(1R,2R)-7'-((3-((R)-2,2-Dimethylcyclopentyl)-4-(5-fluoro-2-methoxypyridin-4-yl)benzyl)oxy)-8'-fluoro-3',4'-dihydro-2'H-spiro[cyclopropane-1,1'-naphthalene]-2-carboxylic acid

ID: ALA2385464

Chembl Id: CHEMBL2385464

PubChem CID: 58379987

Max Phase: Preclinical

Molecular Formula: C33H35F2NO4

Molecular Weight: 547.64

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(-c2ccc(COc3ccc4c(c3F)[C@]3(CCC4)C[C@H]3C(=O)O)cc2[C@@H]2CCCC2(C)C)c(F)cn1

Standard InChI:  InChI=1S/C33H35F2NO4/c1-32(2)12-5-7-24(32)22-14-19(8-10-21(22)23-15-28(39-3)36-17-26(23)34)18-40-27-11-9-20-6-4-13-33(29(20)30(27)35)16-25(33)31(37)38/h8-11,14-15,17,24-25H,4-7,12-13,16,18H2,1-3H3,(H,37,38)/t24-,25-,33+/m0/s1

Standard InChI Key:  WUMCAEVLFYSGKO-UTKFAANNSA-N

Alternative Forms

1. Parent:

   

   ALA2385464

   (1'R,4R)-6-[[3-[(1R)-2,2-dimethylcyclopentyl]-4-(5-fluoro-2-methoxypyridin-4-yl)phenyl]methoxy]-5-fluorospiro[2,3-dihydro-1H-naphthalene-4,2'-cyclopropane]-1'-carboxylic 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: 547.64

Molecular Weight (Monoisotopic): 547.2534

AlogP: 7.59

#Rotatable Bonds: 7

Polar Surface Area: 68.65

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.95

CX Basic pKa: 0.88

CX LogP: 7.75

CX LogD: 4.56

Aromatic Rings: 3

Heavy Atoms: 40

QED Weighted: 0.33

Np Likeness Score: 0.27

References

1. Wang Y, Liu JJ, Dransfield PJ, Zhu L, Wang Z, Du X, Jiao X, Su Y, Li AR, Brown SP, Kasparian A, Vimolratana M, Yu M, Pattaropong V, Houze JB, Swaminath G, Tran T, Nguyen K, Guo Q, Zhang J, Zhuang R, Li F, Miao L, Bartberger MD, Correll TL, Chow D, Wong S, Luo J, Lin DC, Medina JC..  (2013)  Discovery and Optimization of Potent GPR40 Full Agonists Containing Tricyclic Spirocycles.,  4  (6): [PMID:24900707] [10.1021/ml300427u]

Source

Source(1):

• Scientific Literature