9-(2-Amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-6-yl)nonanoic Acid

ID: ALA3086863

PubChem CID: 136241610

Max Phase: Preclinical

Molecular Formula: C15H22N4O3

Molecular Weight: 306.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc2[nH]c(CCCCCCCCC(=O)O)cc2c(=O)[nH]1

Standard InChI:  InChI=1S/C15H22N4O3/c16-15-18-13-11(14(22)19-15)9-10(17-13)7-5-3-1-2-4-6-8-12(20)21/h9H,1-8H2,(H,20,21)(H4,16,17,18,19,22)

Standard InChI Key:  SQEUPDXSHKECRJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 23  0  0  0  0  0  0  0  0999 V2000
   19.2273  -26.1460    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.2262  -26.9655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9342  -27.3745    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.9325  -25.7371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6411  -26.1424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6459  -26.9610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4259  -27.2094    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.9033  -26.5443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4181  -25.8849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5182  -27.3735    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.9300  -24.9199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.7204  -26.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1249  -25.8294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9420  -25.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3464  -25.1145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1636  -25.1096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5680  -24.3995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3852  -24.3947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7896  -23.6846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6068  -23.6798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0072  -22.9706    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.0155  -24.3860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  6  1  0
  5  4  1  0
  4  1  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
  2 10  1  0
  4 11  2  0
  8 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3086863

   ---

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: 306.37

Molecular Weight (Monoisotopic): 306.1692

AlogP: 2.19

#Rotatable Bonds: 9

Polar Surface Area: 124.86

Molecular Species: ACID

HBA: 4

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 5.30

CX Basic pKa: 4.61

CX LogP: 1.72

CX LogD: -0.09

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.53

Np Likeness Score: 0.34

References

1. Wang Y, Cherian C, Orr S, Mitchell-Ryan S, Hou Z, Raghavan S, Matherly LH, Gangjee A..  (2013)  Tumor-targeting with novel non-benzoyl 6-substituted straight chain pyrrolo[2,3-d]pyrimidine antifolates via cellular uptake by folate receptor α and inhibition of de novo purine nucleotide biosynthesis.,  56  (21): [PMID:24111942] [10.1021/jm401139z]

Source

Source(1):

• Scientific Literature