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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2020-02-26 21:41:54 UTC
HMDB IDHMDB0015597
Secondary Accession Numbers
  • HMDB15597
Metabolite Identification
Common NameVoacamine
DescriptionVoacamine, also known as voacanginine, belongs to the class of organic compounds known as ibogan-type alkaloids. These are indole alkaloids with a structure based on the ibogamine skeleton or a derivative thereof. Ibogamine is a pentacyclic heterocyclic compound consisting of an indole fused to an azepane-containing tricyclic moiety ring. Iboga alkaloids arise from the cyclization of a secodine-type precursor through the formation of a 16,21 bond. Voacamine may compete with anticancer drugs such as doxorubicin for P-gp transport, decreasing removal of doxorubicin. It was shown to exhibit in vivo activity with 25.4% and 43.4% inhibition of parasitaemia with 2.5 and 10 mg/kg, respectively. Voacamine is a drug which is used for the treatment of malaria. also under investigation for the modulation of multidrug resistance in cancer cells. It is an antimalarial drug approved for use in several African countries. It is an alkaloid isolated from the bark of the Pescheria fuchsiae folia tree. Voacamine is a very strong basic compound (based on its pKa). Voacamine is also under investigation for use in modulating multidrug-resistance in tumor cells. Voacamine is possibly a substrate for P-glycoprotein (P-gp), an efflux pump responsible for multidrug resistance in tumor cells.
Structure
Data?1582753314
Synonyms
ValueSource
Methyl-12-methoxy-13-(17-methoxy-17-oxovobasan-3alpha-yl)ibogamine-18-carboxylateKegg
Methyl-12-methoxy-13-(17-methoxy-17-oxovobasan-3a-yl)ibogamine-18-carboxylateGenerator
Methyl-12-methoxy-13-(17-methoxy-17-oxovobasan-3a-yl)ibogamine-18-carboxylic acidGenerator
Methyl-12-methoxy-13-(17-methoxy-17-oxovobasan-3alpha-yl)ibogamine-18-carboxylic acidGenerator
Methyl-12-methoxy-13-(17-methoxy-17-oxovobasan-3α-yl)ibogamine-18-carboxylateGenerator
Methyl-12-methoxy-13-(17-methoxy-17-oxovobasan-3α-yl)ibogamine-18-carboxylic acidGenerator
VoacanginineHMDB
VocamineHMDB
Chemical FormulaC43H52N4O5
Average Molecular Weight704.8968
Monoisotopic Molecular Weight704.393770794
IUPAC Namemethyl (1S,15S,17S,18S)-17-ethyl-6-[(1R,12R,14R,15E)-15-ethylidene-18-(methoxycarbonyl)-17-methyl-10,17-diazatetracyclo[12.3.1.0³,¹¹.0⁴,⁹]octadeca-3(11),4,6,8-tetraen-12-yl]-7-methoxy-3,13-diazapentacyclo[13.3.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]nonadeca-2(10),4,6,8-tetraene-1-carboxylate
Traditional Namevoacamine
CAS Registry Number3371-85-5
SMILES
[H][C@@]12C[C@H](CC)[C@]3([H])N(C1)CCC1=C(NC4=CC(=C(OC)C=C14)[C@@]1([H])C[C@]4([H])C(C(=O)OC)[C@@]([H])(CC5=C1NC1=CC=CC=C51)N(C)C\C4=C\C)[C@@]3(C2)C(=O)OC
InChI Identifier
InChI=1S/C43H52N4O5/c1-7-24-15-23-20-43(42(49)52-6)39-27(13-14-47(21-23)40(24)43)29-19-36(50-4)30(17-34(29)45-39)31-16-28-25(8-2)22-46(3)35(37(28)41(48)51-5)18-32-26-11-9-10-12-33(26)44-38(31)32/h8-12,17,19,23-24,28,31,35,37,40,44-45H,7,13-16,18,20-22H2,1-6H3/b25-8-/t23-,24-,28-,31+,35+,37?,40-,43+/m0/s1
InChI KeyVCMIRXRRQJNZJT-XRMSBCOFSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as ibogan-type alkaloids. These are indole alkaloids with a structure based on the ibogamine skeleton or a derivative thereof. Ibogamine is a pentacyclic heterocyclic compound consisting of an indole fused to an azepane-containing tricyclic moiety ring. Iboga alkaloids arise from the cyclization of a secodine-type precursor through the formation of a 16,21 bond.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassIbogan-type alkaloids
Sub ClassNot Available
