ID: ALA486004

Max Phase: Preclinical

Molecular Formula: C27H36N2O5

Molecular Weight: 468.59

Molecule Type: Small molecule

Representations

Synonyms (1): Klugine
Synonyms from Alternative Forms(1):

Canonical SMILES:  CC[C@H]1CN2CCc3cc(O)c(OC)cc3[C@@H]2C[C@@H]1C[C@@]1(O)NCCc2cc(O)c(OC)cc21

Standard InChI:  InChI=1S/C27H36N2O5/c1-4-16-15-29-8-6-17-10-23(30)25(33-2)12-20(17)22(29)9-19(16)14-27(32)21-13-26(34-3)24(31)11-18(21)5-7-28-27/h10-13,16,19,22,28,30-32H,4-9,14-15H2,1-3H3/t16-,19+,22-,27-/m0/s1

Standard InChI Key:  IIFHKWNCTVOSKL-OKGGWNPJSA-N

Molecule Features

Natural Product: Yes

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: 468.59

Molecular Weight (Monoisotopic): 468.2624

AlogP: 3.44

#Rotatable Bonds: 5

Polar Surface Area: 94.42

Molecular Species: BASE

HBA: 7

HBD: 4

#RO5 Violations: 0

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 9.69

CX Basic pKa: 8.61

CX LogP: 3.52

CX LogD: 2.08

Aromatic Rings: 2

Heavy Atoms: 34

QED Weighted: 0.53

Np Likeness Score: 1.44

References

1. Zhou YD, Kim YP, Mohammed KA, Jones DK, Muhammad I, Dunbar DC, Nagle DG..  (2005)  Terpenoid tetrahydroisoquinoline alkaloids emetine, klugine, and isocephaeline inhibit the activation of hypoxia-inducible factor-1 in breast tumor cells.,  68  (6): [PMID:15974627] [10.1021/np050029m]

2. Muhammad I, Dunbar DC, Khan SI, Tekwani BL, Bedir E, Takamatsu S, Ferreira D, Walker LA..  (2003)  Antiparasitic alkaloids from Psychotria klugii.,  66  (7): [PMID:12880315] [10.1021/np030086k]

Source

Source(1):

• Scientific Literature