(2E,4E,6Z,8E)-3,7-dimethyl-8-((R)-4-methyl-3,4-dihydronaphthalen-1(2H)-ylidene)octa-2,4,6-trienoic acid

ID: ALA3098773

Chembl Id: CHEMBL3098773

PubChem CID: 73054430

Max Phase: Preclinical

Molecular Formula: C21H24O2

Molecular Weight: 308.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=C/C=C/C(C)=C/C(=O)O)/C=C1\CC[C@@H](C)c2ccccc21

Standard InChI:  InChI=1S/C21H24O2/c1-15(7-6-8-16(2)14-21(22)23)13-18-12-11-17(3)19-9-4-5-10-20(18)19/h4-10,13-14,17H,11-12H2,1-3H3,(H,22,23)/b8-6+,15-7-,16-14+,18-13+/t17-/m1/s1

Standard InChI Key:  IUAWGSHMQSZQSY-ARGJGUSHSA-N

Alternative Forms

1. Parent:

   

   ALA3098773

   (2E,4E,6Z,8E)-3,7-dimethyl-8-[(4R)-4-methyl-3,4-dihydro-2H-naphthalen-1-ylidene]octa-2,4,6-trienoic acid

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 308.42

Molecular Weight (Monoisotopic): 308.1776

AlogP: 5.50

#Rotatable Bonds: 4

Polar Surface Area: 37.30

Molecular Species: ACID

HBA: 1

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.53

CX Basic pKa: ┄

CX LogP: 5.29

CX LogD: 2.50

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.59

Np Likeness Score: 1.50

References

1. Desphande A, Xia G, Boerma LJ, Vines KK, Atigadda VR, Lobo-Ruppert S, Grubbs CJ, Moeinpour FL, Smith CD, Christov K, Brouillette WJ, Muccio DD..  (2014)  Methyl-substituted conformationally constrained rexinoid agonists for the retinoid X receptors demonstrate improved efficacy for cancer therapy and prevention.,  22  (1): [PMID:24359708] [10.1016/j.bmc.2013.11.039]

2. Atigadda VR, Xia G, Desphande A, Boerma LJ, Lobo-Ruppert S, Grubbs CJ, Smith CD, Brouillette WJ, Muccio DD..  (2014)  Methyl substitution of a rexinoid agonist improves potency and reveals site of lipid toxicity.,  57  (12): [PMID:24801499] [10.1021/jm5004792]

Source

Source(1):

• Scientific Literature