Common Name9-cis-retinoate
Description9-cis-Retinoic acid is an active retinoid that regulates expression of retinoid responsive genes, serving as a ligand for two classes of ligand-dependent transcription factors: the retinoic acid receptors and retinoid X receptors. Retinoids (vitamin A and its analogs) are essential dietary substances that are needed by mammals for reproduction, normal embryogenesis, growth, vision, and maintaining normal cellular differentiation and the integrity of the immune system. Within cells, retinoids regulate gene transcription acting through ligand-dependent transcription factors, the retinoic acid receptors (RARs), and the retinoid X receptors (RXRs). all-trans-Retinoic acid binds only to RARs with high affinity, whereas its 9-cis isomer binds with high affinity to both RARs and RXRs. The actions of all-trans- and 9-cis-retinoic acid in regulating cellular responses are distinct and not interchangeable (PMID: 9115228 ).
Structure
Molecular FormulaC20H28O2
Average Mass300.43510
Monoisotopic Mass300.20893
IUPAC Name(2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid
Traditional Name9-cis-retinoic acid
CAS Registry Number5300-03-08
SMILESCC1=C(/C=C/C(C)=C\C=C\C(C)=C\C(=O)[O-])C(C)(C)CCC1
InChI IdentifierInChI=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+
InChI KeySHGAZHPCJJPHSC-ZVCIMWCZSA-N
CHEBI IDCHEBI:78630
HMDB IDHMDB0002369
Pathways
NameSMPDB/PathBank
Retinol Metabolism
Vitamin A Deficiency
StateSolid
Water Solubility4.77e-03 g/l
logP5.66
logS-4.80
pKa (Strongest Acidic)5.00
pKa (Strongest Basic)Not Available
Hydrogen Acceptor Count2
Hydrogen Donor Count1
Polar Surface Area37.3 Ų
Rotatable Bond Count5
Physiological Charge-1
Formal Charge0
Refractivity97.79 m³·mol⁻¹
Polarizability35.92

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