5-(5-((2,4-diaminopyrimidin-5-yl)methyl)-2,3-dimethoxyphenyl)pent-4-ynoic acid

ID: ALA2282813

PubChem CID: 76312739

Max Phase: Preclinical

Molecular Formula: C18H20N4O4

Molecular Weight: 356.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(Cc2cnc(N)nc2N)cc(C#CCCC(=O)O)c1OC

Standard InChI:  InChI=1S/C18H20N4O4/c1-25-14-9-11(8-13-10-21-18(20)22-17(13)19)7-12(16(14)26-2)5-3-4-6-15(23)24/h7,9-10H,4,6,8H2,1-2H3,(H,23,24)(H4,19,20,21,22)

Standard InChI Key:  NTEDBEJGQHMAKR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 27  0  0  0  0  0  0  0  0999 V2000
   11.7585   -2.5052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4662   -2.0966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1739   -2.5052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0512   -2.0937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3440   -2.5016    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.3436   -3.3197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0562   -3.7281    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.7605   -3.3179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1714   -3.3235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8782   -3.7320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5869   -3.3234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5843   -2.5019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8768   -2.0971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0528   -1.2765    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.6364   -3.7292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.2906   -2.0908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.9997   -2.4969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2952   -3.7310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2963   -4.5482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8778   -4.5492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8716   -5.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8654   -6.1826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5700   -6.5965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2808   -6.1934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9853   -6.6073    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2870   -5.3762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  1  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  1  1  0
  3  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  3  1  0
  4 14  1  0
  6 15  1  0
 12 16  1  0
 16 17  1  0
 11 18  1  0
 18 19  1  0
 10 20  1  0
 20 21  3  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2282813

   5-[5-[(2,4-Diaminopyrimidin-5-yl)methyl]-2,3-dimethoxyphenyl]pent-4-ynoic 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: 356.38

Molecular Weight (Monoisotopic): 356.1485

AlogP: 1.47

#Rotatable Bonds: 6

Polar Surface Area: 133.58

Molecular Species: ACID

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.60

CX Basic pKa: 8.16

CX LogP: 0.30

CX LogD: -0.13

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.66

Np Likeness Score: 0.18

References

1. Kiani YS, Kalsoom S, Riaz N.  (2013)  In silico ligand-based pharmacophore model generation for the identification of novel Pneumocystis carinii DHFR inhibitors,  22  (2): [10.1007/s00044-012-0082-2]

Source

Source(1):

• Scientific Literature