2-{4-[2-(2,4-Diamino-furo[2,3-d]pyrimidin-5-yl)-1-methyl-vinyl]-benzoylamino}-pentanedioic acid (E-isomer)

ID: ALA2092925

Chembl Id: CHEMBL2092925

PubChem CID: 52943039

Max Phase: Preclinical

Molecular Formula: C21H21N5O6

Molecular Weight: 439.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C/C(=C\c1coc2nc(N)nc(N)c12)c1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1

Standard InChI:  InChI=1S/C21H21N5O6/c1-10(8-13-9-32-19-16(13)17(22)25-21(23)26-19)11-2-4-12(5-3-11)18(29)24-14(20(30)31)6-7-15(27)28/h2-5,8-9,14H,6-7H2,1H3,(H,24,29)(H,27,28)(H,30,31)(H4,22,23,25,26)/b10-8+/t14-/m0/s1

Standard InChI Key:  RDIKKVMTSXCIPF-PLWJUESGSA-N

Alternative Forms

1. Parent:

   

   ALA2092925

   (2S)-2-[[4-[(E)-1-(2,4-diaminofuro[2,3-d]pyrimidin-5-yl)prop-1-en-2-yl]benzoyl]amino]pentanedioic 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: 439.43

Molecular Weight (Monoisotopic): 439.1492

AlogP: 2.00

#Rotatable Bonds: 8

Polar Surface Area: 194.66

Molecular Species: ACID

HBA: 8

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.22

CX Basic pKa: 5.21

CX LogP: -0.47

CX LogD: -4.96

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.35

Np Likeness Score: -0.13

References

1. Gangjee A, Zeng Y, McGuire JJ, Kisliuk RL..  (2000)  Effect of C9-methyl substitution and C8-C9 conformational restriction on antifolate and antitumor activity of classical 5-substituted 2,4-diaminofuro[2,3-d]pyrimidines.,  43  (16): [PMID:10956221] [10.1021/jm000130i]

Source

Source(1):

• Scientific Literature