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

ID: ALA1650308

Chembl Id: CHEMBL1650308

PubChem CID: 25033604

Max Phase: Preclinical

Molecular Formula: C32H33N9O4

Molecular Weight: 607.68

Molecule Type: Small molecule

Names and Identifiers

Synonyms: BAL0030545 | CHEMBL1650308|BAL0030545|(E)-3-[5-[(2,4-diaminopyrimidin-5-yl)methyl]-2,3-dimethoxyphenyl]-1-[1-(2-morpholin-4-ylpyrimidin-5-yl)-1H-phthalazin-2-yl]prop-2-en-1-one

Canonical SMILES:  COc1cc(Cc2cnc(N)nc2N)cc(/C=C/C(=O)N2N=Cc3ccccc3C2c2cnc(N3CCOCC3)nc2)c1OC

Standard InChI:  InChI=1S/C32H33N9O4/c1-43-26-15-20(14-23-16-35-31(34)39-30(23)33)13-21(29(26)44-2)7-8-27(42)41-28(25-6-4-3-5-22(25)19-38-41)24-17-36-32(37-18-24)40-9-11-45-12-10-40/h3-8,13,15-19,28H,9-12,14H2,1-2H3,(H4,33,34,35,39)/b8-7+

Standard InChI Key:  YTQNXENPQFRJGI-BQYQJAHWSA-N

Alternative Forms

1. Parent:

   

   ALA1650308

   (E)-3-[5-[(2,4-diaminopyrimidin-5-yl)methyl]-2,3-dimethoxyphenyl]-1-[1-(2-morpholin-4-ylpyrimidin-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: 607.68

Molecular Weight (Monoisotopic): 607.2656

AlogP: 2.85

#Rotatable Bonds: 8

Polar Surface Area: 167.20

Molecular Species: NEUTRAL

HBA: 12

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 13

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa:

CX Basic pKa: 8.16

CX LogP: 3.34

CX LogD: 3.15

Aromatic Rings: 4

Heavy Atoms: 45

QED Weighted: 0.28

Np Likeness Score: -0.49

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