Molecule

Voacangine

AlkaPlorer ID: AK005568

Synonym: None

IUPAC Name: methyl (1S,15S,17S,18S)-17-ethyl-7-methoxy-3,13-diazapentacyclo[13.3.1.02,10.04,9.013,18]nonadeca-2(10),4(9),5,7-tetraene-1-carboxylate

Structure

SMILES: CC[C@H]1C[C@@H]2CN3CCC4=C(NC5=CC=C(OC)C=C45)[C@](C(=O)OC)(C2)[C@H]13

InChI: InChI=1S/C22H28N2O3/c1-4-14-9-13-11-22(21(25)27-3)19-16(7-8-24(12-13)20(14)22)17-10-15(26-2)5-6-18(17)23-19/h5-6,10,13-14,20,23H,4,7-9,11-12H2,1-3H3/t13-,14-,20-,22+/m0/s1

InChIKey: MMAYTCMMKJYIAM-RUGRQLENSA-N

Reference

Activation and Inhibition of Thermosensitive TRP Channels by Voacangine, an Alkaloid Present in <i>Voacanga africana,</i> an African Tree

PubChem CID: 73255

CAS: 510-22-5

LOTUS: LTS0010255

NPASS: NPC96321

data_source: manually

Source

Species	Genus	Family	Order	Class	Phylum	Kingdom	Domain
Tabernaemontana calcarea	Tabernaemontana	Apocynaceae	Gentianales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Tabernaemontana divaricata	Tabernaemontana	Apocynaceae	Gentianales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Voacanga africana	Voacanga	Apocynaceae	Gentianales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota

Properties Information

Molecule Weight: 368.4770000000002

TPSA？: 54.56

MolLogP？: 3.2638000000000016

Number of H-Donors: 1

Number of H-Acceptors: 4

RingCount: 6

Activities Information

Organism	Target Name	Standard Type	Standard Value	Standard Units	doi
Electrophorus electricus	Acetylcholinesterase	IC50	4400.0	nM	10.1016/j.bmcl.2010.08.123
Homo sapiens	A2780	IC50	10.4	ug.mL-1	10.1021/np020548e
Homo sapiens	HCT-116	IC50	40000.0	nM	10.1016/j.bmcl.2015.07.036
Homo sapiens	HEK293	IC50	40000.0	nM	10.1016/j.bmcl.2015.07.036
Homo sapiens	HEK-293T	IC50	40000.0	nM	10.1016/j.bmcl.2015.07.036
Homo sapiens	HEK-293T	Inhibition	nan	%	10.1016/j.bmcl.2015.07.036
Homo sapiens	KB	IC50	25.0	ug.mL-1	10.1016/j.bmcl.2004.06.074
Homo sapiens	RKO	IC50	40000.0	nM	10.1016/j.bmcl.2015.07.036
Homo sapiens	SW480	IC50	40000.0	nM	10.1016/j.bmcl.2015.07.036
Homo sapiens	Transient receptor potential cation channel subfamily A member 1	Activity	85.0	%	10.1021/np500235b
Homo sapiens	Transient receptor potential cation channel subfamily A member 1	Activity	98.0	%	10.1021/np400885u
Homo sapiens	Transient receptor potential cation channel subfamily A member 1	Activity	nan	None	10.1021/np400885u
Homo sapiens	Transient receptor potential cation channel subfamily A member 1	Activity	nan	None	10.1021/np500235b
Homo sapiens	Transient receptor potential cation channel subfamily A member 1	EC50	8000.0	nM	10.1021/np400885u
Homo sapiens	Transient receptor potential cation channel subfamily A member 1	EC50	8000.0	nM	10.1021/np500235b
Homo sapiens	Transient receptor potential cation channel subfamily A member 1	IC50	nan	None	10.1021/np500235b
Homo sapiens	Transient receptor potential cation channel subfamily A member 1	Ratio EC50	15.0	None	10.1021/np400885u
Homo sapiens	Transient receptor potential cation channel subfamily A member 1	Ratio IC50	300.0	None	10.1021/np400885u
Homo sapiens	Transient receptor potential cation channel subfamily A member 1	Ratio IC50	300000.0	None	10.1021/np400885u
Homo sapiens	Transient receptor potential cation channel subfamily V member 2	Activity	nan	None	10.1021/np400885u
Homo sapiens	Transient receptor potential cation channel subfamily V member 3	Activity	nan	None	10.1021/np400885u
Homo sapiens	Vanilloid receptor	Activity	nan	None	10.1021/np400885u
Homo sapiens	Vanilloid receptor	Activity	nan	None	10.1021/np500235b
Homo sapiens	Vanilloid receptor	EC50	nan	None	10.1021/np500235b
Homo sapiens	Vanilloid receptor	IC50	24000.0	nM	10.1021/np400885u
Homo sapiens	Vanilloid receptor	IC50	30000.0	nM	10.1021/np500235b
Homo sapiens	Vanilloid receptor	IC50	50000.0	nM	10.1021/np400885u
Homo sapiens	Vanilloid receptor	Inhibition	nan	%	10.1021/np400885u
Homo sapiens	Vanilloid receptor	Kb	18000.0	nM	10.1021/np400885u
Homo sapiens	Vanilloid receptor	Kd	19952.62	nM	10.1021/np400885u
Mus musculus	Transient receptor potential cation channel subfamily M member 8	Activity	nan	None	10.1021/np400885u
Mus musculus	Transient receptor potential cation channel subfamily M member 8	Activity	nan	None	10.1021/np500235b
Mus musculus	Transient receptor potential cation channel subfamily M member 8	EC50	nan	None	10.1021/np500235b
Mus musculus	Transient receptor potential cation channel subfamily M member 8	IC50	7000.0	nM	10.1021/np500235b
Mus musculus	Transient receptor potential cation channel subfamily M member 8	IC50	9000.0	nM	10.1021/np400885u
Mus musculus	Transient receptor potential cation channel subfamily M member 8	IC50	9000.0	nM	10.1021/np500235b
Mus musculus	Transient receptor potential cation channel subfamily M member 8	IC50	nan	None	10.1021/np500235b
Mus musculus	Transient receptor potential cation channel subfamily M member 8	Inhibition	nan	%	10.1021/np400885u
Mus musculus	Transient receptor potential cation channel subfamily M member 8	Kb	8500.0	nM	10.1021/np400885u
Mus musculus	Transient receptor potential cation channel subfamily M member 8	Kd	7943.28	nM	10.1021/np400885u
Mus musculus	Transient receptor potential cation channel subfamily M member 8	Ratio IC50	15.0	None	10.1021/np400885u
Mus musculus	Transient receptor potential cation channel subfamily M member 8	Ratio IC50	25.0	None	10.1021/np400885u
None	ADMET	Activity	nan	None	10.1021/np500235b
None	NON-PROTEIN TARGET	IC50	40000.0	nM	10.1016/j.bmcl.2015.07.036
None	Unchecked	IC50	11500.0	nM	10.1016/j.bmcl.2015.07.036
None	Unchecked	Inhibition	nan	%	10.1016/j.bmcl.2015.07.036