Standard InChI: InChI=1S/C20H22N4.ClH/c1-23(2)13-12-21-18-15-9-5-7-11-17(15)24(3)20-14-8-4-6-10-16(14)22-19(18)20;/h4-11H,12-13H2,1-3H3,(H,21,22);1H
Standard InChI Key: VKTZJUABBWIAJQ-UHFFFAOYSA-N
Associated Targets(Human)
HUVEC 11049 Activities
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Associated Targets(non-human)
Plasmodium falciparum 966862 Activities
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Vero 26788 Activities
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Rhodesain 1463 Activities
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Cathepsin B-like cysteine protease 88 Activities
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Trypanosoma brucei brucei 13300 Activities
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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
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Properties
Molecular Weight: 319.43
Molecular Weight (Monoisotopic): 319.1917
AlogP: 3.27
#Rotatable Bonds: 4
Polar Surface Area: 34.94
Molecular Species: BASE
HBA: 2
HBD: 2
#RO5 Violations: 0
HBA (Lipinski): 4
HBD (Lipinski): 2
#RO5 Violations (Lipinski): 0
CX Acidic pKa: 9.97
CX Basic pKa: 8.81
CX LogP: -1.80
CX LogD: -2.98
Aromatic Rings: 4
Heavy Atoms: 24
QED Weighted: 0.57
Np Likeness Score: -0.07
References
1.Lavrado J, Paulo A, Gut J, Rosenthal PJ, Moreira R.. (2008) Cryptolepine analogues containing basic aminoalkyl side-chains at C-11: synthesis, antiplasmodial activity, and cytotoxicity., 18 (4):[PMID:18207399][10.1016/j.bmcl.2008.01.015]
2.Lavrado J, Reszka AP, Moreira R, Neidle S, Paulo A.. (2010) C-11 diamino cryptolepine derivatives NSC748392, NSC748393, and NSC748394: anticancer profile and G-quadruplex stabilization., 20 (23):[PMID:20952194][10.1016/j.bmcl.2010.09.110]
3.Lavrado J, Cabal GG, Prudêncio M, Mota MM, Gut J, Rosenthal PJ, Díaz C, Guedes RC, dos Santos DJ, Bichenkova E, Douglas KT, Moreira R, Paulo A.. (2011) Incorporation of basic side chains into cryptolepine scaffold: structure-antimalarial activity relationships and mechanistic studies., 54 (3):[PMID:21207937][10.1021/jm101383f]
4.Lavrado J, Mackey Z, Hansell E, McKerrow JH, Paulo A, Moreira R.. (2012) Antitrypanosomal and cysteine protease inhibitory activities of alkyldiamine cryptolepine derivatives., 22 (19):[PMID:22926067][10.1016/j.bmcl.2012.07.104]
