DL-3-[4-[[(2,4-Diamino-6-pteridinyl)methyl]methylamino]phenyl]-5-(2-carbomethoxyethyl)hydantoin

ID: ALA3245590

PubChem CID: 90655746

Max Phase: Preclinical

Molecular Formula: C21H23N9O4

Molecular Weight: 465.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)CCC1NC(=O)N(c2ccc(N(C)Cc3cnc4nc(N)nc(N)c4n3)cc2)C1=O

Standard InChI:  InChI=1S/C21H23N9O4/c1-29(10-11-9-24-18-16(25-11)17(22)27-20(23)28-18)12-3-5-13(6-4-12)30-19(32)14(26-21(30)33)7-8-15(31)34-2/h3-6,9,14H,7-8,10H2,1-2H3,(H,26,33)(H4,22,23,24,27,28)

Standard InChI Key:  AQLKDVVRYXBITI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 34 37  0  0  0  0  0  0  0  0999 V2000
   12.7530   -8.8081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5815   -9.6151    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.7610   -9.7013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3485  -10.4158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4254   -8.9477    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.0385   -8.3956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9523   -7.5751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5067   -8.4726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1741   -8.9575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9278   -8.6219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5952   -9.1069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0140   -7.8014    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3466   -7.3165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6185   -8.7761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0664   -9.3892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2595   -9.2177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0045   -8.4331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5565   -7.8200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3635   -7.9915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1975   -8.2615    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9840   -7.4647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6142   -8.8449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4266   -7.9908    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2131   -7.1939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7965   -6.6106    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5934   -6.8241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8069   -7.6210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6038   -7.8345    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8173   -8.6314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2339   -9.2147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4370   -9.0012    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2235   -8.2043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1767   -6.2407    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4162   -6.9804    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  2  0
  1  6  1  0
  8  9  1  0
 10 11  2  0
 12 13  1  0
 10 12  1  0
  9 10  1  0
  1  8  1  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
  5 14  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3245590

   Methyl 3-[1-[4-[(2,4-diaminopteridin-6-yl)methyl-methylamino]phenyl]-2,5-dioxoimidazolidin-4-yl]propanoate

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: 465.47

Molecular Weight (Monoisotopic): 465.1873

AlogP: 0.60

#Rotatable Bonds: 7

Polar Surface Area: 182.55

Molecular Species: NEUTRAL

HBA: 11

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 13

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.41

CX Basic pKa: 3.00

CX LogP: 0.05

CX LogD: 0.05

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.33

Np Likeness Score: -0.80

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