methyl (1S,15R,17S,18S)-5-[(1S,12R,14S,15Z,18S)-15-ethylidene-18-(hydroxymethyl)-18-methoxycarbonyl-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: c9cc867c-cabc-48c7-9a6d-5ec8e113fb0e
• Taxonomy: Alkaloids and derivatives > Ibogan-type alkaloids
• IUPAC Name: methyl (1S,15R,17S,18S)-5-[(1S,12R,14S,15Z,18S)-15-ethylidene-18-(hydroxymethyl)-18-methoxycarbonyl-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=C1CNC2CC3=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
• 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
• InChI: InChI=1S/C43H52N4O7/c1-6-24-19-44-34-17-29-25-9-7-8-10-32(25)45-36(29)30(16-31(24)43(34,21-48)41(51)54-5)35-33(52-3)12-11-26-27-13-14-47-20-23-15-28(22(2)49)39(47)42(18-23,40(50)53-4)38(27)46-37(26)35/h6-12,22-23,28,30-31,34,39,44-46,48-49H,13-21H2,1-5H3/b24-6+/t22-,23+,28+,30+,31-,34-,39-,42+,43-/m0/s1
• InChI Key: JISWNPUGSHPACB-BANJEBCRSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₃H₅₂N₄O₇
• Molecular Weight: 736.90 g/mol
• Exact Mass: 736.38360001 g/mol
• Topological Polar Surface Area (TPSA): 149.00 Ų
• XlogP: 3.60
• Atomic LogP (AlogP): 4.48
• H-Bond Acceptor: 9
• H-Bond Donor: 5
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9295	92.95%
Caco-2	-	0.8274	82.74%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.5765	57.65%
OATP2B1 inhibitior	-	0.7197	71.97%
OATP1B1 inhibitior	+	0.8280	82.80%
OATP1B3 inhibitior	+	0.9171	91.71%
MATE1 inhibitior	-	0.8612	86.12%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.9951	99.51%
P-glycoprotein inhibitior	+	0.8185	81.85%
P-glycoprotein substrate	+	0.8679	86.79%
CYP3A4 substrate	+	0.7498	74.98%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.3810	38.10%
CYP3A4 inhibition	-	0.6001	60.01%
CYP2C9 inhibition	-	0.7487	74.87%
CYP2C19 inhibition	-	0.8364	83.64%
CYP2D6 inhibition	-	0.8482	84.82%
CYP1A2 inhibition	-	0.7132	71.32%
CYP2C8 inhibition	+	0.7399	73.99%
CYP inhibitory promiscuity	-	0.6868	68.68%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.5825	58.25%
Eye corrosion	-	0.9865	98.65%
Eye irritation	-	0.9278	92.78%
Skin irritation	-	0.7696	76.96%
Skin corrosion	-	0.9340	93.40%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6915	69.15%
Micronuclear	+	0.7300	73.00%
Hepatotoxicity	-	0.6750	67.50%
skin sensitisation	-	0.8597	85.97%
Respiratory toxicity	+	0.8889	88.89%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	-	0.8258	82.58%
Acute Oral Toxicity (c)	III	0.5914	59.14%
Estrogen receptor binding	+	0.8733	87.33%
Androgen receptor binding	+	0.7803	78.03%
Thyroid receptor binding	+	0.6302	63.02%
Glucocorticoid receptor binding	+	0.8058	80.58%
Aromatase binding	+	0.6477	64.77%
PPAR gamma	+	0.7605	76.05%
Honey bee toxicity	-	0.6439	64.39%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.6600	66.00%
Fish aquatic toxicity	+	0.9583	95.83%

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	99.66%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	99.02%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.86%	91.11%
CHEMBL2581	P07339	Cathepsin D	98.40%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.46%	85.14%
CHEMBL4040	P28482	MAP kinase ERK2	96.30%	83.82%
CHEMBL4302	P08183	P-glycoprotein 1	95.98%	92.98%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.57%	95.56%
CHEMBL4073	P09237	Matrix metalloproteinase 7	92.81%	97.56%
CHEMBL2535	P11166	Glucose transporter	92.55%	98.75%
CHEMBL5608	Q16288	NT-3 growth factor receptor	91.82%	95.89%
CHEMBL3310	Q96DB2	Histone deacetylase 11	91.07%	88.56%
CHEMBL5028	O14672	ADAM10	91.03%	97.50%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	90.38%	90.95%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	89.29%	93.03%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.18%	97.09%
CHEMBL2096618	P11274	Bcr/Abl fusion protein	88.77%	85.83%
CHEMBL4208	P20618	Proteasome component C5	88.37%	90.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.99%	99.17%
CHEMBL340	P08684	Cytochrome P450 3A4	87.24%	91.19%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.99%	89.00%
CHEMBL5103	Q969S8	Histone deacetylase 10	86.14%	90.08%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	85.79%	96.47%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	85.10%	97.50%
CHEMBL253	P34972	Cannabinoid CB2 receptor	84.89%	97.25%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.51%	92.62%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	82.38%	89.67%
CHEMBL1255126	O15151	Protein Mdm4	81.44%	90.20%
CHEMBL255	P29275	Adenosine A2b receptor	81.42%	98.59%
CHEMBL205	P00918	Carbonic anhydrase II	81.19%	98.44%

Plants that contains it

• Garcinia xanthochymus
• Tabernaemontana corymbosa

Cross-Links

• PubChem: 101226046
• LOTUS: LTS0059524
• wikiData: Q105284538