19-Epivoacristine

Details

• Internal ID: 4346cc32-b4bf-4fb0-8e2e-2a34a3627171
• Taxonomy: Alkaloids and derivatives > Ibogan-type alkaloids
• IUPAC Name: methyl (1S,15R,17S,18S)-17-[(1R)-1-hydroxyethyl]-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): CC(C1CC2CC3(C1N(C2)CCC4=C3NC5=C4C=C(C=C5)OC)C(=O)OC)O
• SMILES (Isomeric): C[C@H]([C@H]1C[C@@H]2C[C@@]3([C@H]1N(C2)CCC4=C3NC5=C4C=C(C=C5)OC)C(=O)OC)O
• InChI: InChI=1S/C22H28N2O4/c1-12(25)16-8-13-10-22(21(26)28-3)19-15(6-7-24(11-13)20(16)22)17-9-14(27-2)4-5-18(17)23-19/h4-5,9,12-13,16,20,23,25H,6-8,10-11H2,1-3H3/t12-,13-,16-,20+,22-/m1/s1
• InChI Key: OYMQKBZMKFJPMH-MDIKWQLESA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₈N₂O₄
• Molecular Weight: 384.50 g/mol
• Exact Mass: 384.20490738 g/mol
• Topological Polar Surface Area (TPSA): 74.80 Ų
• XlogP: 2.40
• Atomic LogP (AlogP): 2.23
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

• 20-Epivoacangarine
• 6883-77-8
• Methyl (20R)-20-hydroxy-12-methoxyibogamine-18-carboxylate
• Ibogamine-18-carboxylic acid, 20-hydroxy-12-methoxy-, methyl ester, (20R)-
• DTXSID70218938
• AKOS040734510

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8766	87.66%
Caco-2	+	0.7148	71.48%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.5507	55.07%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9204	92.04%
OATP1B3 inhibitior	+	0.9102	91.02%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	+	0.8455	84.55%
P-glycoprotein inhibitior	-	0.4368	43.68%
P-glycoprotein substrate	+	0.8081	80.81%
CYP3A4 substrate	+	0.6618	66.18%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.4651	46.51%
CYP3A4 inhibition	-	0.5867	58.67%
CYP2C9 inhibition	-	0.8452	84.52%
CYP2C19 inhibition	-	0.8438	84.38%
CYP2D6 inhibition	-	0.6424	64.24%
CYP1A2 inhibition	-	0.7834	78.34%
CYP2C8 inhibition	-	0.8018	80.18%
CYP inhibitory promiscuity	-	0.7701	77.01%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6563	65.63%
Eye corrosion	-	0.9906	99.06%
Eye irritation	-	0.9895	98.95%
Skin irritation	-	0.7936	79.36%
Skin corrosion	-	0.9487	94.87%
Ames mutagenesis	-	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7193	71.93%
Micronuclear	+	0.6200	62.00%
Hepatotoxicity	-	0.5500	55.00%
skin sensitisation	-	0.8781	87.81%
Respiratory toxicity	+	0.8889	88.89%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.9875	98.75%
Nephrotoxicity	-	0.9282	92.82%
Acute Oral Toxicity (c)	III	0.4470	44.70%
Estrogen receptor binding	+	0.7891	78.91%
Androgen receptor binding	+	0.6732	67.32%
Thyroid receptor binding	+	0.5951	59.51%
Glucocorticoid receptor binding	+	0.7862	78.62%
Aromatase binding	+	0.7079	70.79%
PPAR gamma	-	0.5391	53.91%
Honey bee toxicity	-	0.7922	79.22%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	+	0.9087	90.87%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.53%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.48%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	99.14%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.59%	85.14%
CHEMBL2535	P11166	Glucose transporter	96.88%	98.75%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.14%	95.56%
CHEMBL2581	P07339	Cathepsin D	94.05%	98.95%
CHEMBL4208	P20618	Proteasome component C5	93.78%	90.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.95%	97.09%
CHEMBL205	P00918	Carbonic anhydrase II	91.36%	98.44%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	89.64%	96.77%
CHEMBL340	P08684	Cytochrome P450 3A4	89.10%	91.19%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	88.99%	90.71%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	88.99%	94.08%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.98%	95.89%
CHEMBL255	P29275	Adenosine A2b receptor	88.24%	98.59%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	85.20%	95.89%
CHEMBL3437	Q16853	Amine oxidase, copper containing	85.13%	94.00%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	85.06%	97.50%
CHEMBL4073	P09237	Matrix metalloproteinase 7	84.84%	97.56%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.42%	92.62%
CHEMBL2782	P35610	Acyl coenzyme A:cholesterol acyltransferase 1	83.38%	91.65%
CHEMBL4302	P08183	P-glycoprotein 1	83.36%	92.98%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	83.10%	86.92%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	82.95%	91.03%

Plants that contains it

• Tabernaemontana calcarea
• Tabernaemontana catharinensis
• Tabernaemontana dichotoma
• Tabernaemontana divaricata

Cross-Links

• PubChem: 56842093
• LOTUS: LTS0155564
• wikiData: Q83095851