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

ID: ALA104410

PubChem CID: 136056573

Max Phase: Preclinical

Molecular Formula: C25H23FN4O7

Molecular Weight: 510.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C#CCN(Cc1ccc2nc(CO)[nH]c(=O)c2c1)c1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)c(F)c1

Standard InChI:  InChI=1S/C25H23FN4O7/c1-2-9-30(12-14-3-6-19-17(10-14)24(35)29-21(13-31)27-19)15-4-5-16(18(26)11-15)23(34)28-20(25(36)37)7-8-22(32)33/h1,3-6,10-11,20,31H,7-9,12-13H2,(H,28,34)(H,32,33)(H,36,37)(H,27,29,35)/t20-/m0/s1

Standard InChI Key:  RZOKGLLXJIRPFE-FQEVSTJZSA-N

Molfile:  

     RDKit          2D

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   20.5178    1.9120    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

Alternative Forms

1. Parent:

   

   ALA104410

   ---

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: 510.48

Molecular Weight (Monoisotopic): 510.1551

AlogP: 1.24

#Rotatable Bonds: 11

Polar Surface Area: 172.92

Molecular Species: ACID

HBA: 7

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.14

CX Basic pKa: 5.17

CX LogP: -0.30

CX LogD: -5.04

Aromatic Rings: 3

Heavy Atoms: 37

QED Weighted: 0.24

Np Likeness Score: -1.08

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