2-{4-[(2-Methoxy-4-oxo-3,4-dihydro-quinazolin-6-ylmethyl)-prop-2-ynyl-amino]-benzoylamino}-pentanedioic acid

ID: ALA265098

PubChem CID: 135722140

Max Phase: Preclinical

Molecular Formula: C25H24N4O7

Molecular Weight: 492.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C#CCN(Cc1ccc2nc(OC)[nH]c(=O)c2c1)c1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1

Standard InChI:  InChI=1S/C25H24N4O7/c1-3-12-29(14-15-4-9-19-18(13-15)23(33)28-25(27-19)36-2)17-7-5-16(6-8-17)22(32)26-20(24(34)35)10-11-21(30)31/h1,4-9,13,20H,10-12,14H2,2H3,(H,26,32)(H,30,31)(H,34,35)(H,27,28,33)/t20-/m0/s1

Standard InChI Key:  AJJBCKYMURNWIQ-FQEVSTJZSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA265098

   ---

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: 492.49

Molecular Weight (Monoisotopic): 492.1645

AlogP: 1.62

#Rotatable Bonds: 11

Polar Surface Area: 161.92

Molecular Species: ACID

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.20

CX Basic pKa: 4.45

CX LogP: 1.17

CX LogD: -3.97

Aromatic Rings: 3

Heavy Atoms: 36

QED Weighted: 0.29

Np Likeness Score: -0.73

References

1. Jackman AL, Marsham PR, Thornton TJ, Bishop JA, O'Connor BM, Hughes LR, Calvert AH, Jones TR..  (1990)  Quinazoline antifolate thymidylate synthase inhibitors: 2'-fluoro-N10-propargyl-5,8-dideazafolic acid and derivatives with modifications in the C2 position.,  33  (11): [PMID:2231607] [10.1021/jm00173a025]

2. Srivastava V, Gupta SP, Siddiqi MI, Mishra BN..  (2010)  3D-QSAR studies on quinazoline antifolate thymidylate synthase inhibitors by CoMFA and CoMSIA models.,  45  (4): [PMID:20153089] [10.1016/j.ejmech.2009.12.065]

Source

Source(1):

• Scientific Literature