methyl (1R,2S,3R,5R,6S,10S)-2,6-dimethyl-21-oxo-14-oxa-8-azahexacyclo[11.6.1.11,5.02,10.03,8.017,20]henicosa-13(20),17-diene-18-carboxylate

Details

• Internal ID: 80591b0b-07fd-4c92-833b-b21a6114e5cf
• Taxonomy: Organoheterocyclic compounds > Indolizidines
• IUPAC Name: methyl (1R,2S,3R,5R,6S,10S)-2,6-dimethyl-21-oxo-14-oxa-8-azahexacyclo[11.6.1.11,5.02,10.03,8.017,20]henicosa-13(20),17-diene-18-carboxylate
• SMILES (Canonical): CC1CN2CC3CCC4=C5C(=C(CC56C3(C2CC1C6=O)C)C(=O)OC)CCO4
• SMILES (Isomeric): C[C@@H]1CN2C[C@H]3CCC4=C5C(=C(C[C@@]56[C@]3([C@H]2C[C@H]1C6=O)C)C(=O)OC)CCO4
• InChI: InChI=1S/C23H29NO4/c1-12-10-24-11-13-4-5-17-19-14(6-7-28-17)16(21(26)27-3)9-23(19)20(25)15(12)8-18(24)22(13,23)2/h12-13,15,18H,4-11H2,1-3H3/t12-,13-,15-,18-,22-,23-/m1/s1
• InChI Key: TVYCEKHYHLUROK-KANWGXABSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₉NO₄
• Molecular Weight: 383.50 g/mol
• Exact Mass: 383.20965841 g/mol
• Topological Polar Surface Area (TPSA): 55.80 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 2.86
• H-Bond Acceptor: 5
• H-Bond Donor: 0
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9515	95.15%
Caco-2	+	0.8715	87.15%
Blood Brain Barrier	+	0.8500	85.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.5122	51.22%
OATP2B1 inhibitior	-	0.8643	86.43%
OATP1B1 inhibitior	+	0.8834	88.34%
OATP1B3 inhibitior	+	0.9524	95.24%
MATE1 inhibitior	-	0.6200	62.00%
OCT2 inhibitior	-	0.5000	50.00%
BSEP inhibitior	+	0.8950	89.50%
P-glycoprotein inhibitior	-	0.5689	56.89%
P-glycoprotein substrate	+	0.5190	51.90%
CYP3A4 substrate	+	0.7042	70.42%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8261	82.61%
CYP3A4 inhibition	-	0.7830	78.30%
CYP2C9 inhibition	-	0.9503	95.03%
CYP2C19 inhibition	-	0.9395	93.95%
CYP2D6 inhibition	-	0.9064	90.64%
CYP1A2 inhibition	-	0.8885	88.85%
CYP2C8 inhibition	+	0.6041	60.41%
CYP inhibitory promiscuity	-	0.9517	95.17%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.4417	44.17%
Eye corrosion	-	0.9853	98.53%
Eye irritation	-	0.9291	92.91%
Skin irritation	-	0.7634	76.34%
Skin corrosion	-	0.9174	91.74%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7539	75.39%
Micronuclear	+	0.5200	52.00%
Hepatotoxicity	-	0.5250	52.50%
skin sensitisation	-	0.8379	83.79%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	+	0.6572	65.72%
Acute Oral Toxicity (c)	III	0.6280	62.80%
Estrogen receptor binding	+	0.6905	69.05%
Androgen receptor binding	+	0.7341	73.41%
Thyroid receptor binding	-	0.5475	54.75%
Glucocorticoid receptor binding	+	0.8080	80.80%
Aromatase binding	+	0.5935	59.35%
PPAR gamma	+	0.5376	53.76%
Honey bee toxicity	-	0.7915	79.15%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.8788	87.88%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.79%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.44%	96.09%
CHEMBL4040	P28482	MAP kinase ERK2	94.83%	83.82%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.64%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.62%	91.11%
CHEMBL340	P08684	Cytochrome P450 3A4	89.58%	91.19%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.13%	97.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	88.63%	96.77%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.48%	97.25%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	87.31%	94.33%
CHEMBL2581	P07339	Cathepsin D	87.11%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.04%	86.33%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	85.83%	94.78%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.30%	97.14%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.90%	94.00%
CHEMBL2413	P32246	C-C chemokine receptor type 1	81.74%	89.50%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.60%	99.23%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	81.28%	82.69%
CHEMBL5255	O00206	Toll-like receptor 4	80.68%	92.50%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.67%	92.62%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.31%	95.89%

Plants that contains it

• Daphniphyllum himalayense
• Daphniphyllum subverticillatum

Cross-Links

• PubChem: 163106094
• LOTUS: LTS0230864
• wikiData: Q105265620