ID: ALA385072

Max Phase: Preclinical

Molecular Formula: C29H40N8O4S

Molecular Weight: 596.76

Molecule Type: Small molecule

Representations

Canonical SMILES:  Cn1cnc(S(=O)(=O)N(CCN(Cc2cncn2C)c2ccc(C#N)cc2)CC2CCN(C(=O)OC(C)(C)C)CC2)c1

Standard InChI:  InChI=1S/C29H40N8O4S/c1-29(2,3)41-28(38)35-12-10-24(11-13-35)18-37(42(39,40)27-20-33(4)22-32-27)15-14-36(19-26-17-31-21-34(26)5)25-8-6-23(16-30)7-9-25/h6-9,17,20-22,24H,10-15,18-19H2,1-5H3

Standard InChI Key:  NYTPJJDEMIZHPE-UHFFFAOYSA-N

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

Properties

Molecular Weight: 596.76

Molecular Weight (Monoisotopic): 596.2893

AlogP: 3.37

#Rotatable Bonds: 10

Polar Surface Area: 129.59

Molecular Species: NEUTRAL

HBA: 10

HBD: 0

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 0

#RO5 Violations (Lipinski): 2

CX Acidic pKa:

CX Basic pKa: 6.22

CX LogP: 2.63

CX LogD: 2.61

Aromatic Rings: 3

Heavy Atoms: 42

QED Weighted: 0.35

Np Likeness Score: -1.41

References

1. Glenn MP, Chang SY, Hornéy C, Rivas K, Yokoyama K, Pusateri EE, Fletcher S, Cummings CG, Buckner FS, Pendyala PR, Chakrabarti D, Sebti SM, Gelb M, Van Voorhis WC, Hamilton AD..  (2006)  Structurally simple, potent, Plasmodium selective farnesyltransferase inhibitors that arrest the growth of malaria parasites.,  49  (19): [PMID:16970397] [10.1021/jm060081v]

2. Fletcher S, Cummings CG, Rivas K, Katt WP, Hornéy C, Buckner FS, Chakrabarti D, Sebti SM, Gelb MH, Van Voorhis WC, Hamilton AD..  (2008)  Potent, Plasmodium-selective farnesyltransferase inhibitors that arrest the growth of malaria parasites: structure-activity relationships of ethylenediamine-analogue scaffolds and homology model validation.,  51  (17): [PMID:18686940] [10.1021/jm800113p]

3. Fletcher S, Keaney EP, Cummings CG, Blaskovich MA, Hast MA, Glenn MP, Chang SY, Bucher CJ, Floyd RJ, Katt WP, Gelb MH, Van Voorhis WC, Beese LS, Sebti SM, Hamilton AD..  (2010)  Structure-based design and synthesis of potent, ethylenediamine-based, mammalian farnesyltransferase inhibitors as anticancer agents.,  53  (19): [PMID:20822181] [10.1021/jm1001748]

Source

Source(1):

• Scientific Literature