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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:52:03 UTC

HMDB ID

HMDB0015605

Secondary Accession Numbers

HMDB15605

Metabolite Identification

Common Name

Tamibarotene

Description

Tamibarotene is only found in individuals that have used or taken this drug. It is a novel synthetic retinoid for acute promyelocytic leukaemia (APL). Tamibarotene is currently approved in Japan for treatment of recurrent APL, and is undergoing clinical trials in the United States.Tamibarotene is a specific agonist for retinoic acid receptor alpha/beta with possible binding to retinoid X receptors (RXR).

Structure

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


  Mrv0541 02231218012D          

 26 28  0  0  0  0            999 V2000
    5.9962    1.0807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5605   -0.9956    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8413   -2.2303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2769   -0.1541    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.1341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.5159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.2784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.1034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    0.2784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    1.1034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520   -0.8486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.8486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    2.2303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    2.2303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8165   -0.1628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8165    1.5445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5640    0.2612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5640    1.1205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9929    0.2557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7058   -0.1596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4219    0.2501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7026   -0.9846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1347   -0.1651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4155   -1.3999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1316   -0.9901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8445   -1.4053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 19  2  0  0  0  0
  2 26  1  0  0  0  0
  3 26  2  0  0  0  0
  4 17  1  0  0  0  0
  4 19  1  0  0  0  0
  5  7  1  0  0  0  0
  5  9  1  0  0  0  0
  5 11  1  0  0  0  0
  5 12  1  0  0  0  0
  6  8  1  0  0  0  0
  6 10  1  0  0  0  0
  6 13  1  0  0  0  0
  6 14  1  0  0  0  0
  7  8  1  0  0  0  0
  9 10  2  0  0  0  0
  9 15  1  0  0  0  0
 10 16  1  0  0  0  0
 15 17  2  0  0  0  0
 16 18  2  0  0  0  0
 17 18  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
 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

HMDB0015605
     RDKit          3D
Tamibarotene
 51 53  0  0  0  0  0  0  0  0999 V2000
   -4.1651   -1.9069    1.8771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8721   -0.5066    1.3789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1153    0.5304    2.4765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7387   -0.1916    0.2084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0865    0.7822   -0.7553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8134    0.2090   -1.3218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1645    1.2488   -2.2022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0440   -1.0194   -2.1559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9316   -0.1167   -0.1576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5475   -0.0730   -0.3855 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3294   -0.3562    0.6216 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7240   -0.3316    0.4636 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4870   -0.0378   -0.6660 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9593    0.2709   -1.7793 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9607   -0.0694   -0.6274 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6761   -0.6931    0.3560 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0781   -0.6916    0.3583 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7957   -0.0606   -0.6321 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2453   -0.0606   -0.6273 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8862    0.5116   -1.5254 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9160   -0.7024    0.3850 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0642    0.5734   -1.6321 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6884    0.5721   -1.6344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1991   -0.6883    1.8769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5519   -0.7291    2.0925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4160   -0.4419    1.0701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6869   -2.6144    1.1688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7880   -2.0445    2.9245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2675   -2.0747    1.8862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3200    1.3260    2.4332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1144    0.0616    3.4815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0669    1.0625    2.2754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1354   -1.0849   -0.3047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6476    0.3464    0.6072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7956    1.6684   -0.1473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7977    1.1227   -1.5046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5917    1.9546   -1.5697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4680    0.7171   -2.9147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9612    1.7310   -2.7944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0957   -1.6251   -2.1708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2444   -0.7721   -3.2203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8478   -1.6734   -1.7740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1851    0.1886   -1.3714 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2852   -0.5694    1.3440 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1339   -1.2023    1.1455 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6032   -1.1991    1.1584 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5559   -0.5992    1.3269 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6349    1.0744   -2.4187 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1396    1.0745   -2.4269 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4444   -0.9234    2.7168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9481   -0.9924    3.0865 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  6  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 18 22  1  0
 22 23  2  0
 11 24  2  0
 24 25  1  0
 25 26  2  0
 26  2  1  0
 26  9  1  0
 23 15  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  3 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  5 35  1  0
  5 36  1  0
  7 37  1  0
  7 38  1  0
  7 39  1  0
  8 40  1  0
  8 41  1  0
  8 42  1  0
 10 43  1  0
 12 44  1  0
 16 45  1  0
 17 46  1  0
 21 47  1  0
 22 48  1  0
 23 49  1  0
 24 50  1  0
 25 51  1  0
M  END


