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

ID: ALA289923

PubChem CID: 135887124

Max Phase: Preclinical

Molecular Formula: C20H27N7O4

Molecular Weight: 429.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NCCCC(NC(=O)c1ccc(NCC2CNc3nc(N)nc(O)c3C2)cc1)C(=O)O

Standard InChI:  InChI=1S/C20H27N7O4/c21-7-1-2-15(19(30)31)25-17(28)12-3-5-13(6-4-12)23-9-11-8-14-16(24-10-11)26-20(22)27-18(14)29/h3-6,11,15,23H,1-2,7-10,21H2,(H,25,28)(H,30,31)(H4,22,24,26,27,29)

Standard InChI Key:  YYXQTKSKWJEYRP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
    2.2542   -4.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7417   -4.3667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2542   -3.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2250   -3.4625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7417   -3.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2250   -4.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7792   -4.3667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4167   -2.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9417   -2.5667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4625   -1.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7792   -3.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4625   -2.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9042   -2.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7375   -2.5625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4167   -1.6667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9792   -1.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3042   -3.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7042   -4.3667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3417   -3.4625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3042   -4.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9000   -3.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3792   -2.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8625   -3.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8250   -3.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9417   -1.3667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8625   -2.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3792   -3.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5417   -2.2625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9792   -2.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0167   -2.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5000   -2.2625    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  1  1  0
  8 13  1  0
  9  8  1  0
 10 12  1  0
 11  3  1  0
 12  9  1  0
 13 21  2  0
 14  5  1  0
 15  8  2  0
 16 10  2  0
 17 20  1  0
 18  6  1  0
 19 24  1  0
 20  7  1  0
 21 27  1  0
 22 26  2  0
 23 19  1  0
 24 17  1  0
 25 10  1  0
 26 23  1  0
 27 23  2  0
 28 30  1  0
 29 12  1  0
 30 31  1  0
 31 29  1  0
  6  4  2  0
 17 11  1  0
 13 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA289923

   ---

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: 429.48

Molecular Weight (Monoisotopic): 429.2125

AlogP: 0.38

#Rotatable Bonds: 9

Polar Surface Area: 188.51

Molecular Species: ZWITTERION

HBA: 9

HBD: 7

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 9

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.36

CX Basic pKa: 9.89

CX LogP: -2.04

CX LogD: -2.04

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.29

Np Likeness Score: 0.01

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]

2. Singh SK, Singer SC, Ferone R, Waters KA, Mullin RJ, Hynes JB..  (1992)  Synthesis and biological evaluation of N alpha-(5-deaza-5,6,7,8-tetrahydropteroyl)-L-ornithine.,  35  (11): [PMID:1375963] [10.1021/jm00089a009]

Source

Source(1):

• Scientific Literature