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9-cis-Retinoic acid

CAT: 1568-C01809Size: 5 mgDry Ice: NoHazardous: No
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CAS Number
5300-03-8
Synonyms
Alitretinoin, ALRT 1057
SKU
C01809-5mg
Target
Retinoid Receptor
Applications
Metabolism
Additionnal Information
9-cis-Retinoic acid (Alitretinoin, ALRT 1057) is an active metabolite of vitamin A that functions as a high-affinity ligand for retinoid X receptors (RXRs) and also activates retinoic acid receptors (RARs) . It inhibits adipogenesis by activating RXR while simultaneously decreasing RXRα and PPARγ levels in an RXR activation-independent manner.

Chemical Information

9-Cis-Retinoic Acid

9-cis-retinoic acid is a retinoic acid in which the exocyclic double bonds have 7E,9Z,11E,13E geometry. It has a role as a metabolite, an antineoplastic agent, a keratolytic drug and a retinoid X receptor agonist. It is a conjugate acid of a 9-cis-retinoate.

CAS Number5300-03-8
PubChem CID449171
IUPAC Name(2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoic acid
Molecular FormulaC20H28O2
Molecular Weight300.4
XLogP6.3
Topological Polar Surface Area37.3
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count5
Heavy Atom Count22
Formal Charge0
Complexity567
SMILES
CC1=C(C(CCC1)(C)C)/C=C/C(=C\C=C\C(=C\C(=O)O)\C)/C
InChI
InChI=1S/C20H28O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14H,7,10,13H2,1-5H3,(H,21,22)/b9-6+,12-11+,15-8-,16-14+
InChIKey
SHGAZHPCJJPHSC-ZVCIMWCZSA-N
Chemical Structure
2D Structure
2D structure of 9-Cis-Retinoic Acid
CAS: 5300-03-8
CID: 449171
Formula: C20H28O2
MW: 300.4
Interactive 3D Structure
Loading 3D structure...
Computed Properties
PropertyValue
Molecular Weight300.4
XLogP36.3
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count5
Exact Mass300.208930132
Monoisotopic Mass300.208930132
Topological Polar Surface Area37.3 Ų
Heavy Atom Count22
Formal Charge0
Complexity567
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count4
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes