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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (6) Show 6 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:35 UTC

HMDB ID

HMDB0014355

Secondary Accession Numbers

HMDB14355

Metabolite Identification

Common Name

Adapalene

Description

Adapalene, also known as differine or adaferin, 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. Adapalene is an extremely weak basic (essentially neutral) compound (based on its pKa). Adapalene is a potentially toxic compound.

Structure

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

210
  Mrv0541 02231214312D          

 31 36  0  0  0  0            999 V2000
    2.4469   -3.8851    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9958    3.7168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3746    3.3417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0407   -3.4580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1604   -3.8170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4205   -3.4580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7306   -2.2632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3504   -3.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7306   -3.7078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0407   -2.6615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9076   -4.2103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1604   -2.9546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4205   -2.6615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4574   -2.8747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6604   -3.0883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6709   -2.0778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0875   -1.4944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0770   -2.5049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2906   -1.7079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3010   -0.6975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -4.0986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7177   -0.1142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0979   -0.4840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9312    0.6828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3114    0.3129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7280    0.8963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3142    1.2810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9633    1.7228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5302    2.1127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3603    2.3351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5769    3.1312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 15  1  0  0  0  0
  1 21  1  0  0  0  0
  2 31  1  0  0  0  0
  3 31  2  0  0  0  0
  4  8  1  0  0  0  0
  4  9  1  0  0  0  0
  4 10  1  0  0  0  0
  4 14  1  0  0  0  0
  5  8  1  0  0  0  0
  5 11  1  0  0  0  0
  5 12  1  0  0  0  0
  6  9  1  0  0  0  0
  6 11  1  0  0  0  0
  6 13  1  0  0  0  0
  7 10  1  0  0  0  0
  7 12  1  0  0  0  0
  7 13  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 15 18  1  0  0  0  0
 16 17  2  0  0  0  0
 17 19  1  0  0  0  0
 17 20  1  0  0  0  0
 18 19  2  0  0  0  0
 20 22  2  0  0  0  0
 20 23  1  0  0  0  0
 22 24  1  0  0  0  0
 23 25  2  0  0  0  0
 24 26  2  0  0  0  0
 24 27  1  0  0  0  0
 25 26  1  0  0  0  0
 26 28  1  0  0  0  0
 27 29  2  0  0  0  0
 28 30  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
M  END

HMDB0014355
     RDKit          3D
Adapalene
 59 64  0  0  0  0  0  0  0  0999 V2000
   -3.1806   -3.4545   -2.4438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9292   -2.3674   -1.5716 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6237   -1.9984   -1.2988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5586   -2.7085   -1.8900 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7300   -2.3176   -1.5962 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0103   -1.2643   -0.7507 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4019   -0.9066   -0.4827 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4081   -1.8518   -0.4646 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7117   -1.5438   -0.2185 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0794   -0.2388    0.0280 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4178    0.0906    0.2828 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8007    1.3913    0.5311 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1941    1.7207    0.7939 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0921    0.8415    0.8027 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5633    3.0298    1.0436 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8245    2.3629    0.5214 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5006    2.0388    0.2696 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1087    0.7464    0.0212 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7896    0.4019   -0.2327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0677   -0.6041   -0.2000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3950   -0.9558   -0.4617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4650   -0.1840    0.1594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3025    0.4600   -0.9164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4011    1.3493   -0.3658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3073    0.4791    0.4817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4693   -0.1032    1.5833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9197    1.0201    2.4145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9879    1.8133    1.5434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7700    2.4522    0.4204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8852    0.9820    0.9796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3838   -0.9998    1.0270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2730   -3.5125   -2.6243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7553   -4.3993   -2.0451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6548   -3.1981   -3.4057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7988   -3.5356   -2.5536 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5715   -2.8555   -2.0452 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0682   -2.8800   -0.6658 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4447   -2.3348   -0.2201 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1730   -0.6824    0.2873 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0947    3.4891    0.2903 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1410    3.3786    0.7179 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7556    2.8208    0.2682 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0481    1.1946   -0.2320 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1682    0.2153    0.4561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6697    1.1347   -1.5495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7608   -0.3121   -1.5341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9943    1.6993   -1.2161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6594   -0.3577   -0.1859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1475    1.0262    0.9201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1259   -0.7686    2.2144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7741    1.6834    2.6706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4376    0.6944    3.3478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5888    2.6364    2.1599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0050    2.9280   -0.2538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4677    3.2198    0.7592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2823    1.6204    0.3290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2592    0.6071    1.8156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8770   -1.4661    1.8940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9202   -1.7264    0.3906 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 12 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
  6 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 28 30  1  0
 26 31  1  0
 21  3  1  0
 30 22  1  0
 19  7  1  0
 31 22  1  0
 18 10  1  0
 29 24  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  4 35  1  0
  5 36  1  0
  8 37  1  0
  9 38  1  0
 11 39  1  0
 15 40  1  0
 16 41  1  0
 17 42  1  0
 19 43  1  0
 20 44  1  0
 23 45  1  0
 23 46  1  0
 24 47  1  0
 25 48  1  0
 25 49  1  0
 26 50  1  0
 27 51  1  0
 27 52  1  0
 28 53  1  0
 29 54  1  0
 29 55  1  0
 30 56  1  0
 30 57  1  0
 31 58  1  0
 31 59  1  0
M  END

