(S)-2-(5-((2-amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-5-yl)methyl)thiophene-2-carboxamido)pentanedioic acid

ID: ALA2426245

Chembl Id: CHEMBL2426245

PubChem CID: 135465664

Max Phase: Preclinical

Molecular Formula: C17H17N5O6S

Molecular Weight: 419.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc2[nH]cc(Cc3ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)s3)c2c(=O)[nH]1

Standard InChI:  InChI=1S/C17H17N5O6S/c18-17-21-13-12(15(26)22-17)7(6-19-13)5-8-1-3-10(29-8)14(25)20-9(16(27)28)2-4-11(23)24/h1,3,6,9H,2,4-5H2,(H,20,25)(H,23,24)(H,27,28)(H4,18,19,21,22,26)/t9-/m0/s1

Standard InChI Key:  NGUQGNWNDPTPDO-VIFPVBQESA-N

Alternative Forms

1. Parent:

   

   ALA2426245

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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

Calculated Properties

Molecular Weight: 419.42

Molecular Weight (Monoisotopic): 419.0900

AlogP: 0.53

#Rotatable Bonds: 8

Polar Surface Area: 191.26

Molecular Species: ACID

HBA: 7

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.51

CX Basic pKa: 3.06

CX LogP: 0.02

CX LogD: -5.78

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.30

Np Likeness Score: -0.39

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. Wang Y, Mitchell-Ryan S, Raghavan S, George C, Orr S, Hou Z, Matherly LH, Gangjee A..  (2015)  Novel 5-substituted pyrrolo[2,3-d]pyrimidines as dual inhibitors of glycinamide ribonucleotide formyltransferase and 5-aminoimidazole-4-carboxamide ribonucleotide formyltransferase and as potential antitumor agents.,  58  (3): [PMID:25602637] [10.1021/jm501787c]

Source

Source(1):

• Scientific Literature