Details of the Drug

General Information of Drug (ID: DMBN6KU)

Drug Name
PMID27336223-Compound-11
Affected Organisms
Humans and other mammals
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 1 Molecular Weight (mw) 412.5
Logarithm of the Partition Coefficient (xlogp) 7.7
Rotatable Bond Count (rotbonds) 4
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 3
ADMET Property
Absorption AUC
The area under the plot of plasma concentration (AUC) of drug is 8.37 +/- 8.46 mcgh/L [1]
Absorption Cmax
The maximum plasma concentration (Cmax) of drug is 0.553 +/- 0.466 mcg/L [1]
Elimination
Approximately 75% of the drug is excreted by the biliary route remains unchanged [2]
Half-life
The concentration or amount of drug in body reduced by one-half in 7 - 51 hours [1]
Metabolism
The drug is metabolized via the liver [3]
Chemical Identifiers
Formula
C28H28O3
IUPAC Name
6-[3-(1-adamantyl)-4-methoxyphenyl]naphthalene-2-carboxylic acid
Canonical SMILES
COC1=C(C=C(C=C1)C2=CC3=C(C=C2)C=C(C=C3)C(=O)O)C45CC6CC(C4)CC(C6)C5
InChI
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)
InChIKey
LZCDAPDGXCYOEH-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
60164
ChEBI ID
CHEBI:31174
CAS Number
106685-40-9
UNII
1L4806J2QF
DrugBank ID
DB00210
TTD ID
D0W8JK
ACDINA ID
D00808

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Retinoic acid receptor gamma (RARG) TT1Q3IE RARG_HUMAN Agonist [4]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Antigen-presenting glycoprotein CD1d (CD1D) OT3ROU4J CD1D_HUMAN Gene/Protein Processing [5]
Cellular retinoic acid-binding protein 2 (CRABP2) OTY01V9G RABP2_HUMAN Gene/Protein Processing [6]
Interleukin-10 (IL10) OTIRFRXC IL10_HUMAN Gene/Protein Processing [5]
Retinoic acid receptor gamma (RARG) OT8LHMDH RARG_HUMAN Drug Response [7]
Toll-like receptor 2 (TLR2) OTGO5P4R TLR2_HUMAN Gene/Protein Processing [5]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Retinoic acid receptor gamma (RARG) DTT RARG 1.81E-01 0.07 0.2
Retinoic acid receptor gamma (RARG) DTT RARG 1.45E-03 -0.13 -0.39
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 FDA Approved Drug Products: Differin (adapalene) gel
2 Pierard GE, Pierard-Franchimont C, Paquet P, Quatresooz P: Spotlight on adapalene. Expert Opin Drug Metab Toxicol. 2009 Dec;5(12):1565-75. doi: 10.1517/17425250903386269.
3 FDA: Pharmacology/Toxicology Review and Evaluation (adapalene)
4 Therapeutic use of selective synthetic ligands for retinoic acid receptors: a patent review.Expert Opin Ther Pat. 2016 Aug;26(8):957-71.
5 In vitro modulation of TLR-2, CD1d and IL-10 by adapalene on normal human skin and acne inflammatory lesions. Exp Dermatol. 2007 Jun;16(6):500-6. doi: 10.1111/j.1600-0625.2007.00552.x.
6 Comparison of CD271 (adapalene) and all-trans retinoic acid in human skin: dissociation of epidermal effects and CRABP-II mRNA expression. J Invest Dermatol. 1993 Sep;101(3):325-8. doi: 10.1111/1523-1747.ep12365480.
7 Pharmacology of adapalene. Br J Dermatol. 1998 Oct;139 Suppl 52:3-7. doi: 10.1046/j.1365-2133.1998.1390s2003.x.