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Voacamine

CAT: 0804-HY-N6932-02Size: 5 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-N6932-02Size:5 mg
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Description
Voacamine is an indole alkaloid with cannabinoid 1 (CB1) antagonistic activity. Voacamine can inhibit nuclear translocation. Voacamine is effective in enhancing the effect of Doxorubicin as it interferes with the P-glycoprotein (P-gp) function. Voacamine promotes apoptosis-independent autophagic cell death in human osteosarcoma cells. Voacamine activates mitochondrial-associated apoptosis signaling pathway and inhibition of PI3K/Akt/mTOR signaling pathway to suppress breast cancer progression. Voacamine inhibits EGFR to exert oncogenic activity against colorectal cancer[1][2][3][4][5].
CAS Number
3371-85-5
UNSPSC
12352005
Target
Akt; Apoptosis; Autophagy; Cannabinoid Receptor; EGFR; mTOR; P-glycoprotein; PI3K
Type
Natural Products
Related Pathways
Apoptosis; Autophagy; GPCR/G Protein; JAK/STAT Signaling; Membrane Transporter/Ion Channel; Neuronal Signaling; PI3K/Akt/mTOR; Protein Tyrosine Kinase/RTK
Applications
Metabolism-protein/nucleotide metabolism
Field of Research
Cancer; Metabolic Disease
Assay Protocol
https://www.medchemexpress.com/voacamine.html
Purity
99.64
Solubility
DMSO : ≥ 100 mg/mL
Smiles
O=C(OC)[C@]1([C@@H]2[N@](CC(C[C@H]2CC)C1)CC3)C4=C3C(C=C5OC)=C(N4)C=C5[C@](C[C@@H]6[C@H](C(OC)=O)[C@H](N(C)C/C6=C/C)C7)([H])C8=C7C9=C(N8)C=CC=C9
Molecular Formula
C43H52N4O5
Molecular Weight
704.90
References & Citations
[1]Kitajima M, et al. Discovery of indole alkaloids with cannabinoid CB1 receptor antagonistic activity. Bioorg Med Chem Lett. 2011 Apr 1;21 (7) :1962-4.|[2]Pellegrini, E., et al., (2022) . A natural product, voacamine, sensitizes paclitaxel-resistant human ovarian cancer cells. Toxicology and applied pharmacology, 434, 115816.|[3]Zuo, Y., et al., (2022) . Activation of mitochondrial-associated apoptosis signaling pathway and inhibition of PI3K/Akt/mTOR signaling pathway by voacamine suppress breast cancer progression. Phytomedicine : international journal of phytotherapy and phytopharmacology, 99, 154015. |[4]Meschini, S., et al., (2008) . The plant alkaloid voacamine induces apoptosis-independent autophagic cell death on both sensitive and multidrug resistant human osteosarcoma cells. Autophagy, 4 (8), 1020–1033. |[5]Chen, Y., et al., (2022) . Voacamine is a novel inhibitor of EGFR exerting oncogenic activity against colorectal cancer through the mitochondrial pathway. Pharmacological research, 184, 106415.
Shipping Conditions
Room Temperature
Storage Conditions
4°C (Powder, protect from light)
Scientific Category
Natural Products
Clinical Information
No Development Reported

Chemical Information

Voacamine

Voacamine is a citraconoyl group.

CAS Number3371-85-5
PubChem CID11953931
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
Molecular FormulaC43H52N4O5
Molecular Weight704.9
XLogP6.1
Topological Polar Surface Area99.9
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count7
Rotatable Bond Count7
Heavy Atom Count52
Formal Charge0
Complexity1410
SMILES
CC[C@H]1C[C@H]2C[C@@]3([C@H]1N(C2)CCC4=C3NC5=CC(=C(C=C45)OC)[C@H]6C[C@@H]\7C([C@@H](CC8=C6NC9=CC=CC=C89)N(C/C7=C/C)C)C(=O)OC)C(=O)OC
InChI
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
Chemical Structure
2D Structure
2D structure of Voacamine
CAS: 3371-85-5
CID: 11953931
Formula: C43H52N4O5
MW: 704.9
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight704.9
XLogP36.1
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count7
Rotatable Bond Count7
Exact Mass704.39377077
Monoisotopic Mass704.39377077
Topological Polar Surface Area99.9 Ų
Heavy Atom Count52
Formal Charge0
Complexity1410
Isotope Atom Count0
Defined Atom Stereocenter Count7
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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