  Mrv0541 02231218012D          

 26 28  0  0  0  0            999 V2000
    5.9962    1.0807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5605   -0.9956    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8413   -2.2303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2769   -0.1541    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.1341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.5159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.2784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.1034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    0.2784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    1.1034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520   -0.8486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.8486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    2.2303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    2.2303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8165   -0.1628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8165    1.5445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5640    0.2612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5640    1.1205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9929    0.2557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7058   -0.1596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4219    0.2501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7026   -0.9846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1347   -0.1651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4155   -1.3999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1316   -0.9901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8445   -1.4053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 19  2  0  0  0  0
  2 26  1  0  0  0  0
  3 26  2  0  0  0  0
  4 17  1  0  0  0  0
  4 19  1  0  0  0  0
  5  7  1  0  0  0  0
  5  9  1  0  0  0  0
  5 11  1  0  0  0  0
  5 12  1  0  0  0  0
  6  8  1  0  0  0  0
  6 10  1  0  0  0  0
  6 13  1  0  0  0  0
  6 14  1  0  0  0  0
  7  8  1  0  0  0  0
  9 10  2  0  0  0  0
  9 15  1  0  0  0  0
 10 16  1  0  0  0  0
 15 17  2  0  0  0  0
 16 18  2  0  0  0  0
 17 18  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
 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>
HMDB0015605

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1(C)CCC(C)(C)C2=C1C=CC(NC(=O)C1=CC=C(C=C1)C(O)=O)=C2

> <INCHI_IDENTIFIER>
InChI=1S/C22H25NO3/c1-21(2)11-12-22(3,4)18-13-16(9-10-17(18)21)23-19(24)14-5-7-15(8-6-14)20(25)26/h5-10,13H,11-12H2,1-4H3,(H,23,24)(H,25,26)

> <INCHI_KEY>
MUTNCGKQJGXKEM-UHFFFAOYSA-N

> <FORMULA>
C22H25NO3

> <MOLECULAR_WEIGHT>
351.4388

> <EXACT_MASS>
351.183443671

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
39.16348533361369

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)carbamoyl]benzoic acid

> <ALOGPS_LOGP>
4.99

> <JCHEM_LOGP>
5.349100168333335

> <ALOGPS_LOGS>
-5.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.458566925713676

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.693783000823111

> <JCHEM_PKA_STRONGEST_BASIC>
-4.0306430501291635

> <JCHEM_POLAR_SURFACE_AREA>
66.39999999999999

> <JCHEM_REFRACTIVITY>
104.37729999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.75e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tamibarotene

