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

ID: ALA321977

PubChem CID: 135722139

Max Phase: Preclinical

Molecular Formula: C25H24N4O7

Molecular Weight: 492.49

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)cc1

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

Standard InChI Key:  AKLRDMIEXNNAPZ-FQEVSTJZSA-N

Molfile:  

     RDKit          2D

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   -2.7421   -2.5542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    0.8215   -2.1384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5372   -2.5487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  3  7  1  0
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 35 36  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA321977

   ---

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: 1.10

#Rotatable Bonds: 11

Polar Surface Area: 172.92

Molecular Species: ACID

HBA: 7

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.24

CX Basic pKa: 5.20

CX LogP: -0.37

CX LogD: -5.09

Aromatic Rings: 3

Heavy Atoms: 36

QED Weighted: 0.25

Np Likeness Score: -0.85

References

1. Hughes LR, Jackman AL, Oldfield J, Smith RC, Burrows KD, Marsham PR, Bishop JA, Jones TR, O'Connor BM, Calvert AH..  (1990)  Quinazoline antifolate thymidylate synthase inhibitors: alkyl, substituted alkyl, and aryl substituents in the C2 position.,  33  (11): [PMID:2231606] [10.1021/jm00173a024]

2. 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]

3. 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