Direct ParentIbogan-type alkaloids
Alternative Parents
Substituents
  • Ibogan skeleton
  • Vobasan skeleton
  • Catharanthine skeleton
  • Pyrroloazepine
  • 3-alkylindole
  • Indole
  • Indole or derivatives
  • Piperidinecarboxylic acid
  • Anisole
  • Alkyl aryl ether
  • Azepine
  • Aralkylamine
  • Dicarboxylic acid or derivatives
  • Piperidine
  • Benzenoid
  • Pyrrole
  • Methyl ester
  • Heteroaromatic compound
  • Amino acid or derivatives
  • Tertiary aliphatic amine
  • Tertiary amine
  • Carboxylic acid ester
  • Organoheterocyclic compound
  • Azacycle
  • Carboxylic acid derivative
  • Ether
  • Amine
  • Organic nitrogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxygen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0032 g/LNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0032 g/LALOGPS
logP6.26ALOGPS
logP6.21ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)15.56ChemAxon
pKa (Strongest Basic)8.53ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area99.89 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity203.68 m³·mol⁻¹ChemAxon
Number of Rings9ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ab9-0000009500-a1a64a21f7d9ec3401faSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05g1-0001009100-2b2d3c299d1d143b7473Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dr-0000039000-9017d6876d59e4847db3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000004900-deceec71058f12cd75d0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udr-0002009300-7d3cb4a2a467e2e222edSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052r-0013009000-b8e009201a2611beca79Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB04877 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB04877 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB04877
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDC00001785
Chemspider ID10128230
KEGG Compound IDC09252
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkVoacamine
METLIN IDNot Available
PubChem Compound11953931
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Meschini S, Marra M, Calcabrini A, Federici E, Galeffi C, Arancia G: Voacamine, a bisindolic alkaloid from Peschiera fuchsiaefolia, enhances the cytotoxic effect of doxorubicin on multidrug-resistant tumor cells. Int J Oncol. 2003 Dec;23(6):1505-13. [PubMed:14612920 ]
  2. Meschini S, Marra M, Condello M, Calcabrini A, Federici E, Dupuis ML, Cianfriglia M, Arancia G: Voacamine, an alkaloid extracted from Peschiera fuchsiaefolia, inhibits P-glycoprotein action in multidrug-resistant tumor cells. Int J Oncol. 2005 Dec;27(6):1597-603. [PubMed:16273216 ]
  3. Meschini S, Condello M, Marra M, Formisano G, Federici E, Arancia G: Autophagy-mediated chemosensitizing effect of the plant alkaloid voacamine on multidrug resistant cells. Toxicol In Vitro. 2007 Mar;21(2):197-203. Epub 2006 Sep 16. [PubMed:17070665 ]

Transporters

General function:
Involved in ATP binding
Specific function:
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:
ABCB1
Uniprot ID:
P08183
Molecular weight:
141477.3
References
  1. Meschini S, Marra M, Condello M, Calcabrini A, Federici E, Dupuis ML, Cianfriglia M, Arancia G: Voacamine, an alkaloid extracted from Peschiera fuchsiaefolia, inhibits P-glycoprotein action in multidrug-resistant tumor cells. Int J Oncol. 2005 Dec;27(6):1597-603. [PubMed:16273216 ]
  2. Meschini S, Marra M, Calcabrini A, Federici E, Galeffi C, Arancia G: Voacamine, a bisindolic alkaloid from Peschiera fuchsiaefolia, enhances the cytotoxic effect of doxorubicin on multidrug-resistant tumor cells. Int J Oncol. 2003 Dec;23(6):1505-13. [PubMed:14612920 ]