210
  Mrv0541 02231214312D          

 31 36  0  0  0  0            999 V2000
    2.4469   -3.8851    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9958    3.7168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3746    3.3417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0407   -3.4580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1604   -3.8170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4205   -3.4580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7306   -2.2632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3504   -3.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7306   -3.7078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0407   -2.6615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9076   -4.2103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1604   -2.9546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4205   -2.6615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4574   -2.8747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6604   -3.0883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6709   -2.0778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0875   -1.4944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0770   -2.5049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2906   -1.7079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3010   -0.6975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -4.0986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7177   -0.1142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0979   -0.4840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9312    0.6828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3114    0.3129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7280    0.8963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3142    1.2810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9633    1.7228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5302    2.1127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3603    2.3351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5769    3.1312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 15  1  0  0  0  0
  1 21  1  0  0  0  0
  2 31  1  0  0  0  0
  3 31  2  0  0  0  0
  4  8  1  0  0  0  0
  4  9  1  0  0  0  0
  4 10  1  0  0  0  0
  4 14  1  0  0  0  0
  5  8  1  0  0  0  0
  5 11  1  0  0  0  0
  5 12  1  0  0  0  0
  6  9  1  0  0  0  0
  6 11  1  0  0  0  0
  6 13  1  0  0  0  0
  7 10  1  0  0  0  0
  7 12  1  0  0  0  0
  7 13  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 15 18  1  0  0  0  0
 16 17  2  0  0  0  0
 17 19  1  0  0  0  0
 17 20  1  0  0  0  0
 18 19  2  0  0  0  0
 20 22  2  0  0  0  0
 20 23  1  0  0  0  0
 22 24  1  0  0  0  0
 23 25  2  0  0  0  0
 24 26  2  0  0  0  0
 24 27  1  0  0  0  0
 25 26  1  0  0  0  0
 26 28  1  0  0  0  0
 27 29  2  0  0  0  0
 28 30  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014355

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(C=C(C=C1)C1=CC2=C(C=C1)C=C(C=C2)C(O)=O)C12CC3CC(CC(C3)C1)C2

> <INCHI_IDENTIFIER>
InChI=1S/C28H28O3/c1-31-26-7-6-23(21-2-3-22-12-24(27(29)30)5-4-20(22)11-21)13-25(26)28-14-17-8-18(15-28)10-19(9-17)16-28/h2-7,11-13,17-19H,8-10,14-16H2,1H3,(H,29,30)

