| Common Name |
Voacamine
| Description |
Voacamine is only found in individuals that have used or taken this drug. It is an alkaloid isolated from the bark of the Pescheria fuchsiae folia tree. It is an antimalarial drug approved for use in several African countries. Voacamine is also under investigation for use in modliating mlitidrug-resistance in tumor cells. Voacamine is possibly a substrate for P-glycoprotein (P-gp), an efflux pump responsible for mlitidrug resistance in tumor cells. Voacamine may compete with anticancer drugs such as doxorubicin for P-gp transport, decreasing removal of doxorubicin.
| Structure |
| Synonyms |
| Value |
Source |
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 Formlia |
C43H52N4O5
| Average Molecliar Weight |
704.8968
| Monoisotopic Molecliar Weight |
704.393770794
| IUPAC Name |
methyl (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 Name |
voacamine
| CAS Registry Number |
3371-85-5
| 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)CC4=CC)[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 Key |
VCMIRXRRQJNZJT-XRMSBCOFSA-N
| Chemical Taxonomy |
| Description |
This compound belongs to the class of chemical entities 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.
| Kingdom |
Chemical entities
| Super Class |
Organic compounds
| Class |
Alkaloids and derivatives
| Sub Class |
Ibogan-type alkaloids
| Direct Parent |
Ibogan-type alkaloids
| Alternative Parents |
Vobasan alkaloids
3-alkylindoles
Pyrroloazepines
Piperidinecarboxylic acids
Anisoles
Alkyl aryl ethers
Aralkylamines
Azepines
Dicarboxylic acids and derivatives
Pyrroles
Methyl esters
Heteroaromatic compounds
Trialkylamines
Amino acids and derivatives
Azacyclic compounds
Organic oxides
Organopnictogen compounds
Carbonyl compounds
Hydrocarbon derivatives
| 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
| Molecliar Framework |
Aromatic heteropolycyclic compounds
| External Descriptors |
Not Available
| Ontology |
| Status |
Expected but not Quantified
| Origin |
Drug
| Biofunction |
Antimalarial Agents
| Application |
Pharmaceutical
| Cellliar locations |
Membrane
| Physical Properties |
| State |
Solid
| Experimental Properties |
| Property |
Value |
Reference |
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility3.23e-03 g/LNot Available
LogPNot AvailableNot Available
| Predicted Properties |
| Property |
Value |
Source |
Water Solubility0.0032 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity203.68 m3·mol-1ChemAxon
Number of Rings9ChemAxon
Bioavailability0ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
| Spectrum Type |
Description |
Splash Key |
|
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available
| Biological Properties |
| Cellliar Locations |
Membrane
| Biofluid Locations |
Blood
Urine
| Tissue Location |
Not Available
| Pathways |
Not Available
| Normal Concentrations |
| Biofluid |
Status |
Age |
Condition |
Reference |
Details |
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB04877
21059682
details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB04877
21059682
details
|
| Abnormal Concentrations |
|
Not Available
| Associated Disorders and Diseases |
| Disease References |
None
| Associated OMIM IDs |
None
| External Links |
| DrugBank ID |
DB04877
| DrugBank Metabolite ID |
Not Available
| Phenol Explorer Compound ID |
Not Available
| Phenol Explorer Metabolite ID |
Not Available
| FoodDB ID |
Not Available
| KNApSAcK ID |
Not Available
| Chemspider ID |
10128230
| KEGG Compound ID |
C09252
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Not Available
| NuGOwiki Link |
HMDB15597
| Metagene Link |
HMDB15597
| METLIN ID |
Not Available
| PubChem Compound |
11953931
| PDB ID |
Not Available
| ChEBI ID |
Not Available
Product: Amidopyrine
References |
| Synthesis Reference |
Not Available |
| Material Safety Data Sheet (MSDS) |
Not Available |
| General References |
- 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 ]
- 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 ]
- 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
- 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 ]
- 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 ]
PMID: 26320055
