Adapalene - Moligand™, ≥98% , Agonist of Retinoic acid receptor-αAgonist of Retinoic acid receptor-βAgonist of Retinoic acid receptor-γ, CAS No.106685-40-9, Agonist of Retinoic acid receptor-αAgonist of Retinoic acid receptor-βAgonist of Retinoic acid receptor-γ

CAS: 106685-40-9 Cat. No.: A120006 Formula: C₂₈H₂₈O₃ Molecular Weight: 412.52 EC Number: 620-513-9

GRADE & PURITY Moligand™, ≥98%

Synonyms

6-(4-Methoxy-3-tricyclo[3.3.1.13,7]dec-1-ylphenyl)-2-naphthalenecarboxylic acid | Adapaleno [INN-Spanish] | CD271 | CD-271 | STL453114 | UNII-1L4806J2QF | Adaferin | Adapaleno (INN-Spanish) | AKOS015895391 | Differine | HMS3715H16 | SR-01000942194 | Tox21

Storage

Store at 2-8°C

Shipped In

Wet ice

Overview

Adapalene is a dual RAR and RXR agonist, used in the treatment of acne.
Adapalene, a retinoic acid analogue, is a RARβ and RARγ agonist. Adapalene inhibits proliferation and induces apoptosis in colorectal cancer cells in vitro. Adapalene gel is an efficacious treatment for acne vulgaris.

Specifications

Synonyms

6-(4-Methoxy-3-tricyclo[3.3.1.13,7]dec-1-ylphenyl)-2-naphthalenecarboxylic acid | Adapaleno [INN-Spanish] | CD271 | CD-271 | STL453114 | UNII-1L4806J2QF | Adaferin | Adapaleno (INN-Spanish) | AKOS015895391 | Differine | HMS3715H16 | SR-01000942194 | Tox21

Specifications & Purity

Moligand™, ≥98%

Biochemical and Physiological Mechanisms

Retinoic acid analog that is a RARβand RARγagonist (AC50values are 2.2, 9.3, 22 and > 1000 nM for RARβ, RARγ, RARαand RXRαreceptors respectively). Inhibits proliferation and induces apoptosis in colorectal cancer cellin vitro. Displays comedolytic activit

Storage

Store at 2-8°C

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Action Type

AGONIST

Mechanism of action

Agonist of Retinoic acid receptor-αAgonist of Retinoic acid receptor-βAgonist of Retinoic acid receptor-γ

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 488183399
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488183399
• 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
• IUPAC Name: 6-[3-(1-adamantyl)-4-methoxyphenyl]naphthalene-2-carboxylic acid
• InChIKey: LZCDAPDGXCYOEH-UHFFFAOYSA-N
• 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)
• Isomeric SMILES: COC1=C(C=C(C=C1)C2=CC3=C(C=C2)C=C(C=C3)C(=O)O)C45CC6CC(C4)CC(C6)C5
• RTECS: QJ1987000
• Molecular Weight: 412.52
• Reaxy-Rn: 7393980
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=7393980&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Prenol lipids
      • Subclass Retinoids

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Prenol lipids
• Subclass: Retinoids
• Intermediate Tree Nodes: Not available
• Direct Parent: Retinoids
• Alternative Parents: Phenylnaphthalenes Naphthalenecarboxylic acids Phenoxy compounds Methoxybenzenes Anisoles Alkyl aryl ethers Monocarboxylic acids and derivatives Carboxylic acids Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homopolycyclic compounds
• 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
• Description: This compound 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.
• External Descriptors: monocarboxylic acid - adamantanes

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

RARG Tclin Retinoic acid receptor gamma (2 Activities)

Discover Target: RARG

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

RARB Tclin Retinoic acid receptor beta (4 Activities)

Discover Target: RARB

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

RARA Tclin Retinoic acid receptor alpha (2 Activities)

Discover Target: RARA

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

GLRA1 Tclin Glycine receptor subunit alpha-1 (1 Activities)

Discover Target: GLRA1

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

Chemical and Physical Properties

• Solubility: Solvent:DMSO, Max Conc. mg/mL: 10.31, Max Conc. mM: 25
• Sensitivity: Moisture &Heat sensitive
• Melt Point(°C): 301℃
• Molecular Weight: 412.500 g/mol
• XLogP3: 7.700
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 412.204 Da
• Monoisotopic Mass: 412.204 Da
• Topological Polar Surface Area: 46.500 Ų
• Heavy Atom Count: 31
• Formal Charge: 0
• Complexity: 644.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1