> <INCHI_KEY>
LZCDAPDGXCYOEH-UHFFFAOYSA-N

> <FORMULA>
C28H28O3

> <MOLECULAR_WEIGHT>
412.5201

> <EXACT_MASS>
412.203844762

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
47.65154823585963

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-[3-(adamantan-1-yl)-4-methoxyphenyl]naphthalene-2-carboxylic acid

> <ALOGPS_LOGP>
6.06

> <JCHEM_LOGP>
6.458501423666666

> <ALOGPS_LOGS>
-8.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.9892612421177724

> <JCHEM_PKA_STRONGEST_BASIC>
-4.8289204668822325

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
122.07189999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.01e-06 g/l

> <JCHEM_TRADITIONAL_IUPAC>
differin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014355
     RDKit          3D
Adapalene
 59 64  0  0  0  0  0  0  0  0999 V2000
   -3.1806   -3.4545   -2.4438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9292   -2.3674   -1.5716 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6237   -1.9984   -1.2988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5586   -2.7085   -1.8900 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7300   -2.3176   -1.5962 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0103   -1.2643   -0.7507 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4019   -0.9066   -0.4827 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4081   -1.8518   -0.4646 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7117   -1.5438   -0.2185 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0794   -0.2388    0.0280 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4178    0.0906    0.2828 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8007    1.3913    0.5311 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1941    1.7207    0.7939 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0921    0.8415    0.8027 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5633    3.0298    1.0436 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8245    2.3629    0.5214 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5006    2.0388    0.2696 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1087    0.7464    0.0212 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7896    0.4019   -0.2327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0677   -0.6041   -0.2000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3950   -0.9558   -0.4617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4650   -0.1840    0.1594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3025    0.4600   -0.9164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4011    1.3493   -0.3658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3073    0.4791    0.4817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4693   -0.1032    1.5833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9197    1.0201    2.4145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9879    1.8133    1.5434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7700    2.4522    0.4204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8852    0.9820    0.9796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3838   -0.9998    1.0270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2730   -3.5125   -2.6243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7553   -4.3993   -2.0451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6548   -3.1981   -3.4057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7988   -3.5356   -2.5536 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5715   -2.8555   -2.0452 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0682   -2.8800   -0.6658 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4447   -2.3348   -0.2201 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1730   -0.6824    0.2873 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0947    3.4891    0.2903 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1410    3.3786    0.7179 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7556    2.8208    0.2682 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0481    1.1946   -0.2320 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1682    0.2153    0.4561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6697    1.1347   -1.5495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7608   -0.3121   -1.5341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9943    1.6993   -1.2161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6594   -0.3577   -0.1859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1475    1.0262    0.9201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1259   -0.7686    2.2144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7741    1.6834    2.6706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4376    0.6944    3.3478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5888    2.6364    2.1599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0050    2.9280   -0.2538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4677    3.2198    0.7592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2823    1.6204    0.3290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2592    0.6071    1.8156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8770   -1.4661    1.8940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9202   -1.7264    0.3906 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 12 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
  6 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 28 30  1  0
 26 31  1  0
 21  3  1  0
 30 22  1  0
 19  7  1  0
 31 22  1  0
 18 10  1  0
 29 24  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  4 35  1  0
  5 36  1  0
  8 37  1  0
  9 38  1  0
 11 39  1  0
 15 40  1  0
 16 41  1  0
 17 42  1  0
 19 43  1  0
 20 44  1  0
 23 45  1  0
 23 46  1  0
 24 47  1  0
 25 48  1  0
 25 49  1  0
 26 50  1  0
 27 51  1  0
 27 52  1  0
 28 53  1  0
 29 54  1  0
 29 55  1  0
 30 56  1  0
 30 57  1  0
 31 58  1  0
 31 59  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 210                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       4.568  -7.252   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       5.592   6.938   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       8.166   6.238   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       7.543  -6.455   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.766  -7.125   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.118  -6.455   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.830  -4.225   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.254  -7.198   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.830  -6.921   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.543  -4.968   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.161  -7.859   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.766  -5.515   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.118  -4.968   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.454  -5.366   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.966  -5.765   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.852  -3.879   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.763  -2.790   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.877  -4.676   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.276  -3.188   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.162  -1.302   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.080  -7.651   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.073  -0.213   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.649  -0.903   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.472   1.275   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.048   0.584   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.959   1.673   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.320   2.391   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.398   3.216   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.723   3.944   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.273   4.359   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.677   5.845   0.000  0.00  0.00           C+0
CONECT    1   15   21                                                       
CONECT    2   31                                                            
CONECT    3   31                                                            
CONECT    4    8    9   10   14                                             
CONECT    5    8   11   12                                                  
CONECT    6    9   11   13                                                  
CONECT    7   10   12   13                                                  
CONECT    8    4    5                                                       
CONECT    9    4    6                                                       
CONECT   10    4    7                                                       
CONECT   11    5    6                                                       
CONECT   12    5    7                                                       
CONECT   13    6    7                                                       
CONECT   14    4   15   16                                                  
CONECT   15    1   14   18                                                  
CONECT   16   14   17                                                       
CONECT   17   16   19   20                                                  
CONECT   18   15   19                                                       
CONECT   19   17   18                                                       
CONECT   20   17   22   23                                                  
CONECT   21    1                                                            
CONECT   22   20   24                                                       
CONECT   23   20   25                                                       
CONECT   24   22   26   27                                                  
CONECT   25   23   26                                                       
CONECT   26   24   25   28                                                  
CONECT   27   24   29                                                       
CONECT   28   26   30                                                       
CONECT   29   27   30                                                       
CONECT   30   28   29   31                                                  
CONECT   31    2    3   30                                                  
MASTER        0    0    0    0    0    0    0    0   31    0   72    0
END

