ID: ALA374172

Max Phase: Preclinical

Molecular Formula: C21H23N5O6

Molecular Weight: 441.44

Molecule Type: Small molecule

Representations

Canonical SMILES:  Nc1nc2[nH]cc(CCCc3ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc3)c2c(=O)[nH]1

Standard InChI:  InChI=1S/C21H23N5O6/c22-21-25-17-16(19(30)26-21)13(10-23-17)3-1-2-11-4-6-12(7-5-11)18(29)24-14(20(31)32)8-9-15(27)28/h4-7,10,14H,1-3,8-9H2,(H,24,29)(H,27,28)(H,31,32)(H4,22,23,25,26,30)/t14-/m0/s1

Standard InChI Key:  LICPJBQGYLPBOC-AWEZNQCLSA-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: 441.44

Molecular Weight (Monoisotopic): 441.1648

AlogP: 1.06

#Rotatable Bonds: 10

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: 3.32

CX Basic pKa: 4.72

CX LogP: 0.31

CX LogD: -4.92

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.27

Np Likeness Score: 0.07

References

1. Gangjee A, Zeng Y, McGuire JJ, Mehraein F, Kisliuk RL..  (2004)  Synthesis of classical, three-carbon-bridged 5-substituted furo[2,3-d]pyrimidine and 6-substituted pyrrolo[2,3-d]pyrimidine analogues as antifolates.,  47  (27): [PMID:15615538] [10.1021/jm040123k]

2. 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]

3. 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]

Source

Source(1):

• Scientific Literature