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Natural Product (NP) Details

General Information of the NP (ID: NP2784)
Name
Voacamine
Synonyms
VOACAMINE; Voacanginine; Vocamine; 3371-85-5; Methyl 12-methoxy-13-(17-methoxy-17-oxovobasan-3alpha-yl)ibogamine-18-carboxylate; CHEBI:10014; DB04877; C09252; Methyl-12-methoxy-13-(17-methoxy-17-oxovobasan-3alpha-yl)ibogamine-18-carboxylate; methyl (1S,15S,17S,18S)-17-ethyl-6-[(1R,12R,14R,15E)-15-ethylidene-18-(methoxycarbonyl)-17-methyl-10,17-diazatetracyclo[12.3.1.0^{3,11}.0^{4,9}]octadeca-3(11),4,6,8-tetraen-12-yl]-7-methoxy-3,13-diazapentacyclo[13.3.1.0^{2,10}.0^{4,9}.0^{13,18}]nonadeca-2(10),4,6,8-tetraene-1-carboxylate; 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
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Species Origin Voacanga africana ...     Click to Show/Hide
Voacanga africana
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Gentianales
Family: Apocynaceae
Genus: Voacanga
Species: Voacanga africana
Disease Osteosarcoma [ICD-11: 2B51] Investigative [1]
Structure
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2D MOL

3D MOL

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Formula
C43H52N4O5
PubChem CID
11953931
Canonical SMILES
CCC1CC2CC3(C1N(C2)CCC4=C3NC5=CC(=C(C=C45)OC)C6CC7C(C(CC8=C6NC9=CC=CC=C89)N(CC7=CC)C)C(=O)OC)C(=O)OC
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
InChIKey
VCMIRXRRQJNZJT-XRMSBCOFSA-N
CAS Number
CAS 3371-85-5
ChEBI ID
CHEBI:10014
Herb ID
HBIN048150
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Resistance can be Reversed by This NP
          Doxorubicin      Solid tumour/cancer     Click to Show/Hide the Molecular Data of This Drug
                 Reversing Drug Resistance     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Biological
                    Regulation
Induction Autophagic cell death
                    In-vitro Model U2OS CVCL_0042 Osteosarcoma Homo sapiens
U-2 OS R1 CVCL_T429 Osteosarcoma Homo sapiens
                    Experimental
                    Result(s)
Voacamine is capable of enhancing the cytotoxic effect of DOX on MDR cells by favouring a lethal autophagic process.
References
Reference 1 Voacamine: Alkaloid with its essential dimeric units to reverse tumor multidrug resistance. Toxicol In Vitro. 2020 Jun;65:104819.
Reference 2 Autophagy-mediated chemosensitizing effect of the plant alkaloid voacamine on multidrug resistant cells. Toxicol In Vitro. 2007 Mar;21(2):197-203.
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Correspondence

X. N. Sun, Y. T. Zhang, Y. Zhou, X. C. Lian, L. L. Yan, T. Pan, T. Jin, H. Xie, Z. M. Liang, W. Q. Qiu, J. X. Wang, Z. R. Li, F. Zhu*, X. B. Sui*. NPCDR: natural product-based drug combination and its disease-specific molecular regulation. Nucleic Acids Research. 50(D1): 1324-1333 (2020). PMID: 34664659

Prof. Feng ZHU  (zhufeng@zju.edu.cn)

College of Pharmaceutical Sciences, Zhejiang University, Hangzhou, China


Prof. Xinbing SUI  (hzzju@hznu.edu.cn)

School of Pharmacy and Department of Medical Oncology, the Affiliated Hospital of Hangzhou Normal University, Hangzhou Normal University, Hangzhou, China