COMPND    HMDB0014355
HETATM    1  C1  UNL     1      -3.181  -3.454  -2.444  1.00  0.00           C  
HETATM    2  O1  UNL     1      -2.929  -2.367  -1.572  1.00  0.00           O  
HETATM    3  C2  UNL     1      -1.624  -1.998  -1.299  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.559  -2.709  -1.890  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.730  -2.318  -1.596  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.010  -1.264  -0.751  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.402  -0.907  -0.483  1.00  0.00           C  
HETATM    8  C7  UNL     1       3.408  -1.852  -0.465  1.00  0.00           C  
HETATM    9  C8  UNL     1       4.712  -1.544  -0.218  1.00  0.00           C  
HETATM   10  C9  UNL     1       5.079  -0.239   0.028  1.00  0.00           C  
HETATM   11  C10 UNL     1       6.418   0.091   0.283  1.00  0.00           C  
HETATM   12  C11 UNL     1       6.801   1.391   0.531  1.00  0.00           C  
HETATM   13  C12 UNL     1       8.194   1.721   0.794  1.00  0.00           C  
HETATM   14  O2  UNL     1       9.092   0.842   0.803  1.00  0.00           O  
HETATM   15  O3  UNL     1       8.563   3.030   1.044  1.00  0.00           O  
HETATM   16  C13 UNL     1       5.825   2.363   0.521  1.00  0.00           C  
HETATM   17  C14 UNL     1       4.501   2.039   0.270  1.00  0.00           C  
HETATM   18  C15 UNL     1       4.109   0.746   0.021  1.00  0.00           C  
HETATM   19  C16 UNL     1       2.790   0.402  -0.233  1.00  0.00           C  
HETATM   20  C17 UNL     1      -0.068  -0.604  -0.200  1.00  0.00           C  
HETATM   21  C18 UNL     1      -1.395  -0.956  -0.462  1.00  0.00           C  
HETATM   22  C19 UNL     1      -2.465  -0.184   0.159  1.00  0.00           C  
HETATM   23  C20 UNL     1      -3.302   0.460  -0.916  1.00  0.00           C  
HETATM   24  C21 UNL     1      -4.401   1.349  -0.366  1.00  0.00           C  
HETATM   25  C22 UNL     1      -5.307   0.479   0.482  1.00  0.00           C  
HETATM   26  C23 UNL     1      -4.469  -0.103   1.583  1.00  0.00           C  
HETATM   27  C24 UNL     1      -3.920   1.020   2.415  1.00  0.00           C  
HETATM   28  C25 UNL     1      -2.988   1.813   1.543  1.00  0.00           C  
HETATM   29  C26 UNL     1      -3.770   2.452   0.420  1.00  0.00           C  
HETATM   30  C27 UNL     1      -1.885   0.982   0.980  1.00  0.00           C  
HETATM   31  C28 UNL     1      -3.384  -1.000   1.027  1.00  0.00           C  
HETATM   32  H1  UNL     1      -4.273  -3.512  -2.624  1.00  0.00           H  
HETATM   33  H2  UNL     1      -2.755  -4.399  -2.045  1.00  0.00           H  
HETATM   34  H3  UNL     1      -2.655  -3.198  -3.406  1.00  0.00           H  
