4-[5-(2,4-Diamino-pteridin-6-ylmethyl)-5H-dibenzo[b,f]azepin-1-yl]-but-3-ynoic acid

ID: ALA190807

Chembl Id: CHEMBL190807

PubChem CID: 44398535

Max Phase: Preclinical

Molecular Formula: C25H19N7O2

Molecular Weight: 449.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc(N)c2nc(CN3c4ccccc4C=Cc4c(C#CCC(=O)O)cccc43)cnc2n1

Standard InChI:  InChI=1S/C25H19N7O2/c26-23-22-24(31-25(27)30-23)28-13-17(29-22)14-32-19-8-2-1-5-16(19)11-12-18-15(6-3-9-20(18)32)7-4-10-21(33)34/h1-3,5-6,8-9,11-13H,10,14H2,(H,33,34)(H4,26,27,28,30,31)

Standard InChI Key:  KOMMMDLJBSKWOZ-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA190807

   4-[11-[(2,4-Diaminopteridin-6-yl)methyl]benzo[b][1]benzazepin-4-yl]but-3-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: 449.47

Molecular Weight (Monoisotopic): 449.1600

AlogP: 3.23

#Rotatable Bonds: 3

Polar Surface Area: 144.14

Molecular Species: ACID

HBA: 8

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.66

CX Basic pKa: 2.91

CX LogP: 3.15

CX LogD: -0.06

Aromatic Rings: 4

Heavy Atoms: 34

QED Weighted: 0.40

Np Likeness Score: -0.33

References

1. Chan DC, Fu H, Forsch RA, Queener SF, Rosowsky A..  (2005)  Design, synthesis, and antifolate activity of new analogues of piritrexim and other diaminopyrimidine dihydrofolate reductase inhibitors with omega-carboxyalkoxy or omega-carboxy-1-alkynyl substitution in the side chain.,  48  (13): [PMID:15974594] [10.1021/jm0581718]

Source

Source(1):

• Scientific Literature