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015605
     RDKit          3D
Tamibarotene
 51 53  0  0  0  0  0  0  0  0999 V2000
   -4.1651   -1.9069    1.8771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8721   -0.5066    1.3789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1153    0.5304    2.4765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7387   -0.1916    0.2084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0865    0.7822   -0.7553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8134    0.2090   -1.3218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1645    1.2488   -2.2022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0440   -1.0194   -2.1559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9316   -0.1167   -0.1576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5475   -0.0730   -0.3855 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3294   -0.3562    0.6216 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7240   -0.3316    0.4636 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4870   -0.0378   -0.6660 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9593    0.2709   -1.7793 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9607   -0.0694   -0.6274 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6761   -0.6931    0.3560 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0781   -0.6916    0.3583 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7957   -0.0606   -0.6321 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2453   -0.0606   -0.6273 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8862    0.5116   -1.5254 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9160   -0.7024    0.3850 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0642    0.5734   -1.6321 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6884    0.5721   -1.6344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1991   -0.6883    1.8769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5519   -0.7291    2.0925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4160   -0.4419    1.0701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6869   -2.6144    1.1688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7880   -2.0445    2.9245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2675   -2.0747    1.8862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3200    1.3260    2.4332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1144    0.0616    3.4815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0669    1.0625    2.2754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1354   -1.0849   -0.3047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6476    0.3464    0.6072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7956    1.6684   -0.1473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7977    1.1227   -1.5046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5917    1.9546   -1.5697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4680    0.7171   -2.9147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9612    1.7310   -2.7944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0957   -1.6251   -2.1708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2444   -0.7721   -3.2203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8478   -1.6734   -1.7740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1851    0.1886   -1.3714 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2852   -0.5694    1.3440 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1339   -1.2023    1.1455 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6032   -1.1991    1.1584 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5559   -0.5992    1.3269 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6349    1.0744   -2.4187 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1396    1.0745   -2.4269 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4444   -0.9234    2.7168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9481   -0.9924    3.0865 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  6  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 18 22  1  0
 22 23  2  0
 11 24  2  0
 24 25  1  0
 25 26  2  0
 26  2  1  0
 26  9  1  0
 23 15  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  3 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  5 35  1  0
  5 36  1  0
  7 37  1  0
  7 38  1  0
  7 39  1  0
  8 40  1  0
  8 41  1  0
  8 42  1  0
 10 43  1  0
 12 44  1  0
 16 45  1  0
 17 46  1  0
 21 47  1  0
 22 48  1  0
 23 49  1  0
 24 50  1  0
 25 51  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      11.193   2.017   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      17.846  -1.858   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      16.504  -4.163   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       9.850  -0.288   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       4.414  -0.250   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.414   2.830   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.080   0.520   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.080   2.060   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.747   0.520   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.747   2.060   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.644  -1.584   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.184  -1.584   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.644   4.163   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.184   4.163   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.124  -0.304   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.124   2.883   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.519   0.488   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.519   2.092   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.187   0.477   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.517  -0.298   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.854   0.467   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.512  -1.838   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      15.185  -0.308   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      13.842  -2.613   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      15.179  -1.848   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      16.510  -2.623   0.000  0.00  0.00           C+0
CONECT    1   19                                                            
CONECT    2   26                                                            
CONECT    3   26                                                            
CONECT    4   17   19                                                       
CONECT    5    7    9   11   12                                             
CONECT    6    8   10   13   14                                             
CONECT    7    5    8                                                       
CONECT    8    6    7                                                       
CONECT    9    5   10   15                                                  
CONECT   10    6    9   16                                                  
CONECT   11    5                                                            
CONECT   12    5                                                            
CONECT   13    6                                                            
CONECT   14    6                                                            
CONECT   15    9   17                                                       
CONECT   16   10   18                                                       
CONECT   17    4   15   18                                                  
CONECT   18   16   17                                                       
CONECT   19    1    4   20                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20   23                                                       
CONECT   22   20   24                                                       
CONECT   23   21   25                                                       
CONECT   24   22   25                                                       
CONECT   25   23   24   26                                                  
CONECT   26    2    3   25                                                  
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

