6007   -2.2041   -0.3714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3714    0.0546    0.1036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0199    0.7267    1.3823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6983    1.4625    1.3291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4368    1.9665    2.7497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7976    2.7102    0.4617 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2692    0.4004    3.3719 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1113    0.5396    3.1900 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3257    0.5414   -1.1871 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3631    0.4230   -2.4996 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0589   -0.2657   -3.5240 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5599   -0.6238    0.9843 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5357   -0.5191    2.3105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0683    1.4999    2.0284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1071   -2.1297   -1.1291 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2656   -2.1955    0.3109 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9013   -3.0941   -0.3630 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7169   -1.9802   -1.4516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7928    0.4578   -2.3475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3433   -0.5207   -2.3867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7974   -1.3744   -2.5557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7064   -2.3155   -0.5105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3922   -2.5363    0.6597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1220   -2.8125   -1.1520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2722   -0.5893    0.3103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7574    0.8208   -0.6304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8000    1.5235    1.5652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0413    0.0802    2.2677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7352    2.8378    2.6763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3893    2.3693    3.1360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0261    1.1483    3.3595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1163    2.4769   -0.5623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4669    3.4094    0.9931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8022    3.1759    0.4273 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  6 10  1  0
 10 11  2  0
  2 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 15 19  1  0
 19 20  1  0
 19 21  1  0
 19 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  1  0
 11  3  1  0
 17 12  1  0
 24 14  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  5 30  1  0
  9 31  1  0
 10 32  1  0
 11 33  1  0
 13 34  1  0
 16 35  1  0
 18 36  1  0
 18 37  1  0
 18 38  1  0
 20 39  1  0
 20 40  1  0
 20 41  1  0
 21 42  1  0
 21 43  1  0
 21 44  1  0
 22 45  1  0
 22 46  1  0
 23 47  1  0
 23 48  1  0
 25 49  1  0
 25 50  1  0
 25 51  1  0
 26 52  1  0
 26 53  1  0
 26 54  1  0
M  END

307
  Mrv0541 02231214352D          

 26 28  0  0  0  0            999 V2000
    5.9770   -2.7941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5481   -2.7886    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.9411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    2.5911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.3536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    2.1786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    1.3536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    2.1786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    0.2266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    0.2266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    3.3056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    3.3056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8165    0.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8165    2.6197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5640    1.3364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5640    2.1958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2769    0.9212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2769    2.6111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2737    0.0962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9929    1.3309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5577   -0.3136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9866   -0.3191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5545   -1.1386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9834   -1.1441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2673   -1.5538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2641   -2.3788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 26  1  0  0  0  0
  2 26  2  0  0  0  0
  3  5  1  0  0  0  0
  3  7  1  0  0  0  0
  3  9  1  0  0  0  0
  3 10  1  0  0  0  0
  4  6  1  0  0  0  0
  4  8  1  0  0  0  0
  4 11  1  0  0  0  0
  4 12  1  0  0  0  0
  5  6  1  0  0  0  0
  7  8  2  0  0  0  0
  7 13  1  0  0  0  0
  8 14  1  0  0  0  0
 13 15  2  0  0  0  0
 14 16  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 16 18  1  0  0  0  0
 17 19  1  0  0  0  0
 17 20  2  0  0  0  0
 19 21  2  0  0  0  0
 19 22  1  0  0  0  0
 21 23  1  0  0  0  0
 22 24  2  0  0  0  0
 23 25  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014452

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=CC2=C(C=C1C(=C)C1=CC=C(C=C1)C(O)=O)C(C)(C)CCC2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C24H28O2/c1-15-13-20-21(24(5,6)12-11-23(20,3)4)14-19(15)16(2)17-7-9-18(10-8-17)22(25)26/h7-10,13-14H,2,11-12H2,1,3-6H3,(H,25,26)

> <INCHI_KEY>
NAVMQTYZDKMPEU-UHFFFAOYSA-N

> <FORMULA>
C24H28O2

> <MOLECULAR_WEIGHT>
348.4779

> <EXACT_MASS>
348.20893014

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
40.89246091735121

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-[1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)ethenyl]benzoic acid

> <ALOGPS_LOGP>
6.86

> <JCHEM_LOGP>
6.940537397666667

> <ALOGPS_LOGS>
-6.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.070792459533179

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
117.124

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.49e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
bexarotene

