methyl (1S,15R,17S,18S)-17-ethyl-7-methoxy-14-oxo-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: 8443de62-8dd0-45a6-aeb0-02d6dabdf48c
• Taxonomy: Alkaloids and derivatives > Ibogan-type alkaloids
• IUPAC Name: methyl (1S,15R,17S,18S)-17-ethyl-7-methoxy-14-oxo-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=O)CCC4=C3NC5=C4C=C(C=C5)OC)C(=O)OC
• SMILES (Isomeric): CC[C@H]1C[C@@H]2C[C@@]3([C@H]1N(C2=O)CCC4=C3NC5=C4C=C(C=C5)OC)C(=O)OC
• InChI: InChI=1S/C22H26N2O4/c1-4-12-9-13-11-22(21(26)28-3)18-15(7-8-24(19(12)22)20(13)25)16-10-14(27-2)5-6-17(16)23-18/h5-6,10,12-13,19,23H,4,7-9,11H2,1-3H3/t12-,13+,19-,22+/m0/s1
• InChI Key: LTQINICYLGNLHN-IMDACWRGSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₆N₂O₄
• Molecular Weight: 382.50 g/mol
• Exact Mass: 382.18925731 g/mol
• Topological Polar Surface Area (TPSA): 71.60 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 2.79
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

• BDBM50044110

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9304	93.04%
Caco-2	+	0.7934	79.34%
Blood Brain Barrier	+	0.8000	80.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.5905	59.05%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8819	88.19%
OATP1B3 inhibitior	+	0.9199	91.99%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.7072	70.72%
BSEP inhibitior	+	0.9319	93.19%
P-glycoprotein inhibitior	+	0.7115	71.15%
P-glycoprotein substrate	+	0.7691	76.91%
CYP3A4 substrate	+	0.6434	64.34%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8026	80.26%
CYP3A4 inhibition	+	0.5664	56.64%
CYP2C9 inhibition	-	0.5830	58.30%
CYP2C19 inhibition	-	0.5210	52.10%
CYP2D6 inhibition	-	0.8499	84.99%
CYP1A2 inhibition	-	0.6046	60.46%
CYP2C8 inhibition	-	0.6677	66.77%
CYP inhibitory promiscuity	+	0.6936	69.36%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6672	66.72%
Eye corrosion	-	0.9905	99.05%
Eye irritation	-	0.9797	97.97%
Skin irritation	-	0.8200	82.00%
Skin corrosion	-	0.9430	94.30%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7135	71.35%
Micronuclear	+	0.6800	68.00%
Hepatotoxicity	+	0.5125	51.25%
skin sensitisation	-	0.9006	90.06%
Respiratory toxicity	+	0.9000	90.00%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	-	0.8733	87.33%
Acute Oral Toxicity (c)	III	0.5528	55.28%
Estrogen receptor binding	+	0.8012	80.12%
Androgen receptor binding	+	0.7507	75.07%
Thyroid receptor binding	+	0.5961	59.61%
Glucocorticoid receptor binding	+	0.7554	75.54%
Aromatase binding	+	0.6597	65.97%
PPAR gamma	-	0.5000	50.00%
Honey bee toxicity	-	0.8417	84.17%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9414	94.14%

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	99.54%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.36%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.96%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.08%	85.14%
CHEMBL255	P29275	Adenosine A2b receptor	97.44%	98.59%
CHEMBL2581	P07339	Cathepsin D	96.15%	98.95%
CHEMBL205	P00918	Carbonic anhydrase II	95.09%	98.44%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.72%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.77%	95.56%
CHEMBL4208	P20618	Proteasome component C5	92.55%	90.00%
CHEMBL2535	P11166	Glucose transporter	92.19%	98.75%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	90.99%	96.77%
CHEMBL261	P00915	Carbonic anhydrase I	89.39%	96.76%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.18%	95.89%
CHEMBL241	Q14432	Phosphodiesterase 3A	88.08%	92.94%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	87.71%	86.92%
CHEMBL221	P23219	Cyclooxygenase-1	87.07%	90.17%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	86.68%	92.62%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	84.52%	97.50%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	84.21%	91.07%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.36%	94.00%
CHEMBL340	P08684	Cytochrome P450 3A4	81.77%	91.19%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.68%	94.33%

Plants that contains it

• Tabernaemontana citrifolia
• Tabernaemontana cymosa
• Tabernaemontana divaricata
• Tabernaemontana markgrafiana

Cross-Links

• PubChem: 12110672
• LOTUS: LTS0234014
• wikiData: Q104403305