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

ID: ALA3245589

PubChem CID: 90655745

Max Phase: Preclinical

Molecular Formula: C20H23N9O5

Molecular Weight: 469.46

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C20H23N9O5/c1-29(9-11-8-23-17-15(24-11)16(21)27-19(22)28-17)12-4-2-10(3-5-12)25-20(34)26-13(18(32)33)6-7-14(30)31/h2-5,8,13H,6-7,9H2,1H3,(H,30,31)(H,32,33)(H2,25,26,34)(H4,21,22,23,27,28)

Standard InChI Key:  DAOJZAXLOKDWKQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 34 36  0  0  0  0  0  0  0  0999 V2000
   13.8305   -9.2304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4016   -9.2304    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.1160   -9.6429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1160  -10.4679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8305  -10.8804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8305  -11.7054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1160  -12.1179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5450  -12.1179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8305   -8.4054    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5450   -9.6429    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6871   -9.6429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9726   -9.2304    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.6871  -10.4679    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2582   -9.6429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2582  -10.4679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5437  -10.8804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8292  -10.4679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8292   -9.6429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5437   -9.2304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1147  -10.8804    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1147  -11.7054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4003  -10.4679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5424  -12.1179    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8279  -11.7054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8279  -10.8804    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5424  -10.4679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2569  -10.8804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9713  -10.4679    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6858  -10.8804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6858  -11.7054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9713  -12.1179    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2569  -11.7054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5424   -9.6429    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1135  -12.1179    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  1  0
  6  7  2  0
  6  8  1  0
  1  9  2  0
  1 10  1  0
 11 12  1  0
 11 13  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 14 19  2  0
 20 21  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 23 32  2  0
 27 32  1  0
 26 33  1  0
 24 34  1  0
 22 29  1  0
 20 22  1  0
 17 20  1  0
 12 14  1  0
  2 11  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3245589

   2-[[4-[(2,4-Diaminopteridin-6-yl)methyl-methylamino]phenyl]carbamoylamino]pentanedioic 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: 469.46

Molecular Weight (Monoisotopic): 469.1822

AlogP: 0.66

#Rotatable Bonds: 9

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: 3.39

CX Basic pKa: 2.85

CX LogP: -0.14

CX LogD: -6.44

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.25

Np Likeness Score: -0.83

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