ID: ALA512577

Max Phase: Preclinical

Molecular Formula: C10H12N3O9P

Molecular Weight: 349.19

Molecule Type: Small molecule

Representations

Synonyms (2): 6-cyano-UMP | 6-Cyano-Uridine Monophosphate
Synonyms from Alternative Forms(2):

Canonical SMILES:  N#Cc1cc(=O)[nH]c(=O)n1[C@@H]1O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C10H12N3O9P/c11-2-4-1-6(14)12-10(17)13(4)9-8(16)7(15)5(22-9)3-21-23(18,19)20/h1,5,7-9,15-16H,3H2,(H,12,14,17)(H2,18,19,20)/t5-,7-,8-,9-/m1/s1

Standard InChI Key:  GCVKNFUDFHDSJQ-ZOQUXTDFSA-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: 349.19

Molecular Weight (Monoisotopic): 349.0311

AlogP: -2.86

#Rotatable Bonds: 4

Polar Surface Area: 195.10

Molecular Species: ACID

HBA: 9

HBD: 5

#RO5 Violations: 0

HBA (Lipinski): 12

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 1.23

CX Basic pKa:

CX LogP: -2.69

CX LogD: -7.56

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.35

Np Likeness Score: 0.72

References

1. Poduch E, Bello AM, Tang S, Fujihashi M, Pai EF, Kotra LP..  (2006)  Design of inhibitors of orotidine monophosphate decarboxylase using bioisosteric replacement and determination of inhibition kinetics.,  49  (16): [PMID:16884305] [10.1021/jm060202r]

2. Bello AM, Poduch E, Liu Y, Wei L, Crandall I, Wang X, Dyanand C, Kain KC, Pai EF, Kotra LP..  (2008)  Structure-activity relationships of C6-uridine derivatives targeting plasmodia orotidine monophosphate decarboxylase.,  51  (3): [PMID:18189347] [10.1021/jm7010673]

3. Bello AM, Konforte D, Poduch E, Furlonger C, Wei L, Liu Y, Lewis M, Pai EF, Paige CJ, Kotra LP..  (2009)  Structure-activity relationships of orotidine-5'-monophosphate decarboxylase inhibitors as anticancer agents.,  52  (6): [PMID:19260677] [10.1021/jm801224t]

4. Meza-Avina ME, Wei L, Liu Y, Poduch E, Bello AM, Mishra RK, Pai EF, Kotra LP..  (2010)  Structural determinants for the inhibitory ligands of orotidine-5'-monophosphate decarboxylase.,  18  (11): [PMID:20452222] [10.1016/j.bmc.2010.04.017]

Source

Source(1):

• Scientific Literature