(S)-5-Amino-2-{5-[(2-amino-4-oxo-3,4-dihydro-pyrido[2,3-d]pyrimidin-6-ylmethyl)-amino]-1-oxo-1,3-dihydro-isoindol-2-yl}-pentanoic acid

ID: ALA117462

PubChem CID: 135528799

Max Phase: Preclinical

Molecular Formula: C21H23N7O4

Molecular Weight: 437.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NCCC[C@@H](C(=O)O)N1Cc2cc(NCc3cnc4nc(N)nc(O)c4c3)ccc2C1=O

Standard InChI:  InChI=1S/C21H23N7O4/c22-5-1-2-16(20(31)32)28-10-12-7-13(3-4-14(12)19(28)30)24-8-11-6-15-17(25-9-11)26-21(23)27-18(15)29/h3-4,6-7,9,16,24H,1-2,5,8,10,22H2,(H,31,32)(H3,23,25,26,27,29)/t16-/m0/s1

Standard InChI Key:  IRSZGKLLTGEBKA-INIZCTEOSA-N

Molfile:  

     RDKit          2D

 33 36  0  0  1  0  0  0  0  0999 V2000
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    0.2250   -4.3375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8542   -2.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7417   -4.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.3500   -2.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3750   -3.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9042   -3.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9625   -2.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2625   -4.3292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    4.8375   -1.6125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2250   -2.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.7792   -3.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6542   -1.3250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8167   -3.4292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8083   -4.3292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7792   -4.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3375   -3.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3000   -3.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3292   -2.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6667   -1.5542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5792   -4.3000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4042   -2.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7125   -3.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2667   -3.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7042   -2.1250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  5  2  0
  3  1  1  0
  4  6  1  0
  5 13  1  0
  6  7  2  0
  7 15  1  0
  8  2  1  0
  9  3  1  0
 10 11  1  0
 11  1  1  0
 12  1  1  0
 13 24  2  0
 14 12  1  0
 15 20  2  0
 16  9  2  0
 17  3  2  0
 18  6  1  0
 19 10  2  0
 20 26  1  0
 21 14  2  0
 22 25  1  0
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 24 20  1  0
 25 19  1  0
 26 22  1  0
 27 16  1  0
 28 14  1  0
 29 31  1  0
 30 12  1  0
 31 32  1  0
 32 30  1  0
 12 33  1  1
  9 10  1  0
 27 25  2  0
  7  5  1  0
  4  8  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA117462

   ---

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: 437.46

Molecular Weight (Monoisotopic): 437.1812

AlogP: 1.07

#Rotatable Bonds: 8

Polar Surface Area: 180.58

Molecular Species: ZWITTERION

HBA: 9

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.45

CX Basic pKa: 9.72

CX LogP: -1.87

CX LogD: -1.87

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.34

Np Likeness Score: -0.41

References

1. Rosowsky A, Forsch RA, Null A, Moran RG..  (1999)  5-deazafolate analogues with a rotationally restricted glutamate or ornithine side chain: synthesis and binding interaction with folylpolyglutamate synthetase.,  42  (18): [PMID:10479284] [10.1021/jm9807205]

Source

Source(1):

• Scientific Literature