Vocamine

Details

• Internal ID: f7cde035-8bed-4b76-bb91-5e9f7458e8bd
• Taxonomy: Alkaloids and derivatives > Ibogan-type alkaloids
• IUPAC Name: methyl (1S,15S,17S,18S)-17-ethyl-6-[(1S,12R,14S,15Z)-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
• SMILES (Canonical): 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
• SMILES (Isomeric): 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
• InChI Key: VCMIRXRRQJNZJT-DFGFQBNESA-N
• Popularity: 33 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₃H₅₂N₄O₅
• Molecular Weight: 704.90 g/mol
• Exact Mass: 704.39377077 g/mol
• Topological Polar Surface Area (TPSA): 99.90 Ų
• XlogP: 6.10
• Atomic LogP (AlogP): 6.49
• H-Bond Acceptor: 7
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

• Vocamine
• VOACAMINE
• Crystalline compound from Voacanga afracina
• B 606109
• C43H52N4O5
• NSC82591
• NSC-82591
• C43-H52-N4-O5
• 3371-85-5
• 12-Methoxy-13-[(3-alpha)-17-methoxy-17-oxovobasan-3-yl]ibogamine-18-carboxylic acid methyl ester
• Ibogamine-18-carboxylic acid, 12-methoxy-13-[(3.alpha.)-17-methoxy-17-oxovobasan-3-yl]-, methyl ester
• 6,2':1,2]azepino[4,5-b]indole-6-carboxylic acid, 3-(14-carboxy-5-ethylidene-2,3,4,5,6,7,8,9-octahydro-3-methyl-2,6-methano-1H-azecino[5,4-b]indol-8-yl)-7-ethyl-6,6a,7,8,9,10,12,13-octahydro-2-methoxy-, dimethyl ester

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9635	96.35%
Caco-2	-	0.7820	78.20%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.6649	66.49%
OATP2B1 inhibitior	-	0.5711	57.11%
OATP1B1 inhibitior	+	0.8107	81.07%
OATP1B3 inhibitior	+	0.9079	90.79%
MATE1 inhibitior	-	0.6637	66.37%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.9969	99.69%
P-glycoprotein inhibitior	+	0.8603	86.03%
P-glycoprotein substrate	+	0.8825	88.25%
CYP3A4 substrate	+	0.7559	75.59%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.3516	35.16%
CYP3A4 inhibition	+	0.7262	72.62%
CYP2C9 inhibition	-	0.6209	62.09%
CYP2C19 inhibition	-	0.7443	74.43%
CYP2D6 inhibition	-	0.8255	82.55%
CYP1A2 inhibition	-	0.7083	70.83%
CYP2C8 inhibition	+	0.7655	76.55%
CYP inhibitory promiscuity	+	0.5987	59.87%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5947	59.47%
Eye corrosion	-	0.9885	98.85%
Eye irritation	-	0.9312	93.12%
Skin irritation	-	0.7807	78.07%
Skin corrosion	-	0.9382	93.82%
Ames mutagenesis	-	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8039	80.39%
Micronuclear	+	0.7100	71.00%
Hepatotoxicity	-	0.6875	68.75%
skin sensitisation	-	0.8778	87.78%
Respiratory toxicity	+	0.8889	88.89%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	-	0.7530	75.30%
Acute Oral Toxicity (c)	III	0.6435	64.35%
Estrogen receptor binding	+	0.8543	85.43%
Androgen receptor binding	+	0.7674	76.74%
Thyroid receptor binding	+	0.6160	61.60%
Glucocorticoid receptor binding	+	0.8131	81.31%
Aromatase binding	+	0.6523	65.23%
PPAR gamma	+	0.7100	71.00%
Honey bee toxicity	-	0.6505	65.05%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9971	99.71%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.79%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.59%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	97.86%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.80%	94.45%
CHEMBL2581	P07339	Cathepsin D	96.78%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.42%	97.25%
CHEMBL2535	P11166	Glucose transporter	95.85%	98.75%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.60%	85.14%
CHEMBL228	P31645	Serotonin transporter	94.59%	95.51%
CHEMBL255	P29275	Adenosine A2b receptor	94.33%	98.59%
CHEMBL217	P14416	Dopamine D2 receptor	92.89%	95.62%
CHEMBL205	P00918	Carbonic anhydrase II	91.99%	98.44%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.64%	99.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.96%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.95%	89.00%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	85.81%	97.50%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	85.55%	90.95%
CHEMBL4208	P20618	Proteasome component C5	85.48%	90.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.24%	95.89%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	83.12%	89.62%
CHEMBL2096618	P11274	Bcr/Abl fusion protein	80.69%	85.83%
CHEMBL3192	Q9BY41	Histone deacetylase 8	80.68%	93.99%
CHEMBL5028	O14672	ADAM10	80.22%	97.50%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.21%	97.14%

Plants that contains it

• Lycoris radiata

Cross-Links

• PubChem: 54601825
• NPASS: NPC41549