methyl (1S,15R,17S,18S)-5-[(1R,12R,14S,15E,18S)-15-ethylidene-18-(hydroxymethyl)-18-methoxycarbonyl-17-methyl-10,17-diazatetracyclo[12.3.1.03,11.04,9]octadeca-3(11),4,6,8-tetraen-12-yl]-17-[(1S)-1-hydroxyethyl]-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: 579b9d36-0deb-4a2e-8767-079991e8fca9
• Taxonomy: Alkaloids and derivatives > Ibogan-type alkaloids
• IUPAC Name: methyl (1S,15R,17S,18S)-5-[(1R,12R,14S,15E,18S)-15-ethylidene-18-(hydroxymethyl)-18-methoxycarbonyl-17-methyl-10,17-diazatetracyclo[12.3.1.03,11.04,9]octadeca-3(11),4,6,8-tetraen-12-yl]-17-[(1S)-1-hydroxyethyl]-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): CC=C1CN(C2CC3=C(C(CC1C2(CO)C(=O)OC)C4=C(C=CC5=C4NC6=C5CCN7CC8CC(C7C6(C8)C(=O)OC)C(C)O)OC)NC9=CC=CC=C39)C
• SMILES (Isomeric): C/C=C\1/CN([C@@H]2CC3=C([C@H](C[C@@H]1[C@]2(CO)C(=O)OC)C4=C(C=CC5=C4NC6=C5CCN7C[C@@H]8C[C@@H]([C@H]7[C@]6(C8)C(=O)OC)[C@H](C)O)OC)NC9=CC=CC=C39)C
• InChI: InChI=1S/C44H54N4O7/c1-7-25-21-47(3)35-18-30-26-10-8-9-11-33(26)45-37(30)31(17-32(25)44(35,22-49)42(52)55-6)36-34(53-4)13-12-27-28-14-15-48-20-24-16-29(23(2)50)40(48)43(19-24,41(51)54-5)39(28)46-38(27)36/h7-13,23-24,29,31-32,35,40,45-46,49-50H,14-22H2,1-6H3/b25-7-/t23-,24+,29+,31+,32-,35+,40-,43+,44-/m0/s1
• InChI Key: ZDXOLFVIYJGKKI-HDQDQCGBSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₄H₅₄N₄O₇
• Molecular Weight: 750.90 g/mol
• Exact Mass: 750.39925007 g/mol
• Topological Polar Surface Area (TPSA): 140.00 Ų
• XlogP: 4.10
• Atomic LogP (AlogP): 4.82
• H-Bond Acceptor: 9
• H-Bond Donor: 4
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9266	92.66%
Caco-2	-	0.8122	81.22%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.6316	63.16%
OATP2B1 inhibitior	-	0.7225	72.25%
OATP1B1 inhibitior	+	0.8316	83.16%
OATP1B3 inhibitior	+	0.9056	90.56%
MATE1 inhibitior	-	0.8812	88.12%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	+	0.9953	99.53%
P-glycoprotein inhibitior	+	0.8288	82.88%
P-glycoprotein substrate	+	0.8630	86.30%
CYP3A4 substrate	+	0.7553	75.53%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.3792	37.92%
CYP3A4 inhibition	+	0.5984	59.84%
CYP2C9 inhibition	-	0.7376	73.76%
CYP2C19 inhibition	-	0.8397	83.97%
CYP2D6 inhibition	-	0.8719	87.19%
CYP1A2 inhibition	-	0.7382	73.82%
CYP2C8 inhibition	+	0.7170	71.70%
CYP inhibitory promiscuity	-	0.6582	65.82%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.5626	56.26%
Eye corrosion	-	0.9873	98.73%
Eye irritation	-	0.9247	92.47%
Skin irritation	-	0.7765	77.65%
Skin corrosion	-	0.9371	93.71%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7451	74.51%
Micronuclear	+	0.7200	72.00%
Hepatotoxicity	-	0.6625	66.25%
skin sensitisation	-	0.8743	87.43%
Respiratory toxicity	+	0.8889	88.89%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.9500	95.00%
Nephrotoxicity	-	0.8387	83.87%
Acute Oral Toxicity (c)	III	0.6360	63.60%
Estrogen receptor binding	+	0.8663	86.63%
Androgen receptor binding	+	0.7757	77.57%
Thyroid receptor binding	+	0.6478	64.78%
Glucocorticoid receptor binding	+	0.8292	82.92%
Aromatase binding	+	0.6324	63.24%
PPAR gamma	+	0.7791	77.91%
Honey bee toxicity	-	0.6390	63.90%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.9882	98.82%

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	99.78%	96.09%
CHEMBL4040	P28482	MAP kinase ERK2	98.73%	83.82%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.69%	94.45%
CHEMBL2581	P07339	Cathepsin D	98.29%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	97.32%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.49%	91.11%
CHEMBL4073	P09237	Matrix metalloproteinase 7	94.31%	97.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.17%	85.14%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.71%	97.25%
CHEMBL2096618	P11274	Bcr/Abl fusion protein	92.28%	85.83%
CHEMBL1914	P06276	Butyrylcholinesterase	92.11%	95.00%
CHEMBL4208	P20618	Proteasome component C5	91.78%	90.00%
CHEMBL2535	P11166	Glucose transporter	91.73%	98.75%
CHEMBL4302	P08183	P-glycoprotein 1	90.73%	92.98%
CHEMBL255	P29275	Adenosine A2b receptor	90.23%	98.59%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	89.86%	90.95%
CHEMBL5028	O14672	ADAM10	88.60%	97.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.66%	95.89%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.63%	99.17%
CHEMBL3310	Q96DB2	Histone deacetylase 11	87.62%	88.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.15%	89.00%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	87.03%	97.50%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.07%	97.09%
CHEMBL2885	P07451	Carbonic anhydrase III	84.65%	87.45%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	83.22%	94.08%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.09%	95.89%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.96%	96.00%
CHEMBL1255126	O15151	Protein Mdm4	81.25%	90.20%

Plants that contains it

• Tabernaemontana corymbosa

Cross-Links

• PubChem: 162890049
• LOTUS: LTS0011828
• wikiData: Q105372819