COMPND    HMDB0015605
HETATM    1  C1  UNL     1      -4.165  -1.907   1.877  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.872  -0.507   1.379  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.115   0.530   2.477  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.739  -0.192   0.208  1.00  0.00           C  
HETATM    5  C5  UNL     1      -4.086   0.782  -0.755  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.813   0.209  -1.322  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.164   1.249  -2.202  1.00  0.00           C  
HETATM    8  C8  UNL     1      -3.044  -1.019  -2.156  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.932  -0.117  -0.158  1.00  0.00           C  
HETATM   10  C10 UNL     1      -0.548  -0.073  -0.386  1.00  0.00           C  
HETATM   11  C11 UNL     1       0.329  -0.356   0.622  1.00  0.00           C  
HETATM   12  N1  UNL     1       1.724  -0.332   0.464  1.00  0.00           N  
HETATM   13  C12 UNL     1       2.487  -0.038  -0.666  1.00  0.00           C  
HETATM   14  O1  UNL     1       1.959   0.271  -1.779  1.00  0.00           O  
HETATM   15  C13 UNL     1       3.961  -0.069  -0.627  1.00  0.00           C  
HETATM   16  C14 UNL     1       4.676  -0.693   0.356  1.00  0.00           C  
HETATM   17  C15 UNL     1       6.078  -0.692   0.358  1.00  0.00           C  
HETATM   18  C16 UNL     1       6.796  -0.061  -0.632  1.00  0.00           C  
HETATM   19  C17 UNL     1       8.245  -0.061  -0.627  1.00  0.00           C  
HETATM   20  O2  UNL     1       8.886   0.512  -1.525  1.00  0.00           O  
HETATM   21  O3  UNL     1       8.916  -0.702   0.385  1.00  0.00           O  
HETATM   22  C18 UNL     1       6.064   0.573  -1.632  1.00  0.00           C  
HETATM   23  C19 UNL     1       4.688   0.572  -1.634  1.00  0.00           C  
HETATM   24  C20 UNL     1      -0.199  -0.688   1.877  1.00  0.00           C  
HETATM   25  C21 UNL     1      -1.552  -0.729   2.092  1.00  0.00           C  
HETATM   26  C22 UNL     1      -2.416  -0.442   1.070  1.00  0.00           C  
HETATM   27  H1  UNL     1      -3.687  -2.614   1.169  1.00  0.00           H  
HETATM   28  H2  UNL     1      -3.788  -2.044   2.924  1.00  0.00           H  
HETATM   29  H3  UNL     1      -5.267  -2.075   1.886  1.00  0.00           H  
HETATM   30  H4  UNL     1      -3.320   1.326   2.433  1.00  0.00           H  
HETATM   31  H5  UNL     1      -4.114   0.062   3.482  1.00  0.00           H  
HETATM   32  H6  UNL     1      -5.067   1.062   2.275  1.00  0.00           H  
HETATM   33  H7  UNL     1      -5.135  -1.085  -0.305  1.00  0.00           H  
HETATM   34  H8  UNL     1      -5.648   0.346   0.607  1.00  0.00           H  
HETATM   35  H9  UNL     1      -3.796   1.668  -0.147  1.00  0.00           H  
HETATM   36  H10 UNL     1      -4.798   1.123  -1.505  1.00  0.00           H  
HETATM   37  H11 UNL     1      -1.592   1.955  -1.570  1.00  0.00           H  
HETATM   38  H12 UNL     1      -1.468   0.717  -2.915  1.00  0.00           H  
HETATM   39  H13 UNL     1      -2.961   1.731  -2.794  1.00  0.00           H  
HETATM   40  H14 UNL     1      -2.096  -1.625  -2.171  1.00  0.00           H  
HETATM   41  H15 UNL     1      -3.244  -0.772  -3.220  1.00  0.00           H  
HETATM   42  H16 UNL     1      -3.848  -1.673  -1.774  1.00  0.00           H  
HETATM   43  H17 UNL     1      -0.185   0.189  -1.371  1.00  0.00           H  
HETATM   44  H18 UNL     1       2.285  -0.569   1.344  1.00  0.00           H  
HETATM   45  H19 UNL     1       4.134  -1.202   1.146  1.00  0.00           H  
HETATM   46  H20 UNL     1       6.603  -1.199   1.158  1.00  0.00           H  
HETATM   47  H21 UNL     1       8.556  -0.599   1.327  1.00  0.00           H  
HETATM   48  H22 UNL     1       6.635   1.074  -2.419  1.00  0.00           H  
HETATM   49  H23 UNL     1       4.140   1.075  -2.427  1.00  0.00           H  
HETATM   50  H24 UNL     1       0.444  -0.923   2.717  1.00  0.00           H  
HETATM   51  H25 UNL     1      -1.948  -0.992   3.087  1.00  0.00           H  
CONECT    1    2   27   28   29
CONECT    2    3    4   26
CONECT    3   30   31   32
CONECT    4    5   33   34
CONECT    5    6   35   36
CONECT    6    7    8    9
CONECT    7   37   38   39
CONECT    8   40   41   42
CONECT    9   10   10   26
CONECT   10   11   43
CONECT   11   12   24   24
CONECT   12   13   44
CONECT   13   14   14   15
CONECT   15   16   16   23
CONECT   16   17   45
CONECT   17   18   18   46
CONECT   18   19   22
CONECT   19   20   20   21
CONECT   21   47
CONECT   22   23   23   48
CONECT   23   49
CONECT   24   25   50
CONECT   25   26   26   51
END

