(R)-2-(9-chloro-7-(3-cyano-4-isopropoxybenzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetic acid

ID: ALA3359522

Chembl Id: CHEMBL3359522

PubChem CID: 67250226

Max Phase: Preclinical

Molecular Formula: C24H23ClN2O4

Molecular Weight: 438.91

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)Oc1ccc(COc2ccc3c(c2)c(Cl)c2n3CC[C@@H]2CC(=O)O)cc1C#N

Standard InChI:  InChI=1S/C24H23ClN2O4/c1-14(2)31-21-6-3-15(9-17(21)12-26)13-30-18-4-5-20-19(11-18)23(25)24-16(10-22(28)29)7-8-27(20)24/h3-6,9,11,14,16H,7-8,10,13H2,1-2H3,(H,28,29)/t16-/m1/s1

Standard InChI Key:  RWFBHHNEDFDSPE-MRXNPFEDSA-N

Alternative Forms

1. Parent:

   

   ALA3359522

   2-[(3R)-4-chloro-6-[(3-cyano-4-propan-2-yloxyphenyl)methoxy]-2,3-dihydro-1H-pyrrolo[1,2-a]indol-3-yl]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: 438.91

Molecular Weight (Monoisotopic): 438.1346

AlogP: 5.49

#Rotatable Bonds: 7

Polar Surface Area: 84.48

Molecular Species: ACID

HBA: 5

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.02

CX Basic pKa: ┄

CX LogP: 4.68

CX LogD: 1.53

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.53

Np Likeness Score: -0.69

References

1. Buzard DJ, Lopez L, Moody J, Kawasaki A, Schrader TO, Kasem M, Johnson B, Zhu X, Thoresen L, Kim SH, Gharbaoui T, Sengupta D, Calvano L, Krishnan A, Gao Y, Semple G, Edwards J, Barden J, Morgan M, Usmani K, Chen C, Sadeque A, Chen W, Christopher RJ, Thatte J, Fu L, Solomon M, Whelan K, Al-Shamma H, Gatlin J, Gaidarov I, Anthony T, Le M, Unett DJ, Stirn S, Blackburn A, Behan DP, Jones RM..  (2014)  (7-Benzyloxy-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetic Acids as S1P1 Functional Antagonists.,  5  (12): [PMID:25516794] [10.1021/ml500422m]

Source

Source(1):

• Scientific Literature