HETATM   35  H4  UNL     1      -0.799  -3.536  -2.554  1.00  0.00           H  
HETATM   36  H5  UNL     1       1.572  -2.855  -2.045  1.00  0.00           H  
HETATM   37  H6  UNL     1       3.068  -2.880  -0.666  1.00  0.00           H  
HETATM   38  H7  UNL     1       5.445  -2.335  -0.220  1.00  0.00           H  
HETATM   39  H8  UNL     1       7.173  -0.682   0.287  1.00  0.00           H  
HETATM   40  H9  UNL     1       9.095   3.489   0.290  1.00  0.00           H  
HETATM   41  H10 UNL     1       6.141   3.379   0.718  1.00  0.00           H  
HETATM   42  H11 UNL     1       3.756   2.821   0.268  1.00  0.00           H  
HETATM   43  H12 UNL     1       2.048   1.195  -0.232  1.00  0.00           H  
HETATM   44  H13 UNL     1       0.168   0.215   0.456  1.00  0.00           H  
HETATM   45  H14 UNL     1      -2.670   1.135  -1.549  1.00  0.00           H  
HETATM   46  H15 UNL     1      -3.761  -0.312  -1.534  1.00  0.00           H  
HETATM   47  H16 UNL     1      -4.994   1.699  -1.216  1.00  0.00           H  
HETATM   48  H17 UNL     1      -5.659  -0.358  -0.186  1.00  0.00           H  
HETATM   49  H18 UNL     1      -6.148   1.026   0.920  1.00  0.00           H  
HETATM   50  H19 UNL     1      -5.126  -0.769   2.214  1.00  0.00           H  
HETATM   51  H20 UNL     1      -4.774   1.683   2.671  1.00  0.00           H  
HETATM   52  H21 UNL     1      -3.438   0.694   3.348  1.00  0.00           H  
HETATM   53  H22 UNL     1      -2.589   2.636   2.160  1.00  0.00           H  
HETATM   54  H23 UNL     1      -3.005   2.928  -0.254  1.00  0.00           H  
HETATM   55  H24 UNL     1      -4.468   3.220   0.759  1.00  0.00           H  
HETATM   56  H25 UNL     1      -1.282   1.620   0.329  1.00  0.00           H  
HETATM   57  H26 UNL     1      -1.259   0.607   1.816  1.00  0.00           H  
HETATM   58  H27 UNL     1      -2.877  -1.466   1.894  1.00  0.00           H  
HETATM   59  H28 UNL     1      -3.920  -1.726   0.391  1.00  0.00           H  
CONECT    1    2   32   33   34
CONECT    2    3
CONECT    3    4    4   21
CONECT    4    5   35
CONECT    5    6    6   36
CONECT    6    7   20
CONECT    7    8    8   19
CONECT    8    9   37
CONECT    9   10   10   38
CONECT   10   11   18
CONECT   11   12   12   39
CONECT   12   13   16
CONECT   13   14   14   15
CONECT   15   40
CONECT   16   17   17   41
CONECT   17   18   42
CONECT   18   19   19
CONECT   19   43
CONECT   20   21   21   44
CONECT   21   22
CONECT   22   23   30   31
CONECT   23   24   45   46
CONECT   24   25   29   47
CONECT   25   26   48   49
CONECT   26   27   31   50
CONECT   27   28   51   52
CONECT   28   29   30   53
CONECT   29   54   55
CONECT   30   56   57
CONECT   31   58   59
END

