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

ID: ALA420280

PubChem CID: 136035435

Max Phase: Preclinical

Molecular Formula: C24H21FN4O6

Molecular Weight: 480.45

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C24H21FN4O6/c1-2-9-29(12-14-3-6-19-17(10-14)22(32)27-13-26-19)15-4-5-16(18(25)11-15)23(33)28-20(24(34)35)7-8-21(30)31/h1,3-6,10-11,13,20H,7-9,12H2,(H,28,33)(H,30,31)(H,34,35)(H,26,27,32)/t20-/m0/s1

Standard InChI Key:  QZKRJYITWJUYDS-FQEVSTJZSA-N

Molfile:  

     RDKit          2D

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M  END

Alternative Forms

1. Parent:

   

   ALA420280

   ---

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: 480.45

Molecular Weight (Monoisotopic): 480.1445

AlogP: 1.75

#Rotatable Bonds: 10

Polar Surface Area: 152.69

Molecular Species: ACID

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.14

CX Basic pKa: 5.03

CX LogP: 0.54

CX LogD: -4.54

Aromatic Rings: 3

Heavy Atoms: 35

QED Weighted: 0.32

Np Likeness Score: -1.06

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