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0014452
     RDKit          3D
Bexarotene
 54 56  0  0  0  0  0  0  0  0999 V2000
    2.1531    0.3565    2.7642 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0423    0.0777    1.4698 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2545    0.0241    0.6726 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2447    0.2803   -0.6799 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4031    0.2167   -1.4403 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6139   -0.1091   -0.8554 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8464   -0.1865   -1.6117 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9171   -0.4825   -1.0525 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8305    0.0708   -2.9636 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6357   -0.3660    0.4898 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4675   -0.2969    1.2284 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6941   -0.1286    0.9243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3416    0.7146    1.3327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6275    0.5541    0.8770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9239   -0.4577   -0.0052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9250   -1.3082   -0.4277 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3861   -1.1248    0.0536 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4370   -2.0888   -0.3856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2820   -0.7139   -0.5573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2725   -0.4957   -2.0718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6007   -2.2041   -0.3714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3714    0.0546    0.1036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0199    0.7267    1.3823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6983    1.4625    1.3291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4368    1.9665    2.7497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7976    2.7102    0.4617 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2692    0.4004    3.3719 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1113    0.5396    3.1900 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3257    0.5414   -1.1871 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3631    0.4230   -2.4996 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0589   -0.2657   -3.5240 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5599   -0.6238    0.9843 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5357   -0.5191    2.3105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0683    1.4999    2.0284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1071   -2.1297   -1.1291 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2656   -2.1955    0.3109 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9013   -3.0941   -0.3630 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7169   -1.9802   -1.4516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7928    0.4578   -2.3475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3433   -0.5207   -2.3867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7974   -1.3744   -2.5557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7064   -2.3155   -0.5105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3922   -2.5363    0.6597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1220   -2.8125   -1.1520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2722   -0.5893    0.3103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7574    0.8208   -0.6304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8000    1.5235    1.5652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0413    0.0802    2.2677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7352    2.8378    2.6763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3893    2.3693    3.1360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0261    1.1483    3.3595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1163    2.4769   -0.5623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4669    3.4094    0.9931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8022    3.1759    0.4273 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  6 10  1  0
 10 11  2  0
  2 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 15 19  1  0
 19 20  1  0
 19 21  1  0
 19 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  1  0
 11  3  1  0
 17 12  1  0
 24 14  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  5 30  1  0
  9 31  1  0
 10 32  1  0
 11 33  1  0
 13 34  1  0
 16 35  1  0
 18 36  1  0
 18 37  1  0
 18 38  1  0
 20 39  1  0
 20 40  1  0
 20 41  1  0
 21 42  1  0
 21 43  1  0
 21 44  1  0
 22 45  1  0
 22 46  1  0
 23 47  1  0
 23 48  1  0
 25 49  1  0
 25 50  1  0
 25 51  1  0
 26 52  1  0
 26 53  1  0
 26 54  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 307                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      11.157  -5.216   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       8.490  -5.205   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.414   1.757   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.414   4.837   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.080   2.527   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.080   4.067   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.747   2.527   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.747   4.067   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.644   0.423   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.184   0.423   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.644   6.170   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.184   6.170   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.124   1.703   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.124   4.890   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.519   2.495   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.519   4.099   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.850   1.720   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.850   4.874   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.844   0.180   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.187   2.484   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.508  -0.585   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.175  -0.596   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.502  -2.125   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.169  -2.136   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.832  -2.900   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.826  -4.440   0.000  0.00  0.00           C+0
CONECT    1   26                                                            
CONECT    2   26                                                            
CONECT    3    5    7    9   10                                             
CONECT    4    6    8   11   12                                             
CONECT    5    3    6                                                       
CONECT    6    4    5                                                       
CONECT    7    3    8   13                                                  
CONECT    8    4    7   14                                                  
CONECT    9    3                                                            
CONECT   10    3                                                            
CONECT   11    4                                                            
CONECT   12    4                                                            
CONECT   13    7   15                                                       
CONECT   14    8   16                                                       
CONECT   15   13   16   17                                                  
CONECT   16   14   15   18                                                  
CONECT   17   15   19   20                                                  
CONECT   18   16                                                            
CONECT   19   17   21   22                                                  
CONECT   20   17                                                            
CONECT   21   19   23                                                       
CONECT   22   19   24                                                       
CONECT   23   21   25                                                       
CONECT   24   22   25                                                       
CONECT   25   23   24   26                                                  
CONECT   26    1    2   25                                                  
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