HMDB0014355
     RDKit          3D
Adapalene
 59 64  0  0  0  0  0  0  0  0999 V2000
   -3.1806   -3.4545   -2.4438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9292   -2.3674   -1.5716 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6237   -1.9984   -1.2988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5586   -2.7085   -1.8900 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7300   -2.3176   -1.5962 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0103   -1.2643   -0.7507 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4019   -0.9066   -0.4827 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4081   -1.8518   -0.4646 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7117   -1.5438   -0.2185 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0794   -0.2388    0.0280 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4178    0.0906    0.2828 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8007    1.3913    0.5311 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1941    1.7207    0.7939 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0921    0.8415    0.8027 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5633    3.0298    1.0436 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8245    2.3629    0.5214 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5006    2.0388    0.2696 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1087    0.7464    0.0212 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7896    0.4019   -0.2327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0677   -0.6041   -0.2000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3950   -0.9558   -0.4617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4650   -0.1840    0.1594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3025    0.4600   -0.9164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4011    1.3493   -0.3658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3073    0.4791    0.4817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4693   -0.1032    1.5833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9197    1.0201    2.4145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9879    1.8133    1.5434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7700    2.4522    0.4204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8852    0.9820    0.9796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3838   -0.9998    1.0270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2730   -3.5125   -2.6243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7553   -4.3993   -2.0451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6548   -3.1981   -3.4057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7988   -3.5356   -2.5536 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5715   -2.8555   -2.0452 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0682   -2.8800   -0.6658 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4447   -2.3348   -0.2201 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1730   -0.6824    0.2873 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0947    3.4891    0.2903 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1410    3.3786    0.7179 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7556    2.8208    0.2682 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0481    1.1946   -0.2320 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1682    0.2153    0.4561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6697    1.1347   -1.5495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7608   -0.3121   -1.5341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9943    1.6993   -1.2161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6594   -0.3577   -0.1859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1475    1.0262    0.9201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1259   -0.7686    2.2144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7741    1.6834    2.6706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4376    0.6944    3.3478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5888    2.6364    2.1599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0050    2.9280   -0.2538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4677    3.2198    0.7592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2823    1.6204    0.3290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2592    0.6071    1.8156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8770   -1.4661    1.8940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9202   -1.7264    0.3906 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 12 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
  6 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 28 30  1  0
 26 31  1  0
 21  3  1  0
 30 22  1  0
 19  7  1  0
 31 22  1  0
 18 10  1  0
 29 24  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  4 35  1  0
  5 36  1  0
  8 37  1  0
  9 38  1  0
 11 39  1  0
 15 40  1  0
 16 41  1  0
 17 42  1  0
 19 43  1  0
 20 44  1  0
 23 45  1  0
 23 46  1  0
 24 47  1  0
 25 48  1  0
 25 49  1  0
 26 50  1  0
 27 51  1  0
 27 52  1  0
 28 53  1  0
 29 54  1  0
 29 55  1  0
 30 56  1  0
 30 57  1  0
 31 58  1  0
 31 59  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
6-(3-(1-Adamantyl)-4-methoxyphenyl)-2-naphthoic acid	ChEBI
Adaferin	ChEBI
Adapaleno	ChEBI
Adapalenum	ChEBI
Differine	ChEBI
Differin	Kegg
6-(3-(1-Adamantyl)-4-methoxyphenyl)-2-naphthoate	Generator
271, CD	HMDB

