2-{4-[(2-Amino-4-oxo-3,4,5,6,7,8-hexahydro-pyrido[2,3-d]pyrimidin-6-ylmethyl)-amino]-benzoylamino}-4-sulfo-butyric acid

ID: ALA417696

PubChem CID: 135887125

Max Phase: Preclinical

Molecular Formula: C19H24N6O7S

Molecular Weight: 480.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc(O)c2c(n1)NCC(CNc1ccc(C(=O)NC(CCS(=O)(=O)O)C(=O)O)cc1)C2

Standard InChI:  InChI=1S/C19H24N6O7S/c20-19-24-15-13(17(27)25-19)7-10(9-22-15)8-21-12-3-1-11(2-4-12)16(26)23-14(18(28)29)5-6-33(30,31)32/h1-4,10,14,21H,5-9H2,(H,23,26)(H,28,29)(H,30,31,32)(H4,20,22,24,25,27)

Standard InChI Key:  RYAKEVWNSQUJCU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 33 35  0  0  0  0  0  0  0  0999 V2000
    2.4125   -4.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8917   -4.3667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4125   -3.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3750   -3.4625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8917   -3.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3750   -4.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1667   -2.5625    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.9292   -4.3667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5667   -2.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0917   -2.5667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6125   -1.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6125   -2.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9292   -3.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1667   -3.1625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6917   -2.2625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0542   -2.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8875   -2.5625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    8.6500   -2.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5667   -1.6667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1292   -1.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4542   -3.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8542   -4.3667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.7500   -2.7167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4917   -3.4625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4542   -4.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0500   -3.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5292   -2.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0125   -3.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9750   -3.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0917   -1.3667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0125   -2.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5292   -3.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  1  1  0
  4  5  1  0
  5  3  2  0
  6  2  1  0
  7 19  1  0
  8  1  1  0
  9 16  1  0
 10  9  1  0
 11 12  1  0
 12 10  1  0
 13  3  1  0
 14  7  2  0
 15  7  2  0
 16 27  2  0
 17  5  1  0
 18 12  1  0
 19 18  1  0
 20  9  2  0
 21 11  2  0
 22 26  1  0
 23  6  1  0
 24  7  1  0
 25 30  1  0
 26  8  1  0
 27 33  1  0
 28 32  2  0
 29 25  1  0
 30 22  1  0
 31 11  1  0
 32 29  1  0
 33 29  2  0
  4  6  2  0
 13 22  1  0
 28 16  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA417696

   ---

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: 480.50

Molecular Weight (Monoisotopic): 480.1427

AlogP: -0.08

#Rotatable Bonds: 9

Polar Surface Area: 216.86

Molecular Species: ACID

HBA: 10

HBD: 7

#RO5 Violations: 1

HBA (Lipinski): 13

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 2

CX Acidic pKa: -1.41

CX Basic pKa: 4.07

CX LogP: -2.27

CX LogD: -6.29

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.23

Np Likeness Score: -0.18

References

1. Rosowsky A, Forsch RA, Reich VE, Freisheim JH, Moran RG..  (1992)  Side chain modified 5-deazafolate and 5-deazatetrahydrofolate analogues as mammalian folylpolyglutamate synthetase and glycinamide ribonucleotide formyltransferase inhibitors: synthesis and in vitro biological evaluation.,  35  (9): [PMID:1578484] [10.1021/jm00087a012]

Source

Source(1):

• Scientific Literature