ID: ALA408444

Max Phase: Preclinical

Molecular Formula: C22H24FN5O4

Molecular Weight: 441.46

Molecule Type: Small molecule

Representations

Synonyms (1): BMS-582664
Synonyms from Alternative Forms(1):

Canonical SMILES:  Cc1cc2c(F)c(Oc3ncnn4cc(OC[C@@H](C)OC(=O)[C@@H](C)N)c(C)c34)ccc2[nH]1

Standard InChI:  InChI=1S/C22H24FN5O4/c1-11-7-15-16(27-11)5-6-17(19(15)23)32-21-20-13(3)18(8-28(20)26-10-25-21)30-9-12(2)31-22(29)14(4)24/h5-8,10,12,14,27H,9,24H2,1-4H3/t12-,14-/m1/s1

Standard InChI Key:  LTEJRLHKIYCEOX-TZMCWYRMSA-N

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

Properties

Molecular Weight: 441.46

Molecular Weight (Monoisotopic): 441.1812

AlogP: 3.42

#Rotatable Bonds: 7

Polar Surface Area: 116.76

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa: 7.34

CX LogP: 3.50

CX LogD: 3.23

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.42

Np Likeness Score: -0.89

References

1. Cai ZW, Zhang Y, Borzilleri RM, Qian L, Barbosa S, Wei D, Zheng X, Wu L, Fan J, Shi Z, Wautlet BS, Mortillo S, Jeyaseelan R, Kukral DW, Kamath A, Marathe P, D'Arienzo C, Derbin G, Barrish JC, Robl JA, Hunt JT, Lombardo LJ, Fargnoli J, Bhide RS..  (2008)  Discovery of brivanib alaninate ((S)-((R)-1-(4-(4-fluoro-2-methyl-1H-indol-5-yloxy)-5-methylpyrrolo[2,1-f][1,2,4]triazin-6-yloxy)propan-2-yl)2-aminopropanoate), a novel prodrug of dual vascular endothelial growth factor receptor-2 and fibroblast growth factor receptor-1 kinase inhibitor (BMS-540215).,  51  (6): [PMID:18288793] [10.1021/jm7013309]

Source

Source(1):

• Scientific Literature