4-[(E)-1-Methyl-2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-vinyl]-benzoic acid

ID: ALA285179

Chembl Id: CHEMBL285179

Cas Number: 119999-05-2

PubChem CID: 6440346

Max Phase: Preclinical

Molecular Formula: C24H28O2

Molecular Weight: 348.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C/C(=C\c1ccc2c(c1)C(C)(C)CCC2(C)C)c1ccc(C(=O)O)cc1

Standard InChI:  InChI=1S/C24H28O2/c1-16(18-7-9-19(10-8-18)22(25)26)14-17-6-11-20-21(15-17)24(4,5)13-12-23(20,2)3/h6-11,14-15H,12-13H2,1-5H3,(H,25,26)/b16-14+

Standard InChI Key:  NUSIBKZXKHKYDB-JQIJEIRASA-N

Alternative Forms

1. Parent:

   

   ALA285179

   Benzoic acid, 4-(1-methyl-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)ethenyl)-, (E)-

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: 348.49

Molecular Weight (Monoisotopic): 348.2089

AlogP: 6.29

#Rotatable Bonds: 3

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: 4.11

CX Basic pKa: ┄

CX LogP: 6.90

CX LogD: 3.80

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.66

Np Likeness Score: 0.33

References

1. Beard RL, Gil DW, Marler DK, Henry E, Colon DF, Gillett SJ, Arefieg T, Breen TS, Krauss H, Davies PJ, Chandraratna RA.  (1994)  Structural basis for the differential RXR & RAR activity of stilbene retinoid analogs,  4  (12): [10.1016/S0960-894X(01)80511-4]

2. Dawson MI, Hobbs PD, Derdzinski KA, Chao WR, Frenking G, Loew GH, Jetten AM, Napoli JL, Williams JB, Sani BP..  (1989)  Effect of structural modifications in the C7-C11 region of the retinoid skeleton on biological activity in a series of aromatic retinoids.,  32  (7): [PMID:2738885] [10.1021/jm00127a018]

3. Bonchev D, Seitz WA, Mountain CF, Balaban AT..  (1994)  Modeling the anticarcinogenic action of retinoids by making use of the OASIS method. 3. Inhibition of the induction of ornithine decarboxylase by arotinoids.,  37  (15): [PMID:8057279] [10.1021/jm00041a008]

4. Jong L, Lehmann JM, Hobbs PD, Harlev E, Huffman JC, Pfahl M, Dawson MI..  (1993)  Conformational effects on retinoid receptor selectivity. 1. Effect of 9-double bond geometry on retinoid X receptor activity.,  36  (18): [PMID:8410972] [10.1021/jm00070a003]

Source

Source(1):

• Scientific Literature