Chemical Formula

C₂₈H₂₈O₃

Average Molecular Weight

412.5201

Monoisotopic Molecular Weight

412.203844762

IUPAC Name

6-[3-(adamantan-1-yl)-4-methoxyphenyl]naphthalene-2-carboxylic acid

Traditional Name

differin

CAS Registry Number

106685-40-9

SMILES

COC1=C(C=C(C=C1)C1=CC2=C(C=C1)C=C(C=C2)C(O)=O)C12CC3CC(CC(C3)C1)C2

InChI Identifier

InChI=1S/C28H28O3/c1-31-26-7-6-23(21-2-3-22-12-24(27(29)30)5-4-20(22)11-21)13-25(26)28-14-17-8-18(15-28)10-19(9-17)16-28/h2-7,11-13,17-19H,8-10,14-16H2,1H3,(H,29,30)

InChI Key

LZCDAPDGXCYOEH-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

Adapalene
Phenylnaphthalene
2-naphthalenecarboxylic acid
2-naphthalenecarboxylic acid or derivatives
Naphthalene
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Monocarboxylic acid or derivatives
Ether
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

monocarboxylic acid (CHEBI:31174 )
adamantanes (CHEBI:31174 )

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

Source

Exogenous

Exogenous (HMDB: HMDB0014355)

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	4.0e-06 g/L	Not Available
LogP	8.6	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	4.0e-06 g/L	ALOGPS
logP	6.06	ALOGPS
logP	6.46	ChemAxon
logS	-8	ALOGPS
pKa (Strongest Acidic)	3.99	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	122.07 m³·mol⁻¹	ChemAxon
Polarizability	47.65 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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]+	197.057	31661259
DarkChem	[M-H]-	198.097	31661259
DeepCCS	[M-2H]-	230.742	30932474
DeepCCS	[M+Na]+	205.788	30932474
AllCCS	[M+H]+	205.6	32859911
AllCCS	[M+H-H2O]+	203.2	32859911
AllCCS	[M+NH4]+	207.9	32859911
AllCCS	[M+Na]+	208.5	32859911
AllCCS	[M-H]-	207.5	32859911
AllCCS	[M+Na-2H]-	207.7	32859911
AllCCS	[M+HCOO]-	208.1	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.	9.22 minutes	32390414
Predicted by Siyang on May 30, 2022	21.3146 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.63 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2862.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	585.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	298.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	271.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	569.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	934.9 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	866.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	116.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1719.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	696.6 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	1845.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	548.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	525.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	362.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	384.9 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	16.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Adapalene	COC1=C(C=C(C=C1)C1=CC2=C(C=C1)C=C(C=C2)C(O)=O)C12CC3CC(CC(C3)C1)C2	4687.6	Standard polar	33892256
Adapalene	COC1=C(C=C(C=C1)C1=CC2=C(C=C1)C=C(C=C2)C(O)=O)C12CC3CC(CC(C3)C1)C2	3536.6	Standard non polar	33892256
Adapalene	COC1=C(C=C(C=C1)C1=CC2=C(C=C1)C=C(C=C2)C(O)=O)C12CC3CC(CC(C3)C1)C2	4047.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Adapalene,1TMS,isomer #1	COC1=CC=C(C2=CC=C3C=C(C(=O)O[Si](C)(C)C)C=CC3=C2)C=C1C12CC3CC(CC(C3)C1)C2	3947.3	Semi standard non polar	33892256
Adapalene,1TBDMS,isomer #1	COC1=CC=C(C2=CC=C3C=C(C(=O)O[Si](C)(C)C(C)(C)C)C=CC3=C2)C=C1C12CC3CC(CC(C3)C1)C2	4185.5	Semi standard non polar	33892256

Spectra

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 DB00210	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00210	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00210

