(2E,4E,6Z,8E)-8-[6'-Methyl-3',4'-dihydro-1'(2'H)-naphthalen-1'-ylidene]-3,7-dimethyl-2,4,6-octatrienoic Acid

ID: ALA3289658

Chembl Id: CHEMBL3289658

PubChem CID: 59444434

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\CCCc2cc(C)ccc21

Standard InChI:  InChI=1S/C21H24O2/c1-15(6-4-7-16(2)14-21(22)23)12-18-8-5-9-19-13-17(3)10-11-20(18)19/h4,6-7,10-14H,5,8-9H2,1-3H3,(H,22,23)/b7-4+,15-6-,16-14+,18-12+

Standard InChI Key:  KHXSEEGTXMJURJ-JUPRZYRNSA-N

Alternative Forms

1. Parent:

   

   ALA3289658

   (2e,4e,6z,8e)-3,7-Dimethyl-8-(6-Methyl-3,4-Dihydronaphthalen-1(2h)-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: 5.25

#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: 4.55

CX Basic pKa: ┄

CX LogP: 5.51

CX LogD: 2.74

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.61

Np Likeness Score: 0.98

References

1. 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]

2. Atigadda VR, Xia G, Deshpande A, Wu L, Kedishvili N, Smith CD, Krontiras H, Bland KI, Grubbs CJ, Brouillette WJ, Muccio DD..  (2015)  Conformationally Defined Rexinoids and Their Efficacy in the Prevention of Mammary Cancers.,  58  (19): [PMID:26331194] [10.1021/acs.jmedchem.5b00829]

Source

Source(1):

• Scientific Literature