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Phytochemical Details

01. General Information

Name	Voacamine
PubChem CID	11953931
Molecular Weight	704.9g/mol
Synonyms	voacamine
Formula	C₄₃H₅₂N₄O₅
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	3371-85-5
ChEBI ID	CHEBI:10014
Herb ID	HBIN048150
Drug Bank ID	DB04877
KEGG ID	C09252
Structure		Download 2D MOL 3D MOL

02. Source Information of Phytochemical

(1) Nerium indicum Cold

Chineses Pinyin	JiaZhuTao
Use Part	Leaf, Bark
Habitat	China
Flavor	Bitter
Meridian Tropism	Heart
Species	>Kingdom: Viridiplantae 　-->Phylum: Streptophyta 　　-->Class: Equisetopsida 　　　-->Order: Gentianales 　　　　-->Family: Apocynaceae 　　　　　-->Genus: Nerium 　　　　　　-->Species: Nerium indicum

(2) Lycoris radiata Warm

Chineses Pinyin	ShiSuan
Use Part	Bulb
Habitat	JiangSu, ZheJiang, AnHui, FuJian, JiangXi, ShanDong, ShangHai, HeNan, HuNan, HuBei, GuangDong, GuangXi, HaiNan, SiChuan, GuiZhou, YunNan, XiZang, ChongQing, ShanXi, HeNan, JiangSu, ZheJiang
Flavor	Pungent, Sweet
Meridian Tropism	Lung, Stomach, Liver
Species	>Kingdom: Viridiplantae 　-->Phylum: Streptophyta 　　-->Class: Equisetopsida 　　　-->Order: Asparagales 　　　　-->Family: Amaryllidaceae 　　　　　-->Genus: Lycoris 　　　　　　-->Species: Lycoris radiata

(3) Voacanga africana Unknown

Chineses Pinyin	FeiZhouMaLingGuo
Species	>Kingdom: Viridiplantae 　-->Phylum: Streptophyta 　　-->Class: Equisetopsida 　　　-->Order: Gentianales 　　　　-->Family: Apocynaceae 　　　　　-->Genus: Voacanga 　　　　　　-->Species: Voacanga africana

03. Combinatorial Therapeutic Effect(s)

Synergistic Effect

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Drug(s) whose efficacy can be enhanced by this phytochemical

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Combination Pair ID: 614

Ref_1

Pair Name	Voacamine, Paclitaxel
Partner Name	Paclitaxel
Disease Info	[ICD-11: 2C73]	Ovarian cancer		Investigative
Biological Phenomena	Induction-->Apoptosis
Gene Regulation	Up-regulation	Cleavage	PARP1	hsa142
Gene Regulation	Down-regulation	Expression	RELA	hsa5970
In Vitro Model	A2780	Ovarian endometrioid adenocarcinoma	Homo sapiens (Human)	CVCL_0134
Result	Our data show the specific effect of VOA which only works on drugs known to be substrates of P-gp.

Drug(s) whose resistance can be reversed by this phytochemical

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Combination Pair ID: 966

Ref_2

Pair Name	Voacamine, Doxorubicin
Partner Name	Doxorubicin
Disease Info	[ICD-11: 2B51]	Osteosarcoma		Investigative
Biological Phenomena	Induction-->Autophagy
In Vitro Model	U2OS	Osteosarcoma	Homo sapiens (Human)	CVCL_0042
In Vitro Model	U-2 OS R1	Osteosarcoma	Homo sapiens (Human)	CVCL_T429
Result	Voacamine is capable of enhancing the cytotoxic effect of DOX on MDR cells by favouring a lethal autophagic process

04. Reference

No.	Title	Href
1	A natural product, voacamine, sensitizes paclitaxel-resistant human ovarian cancer cells. Toxicol Appl Pharmacol. 2022 Jan 1;434:115816. doi: 10.1016/j.taap.2021.115816.	`Click`
2	Autophagy-mediated chemosensitizing effect of the plant alkaloid voacamine on multidrug resistant cells. Toxicol In Vitro. 2007 Mar;21(2):197-203. doi: 10.1016/j.tiv.2006.09.007.	`Click`