HMDB0015605
     RDKit          3D
Tamibarotene
 51 53  0  0  0  0  0  0  0  0999 V2000
   -4.1651   -1.9069    1.8771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8721   -0.5066    1.3789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1153    0.5304    2.4765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7387   -0.1916    0.2084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0865    0.7822   -0.7553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8134    0.2090   -1.3218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1645    1.2488   -2.2022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0440   -1.0194   -2.1559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9316   -0.1167   -0.1576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5475   -0.0730   -0.3855 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3294   -0.3562    0.6216 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7240   -0.3316    0.4636 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4870   -0.0378   -0.6660 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9593    0.2709   -1.7793 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9607   -0.0694   -0.6274 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6761   -0.6931    0.3560 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0781   -0.6916    0.3583 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7957   -0.0606   -0.6321 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2453   -0.0606   -0.6273 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8862    0.5116   -1.5254 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9160   -0.7024    0.3850 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0642    0.5734   -1.6321 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6884    0.5721   -1.6344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1991   -0.6883    1.8769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5519   -0.7291    2.0925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4160   -0.4419    1.0701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6869   -2.6144    1.1688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7880   -2.0445    2.9245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2675   -2.0747    1.8862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3200    1.3260    2.4332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1144    0.0616    3.4815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0669    1.0625    2.2754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1354   -1.0849   -0.3047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6476    0.3464    0.6072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7956    1.6684   -0.1473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7977    1.1227   -1.5046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5917    1.9546   -1.5697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4680    0.7171   -2.9147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9612    1.7310   -2.7944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0957   -1.6251   -2.1708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2444   -0.7721   -3.2203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8478   -1.6734   -1.7740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1851    0.1886   -1.3714 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2852   -0.5694    1.3440 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1339   -1.2023    1.1455 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6032   -1.1991    1.1584 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5559   -0.5992    1.3269 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6349    1.0744   -2.4187 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1396    1.0745   -2.4269 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4444   -0.9234    2.7168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9481   -0.9924    3.0865 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  6  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 18 22  1  0
 22 23  2  0
 11 24  2  0
 24 25  1  0
 25 26  2  0
 26  2  1  0
 26  9  1  0
 23 15  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  3 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  5 35  1  0
  5 36  1  0
  7 37  1  0
  7 38  1  0
  7 39  1  0
  8 40  1  0
  8 41  1  0
  8 42  1  0
 10 43  1  0
 12 44  1  0
 16 45  1  0
 17 46  1  0
 21 47  1  0
 22 48  1  0
 23 49  1  0
 24 50  1  0
 25 51  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Am 80	ChEBI
Am-80	ChEBI
Amnoid	ChEBI
Retinobenzoic acid	ChEBI
Tamibaro	ChEBI
Retinobenzoate	Generator
4-((5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)carbamoyl)benzoic acid	HMDB

Chemical Formula

C₂₂H₂₅NO₃

Average Molecular Weight

351.4388

Monoisotopic Molecular Weight

351.183443671

IUPAC Name

4-[(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)carbamoyl]benzoic acid

Traditional Name

tamibarotene

CAS Registry Number

94497-51-5

SMILES

CC1(C)CCC(C)(C)C2=C1C=CC(NC(=O)C1=CC=C(C=C1)C(O)=O)=C2

InChI Identifier

InChI=1S/C22H25NO3/c1-21(2)11-12-22(3,4)18-13-16(9-10-17(18)21)23-19(24)14-5-7-15(8-6-14)20(25)26/h5-10,13H,11-12H2,1-4H3,(H,23,24)(H,25,26)

