(E)-3-[5'-(Adamant-1-yl)-2-chloro-4'-hydroxy-2'-methylbiphenyl-4-yl]acrylic acid

ID: ALA554740

Chembl Id: CHEMBL554740

PubChem CID: 44127469

Max Phase: Preclinical

Molecular Formula: C26H27ClO3

Molecular Weight: 422.95

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(O)c(C23CC4CC(CC(C4)C2)C3)cc1-c1ccc(/C=C/C(=O)O)cc1Cl

Standard InChI:  InChI=1S/C26H27ClO3/c1-15-6-24(28)22(26-12-17-7-18(13-26)9-19(8-17)14-26)11-21(15)20-4-2-16(10-23(20)27)3-5-25(29)30/h2-6,10-11,17-19,28H,7-9,12-14H2,1H3,(H,29,30)/b5-3+

Standard InChI Key:  HZSNUNIQSKOBFH-HWKANZROSA-N

Alternative Forms

1. Parent:

   

   ALA554740

   (E)-3-[4-[5-(1-adamantyl)-4-hydroxy-2-methylphenyl]-3-chlorophenyl]prop-2-enoic 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: 422.95

Molecular Weight (Monoisotopic): 422.1649

AlogP: 6.59

#Rotatable Bonds: 4

Polar Surface Area: 57.53

Molecular Species: ACID

HBA: 2

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.85

CX Basic pKa: ┄

CX LogP: 6.95

CX LogD: 3.71

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.55

Np Likeness Score: 0.23

References

1. Pérez-Rodríguez S, Ortiz MA, Pereira R, Rodríguez-Barrios F, de Lera AR, Piedrafita FJ..  (2009)  Highly twisted adamantyl arotinoids: synthesis, antiproliferative effects and RXR transactivation profiles.,  44  (6): [PMID:19216008] [10.1016/j.ejmech.2009.01.011]

2. García-Rodríguez J, Pérez-Rodríguez S, Ortiz MA, Pereira R, de Lera AR, Piedrafita FJ..  (2014)  Inhibition of IκB kinase-β and IκB kinase-α by heterocyclic adamantyl arotinoids.,  22  (4): [PMID:24457093] [10.1016/j.bmc.2014.01.006]

Source

Source(1):

• Scientific Literature