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

ID: ALA388340

Chembl Id: CHEMBL388340

PubChem CID: 135431649

Max Phase: Preclinical

Molecular Formula: C19H18FN5O6S

Molecular Weight: 463.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1[nH]c2nc(N)[nH]c(=O)c2c1Sc1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)c(F)c1

Standard InChI:  InChI=1S/C19H18FN5O6S/c1-7-14(13-15(22-7)24-19(21)25-17(13)29)32-8-2-3-9(10(20)6-8)16(28)23-11(18(30)31)4-5-12(26)27/h2-3,6,11H,4-5H2,1H3,(H,23,28)(H,26,27)(H,30,31)(H4,21,22,24,25,29)/t11-/m0/s1

Standard InChI Key:  LTCOTSRHIWKZTK-NSHDSACASA-N

Alternative Forms

1. Parent:

   

   ALA388340

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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: 463.45

Molecular Weight (Monoisotopic): 463.0962

AlogP: 1.48

#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: 2.97

CX Basic pKa: 2.38

CX LogP: 0.51

CX LogD: -5.80

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.29

Np Likeness Score: -0.70

References

1. Gangjee A, Jain HD, McGuire JJ, Kisliuk RL..  (2004)  Benzoyl ring halogenated classical 2-amino-6-methyl-3,4-dihydro-4-oxo-5-substituted thiobenzoyl-7H-pyrrolo[2,3-d]pyrimidine antifolates as inhibitors of thymidylate synthase and as antitumor agents.,  47  (27): [PMID:15615522] [10.1021/jm040144e]

Source

Source(1):

• Scientific Literature