COMPND    HMDB0014452
HETATM    1  C1  UNL     1       2.153   0.356   2.764  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.042   0.078   1.470  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.254   0.024   0.673  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.245   0.280  -0.680  1.00  0.00           C  
HETATM    5  C5  UNL     1       4.403   0.217  -1.440  1.00  0.00           C  
HETATM    6  C6  UNL     1       5.614  -0.109  -0.855  1.00  0.00           C  
HETATM    7  C7  UNL     1       6.846  -0.186  -1.612  1.00  0.00           C  
HETATM    8  O1  UNL     1       7.917  -0.482  -1.052  1.00  0.00           O  
HETATM    9  O2  UNL     1       6.830   0.071  -2.964  1.00  0.00           O  
HETATM   10  C8  UNL     1       5.636  -0.366   0.490  1.00  0.00           C  
HETATM   11  C9  UNL     1       4.468  -0.297   1.228  1.00  0.00           C  
HETATM   12  C10 UNL     1       0.694  -0.129   0.924  1.00  0.00           C  
HETATM   13  C11 UNL     1      -0.342   0.715   1.333  1.00  0.00           C  
HETATM   14  C12 UNL     1      -1.628   0.554   0.877  1.00  0.00           C  
HETATM   15  C13 UNL     1      -1.924  -0.458  -0.005  1.00  0.00           C  
HETATM   16  C14 UNL     1      -0.925  -1.308  -0.428  1.00  0.00           C  
HETATM   17  C15 UNL     1       0.386  -1.125   0.054  1.00  0.00           C  
HETATM   18  C16 UNL     1       1.437  -2.089  -0.386  1.00  0.00           C  
HETATM   19  C17 UNL     1      -3.282  -0.714  -0.557  1.00  0.00           C  
HETATM   20  C18 UNL     1      -3.272  -0.496  -2.072  1.00  0.00           C  
HETATM   21  C19 UNL     1      -3.601  -2.204  -0.371  1.00  0.00           C  
HETATM   22  C20 UNL     1      -4.371   0.055   0.104  1.00  0.00           C  
HETATM   23  C21 UNL     1      -4.020   0.727   1.382  1.00  0.00           C  
HETATM   24  C22 UNL     1      -2.698   1.463   1.329  1.00  0.00           C  
HETATM   25  C23 UNL     1      -2.437   1.966   2.750  1.00  0.00           C  
HETATM   26  C24 UNL     1      -2.798   2.710   0.462  1.00  0.00           C  
HETATM   27  H1  UNL     1       1.269   0.400   3.372  1.00  0.00           H  
HETATM   28  H2  UNL     1       3.111   0.540   3.190  1.00  0.00           H  
HETATM   29  H3  UNL     1       2.326   0.541  -1.187  1.00  0.00           H  
HETATM   30  H4  UNL     1       4.363   0.423  -2.500  1.00  0.00           H  
HETATM   31  H5  UNL     1       6.059  -0.266  -3.524  1.00  0.00           H  
HETATM   32  H6  UNL     1       6.560  -0.624   0.984  1.00  0.00           H  
HETATM   33  H7  UNL     1       4.536  -0.519   2.310  1.00  0.00           H  
HETATM   34  H8  UNL     1      -0.068   1.500   2.028  1.00  0.00           H  
HETATM   35  H9  UNL     1      -1.107  -2.130  -1.129  1.00  0.00           H  
HETATM   36  H10 UNL     1       2.266  -2.196   0.311  1.00  0.00           H  
HETATM   37  H11 UNL     1       0.901  -3.094  -0.363  1.00  0.00           H  
HETATM   38  H12 UNL     1       1.717  -1.980  -1.452  1.00  0.00           H  
HETATM   39  H13 UNL     1      -2.793   0.458  -2.347  1.00  0.00           H  
HETATM   40  H14 UNL     1      -4.343  -0.521  -2.387  1.00  0.00           H  
HETATM   41  H15 UNL     1      -2.797  -1.374  -2.556  1.00  0.00           H  
HETATM   42  H16 UNL     1      -4.706  -2.316  -0.510  1.00  0.00           H  
HETATM   43  H17 UNL     1      -3.392  -2.536   0.660  1.00  0.00           H  
HETATM   44  H18 UNL     1      -3.122  -2.812  -1.152  1.00  0.00           H  
HETATM   45  H19 UNL     1      -5.272  -0.589   0.310  1.00  0.00           H  
HETATM   46  H20 UNL     1      -4.757   0.821  -0.630  1.00  0.00           H  
HETATM   47  H21 UNL     1      -4.800   1.523   1.565  1.00  0.00           H  
HETATM   48  H22 UNL     1      -4.041   0.080   2.268  1.00  0.00           H  
HETATM   49  H23 UNL     1      -1.735   2.838   2.676  1.00  0.00           H  
HETATM   50  H24 UNL     1      -3.389   2.369   3.136  1.00  0.00           H  
HETATM   51  H25 UNL     1      -2.026   1.148   3.360  1.00  0.00           H  
HETATM   52  H26 UNL     1      -3.116   2.477  -0.562  1.00  0.00           H  
HETATM   53  H27 UNL     1      -3.467   3.409   0.993  1.00  0.00           H  
HETATM   54  H28 UNL     1      -1.802   3.176   0.427  1.00  0.00           H  
CONECT    1    2    2   27   28
CONECT    2    3   12
CONECT    3    4    4   11
CONECT    4    5   29
CONECT    5    6    6   30
CONECT    6    7   10
CONECT    7    8    8    9
CONECT    9   31
CONECT   10   11   11   32
CONECT   11   33
CONECT   12   13   13   17
CONECT   13   14   34
CONECT   14   15   15   24
CONECT   15   16   19
CONECT   16   17   17   35
CONECT   17   18
CONECT   18   36   37   38
CONECT   19   20   21   22
CONECT   20   39   40   41
CONECT   21   42   43   44
CONECT   22   23   45   46
CONECT   23   24   47   48
CONECT   24   25   26
CONECT   25   49   50   51
CONECT   26   52   53   54
END

