methyl (1S,15S,17S,18S)-17-ethyl-5-[(1S,12R,14S,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]-6-methoxy-3,13-diazapentacyclo[13.3.1.02,10.04,9.013,18]nonadeca-2(10),4(9),5,7-tetraene-1-carboxylate

Details

• Internal ID: 5aeef989-bfe6-4704-a12c-cd7cdc6a4946
• Taxonomy: Alkaloids and derivatives > Ibogan-type alkaloids
• IUPAC Name: methyl (1S,15S,17S,18S)-17-ethyl-5-[(1S,12R,14S,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]-6-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=CC(=C5C6CC7C(C(CC8=C6NC9=CC=CC=C89)N(CC7=CC)C)C(=O)OC)OC)C(=O)OC
• SMILES (Isomeric): CC[C@H]1C[C@H]2C[C@@]3([C@H]1N(C2)CCC4=C3NC5=C4C=CC(=C5[C@H]6C[C@H]\7C([C@H](CC8=C6NC9=CC=CC=C89)N(C/C7=C/C)C)C(=O)OC)OC)C(=O)OC
• InChI: InChI=1S/C43H52N4O5/c1-7-24-17-23-20-43(42(49)52-6)39-28(15-16-47(21-23)40(24)43)27-13-14-34(50-4)36(38(27)45-39)31-18-29-25(8-2)22-46(3)33(35(29)41(48)51-5)19-30-26-11-9-10-12-32(26)44-37(30)31/h8-14,23-24,29,31,33,35,40,44-45H,7,15-22H2,1-6H3/b25-8-/t23-,24-,29+,31+,33-,35?,40-,43+/m0/s1
• InChI Key: QJHYXWBJZHUJGS-JCHBZIMUSA-N
• Popularity: 1 reference 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

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9635	96.35%
Caco-2	-	0.7709	77.09%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.6649	66.49%
OATP2B1 inhibitior	-	0.5727	57.27%
OATP1B1 inhibitior	+	0.8279	82.79%
OATP1B3 inhibitior	+	0.9079	90.79%
MATE1 inhibitior	-	0.6637	66.37%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	1.0000	100.00%
P-glycoprotein inhibitior	+	0.8883	88.83%
P-glycoprotein substrate	+	0.8829	88.29%
CYP3A4 substrate	+	0.7587	75.87%
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	+	0.7793	77.93%
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	-	0.9348	93.48%
Skin irritation	-	0.7807	78.07%
Skin corrosion	-	0.9382	93.82%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8147	81.47%
Micronuclear	+	0.7100	71.00%
Hepatotoxicity	-	0.6375	63.75%
skin sensitisation	-	0.8778	87.78%
Respiratory toxicity	+	0.8667	86.67%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	+	0.4519	45.19%
Acute Oral Toxicity (c)	III	0.6435	64.35%
Estrogen receptor binding	+	0.8646	86.46%
Androgen receptor binding	+	0.7836	78.36%
Thyroid receptor binding	+	0.6146	61.46%
Glucocorticoid receptor binding	+	0.8402	84.02%
Aromatase binding	+	0.6610	66.10%
PPAR gamma	+	0.7741	77.41%
Honey bee toxicity	-	0.6451	64.51%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.5200	52.00%
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	99.71%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	97.59%	95.56%
CHEMBL255	P29275	Adenosine A2b receptor	97.47%	98.59%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.19%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.64%	97.25%
CHEMBL2581	P07339	Cathepsin D	95.53%	98.95%
CHEMBL2535	P11166	Glucose transporter	94.00%	98.75%
CHEMBL228	P31645	Serotonin transporter	92.76%	95.51%
CHEMBL2096618	P11274	Bcr/Abl fusion protein	92.15%	85.83%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.40%	91.11%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	87.87%	90.95%
CHEMBL205	P00918	Carbonic anhydrase II	87.79%	98.44%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.60%	85.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.50%	97.09%
CHEMBL4208	P20618	Proteasome component C5	86.41%	90.00%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	86.21%	97.50%
CHEMBL217	P14416	Dopamine D2 receptor	84.88%	95.62%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.93%	99.17%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	82.75%	89.62%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.47%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.09%	95.89%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	80.75%	82.38%
CHEMBL5028	O14672	ADAM10	80.50%	97.50%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	80.11%	93.03%

Plants that contains it

• Tabernaemontana africana
• Tabernaemontana catharinensis
• Tabernaemontana corymbosa
• Tabernaemontana laeta
• Tabernaemontana pachysiphon
• Tabernaemontana pandacaqui
• Tabernaemontana vanheurckii

Cross-Links

• PubChem: 134714950
• LOTUS: LTS0082104
• wikiData: Q104403497