2-{4-[(2,4-Diamino-furo[2,3-d]pyrimidin-5-ylmethyl)-amino]-benzoylamino}-pentanedioic acid

ID: ALA17383

Chembl Id: CHEMBL17383

PubChem CID: 468708

Max Phase: Preclinical

Molecular Formula: C19H20N6O6

Molecular Weight: 428.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc(N)c2c(CNc3ccc(C(=O)NC(CCC(=O)O)C(=O)O)cc3)coc2n1

Standard InChI:  InChI=1S/C19H20N6O6/c20-15-14-10(8-31-17(14)25-19(21)24-15)7-22-11-3-1-9(2-4-11)16(28)23-12(18(29)30)5-6-13(26)27/h1-4,8,12,22H,5-7H2,(H,23,28)(H,26,27)(H,29,30)(H4,20,21,24,25)

Standard InChI Key:  ACXZKUHGYNILFP-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA17383

   2-[[4-[(2,4-Diaminofuro[2,3-d]pyrimidin-5-yl)methylamino]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: 428.41

Molecular Weight (Monoisotopic): 428.1444

AlogP: 1.05

#Rotatable Bonds: 9

Polar Surface Area: 206.69

Molecular Species: ACID

HBA: 9

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.31

CX Basic pKa: 5.20

CX LogP: -1.89

CX LogD: -6.33

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.28

Np Likeness Score: -0.41

References

1. Gangjee A, Devraj R, McGuire JJ, Kisliuk RL, Queener SF, Barrows LR..  (1994)  Classical and nonclassical furo[2,3-d]pyrimidines as novel antifolates: synthesis and biological activities.,  37  (8): [PMID:8164259] [10.1021/jm00034a015]

2. Gangjee A, Elzein E, Queener SF, McGuire JJ..  (1998)  Synthesis and biological activities of tricyclic conformationally restricted tetrahydropyrido annulated furo[2,3-d]pyrimidines as inhibitors of dihydrofolate reductases.,  41  (9): [PMID:9554874] [10.1021/jm9705420]

Source

Source(1):

• Scientific Literature