HMDB0014452
     RDKit          3D
Bexarotene
 54 56  0  0  0  0  0  0  0  0999 V2000
    2.1531    0.3565    2.7642 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0423    0.0777    1.4698 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2545    0.0241    0.6726 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2447    0.2803   -0.6799 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4031    0.2167   -1.4403 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6139   -0.1091   -0.8554 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8464   -0.1865   -1.6117 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9171   -0.4825   -1.0525 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8305    0.0708   -2.9636 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6357   -0.3660    0.4898 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4675   -0.2969    1.2284 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6941   -0.1286    0.9243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3416    0.7146    1.3327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6275    0.5541    0.8770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9239   -0.4577   -0.0052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9250   -1.3082   -0.4277 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3861   -1.1248    0.0536 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4370   -2.0888   -0.3856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2820   -0.7139   -0.5573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2725   -0.4957   -2.0718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6007   -2.2041   -0.3714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3714    0.0546    0.1036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0199    0.7267    1.3823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6983    1.4625    1.3291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4368    1.9665    2.7497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7976    2.7102    0.4617 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2692    0.4004    3.3719 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1113    0.5396    3.1900 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3257    0.5414   -1.1871 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3631    0.4230   -2.4996 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0589   -0.2657   -3.5240 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5599   -0.6238    0.9843 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5357   -0.5191    2.3105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0683    1.4999    2.0284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1071   -2.1297   -1.1291 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2656   -2.1955    0.3109 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9013   -3.0941   -0.3630 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7169   -1.9802   -1.4516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7928    0.4578   -2.3475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3433   -0.5207   -2.3867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7974   -1.3744   -2.5557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7064   -2.3155   -0.5105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3922   -2.5363    0.6597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1220   -2.8125   -1.1520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2722   -0.5893    0.3103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7574    0.8208   -0.6304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8000    1.5235    1.5652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0413    0.0802    2.2677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7352    2.8378    2.6763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3893    2.3693    3.1360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0261    1.1483    3.3595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1163    2.4769   -0.5623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4669    3.4094    0.9931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8022    3.1759    0.4273 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  6 10  1  0
 10 11  2  0
  2 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 15 19  1  0
 19 20  1  0
 19 21  1  0
 19 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  1  0
 11  3  1  0
 17 12  1  0
 24 14  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  5 30  1  0
  9 31  1  0
 10 32  1  0
 11 33  1  0
 13 34  1  0
 16 35  1  0
 18 36  1  0
 18 37  1  0
 18 38  1  0
 20 39  1  0
 20 40  1  0
 20 41  1  0
 21 42  1  0
 21 43  1  0
 21 44  1  0
 22 45  1  0
 22 46  1  0
 23 47  1  0
 23 48  1  0
 25 49  1  0
 25 50  1  0
 25 51  1  0
 26 52  1  0
 26 53  1  0
 26 54  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Bexaroteno	ChEBI
Bexarotenum	ChEBI
p-(1-(5,6,7,8-Tetrahydro-3,5,5,8,8-pentamethyl-2-naphthyl)vinyl)benzoic acid	ChEBI
Targretin	Kegg
p-(1-(5,6,7,8-Tetrahydro-3,5,5,8,8-pentamethyl-2-naphthyl)vinyl)benzoate	Generator
3-Methyl-ttneb	HMDB
4-(1-(3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)ethenyl)benzoic acid	HMDB
Elan brand OF bexarotene	HMDB
Ligand brand OF bexarotene	HMDB
LG69 Compound	HMDB

