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

ID: ALA1650307

Chembl Id: CHEMBL1650307

PubChem CID: 25033603

Max Phase: Preclinical

Molecular Formula: C30H31N9O3

Molecular Weight: 565.64

Molecule Type: Small molecule

Names and Identifiers

Synonyms: BAL0030544 | CHEMBL1650307|BAL0030544|(E)-3-[5-[(2,4-diaminopyrimidin-5-yl)methyl]-2,3-dimethoxyphenyl]-1-[1-[2-(dimethylamino)pyrimidin-5-yl]-1H-phthalazin-2-yl]prop-2-en-1-one

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

Standard InChI:  InChI=1S/C30H31N9O3/c1-38(2)30-34-15-22(16-35-30)26-23-8-6-5-7-20(23)17-36-39(26)25(40)10-9-19-11-18(13-24(41-3)27(19)42-4)12-21-14-33-29(32)37-28(21)31/h5-11,13-17,26H,12H2,1-4H3,(H4,31,32,33,37)/b10-9+

Standard InChI Key:  MMLDINXSLFMQNR-MDZDMXLPSA-N

Alternative Forms

1. Parent:

   

   ALA1650307

   (E)-3-[5-[(2,4-diaminopyrimidin-5-yl)methyl]-2,3-dimethoxyphenyl]-1-[1-[2-(dimethylamino)pyrimidin-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: 565.64

Molecular Weight (Monoisotopic): 565.2550

AlogP: 3.08

#Rotatable Bonds: 8

Polar Surface Area: 157.97

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: 3.56

CX LogD: 3.37

Aromatic Rings: 4

Heavy Atoms: 42

QED Weighted: 0.30

Np Likeness Score: -0.26

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