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

54244

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Adapalene

METLIN ID

Not Available

PubChem Compound

60164

PDB ID

Not Available

ChEBI ID

31174

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

Rolewski SL: Clinical review: topical retinoids. Dermatol Nurs. 2003 Oct;15(5):447-50, 459-65. [PubMed:14619325 ]
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. Retinoic acid receptor gamma

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:: RARG
Uniprot ID:: P13631
Molecular weight:: 50341.4

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 ]
Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]

Enzyme Details

2. 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

Shroot B, Michel S: Pharmacology and chemistry of adapalene. J Am Acad Dermatol. 1997 Jun;36(6 Pt 2):S96-103. [PubMed:9204085 ]
Griffiths CE, Ancian P, Humphries J, Poncet M, Rizova E, Michel S, Clucas A: Adapalene 0.1% gel and adapalene 0.1% cream stimulate retinoic acid receptor mediated gene transcription without significant irritative effects in the skin of healthy human volunteers. Br J Dermatol. 1998 Oct;139 Suppl 52:12-6. [PubMed:9990415 ]
Michel S, Jomard A, Demarchez M: Pharmacology of adapalene. Br J Dermatol. 1998 Oct;139 Suppl 52:3-7. [PubMed:9990413 ]
Shroot B, Michel S, Allec J, Chatelus A, Wagner N: A new concept of drug delivery for acne. Dermatology. 1998;196(1):165-70. [PubMed:9557255 ]
Kim MJ, Ciletti N, Michel S, Reichert U, Rosenfield RL: The role of specific retinoid receptors in sebocyte growth and differentiation in culture. J Invest Dermatol. 2000 Feb;114(2):349-53. [PubMed:10651997 ]

Enzyme Details

3. 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

Shroot B, Michel S: Pharmacology and chemistry of adapalene. J Am Acad Dermatol. 1997 Jun;36(6 Pt 2):S96-103. [PubMed:9204085 ]
Shroot B, Michel S, Allec J, Chatelus A, Wagner N: A new concept of drug delivery for acne. Dermatology. 1998;196(1):165-70. [PubMed:9557255 ]
Michel S, Jomard A, Demarchez M: Pharmacology of adapalene. Br J Dermatol. 1998 Oct;139 Suppl 52:3-7. [PubMed:9990413 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

4. 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 ]
Kim MJ, Ciletti N, Michel S, Reichert U, Rosenfield RL: The role of specific retinoid receptors in sebocyte growth and differentiation in culture. J Invest Dermatol. 2000 Feb;114(2):349-53. [PubMed:10651997 ]

Enzyme Details

5. 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

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 ]
Kim MJ, Ciletti N, Michel S, Reichert U, Rosenfield RL: The role of specific retinoid receptors in sebocyte growth and differentiation in culture. J Invest Dermatol. 2000 Feb;114(2):349-53. [PubMed:10651997 ]

Enzyme Details

6. 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

Bernard BA: Adapalene, a new chemical entity with retinoid activity. Skin Pharmacol. 1993;6 Suppl 1:61-9. [PubMed:8142113 ]
Kim MJ, Ciletti N, Michel S, Reichert U, Rosenfield RL: The role of specific retinoid receptors in sebocyte growth and differentiation in culture. J Invest Dermatol. 2000 Feb;114(2):349-53. [PubMed:10651997 ]

Showing metabocard for Adapalene (HMDB0014355)

MOL for HMDB0014355 (Adapalene)

3D MOL for HMDB0014355 (Adapalene)

3D SDF for HMDB0014355 (Adapalene)

3D-SDF for HMDB0014355 (Adapalene)

PDB for HMDB0014355 (Adapalene)

3D PDB for HMDB0014355 (Adapalene)

SMILES for HMDB0014355 (Adapalene)

INCHI for HMDB0014355 (Adapalene)

Structure for HMDB0014355 (Adapalene)

3D Structure for HMDB0014355 (Adapalene)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

Enzymes

References

References

References

References

References

References