Posted inUncategorized

Voacamine

July 24, 2017
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

MOLSDFPDBSMILESInChI

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 Value Age Sex 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
    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 ]
    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 ]

    PMID: 26320055

    Last updated on