Chemical Formula

C₂₄H₂₈O₂

Average Molecular Weight

348.4779

Monoisotopic Molecular Weight

348.20893014

IUPAC Name

4-[1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)ethenyl]benzoic acid

Traditional Name

bexarotene

CAS Registry Number

153559-49-0

SMILES

CC1=CC2=C(C=C1C(=C)C1=CC=C(C=C1)C(O)=O)C(C)(C)CCC2(C)C

InChI Identifier

InChI=1S/C24H28O2/c1-15-13-20-21(24(5,6)12-11-23(20,3)4)14-19(15)16(2)17-7-9-18(10-8-17)22(25)26/h7-10,13-14H,2,11-12H2,1,3-6H3,(H,25,26)

InChI Key

NAVMQTYZDKMPEU-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

Bexarotene
Sesquiterpenoid
Bisabolane sesquiterpenoid
Tetralin
Benzoic acid
Benzoic acid or derivatives
Styrene
Benzoyl
Monocyclic benzene moiety
Benzenoid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

retinoid (CHEBI:50859 )
naphthalenes (CHEBI:50859 )
benzoic acids (CHEBI:50859 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.00015 g/L	Not Available
LogP	6.9	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00015 g/L	ALOGPS
logP	6.86	ALOGPS
logP	6.94	ChemAxon
logS	-6.4	ALOGPS
pKa (Strongest Acidic)	4.07	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	117.12 m³·mol⁻¹	ChemAxon
Polarizability	40.89 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
DarkChem	[M+H]+	183.356	31661259
DarkChem	[M-H]-	184.008	31661259
DeepCCS	[M+H]+	189.28	30932474
DeepCCS	[M-H]-	186.922	30932474
DeepCCS	[M-2H]-	220.75	30932474
DeepCCS	[M+Na]+	195.947	30932474
AllCCS	[M+H]+	186.0	32859911
AllCCS	[M+H-H2O]+	183.0	32859911
AllCCS	[M+NH4]+	188.8	32859911
AllCCS	[M+Na]+	189.6	32859911
AllCCS	[M-H]-	193.7	32859911
AllCCS	[M+Na-2H]-	193.4	32859911
AllCCS	[M+HCOO]-	193.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Bexarotene	CC1=CC2=C(C=C1C(=C)C1=CC=C(C=C1)C(O)=O)C(C)(C)CCC2(C)C	4012.0	Standard polar	33892256
Bexarotene	CC1=CC2=C(C=C1C(=C)C1=CC=C(C=C1)C(O)=O)C(C)(C)CCC2(C)C	2875.3	Standard non polar	33892256
Bexarotene	CC1=CC2=C(C=C1C(=C)C1=CC=C(C=C1)C(O)=O)C(C)(C)CCC2(C)C	2765.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Bexarotene,1TMS,isomer #1	C=C(C1=CC=C(C(=O)O[Si](C)(C)C)C=C1)C1=CC2=C(C=C1C)C(C)(C)CCC2(C)C	2828.4	Semi standard non polar	33892256
Bexarotene,1TBDMS,isomer #1	C=C(C1=CC=C(C(=O)O[Si](C)(C)C(C)(C)C)C=C1)C1=CC2=C(C=C1C)C(C)(C)CCC2(C)C	3089.4	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 - Bexarotene GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-0039000000-67c145e4b6291137b828	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bexarotene GC-MS (1 TMS) - 70eV, Positive	splash10-0a4i-5138900000-2dd8135f74c794067a51	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bexarotene 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bexarotene LC-ESI-QFT , negative-QTOF	splash10-0002-0009000000-f46ef667393584a6300e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bexarotene LC-ESI-QFT , negative-QTOF	splash10-0udj-0009000000-9b87e4750a290eb82a7e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bexarotene LC-ESI-QFT , negative-QTOF	splash10-0udi-0009000000-3ce7b47cafecba720b63	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bexarotene LC-ESI-QFT , negative-QTOF	splash10-0udi-0009000000-91e32292babb45759b5d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bexarotene LC-ESI-QFT , positive-QTOF	splash10-0002-0009000000-885779b7401a85dbf649	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bexarotene LC-ESI-QFT , positive-QTOF	splash10-0002-0029000000-e65f7a4f9e6ecad40c0b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bexarotene LC-ESI-QFT , positive-QTOF	splash10-00os-1594000000-b4c3e389bf263ae949a1	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bexarotene LC-ESI-QFT , positive-QTOF	splash10-00kb-1941000000-7e96ac6cea878d4fd773	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bexarotene LC-ESI-QFT , positive-QTOF	splash10-0f6w-1920000000-ca6fbe2847a1daae3bd0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bexarotene LC-ESI-QFT , positive-QTOF	splash10-0f97-1920000000-f8a80e931ae20d42408c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bexarotene , positive-QTOF	splash10-0002-0239000000-3289f3a345e8948cb1c5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bexarotene 30V, Positive-QTOF	splash10-0002-0029000000-f764419e05b00fc56504	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bexarotene 15V, Positive-QTOF	splash10-0002-0009000000-4625185abcfa2bc898af	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bexarotene 30V, Negative-QTOF	splash10-0udj-0009000000-83ae23d7652e10271f8c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bexarotene 45V, Negative-QTOF	splash10-0udi-0009000000-125b9b35e572e36812d1	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bexarotene 75V, Positive-QTOF	splash10-0f6w-1920000000-0ff29face94138088db6	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bexarotene 15V, Negative-QTOF	splash10-0002-0009000000-f46ef667393584a6300e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bexarotene 60V, Negative-QTOF	splash10-0udi-0009000000-91e32292babb45759b5d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bexarotene 15V, Negative-QTOF	splash10-0002-0009000000-7ebaeaf5837b3860398a	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bexarotene 10V, Positive-QTOF	splash10-000t-0019000000-32d412923e98400a6964	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bexarotene 20V, Positive-QTOF	splash10-0f89-1159000000-92fbbb76dae0d7ba5527	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bexarotene 40V, Positive-QTOF	splash10-002r-2291000000-1736e07264d4f60fc414	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bexarotene 10V, Negative-QTOF	splash10-0002-0009000000-5c24e39715a45a65b007	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bexarotene 20V, Negative-QTOF	splash10-0udj-0009000000-8a946560cca4b67e29ca	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bexarotene 40V, Negative-QTOF	splash10-0f79-1298000000-4ea4093117f28c7caa9c	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00307	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00307	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00307

