6-[5-(Adamant-1-yl)-4-[(2-methoxyethoxy)methoxy]-2-methylphenyl]-5-chloro-2-naphthoic acid

ID: ALA563805

Chembl Id: CHEMBL563805

PubChem CID: 44127365

Max Phase: Preclinical

Molecular Formula: C32H35ClO5

Molecular Weight: 535.08

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COCCOCOc1cc(C)c(-c2ccc3cc(C(=O)O)ccc3c2Cl)cc1C12CC3CC(CC(C3)C1)C2

Standard InChI:  InChI=1S/C32H35ClO5/c1-19-9-29(38-18-37-8-7-36-2)28(32-15-20-10-21(16-32)12-22(11-20)17-32)14-27(19)26-6-3-23-13-24(31(34)35)4-5-25(23)30(26)33/h3-6,9,13-14,20-22H,7-8,10-12,15-18H2,1-2H3,(H,34,35)

Standard InChI Key:  GTQRCNNQKSSSCI-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA563805

   6-[5-(Adamant-1-yl)-4-[(2-methoxyethoxy)methoxy]-2-methylphenyl]-5-chloro-2-naphthoic 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: 535.08

Molecular Weight (Monoisotopic): 534.2173

AlogP: 7.63

#Rotatable Bonds: 9

Polar Surface Area: 64.99

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.99

CX Basic pKa: ┄

CX LogP: 7.59

CX LogD: 4.43

Aromatic Rings: 3

Heavy Atoms: 38

QED Weighted: 0.23

Np Likeness Score: 0.07

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