N-{4-[(2-amino-4-oxo-5-methyl-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-6-yl)thio]benzoyl}-L-glutamic acid

ID: ALA224974

Chembl Id: CHEMBL224974

PubChem CID: 135399760

Max Phase: Preclinical

Molecular Formula: C19H19N5O6S

Molecular Weight: 445.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1c(Sc2ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc2)[nH]c2nc(N)[nH]c(=O)c12

Standard InChI:  InChI=1S/C19H19N5O6S/c1-8-13-14(23-19(20)24-16(13)28)22-17(8)31-10-4-2-9(3-5-10)15(27)21-11(18(29)30)6-7-12(25)26/h2-5,11H,6-7H2,1H3,(H,21,27)(H,25,26)(H,29,30)(H4,20,22,23,24,28)/t11-/m0/s1

Standard InChI Key:  DGRMTNYOVDPDTP-NSHDSACASA-N

Alternative Forms

1. Parent:

   

   ALA224974

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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: 445.46

Molecular Weight (Monoisotopic): 445.1056

AlogP: 1.34

#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: 3.13

CX Basic pKa: 2.58

CX LogP: 0.80

CX LogD: -5.44

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.30

Np Likeness Score: -0.30

References

1. Gangjee A, Lin X, Kisliuk RL, McGuire JJ..  (2005)  Synthesis of N-{4-[(2,4-diamino-5-methyl-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-6-yl)thio]benzoyl}-L-glutamic acid and N-{4-[(2-amino-4-oxo-5-methyl-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-6-yl)thio]benzoyl}-L-glutamic acid as dual inhibitors of dihydrofolate reductase and thymidylate synthase and as potential antitumor agents.,  48  (23): [PMID:16279780] [10.1021/jm058234m]

Source

Source(1):

• Scientific Literature