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

74139

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Bexarotene

METLIN ID

Not Available

PubChem Compound

82146

PDB ID

Not Available

ChEBI ID

50859

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

Lowe MN, Plosker GL: Bexarotene. Am J Clin Dermatol. 2000 Jul-Aug;1(4):245-50; discussion 251-2. [PubMed:11702369 ]
Yen WC, Prudente RY, Corpuz MR, Negro-Vilar A, Lamph WW: A selective retinoid X receptor agonist bexarotene (LGD1069, targretin) inhibits angiogenesis and metastasis in solid tumours. Br J Cancer. 2006 Mar 13;94(5):654-60. [PubMed:16495926 ]
Farol LT, Hymes KB: Bexarotene: a clinical review. Expert Rev Anticancer Ther. 2004 Apr;4(2):180-8. [PubMed:15056048 ]
Dragnev KH, Petty WJ, Shah SJ, Lewis LD, Black CC, Memoli V, Nugent WC, Hermann T, Negro-Vilar A, Rigas JR, Dmitrovsky E: A proof-of-principle clinical trial of bexarotene in patients with non-small cell lung cancer. Clin Cancer Res. 2007 Mar 15;13(6):1794-800. [PubMed:17363535 ]
Smit JW, Stokkel MP, Pereira AM, Romijn JA, Visser TJ: Bexarotene-induced hypothyroidism: bexarotene stimulates the peripheral metabolism of thyroid hormones. J Clin Endocrinol Metab. 2007 Jul;92(7):2496-9. Epub 2007 Apr 17. [PubMed:17440015 ]
Gniadecki R, Assaf C, Bagot M, Dummer R, Duvic M, Knobler R, Ranki A, Schwandt P, Whittaker S: The optimal use of bexarotene in cutaneous T-cell lymphoma. Br J Dermatol. 2007 Sep;157(3):433-40. Epub 2007 Jun 6. [PubMed:17553039 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

2. Cytochrome P450 2C9

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:: CYP2C9
Uniprot ID:: P11712
Molecular weight:: 55627.365

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

3. Retinoic acid receptor RXR-beta

General function:: Involved in sequence-specific DNA binding transcription factor activity
Specific function:: Nuclear hormone receptor. Involved in the retinoic acid response pathway. Binds 9-cis retinoic acid (9C-RA)
Gene Name:: RXRB
Uniprot ID:: P28702
Molecular weight:: 56921.4