InChI Key

MUTNCGKQJGXKEM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetralins. These are polycyclic aromatic compounds containing a tetralin moiety, which consists of a benzene fused to a cyclohexane.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Tetralins

Sub Class

Not Available

Direct Parent

Tetralins

Alternative Parents

Substituents

Tetralin
Benzamide
Benzoic acid or derivatives
Benzoic acid
Benzoyl
Monocyclic benzene moiety
Secondary carboxylic acid amide
Carboxamide group
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

retinoid (CHEBI:32181 )
dicarboxylic acid monoamide (CHEBI:32181 )
tetralins (CHEBI:32181 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0015605)

Source

Exogenous

Exogenous (HMDB: HMDB0015605)

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	0.00058 g/L	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00058 g/L	ALOGPS
logP	4.99	ALOGPS
logP	5.35	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	3.69	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.4 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	104.38 m³·mol⁻¹	ChemAxon
Polarizability	39.16 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	185.664	31661259
DarkChem	[M-H]-	184.173	31661259
DeepCCS	[M+H]+	193.619	30932474
DeepCCS	[M-H]-	191.261	30932474
DeepCCS	[M-2H]-	225.2	30932474
DeepCCS	[M+Na]+	200.526	30932474
AllCCS	[M+H]+	187.7	32859911
AllCCS	[M+H-H2O]+	184.9	32859911
AllCCS	[M+NH4]+	190.3	32859911
AllCCS	[M+Na]+	191.0	32859911
AllCCS	[M-H]-	191.0	32859911
AllCCS	[M+Na-2H]-	190.8	32859911
AllCCS	[M+HCOO]-	190.8	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	7.86 minutes	32390414
Predicted by Siyang on May 30, 2022	16.3145 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.28 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	27.3 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2695.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	369.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	189.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	181.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	129.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	715.2 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	858.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	83.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1322.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	573.1 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1630.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	440.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	472.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	238.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	250.2 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	9.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Tamibarotene	CC1(C)CCC(C)(C)C2=C1C=CC(NC(=O)C1=CC=C(C=C1)C(O)=O)=C2	4335.3	Standard polar	33892256
Tamibarotene	CC1(C)CCC(C)(C)C2=C1C=CC(NC(=O)C1=CC=C(C=C1)C(O)=O)=C2	3067.5	Standard non polar	33892256
Tamibarotene	CC1(C)CCC(C)(C)C2=C1C=CC(NC(=O)C1=CC=C(C=C1)C(O)=O)=C2	3375.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Tamibarotene,1TMS,isomer #1	CC1(C)CCC(C)(C)C2=CC(NC(=O)C3=CC=C(C(=O)O[Si](C)(C)C)C=C3)=CC=C21	3310.1	Semi standard non polar	33892256
Tamibarotene,1TMS,isomer #2	CC1(C)CCC(C)(C)C2=CC(N(C(=O)C3=CC=C(C(=O)O)C=C3)[Si](C)(C)C)=CC=C21	3170.3	Semi standard non polar	33892256
Tamibarotene,2TMS,isomer #1	CC1(C)CCC(C)(C)C2=CC(N(C(=O)C3=CC=C(C(=O)O[Si](C)(C)C)C=C3)[Si](C)(C)C)=CC=C21	2978.9	Semi standard non polar	33892256
Tamibarotene,2TMS,isomer #1	CC1(C)CCC(C)(C)C2=CC(N(C(=O)C3=CC=C(C(=O)O[Si](C)(C)C)C=C3)[Si](C)(C)C)=CC=C21	2980.7	Standard non polar	33892256
Tamibarotene,2TMS,isomer #1	CC1(C)CCC(C)(C)C2=CC(N(C(=O)C3=CC=C(C(=O)O[Si](C)(C)C)C=C3)[Si](C)(C)C)=CC=C21	2941.7	Standard polar	33892256
Tamibarotene,1TBDMS,isomer #1	CC1(C)CCC(C)(C)C2=CC(NC(=O)C3=CC=C(C(=O)O[Si](C)(C)C(C)(C)C)C=C3)=CC=C21	3561.9	Semi standard non polar	33892256
Tamibarotene,1TBDMS,isomer #2	CC1(C)CCC(C)(C)C2=CC(N(C(=O)C3=CC=C(C(=O)O)C=C3)[Si](C)(C)C(C)(C)C)=CC=C21	3437.6	Semi standard non polar	33892256
Tamibarotene,2TBDMS,isomer #1	CC1(C)CCC(C)(C)C2=CC(N(C(=O)C3=CC=C(C(=O)O[Si](C)(C)C(C)(C)C)C=C3)[Si](C)(C)C(C)(C)C)=CC=C21	3498.6	Semi standard non polar	33892256
Tamibarotene,2TBDMS,isomer #1	CC1(C)CCC(C)(C)C2=CC(N(C(=O)C3=CC=C(C(=O)O[Si](C)(C)C(C)(C)C)C=C3)[Si](C)(C)C(C)(C)C)=CC=C21	3400.9	Standard non polar	33892256
Tamibarotene,2TBDMS,isomer #1	CC1(C)CCC(C)(C)C2=CC(N(C(=O)C3=CC=C(C(=O)O[Si](C)(C)C(C)(C)C)C=C3)[Si](C)(C)C(C)(C)C)=CC=C21	3184.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Tamibarotene GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-0926000000-4e20d564460f24f3bee6	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tamibarotene GC-MS (1 TMS) - 70eV, Positive	splash10-00di-3195400000-2f9ea0b192db22b23e34	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tamibarotene 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 - Tamibarotene 10V, Positive-QTOF	splash10-0ue9-0009000000-dbfed4dced06a8666457	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tamibarotene 20V, Positive-QTOF	splash10-053r-1239000000-eb277707477e13926eb0	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tamibarotene 40V, Positive-QTOF	splash10-0kii-4930000000-87f3d164d219001d818b	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tamibarotene 10V, Negative-QTOF	splash10-0udi-0009000000-8077c73aa7a0b3a0493f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tamibarotene 20V, Negative-QTOF	splash10-0pb9-1119000000-0596ca0316feae6135e6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tamibarotene 40V, Negative-QTOF	splash10-00bc-9621000000-472a8ced02b76b7e0310	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tamibarotene 10V, Positive-QTOF	splash10-0udi-0019000000-d9e09ce3c5ade8ebd024	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tamibarotene 20V, Positive-QTOF	splash10-0gwb-0369000000-6c232cbaf08e18c9b277	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tamibarotene 40V, Positive-QTOF	splash10-0a4j-3921000000-fbd8a12bd61c31548a10	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tamibarotene 10V, Negative-QTOF	splash10-0udi-0009000000-3ef35313b76eb3af9c7e	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tamibarotene 20V, Negative-QTOF	splash10-0udi-0009000000-986ece158863bf5eb6b0	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tamibarotene 40V, Negative-QTOF	splash10-001i-2090000000-faa1fb3b6d57e52a9c4c	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

