N-[4-[[(2,4-Diamino-6-pteridinyl)methyl]methylamino]phenylcarbamoyl]-DL-asparticAcid

ID: ALA3245588

PubChem CID: 90655744

Max Phase: Preclinical

Molecular Formula: C19H21N9O5

Molecular Weight: 455.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(Cc1cnc2nc(N)nc(N)c2n1)c1ccc(NC(=O)NC(CC(=O)O)C(=O)O)cc1

Standard InChI:  InChI=1S/C19H21N9O5/c1-28(8-10-7-22-16-14(23-10)15(20)26-18(21)27-16)11-4-2-9(3-5-11)24-19(33)25-12(17(31)32)6-13(29)30/h2-5,7,12H,6,8H2,1H3,(H,29,30)(H,31,32)(H2,24,25,33)(H4,20,21,22,26,27)

Standard InChI Key:  PQDTXBOBMMIMKI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 33 35  0  0  0  0  0  0  0  0999 V2000
   12.6343   -8.1579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2053   -8.1579    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.9198   -8.5704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9198   -9.3954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6343   -9.8079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6343  -10.6329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3487   -9.3954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6343   -7.3329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3487   -8.5704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4909   -8.5704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7764   -8.1579    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4909   -9.3954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0619   -8.5704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0619   -9.3954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3474   -9.8079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6330   -9.3954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6330   -8.5704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3474   -8.1579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9185   -9.8079    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9185  -10.6329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2040   -9.3954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3461  -11.0454    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6317  -10.6329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6317   -9.8079    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3461   -9.3954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0606   -9.8079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7751   -9.3954    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4896   -9.8079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4896  -10.6329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7751  -11.0454    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0606  -10.6329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3461   -8.5704    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9172  -11.0454    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  1  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  1  8  2  0
  1  9  1  0
 10 11  1  0
 10 12  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 13 18  2  0
 19 20  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 22 31  2  0
 26 31  1  0
 25 32  1  0
 23 33  1  0
 21 28  1  0
 19 21  1  0
 16 19  1  0
 11 13  1  0
  2 10  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3245588

   2-[[4-[(2,4-Diaminopteridin-6-yl)methyl-methylamino]phenyl]carbamoylamino]butanedioic acid

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: 455.44

Molecular Weight (Monoisotopic): 455.1666

AlogP: 0.27

#Rotatable Bonds: 8

Polar Surface Area: 222.57

Molecular Species: ACID

HBA: 10

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 14

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.43

CX Basic pKa: 2.86

CX LogP: -0.41

CX LogD: -5.69

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.27

Np Likeness Score: -0.92

References

1. Martinelli JE, Chaykovsky M, Kisliuk RL, Gaumont Y, Gittelman MC..  (1979)  Methotrexate analogues. 12. Synthesis and biological properties of some aza homologues.,  22  (7): [PMID:109616] [10.1021/jm00193a022]

Source

Source(1):

• Scientific Literature