ID: ALA1627258

Max Phase: Preclinical

Molecular Formula: C14H22N7O9PS

Molecular Weight: 495.41

Molecule Type: Small molecule

Representations

Canonical SMILES:  C[S+]([O-])(C[C@H](N)C(=O)O)=NP(=O)(O)OC[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C14H22N7O9PS/c1-32(28,3-6(15)14(24)25)20-31(26,27)29-2-7-9(22)10(23)13(30-7)21-5-19-8-11(16)17-4-18-12(8)21/h4-7,9-10,13,22-23H,2-3,15H2,1H3,(H4-,16,17,18,20,24,25,26,27,28)/t6-,7+,9+,10+,13+,32?/m0/s1

Standard InChI Key:  ZPBYYGXZHJOFIV-XPSMFXCBSA-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: 495.41

Molecular Weight (Monoisotopic): 495.0937

AlogP: -2.35

#Rotatable Bonds: 8

Polar Surface Area: 264.58

Molecular Species: ACID

HBA: 13

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 16

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 2

CX Acidic pKa: -3.29

CX Basic pKa: 7.89

CX LogP: -8.80

CX LogD: -9.21

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.17

Np Likeness Score: 0.89

References

1. Ikeuchi H, Meyer ME, Ding Y, Hiratake J, Richards NG..  (2009)  A critical electrostatic interaction mediates inhibitor recognition by human asparagine synthetase.,  17  (18): [PMID:19683931] [10.1016/j.bmc.2009.07.071]

2. Ikeuchi H, Ahn YM, Otokawa T, Watanabe B, Hegazy L, Hiratake J, Richards NG..  (2012)  A sulfoximine-based inhibitor of human asparagine synthetase kills L-asparaginase-resistant leukemia cells.,  20  (19): [PMID:22951255] [10.1016/j.bmc.2012.07.047]

Source

Source(1):

• Scientific Literature