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 DB04942	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB04942	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB04942

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

97231

KEGG Compound ID

C12864

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Tamibarotene

METLIN ID

Not Available

PubChem Compound

108143

PDB ID

A80

ChEBI ID

32181

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

Miwako I, Kagechika H: Tamibarotene. Drugs Today (Barc). 2007 Aug;43(8):563-8. [PubMed:17925887 ]
Sanda T, Kuwano T, Nakao S, Iida S, Ishida T, Komatsu H, Shudo K, Kuwano M, Ono M, Ueda R: Antimyeloma effects of a novel synthetic retinoid Am80 (Tamibarotene) through inhibition of angiogenesis. Leukemia. 2005 Jun;19(6):901-9. [PubMed:15843826 ]
Authors unspecified: Tamibarotene: AM 80, retinobenzoic acid, Tamibaro. Drugs R D. 2004;5(6):359-62. [PubMed:15563242 ]
Mizojiri K, Okabe H, Sugeno K, Misaki A, Ito M, Kominami G, Esumi Y, Takaichi M, Harada T, Seki H, Inaba A: Studies on the metabolism and disposition of the new retinoid 4-[(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)carbamoyl] benzoic acid. 4th communication: absorption, metabolism, excretion and plasma protein binding in various animals and man. Arzneimittelforschung. 1997 Mar;47(3):259-69. [PubMed:9105544 ]
Takeuchi M: [Clinical experience with a new synthetic retinoid, tamibarotene (Am-80) for relapsed or refractory acute promyelocytic leukemia]. Gan To Kagaku Ryoho. 2006 Mar;33(3):397-401. [PubMed:16531727 ]