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Tsai DE, Luger SM, Andreadis C, Vogl DT, Kemner A, Potuzak M, Goradia A, Loren AW, Perl AE, Schuster SJ, Porter DL, Stadtmauer EA, Goldstein SC, Thompson JE, Swider C, Bagg A, Mato AR, Carroll M: A phase I study of bexarotene, a retinoic X receptor agonist, in non-M3 acute myeloid leukemia. Clin Cancer Res. 2008 Sep 1;14(17):5619-25. doi: 10.1158/1078-0432.CCR-07-5185. [PubMed:18765556 ]
Tooker P, Yen WC, Ng SC, Negro-Vilar A, Hermann TW: Bexarotene (LGD1069, Targretin), a selective retinoid X receptor agonist, prevents and reverses gemcitabine resistance in NSCLC cells by modulating gene amplification. Cancer Res. 2007 May 1;67(9):4425-33. [PubMed:17483357 ]
Lalloyer F, Fievet C, Lestavel S, Torpier G, van der Veen J, Touche V, Bultel S, Yous S, Kuipers F, Paumelle R, Fruchart JC, Staels B, Tailleux A: The RXR agonist bexarotene improves cholesterol homeostasis and inhibits atherosclerosis progression in a mouse model of mixed dyslipidemia. Arterioscler Thromb Vasc Biol. 2006 Dec;26(12):2731-7. Epub 2006 Sep 28. [PubMed:17008586 ]
Yen WC, Lamph WW: The selective retinoid X receptor agonist bexarotene (LGD1069, Targretin) prevents and overcomes multidrug resistance in advanced breast carcinoma. Mol Cancer Ther. 2005 May;4(5):824-34. [PubMed:15897247 ]
Yen WC, Prudente RY, Corpuz MR, Negro-Vilar A, Lamph WW: A selective retinoid X receptor agonist bexarotene (LGD1069, targretin) inhibits angiogenesis and metastasis in solid tumours. Br J Cancer. 2006 Mar 13;94(5):654-60. [PubMed:16495926 ]
Rizvi N, Hawkins MJ, Eisenberg PD, Yocum RC, Reich SD: Placebo-controlled trial of bexarotene, a retinoid x receptor agonist, as maintenance therapy for patients treated with chemotherapy for advanced non-small-cell lung cancer. Clin Lung Cancer. 2001 Feb;2(3):210-5. [PubMed:14700480 ]
Rigas JR, Dragnev KH: Emerging role of rexinoids in non-small cell lung cancer: focus on bexarotene. Oncologist. 2005 Jan;10(1):22-33. [PubMed:15632250 ]
Farol LT, Hymes KB: Bexarotene: a clinical review. Expert Rev Anticancer Ther. 2004 Apr;4(2):180-8. [PubMed:15056048 ]
Lowe MN, Plosker GL: Bexarotene. Am J Clin Dermatol. 2000 Jul-Aug;1(4):245-50; discussion 251-2. [PubMed:11702369 ]

Enzyme Details

4. Retinoic acid receptor RXR-gamma

General function:: Involved in sequence-specific DNA binding transcription factor activity
Specific function:: Nuclear hormone receptor. Involved in the retinoic acid response pathway. Binds 9-cis retinoic acid (9C-RA)
Gene Name:: RXRG
Uniprot ID:: P48443
Molecular weight:: 50870.7

