ID: ALA2426247

Max Phase: Preclinical

Molecular Formula: C19H19N5O6

Molecular Weight: 413.39

Molecule Type: Small molecule

Representations

Canonical SMILES:  Nc1nc2[nH]cc(Cc3ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc3)c2c(=O)[nH]1

Standard InChI:  InChI=1S/C19H19N5O6/c20-19-23-15-14(17(28)24-19)11(8-21-15)7-9-1-3-10(4-2-9)16(27)22-12(18(29)30)5-6-13(25)26/h1-4,8,12H,5-7H2,(H,22,27)(H,25,26)(H,29,30)(H4,20,21,23,24,28)/t12-/m0/s1

Standard InChI Key:  VDHBMZRBPMTLGE-LBPRGKRZSA-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: 413.39

Molecular Weight (Monoisotopic): 413.1335

AlogP: 0.47

#Rotatable Bonds: 8

Polar Surface Area: 191.26

Molecular Species: ACID

HBA: 6

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.29

CX Basic pKa: 3.01

CX LogP: -0.10

CX LogD: -6.02

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.31

Np Likeness Score: 0.02

References

1. Kumar VP, Frey KM, Wang Y, Jain HK, Gangjee A, Anderson KS..  (2013)  Substituted pyrrolo[2,3-d]pyrimidines as Cryptosporidium hominis thymidylate synthase inhibitors.,  23  (19): [PMID:23927969] [10.1016/j.bmcl.2013.07.037]

2. Mitchell-Ryan S, Wang Y, Raghavan S, Ravindra MP, Hales E, Orr S, Cherian C, Hou Z, Matherly LH, Gangjee A..  (2013)  Discovery of 5-substituted pyrrolo[2,3-d]pyrimidine antifolates as dual-acting inhibitors of glycinamide ribonucleotide formyltransferase and 5-aminoimidazole-4-carboxamide ribonucleotide formyltransferase in de novo purine nucleotide biosynthesis: implications of inhibiting 5-aminoimidazole-4-carboxamide ribonucleotide formyltransferase to ampk activation and antitumor activity.,  56  (24): [PMID:24256410] [10.1021/jm401328u]

3. Kumar VP, Cisneros JA, Frey KM, Castellanos-Gonzalez A, Wang Y, Gangjee A, White AC, Jorgensen WL, Anderson KS..  (2014)  Structural studies provide clues for analog design of specific inhibitors of Cryptosporidium hominis thymidylate synthase-dihydrofolate reductase.,  24  (17): [PMID:25127103] [10.1016/j.bmcl.2014.07.049]

Source

Source(1):

• Scientific Literature