(S)-4-((S)-1-Carboxy-ethylcarbamoyl)-2-{4-[(2-methyl-4-oxo-3,4-dihydro-quinazolin-6-ylmethyl)-prop-2-ynyl-amino]-benzoylamino}-butyric acid

ID: ALA168450

PubChem CID: 135474792

Max Phase: Preclinical

Molecular Formula: C28H29N5O7

Molecular Weight: 547.57

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C#CCN(Cc1ccc2nc(C)nc(O)c2c1)c1ccc(C(=O)N[C@@H](CCC(=O)N[C@@H](C)C(=O)O)C(=O)O)cc1

Standard InChI:  InChI=1S/C28H29N5O7/c1-4-13-33(15-18-5-10-22-21(14-18)26(36)31-17(3)30-22)20-8-6-19(7-9-20)25(35)32-23(28(39)40)11-12-24(34)29-16(2)27(37)38/h1,5-10,14,16,23H,11-13,15H2,2-3H3,(H,29,34)(H,32,35)(H,37,38)(H,39,40)(H,30,31,36)/t16-,23-/m0/s1

Standard InChI Key:  KWTPVLRPVDASNH-HJPURHCSSA-N

Molfile:  

     RDKit          2D

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    1.8167   -5.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.1042   -6.5750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8167   -6.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3792   -6.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5542   -3.6375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2667   -4.0500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8417   -5.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9667   -1.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.0917   -4.0875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    9.5417   -5.6875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4417   -0.4542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5417   -6.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2542   -3.8625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.4042   -4.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1167   -5.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7542   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9167   -3.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.0792   -5.5875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7917   -1.0500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2542   -6.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.7042   -1.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  2  0
  4  6  2  0
  5  2  2  0
  6  3  1  0
  7 18  1  0
  8  7  1  0
  9 14  1  0
 10 19  1  0
 11 15  1  0
 12 22  1  0
 13 35  1  0
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 16 13  3  0
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 21  1  1  0
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 29 32  1  0
 30 31  2  0
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 32 20  2  0
 14 33  1  1
 34 33  1  0
 35 12  1  0
 36  9  1  0
 37 10  1  0
 38 24  1  0
 39  6  1  0
 19 40  1  1
  4  5  1  0
 27 38  2  0
 18 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA168450

   ---

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: 547.57

Molecular Weight (Monoisotopic): 547.2067

AlogP: 1.84

#Rotatable Bonds: 12

Polar Surface Area: 182.05

Molecular Species: ACID

HBA: 8

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.15

CX Basic pKa: 1.75

CX LogP: 2.41

CX LogD: -4.16

Aromatic Rings: 3

Heavy Atoms: 40

QED Weighted: 0.21

Np Likeness Score: -1.00

References

1. Bavetsias V, Jackman AL, Kimbell R, Gibson W, Boyle FT, Bisset GM..  (1996)  Quinazoline antifolate thymidylate synthase inhibitors: gamma-linked L-D, D-D, and D-L dipeptide analogues of 2-desamino-2-methyl-N10-propargyl-5,8-dideazafolic acid (ICI 198583).,  39  (1): [PMID:8568829] [10.1021/jm950471+]

Source

Source(1):

• Scientific Literature