dimethyl N-[4-[[(2,4-Diamino-6-pteridinyl)methyl]-methylamino]phenylcarbamoyl]-L-aspartate

ID: ALA3245586

PubChem CID: 90655742

Max Phase: Preclinical

Molecular Formula: C21H25N9O5

Molecular Weight: 483.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)C[C@H](NC(=O)Nc1ccc(N(C)Cc2cnc3nc(N)nc(N)c3n2)cc1)C(=O)OC

Standard InChI:  InChI=1S/C21H25N9O5/c1-30(10-12-9-24-18-16(25-12)17(22)28-20(23)29-18)13-6-4-11(5-7-13)26-21(33)27-14(19(32)35-3)8-15(31)34-2/h4-7,9,14H,8,10H2,1-3H3,(H2,26,27,33)(H4,22,23,24,28,29)/t14-/m0/s1

Standard InChI Key:  UCRGOHIYSDFDLY-AWEZNQCLSA-N

Molfile:  

     RDKit          2D

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   12.4280   -6.7760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9991   -6.7760    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.7135   -7.1885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7135   -8.0135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4280   -8.4260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4280   -9.2510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   10.2846   -7.1885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5701   -6.7760    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.2846   -8.0135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8557   -7.1885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8557   -8.0135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1412   -8.4260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.9978   -8.0135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1399   -9.6635    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4254   -9.2510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4254   -8.4260    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1399   -8.0135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8544   -8.4260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5688   -8.0135    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2833   -8.4260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2833   -9.2510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5688   -9.6635    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8544   -9.2510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1399   -7.1885    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7110   -9.6635    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.8570   -6.7760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8570   -8.4260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  6
  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
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 15 16  1  0
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 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
  9 34  1  0
  7 35  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3245586

   dimethyl (2S)-2-[[4-[(2,4-diaminopteridin-6-yl)methyl-methylamino]phenyl]carbamoylamino]butanedioate

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: 483.49

Molecular Weight (Monoisotopic): 483.1979

AlogP: 0.45

#Rotatable Bonds: 8

Polar Surface Area: 200.57

Molecular Species: NEUTRAL

HBA: 12

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 14

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: 3.00

CX LogP: 0.05

CX LogD: 0.05

Aromatic Rings: 3

Heavy Atoms: 35

QED Weighted: 0.32

Np Likeness Score: -0.96

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