Enzymes

Enzyme Details

1. Retinoic acid receptor alpha

General function:: Involved in sequence-specific DNA binding transcription factor activity
Specific function:: This is a receptor for retinoic acid. Retinoic acid has profound effects on vertebrate development, is a morphogen and is a powerful teratogen. This receptor controls cell function by directly regulating gene expression. Regulates expression of target genes in a ligand-dependent manner by recruiting chromatin complexes containing MLL5. Mediates retinoic acid-induced granulopoiesis
Gene Name:: RARA
Uniprot ID:: P10276
Molecular weight:: 50770.8

References

Miwako I, Kagechika H: Tamibarotene. Drugs Today (Barc). 2007 Aug;43(8):563-8. [PubMed:17925887 ]
Sanda T, Kuwano T, Nakao S, Iida S, Ishida T, Komatsu H, Shudo K, Kuwano M, Ono M, Ueda R: Antimyeloma effects of a novel synthetic retinoid Am80 (Tamibarotene) through inhibition of angiogenesis. Leukemia. 2005 Jun;19(6):901-9. [PubMed:15843826 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Jimi S, Mashima K, Matsumoto T, Hara S, Suzumiya J, Tamura K: RARalpha is a regulatory factor for Am-80-induced cell growth inhibition of hematologic malignant cells. Int J Oncol. 2007 Aug;31(2):397-404. [PubMed:17611697 ]
Authors unspecified: Tamibarotene: AM 80, retinobenzoic acid, Tamibaro. Drugs R D. 2004;5(6):359-62. [PubMed:15563242 ]

Enzyme Details

2. Retinoic acid receptor beta

General function:: Involved in sequence-specific DNA binding transcription factor activity
Specific function:: This is a receptor for retinoic acid. This metabolite has profound effects on vertebrate development. Retinoic acid is a morphogen and is a powerful teratogen. This receptor controls cell function by directly regulating gene expression
Gene Name:: RARB
Uniprot ID:: P10826
Molecular weight:: 50488.6

References

Miwako I, Kagechika H: Tamibarotene. Drugs Today (Barc). 2007 Aug;43(8):563-8. [PubMed:17925887 ]
Sanda T, Kuwano T, Nakao S, Iida S, Ishida T, Komatsu H, Shudo K, Kuwano M, Ono M, Ueda R: Antimyeloma effects of a novel synthetic retinoid Am80 (Tamibarotene) through inhibition of angiogenesis. Leukemia. 2005 Jun;19(6):901-9. [PubMed:15843826 ]
Jimi S, Mashima K, Matsumoto T, Hara S, Suzumiya J, Tamura K: RARalpha is a regulatory factor for Am-80-induced cell growth inhibition of hematologic malignant cells. Int J Oncol. 2007 Aug;31(2):397-404. [PubMed:17611697 ]
Authors unspecified: Tamibarotene: AM 80, retinobenzoic acid, Tamibaro. Drugs R D. 2004;5(6):359-62. [PubMed:15563242 ]

Showing metabocard for Tamibarotene (HMDB0015605)

MOL for HMDB0015605 (Tamibarotene)

3D MOL for HMDB0015605 (Tamibarotene)

3D SDF for HMDB0015605 (Tamibarotene)

3D-SDF for HMDB0015605 (Tamibarotene)

PDB for HMDB0015605 (Tamibarotene)

3D PDB for HMDB0015605 (Tamibarotene)

SMILES for HMDB0015605 (Tamibarotene)

INCHI for HMDB0015605 (Tamibarotene)

Structure for HMDB0015605 (Tamibarotene)

3D Structure for HMDB0015605 (Tamibarotene)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References