ID: ALA519546

Max Phase: Preclinical

Molecular Formula: C27H36N2O4

Molecular Weight: 452.60

Molecule Type: Small molecule

Representations

Synonyms (1): 7'-O-Demethylisocephaeline
Synonyms from Alternative Forms(1):

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

Standard InChI:  InChI=1S/C27H36N2O4/c1-4-16-15-29-8-6-18-12-26(32-2)27(33-3)14-21(18)23(29)10-19(16)9-22-20-13-25(31)24(30)11-17(20)5-7-28-22/h11-14,16,19,22-23,28,30-31H,4-10,15H2,1-3H3/t16-,19-,22-,23-/m0/s1

Standard InChI Key:  HGQNZTBYUKKJLH-CQOCVSQPSA-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: 452.60

Molecular Weight (Monoisotopic): 452.2675

AlogP: 4.34

#Rotatable Bonds: 5

Polar Surface Area: 74.19

Molecular Species: BASE

HBA: 6

HBD: 3

#RO5 Violations: 0

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 9.62

CX Basic pKa: 8.91

CX LogP: 3.65

CX LogD: 1.50

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.59

Np Likeness Score: 1.30

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