References

Lowe MN, Plosker GL: Bexarotene. Am J Clin Dermatol. 2000 Jul-Aug;1(4):245-50; discussion 251-2. [PubMed:11702369 ]
Tsai DE, Luger SM, Andreadis C, Vogl DT, Kemner A, Potuzak M, Goradia A, Loren AW, Perl AE, Schuster SJ, Porter DL, Stadtmauer EA, Goldstein SC, Thompson JE, Swider C, Bagg A, Mato AR, Carroll M: A phase I study of bexarotene, a retinoic X receptor agonist, in non-M3 acute myeloid leukemia. Clin Cancer Res. 2008 Sep 1;14(17):5619-25. doi: 10.1158/1078-0432.CCR-07-5185. [PubMed:18765556 ]
Tooker P, Yen WC, Ng SC, Negro-Vilar A, Hermann TW: Bexarotene (LGD1069, Targretin), a selective retinoid X receptor agonist, prevents and reverses gemcitabine resistance in NSCLC cells by modulating gene amplification. Cancer Res. 2007 May 1;67(9):4425-33. [PubMed:17483357 ]
Lalloyer F, Fievet C, Lestavel S, Torpier G, van der Veen J, Touche V, Bultel S, Yous S, Kuipers F, Paumelle R, Fruchart JC, Staels B, Tailleux A: The RXR agonist bexarotene improves cholesterol homeostasis and inhibits atherosclerosis progression in a mouse model of mixed dyslipidemia. Arterioscler Thromb Vasc Biol. 2006 Dec;26(12):2731-7. Epub 2006 Sep 28. [PubMed:17008586 ]
Yen WC, Lamph WW: The selective retinoid X receptor agonist bexarotene (LGD1069, Targretin) prevents and overcomes multidrug resistance in advanced breast carcinoma. Mol Cancer Ther. 2005 May;4(5):824-34. [PubMed:15897247 ]
Yen WC, Prudente RY, Corpuz MR, Negro-Vilar A, Lamph WW: A selective retinoid X receptor agonist bexarotene (LGD1069, targretin) inhibits angiogenesis and metastasis in solid tumours. Br J Cancer. 2006 Mar 13;94(5):654-60. [PubMed:16495926 ]
Rizvi N, Hawkins MJ, Eisenberg PD, Yocum RC, Reich SD: Placebo-controlled trial of bexarotene, a retinoid x receptor agonist, as maintenance therapy for patients treated with chemotherapy for advanced non-small-cell lung cancer. Clin Lung Cancer. 2001 Feb;2(3):210-5. [PubMed:14700480 ]
Rigas JR, Dragnev KH: Emerging role of rexinoids in non-small cell lung cancer: focus on bexarotene. Oncologist. 2005 Jan;10(1):22-33. [PubMed:15632250 ]
Farol LT, Hymes KB: Bexarotene: a clinical review. Expert Rev Anticancer Ther. 2004 Apr;4(2):180-8. [PubMed:15056048 ]

Enzyme Details

5. Retinoic acid receptor RXR-alpha

General function:: Involved in sequence-specific DNA binding transcription factor activity
Specific function:: Nuclear hormone receptor. Involved in the retinoic acid response pathway. Binds 9-cis retinoic acid (9C-RA). ARF6 acts as a key regulator of the tissue-specific adipocyte P2 (aP2) enhancer
Gene Name:: RXRA
Uniprot ID:: P19793
Molecular weight:: 50810.8

References

Lowe MN, Plosker GL: Bexarotene. Am J Clin Dermatol. 2000 Jul-Aug;1(4):245-50; discussion 251-2. [PubMed:11702369 ]
Tsai DE, Luger SM, Andreadis C, Vogl DT, Kemner A, Potuzak M, Goradia A, Loren AW, Perl AE, Schuster SJ, Porter DL, Stadtmauer EA, Goldstein SC, Thompson JE, Swider C, Bagg A, Mato AR, Carroll M: A phase I study of bexarotene, a retinoic X receptor agonist, in non-M3 acute myeloid leukemia. Clin Cancer Res. 2008 Sep 1;14(17):5619-25. doi: 10.1158/1078-0432.CCR-07-5185. [PubMed:18765556 ]
Tooker P, Yen WC, Ng SC, Negro-Vilar A, Hermann TW: Bexarotene (LGD1069, Targretin), a selective retinoid X receptor agonist, prevents and reverses gemcitabine resistance in NSCLC cells by modulating gene amplification. Cancer Res. 2007 May 1;67(9):4425-33. [PubMed:17483357 ]
Lalloyer F, Fievet C, Lestavel S, Torpier G, van der Veen J, Touche V, Bultel S, Yous S, Kuipers F, Paumelle R, Fruchart JC, Staels B, Tailleux A: The RXR agonist bexarotene improves cholesterol homeostasis and inhibits atherosclerosis progression in a mouse model of mixed dyslipidemia. Arterioscler Thromb Vasc Biol. 2006 Dec;26(12):2731-7. Epub 2006 Sep 28. [PubMed:17008586 ]
Yen WC, Lamph WW: The selective retinoid X receptor agonist bexarotene (LGD1069, Targretin) prevents and overcomes multidrug resistance in advanced breast carcinoma. Mol Cancer Ther. 2005 May;4(5):824-34. [PubMed:15897247 ]
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Showing metabocard for Bexarotene (HMDB0014452)

MOL for HMDB0014452 (Bexarotene)

3D MOL for HMDB0014452 (Bexarotene)

3D SDF for HMDB0014452 (Bexarotene)

3D-SDF for HMDB0014452 (Bexarotene)

PDB for HMDB0014452 (Bexarotene)

3D PDB for HMDB0014452 (Bexarotene)

SMILES for HMDB0014452 (Bexarotene)

INCHI for HMDB0014452 (Bexarotene)

Structure for HMDB0014452 (Bexarotene)

3D Structure for HMDB0014452 (Bexarotene)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References

References