Voacangine

Details

• Internal ID: 53287941-4b76-49e7-9b54-09cc3df6da5f
• Taxonomy: Alkaloids and derivatives > Ibogan-type alkaloids
• 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
• SMILES (Canonical): CCC1CC2CC3(C1N(C2)CCC4=C3NC5=C4C=C(C=C5)OC)C(=O)OC
• SMILES (Isomeric): CC[C@H]1C[C@H]2C[C@@]3([C@H]1N(C2)CCC4=C3NC5=C4C=C(C=C5)OC)C(=O)OC
• 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
• InChI Key: MMAYTCMMKJYIAM-RUGRQLENSA-N
• Popularity: 23 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₈N₂O₃
• Molecular Weight: 368.50 g/mol
• Exact Mass: 368.20999276 g/mol
• Topological Polar Surface Area (TPSA): 54.60 Ų
• XlogP: 3.50
• Atomic LogP (AlogP): 3.26
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

• (-)-Voacangine
• Carbomethoxyibogaine
• 510-22-5
• 12-Methoxyibogamine-18-carboxylic acid methyl ester
• 9SY76D3YUK
• CHEBI:141966
• 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
• Ibogamine-18-carboxylic acid, 12-methoxy-, methyl ester
• 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
• RefChem:194597
• methyl (1S,15R,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
• methyl 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
• CHEMBL182120
• methyl ethyl(methoxy)[?]carboxylate
• DTXSID50965276
• MMAYTCMMKJYIAM-RUGRQLENSA-N
• Methyl 12-methoxyibogamine-18-carboxylate
• UNII-9SY76D3YUK
• SCHEMBL30443870
• BDBM50329104
• FS-7615
• methyl (6xi)-12-methoxy-2alpha-ibogamine-18-carboxylate
• Methyl (1S)-3,13-diaza-17-ethyl-7-methoxypentacyclo[13.3.1.0<2,10>.0<4,9>.0<13,18>]nonadeca-2(10),4,6,8-tetraenecarboxylate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9787	97.87%
Caco-2	+	0.8268	82.68%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.4914	49.14%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9104	91.04%
OATP1B3 inhibitior	+	0.9195	91.95%
MATE1 inhibitior	-	0.7437	74.37%
OCT2 inhibitior	-	0.5000	50.00%
BSEP inhibitior	+	0.9050	90.50%
P-glycoprotein inhibitior	+	0.7147	71.47%
P-glycoprotein substrate	+	0.8332	83.32%
CYP3A4 substrate	+	0.6460	64.60%
CYP2C9 substrate	-	0.8032	80.32%
CYP2D6 substrate	+	0.4622	46.22%
CYP3A4 inhibition	+	0.5000	50.00%
CYP2C9 inhibition	-	0.8358	83.58%
CYP2C19 inhibition	-	0.8664	86.64%
CYP2D6 inhibition	+	0.6327	63.27%
CYP1A2 inhibition	-	0.6583	65.83%
CYP2C8 inhibition	-	0.7233	72.33%
CYP inhibitory promiscuity	+	0.5062	50.62%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6768	67.68%
Eye corrosion	-	0.9919	99.19%
Eye irritation	-	0.9832	98.32%
Skin irritation	-	0.8079	80.79%
Skin corrosion	-	0.9489	94.89%
Ames mutagenesis	-	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8647	86.47%
Micronuclear	+	0.5800	58.00%
Hepatotoxicity	-	0.5000	50.00%
skin sensitisation	-	0.8784	87.84%
Respiratory toxicity	+	0.8667	86.67%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	-	0.9200	92.00%
Acute Oral Toxicity (c)	III	0.4768	47.68%
Estrogen receptor binding	+	0.7638	76.38%
Androgen receptor binding	+	0.7128	71.28%
Thyroid receptor binding	+	0.6205	62.05%
Glucocorticoid receptor binding	+	0.7224	72.24%
Aromatase binding	+	0.7231	72.31%
PPAR gamma	-	0.5678	56.78%
Honey bee toxicity	-	0.8160	81.60%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.9412	94.12%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL6007	O75762	Transient receptor potential cation channel subfamily A member 1	8000 nM; 8000 nM	EC50; EC50	PMID: 21899267; PMID: 21051535
CHEMBL4794	Q8NER1	Vanilloid receptor	24000 nM; 30000 nM	IC50; IC50	DOI: 10.6019/CHEMBL1201861; PMID: 16413779

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.60%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.35%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.97%	94.45%
CHEMBL255	P29275	Adenosine A2b receptor	95.09%	98.59%
CHEMBL2535	P11166	Glucose transporter	94.24%	98.75%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.71%	85.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.33%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.23%	95.56%
CHEMBL2581	P07339	Cathepsin D	91.07%	98.95%
CHEMBL4208	P20618	Proteasome component C5	90.43%	90.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	88.22%	92.94%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	86.75%	97.50%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	86.72%	96.77%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	86.40%	92.62%
CHEMBL205	P00918	Carbonic anhydrase II	86.07%	98.44%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.02%	95.89%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	84.74%	86.92%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.57%	99.17%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	83.44%	94.33%
CHEMBL340	P08684	Cytochrome P450 3A4	83.13%	91.19%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.06%	90.71%

Plants that contains it

• Tabernaemontana calcarea
• Tabernaemontana divaricata

Cross-Links

• PubChem: 73255
• NPASS: NPC96321
• ChEMBL: CHEMBL182120