ID: ALA486005

Max Phase: Preclinical

Molecular Formula: C28H38N2O4

Molecular Weight: 466.62

Molecule Type: Small molecule

Representations

Synonyms (1): Isocephaeline
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(OC)cc21

Standard InChI:  InChI=1S/C28H38N2O4/c1-5-17-16-30-9-7-19-13-27(33-3)28(34-4)15-22(19)24(30)11-20(17)10-23-21-14-26(32-2)25(31)12-18(21)6-8-29-23/h12-15,17,20,23-24,29,31H,5-11,16H2,1-4H3/t17-,20-,23-,24-/m0/s1

Standard InChI Key:  DTGZHCFJNDAHEN-IAUHIMIASA-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: 466.62

Molecular Weight (Monoisotopic): 466.2832

AlogP: 4.64

#Rotatable Bonds: 6

Polar Surface Area: 63.19

Molecular Species: BASE

HBA: 6

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 10.09

CX Basic pKa: 9.15

CX LogP: 3.95

CX LogD: 1.36

Aromatic Rings: 2

Heavy Atoms: 34

QED Weighted: 0.65

Np Likeness Score: 1.22

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]

3. Cai YS, Wang C, Tian C, Sun WT, Chen L, Xiao D, Zhou SY, Qiu G, Yu J, Zhu K, Yang SP..  (2019)  Octahydro-Protoberberine and Protoemetine-Type Alkaloids from the Stems of Alangium salviifolium and Their Cytotoxicity.,  82  (9): [PMID:31513408] [10.1021/acs.jnatprod.9b00670]

Source

Source(1):

• Scientific Literature