6-(((3,4-dichlorophenyl)(propyl)amino)methyl)pteridine-2,4-diamine

ID: ALA3272500

PubChem CID: 12417555

Max Phase: Preclinical

Molecular Formula: C16H17Cl2N7

Molecular Weight: 378.27

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCN(Cc1cnc2nc(N)nc(N)c2n1)c1ccc(Cl)c(Cl)c1

Standard InChI:  InChI=1S/C16H17Cl2N7/c1-2-5-25(10-3-4-11(17)12(18)6-10)8-9-7-21-15-13(22-9)14(19)23-16(20)24-15/h3-4,6-7H,2,5,8H2,1H3,(H4,19,20,21,23,24)

Standard InChI Key:  BOULTKNOXWAXNT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    4.2105   -3.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2094   -4.5431    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9234   -4.9556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9216   -3.3044    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6363   -3.7131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6351   -4.5452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3511   -4.9600    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0730   -4.5473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0742   -3.7151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3536   -3.2957    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9231   -5.7797    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4968   -3.3049    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7856   -4.9613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5003   -4.5513    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2129   -4.9654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2055   -5.7905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9172   -6.2044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6331   -5.7944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6327   -4.9661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9204   -4.5557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3461   -4.5535    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   11.3461   -6.2074    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.5028   -3.7193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2244   -3.3054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2267   -2.4734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  5 10  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  3 11  1  0
  1 12  1  0
  8 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
 19 21  1  0
 18 22  1  0
 14 23  1  0
 23 24  1  0
 24 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3272500

   6-[(3,4-dichloro-N-propylanilino)methyl]pteridine-2,4-diamine

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: 378.27

Molecular Weight (Monoisotopic): 377.0922

AlogP: 3.31

#Rotatable Bonds: 5

Polar Surface Area: 106.84

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 1.81

CX LogP: 3.32

CX LogD: 3.32

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.70

Np Likeness Score: -1.22

References

1. Worth DF, Johnson J, Elslager EF, Werbel LM..  (1978)  Folate antagonists. 10. Synthesis and antimalarial effects of 6-[[(aryl and aralkyl)amino]methyl]-2,4-pteridinediamines and -pteridinediamine 8-oxides.,  21  (4): [PMID:349157] [10.1021/jm00202a003]

Source

Source(1):

• Scientific Literature