3-(5-((2,4-diaminopyrimidin-5-yl)methyl)-2,3-dimethoxyphenyl)-1-(1-(2-methoxypyrimidin-5-yl)phthalazin-2(1H)-yl)prop-2-en-1-one

ID: ALA1650306

Chembl Id: CHEMBL1650306

PubChem CID: 53321902

Max Phase: Preclinical

Molecular Formula: C29H28N8O4

Molecular Weight: 552.60

Molecule Type: Small molecule

Names and Identifiers

Synonyms: BAL0030543 | CHEMBL1650306|BAL0030543

Canonical SMILES:  COc1ncc(C2c3ccccc3C=NN2C(=O)/C=C/c2cc(Cc3cnc(N)nc3N)cc(OC)c2OC)cn1

Standard InChI:  InChI=1S/C29H28N8O4/c1-39-23-12-17(11-20-13-32-28(31)36-27(20)30)10-18(26(23)40-2)8-9-24(38)37-25(21-14-33-29(41-3)34-15-21)22-7-5-4-6-19(22)16-35-37/h4-10,12-16,25H,11H2,1-3H3,(H4,30,31,32,36)/b9-8+

Standard InChI Key:  DQACSDIFXYEAFK-CMDGGOBGSA-N

Alternative Forms

1. Parent:

   

   ALA1650306

   (E)-3-[5-[(2,4-diaminopyrimidin-5-yl)methyl]-2,3-dimethoxyphenyl]-1-[1-(2-methoxypyrimidin-5-yl)-1H-phthalazin-2-yl]prop-2-en-1-one

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: 552.60

Molecular Weight (Monoisotopic): 552.2234

AlogP: 3.03

#Rotatable Bonds: 8

Polar Surface Area: 163.96

Molecular Species: NEUTRAL

HBA: 11

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa:

CX Basic pKa: 8.16

CX LogP: 3.29

CX LogD: 3.11

Aromatic Rings: 4

Heavy Atoms: 41

QED Weighted: 0.31

Np Likeness Score: -0.18

References

1. Bowker KE, Caspers P, Gaucher B, MacGowan AP..  (2009)  In vitro activities of three new dihydrofolate reductase inhibitors against clinical isolates of gram-positive bacteria.,  53  (11): [PMID:19738027] [10.1128/aac.00845-09]

2. Clark C, Ednie LM, Lin G, Smith K, Kosowska-Shick K, McGhee P, Dewasse B, Beachel L, Caspers P, Gaucher B, Mert G, Shapiro S, Appelbaum PC..  (2009)  Antistaphylococcal activity of dihydrophthalazine antifolates, a family of novel antibacterial drugs.,  53  (4): [PMID:19188385] [10.1128/aac.01619-08]

3. Caspers P, Bury L, Gaucher B, Heim J, Shapiro S, Siegrist S, Schmitt-Hoffmann A, Thenoz L, Urwyler H..  (2009)  In vitro and in vivo properties of dihydrophthalazine antifolates, a novel family of antibacterial drugs.,  53  (9): [PMID:19546364] [10.1128/aac.00377-09]

Source

Source(1):

• Scientific Literature