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

ID: ALA104230

PubChem CID: 136056574

Max Phase: Preclinical

Molecular Formula: C24H22FN5O6

Molecular Weight: 495.47

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C24H22FN5O6/c1-2-9-30(12-13-3-6-18-16(10-13)22(34)29-24(26)28-18)14-4-5-15(17(25)11-14)21(33)27-19(23(35)36)7-8-20(31)32/h1,3-6,10-11,19H,7-9,12H2,(H,27,33)(H,31,32)(H,35,36)(H3,26,28,29,34)/t19-/m0/s1

Standard InChI Key:  SQQYANUOIIXAQM-IBGZPJMESA-N

Molfile:  

     RDKit          2D

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   -2.9630  -17.9917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    4.1555  -13.8493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0124  -14.2738    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  3  7  1  0
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  1  4  1  0
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 33 35  3  0
 16 17  2  0
 18 36  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA104230

   ---

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: 495.47

Molecular Weight (Monoisotopic): 495.1554

AlogP: 1.33

#Rotatable Bonds: 10

Polar Surface Area: 178.71

Molecular Species: ACID

HBA: 7

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.14

CX Basic pKa: 5.19

CX LogP: 0.24

CX LogD: -4.67

Aromatic Rings: 3

Heavy Atoms: 36

QED Weighted: 0.26

Np Likeness Score: -0.97

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