2-[5'-(Adamant-1-yl)-2-chloro-4'-[(2-methoxyethoxy)methoxy]-2'-methylbiphenyl-4-yl]acetic Acid

ID: ALA560351

Chembl Id: CHEMBL560351

PubChem CID: 44127258

Max Phase: Preclinical

Molecular Formula: C29H35ClO5

Molecular Weight: 499.05

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COCCOCOc1cc(C)c(-c2ccc(CC(=O)O)cc2Cl)cc1C12CC3CC(CC(C3)C1)C2

Standard InChI:  InChI=1S/C29H35ClO5/c1-18-7-27(35-17-34-6-5-33-2)25(29-14-20-8-21(15-29)10-22(9-20)16-29)13-24(18)23-4-3-19(11-26(23)30)12-28(31)32/h3-4,7,11,13,20-22H,5-6,8-10,12,14-17H2,1-2H3,(H,31,32)

Standard InChI Key:  HDBFHIYGUZDEQB-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA560351

   2-[4-[5-(1-Adamantyl)-4-(2-methoxyethoxymethoxy)-2-methylphenyl]-3-chlorophenyl]acetic 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: 499.05

Molecular Weight (Monoisotopic): 498.2173

AlogP: 6.41

#Rotatable Bonds: 10

Polar Surface Area: 64.99

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.16

CX Basic pKa: ┄

CX LogP: 6.58

CX LogD: 3.52

Aromatic Rings: 2

Heavy Atoms: 35

QED Weighted: 0.30

Np Likeness Score: -0.13

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