5-Amino-2-{4-[(2-amino-4-oxo-5-trifluoromethyl-3,4-dihydro-quinazolin-6-ylmethyl)-amino]-benzoylamino}-pentanoic acid

ID: ALA130518

PubChem CID: 136046106

Max Phase: Preclinical

Molecular Formula: C22H23F3N6O4

Molecular Weight: 492.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NCCCC(NC(=O)c1ccc(NCc2ccc3nc(N)nc(O)c3c2C(F)(F)F)cc1)C(=O)O

Standard InChI:  InChI=1S/C22H23F3N6O4/c23-22(24,25)17-12(5-8-14-16(17)19(33)31-21(27)30-14)10-28-13-6-3-11(4-7-13)18(32)29-15(20(34)35)2-1-9-26/h3-8,15,28H,1-2,9-10,26H2,(H,29,32)(H,34,35)(H3,27,30,31,33)

Standard InChI Key:  QMDKLKMYZJMJMO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   -1.4333   -2.5792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3958   -2.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.2042   -2.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3125   -0.4542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1917   -1.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7167   -2.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8750   -1.3542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3167   -1.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3542   -1.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8375   -1.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  1  1  0
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  6  3  2  0
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 20 14  1  0
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 22 14  1  0
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 24  8  1  0
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 26 31  1  0
 27 30  2  0
 28 18  1  0
 29 11  1  0
 30 28  1  0
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 32 34  1  0
 33 12  1  0
 34 35  1  0
 35 33  1  0
  4  5  2  0
 16 22  2  0
 15 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA130518

   ---

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: 492.46

Molecular Weight (Monoisotopic): 492.1733

AlogP: 2.47

#Rotatable Bonds: 9

Polar Surface Area: 176.48

Molecular Species: ZWITTERION

HBA: 8

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.48

CX Basic pKa: 9.82

CX LogP: -0.08

CX LogD: -0.08

Aromatic Rings: 3

Heavy Atoms: 35

QED Weighted: 0.26

Np Likeness Score: -0.54

References

1. Hynes JB, Singh SK, Fetzer O, Shane B..  (1992)  Inhibition of hog liver folylpolyglutamate synthetase by 5-substituted 5,8-dideaza analogues of folic acid bearing a terminal L-ornithine residue.,  35  (22): [PMID:1433214] [10.1021/jm00100a013]

Source

Source(1):

• Scientific Literature