(1R,2S,3R,5R,7S,10R,11S,13S,14S,16S,17S,18S,19R)-4-ethyl-16-methoxy-10-methyl-6-oxa-4-azaheptacyclo[15.2.1.02,7.02,11.03,13.05,10.014,19]icosane-14,18-diol

Details

• Internal ID: 2fc71785-d68f-4a1b-b3a5-d79f6b6cd158
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Aconitane-type diterpenoid alkaloids
• IUPAC Name: (1R,2S,3R,5R,7S,10R,11S,13S,14S,16S,17S,18S,19R)-4-ethyl-16-methoxy-10-methyl-6-oxa-4-azaheptacyclo[15.2.1.02,7.02,11.03,13.05,10.014,19]icosane-14,18-diol
• SMILES (Canonical): CCN1C2C3CC4C2(C5CCC4(C1O5)C)C6CC7C(CC3(C6C7O)O)OC
• SMILES (Isomeric): CCN1[C@@H]2[C@@H]3C[C@H]4[C@@]2([C@@H]5CC[C@]4([C@H]1O5)C)[C@@H]6C[C@@H]7[C@H](C[C@]3([C@H]6[C@H]7O)O)OC
• InChI: InChI=1S/C22H33NO4/c1-4-23-18-12-8-14-20(2)6-5-15(27-19(20)23)22(14,18)11-7-10-13(26-3)9-21(12,25)16(11)17(10)24/h10-19,24-25H,4-9H2,1-3H3/t10-,11-,12+,13+,14-,15+,16-,17+,18-,19-,20-,21+,22-/m1/s1
• InChI Key: RYTZLEVRXNSDGJ-SRKQURDMSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₃₃NO₄
• Molecular Weight: 375.50 g/mol
• Exact Mass: 375.24095853 g/mol
• Topological Polar Surface Area (TPSA): 62.20 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 1.61
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7671	76.71%
Caco-2	-	0.5344	53.44%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Lysosomes	0.6605	66.05%
OATP2B1 inhibitior	-	0.8576	85.76%
OATP1B1 inhibitior	+	0.9147	91.47%
OATP1B3 inhibitior	+	0.9370	93.70%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.6255	62.55%
P-glycoprotein inhibitior	-	0.8961	89.61%
P-glycoprotein substrate	+	0.5332	53.32%
CYP3A4 substrate	+	0.7246	72.46%
CYP2C9 substrate	-	0.8027	80.27%
CYP2D6 substrate	-	0.7533	75.33%
CYP3A4 inhibition	-	0.9478	94.78%
CYP2C9 inhibition	-	0.8383	83.83%
CYP2C19 inhibition	-	0.8024	80.24%
CYP2D6 inhibition	-	0.8950	89.50%
CYP1A2 inhibition	-	0.8804	88.04%
CYP2C8 inhibition	-	0.6640	66.40%
CYP inhibitory promiscuity	-	0.8925	89.25%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6453	64.53%
Eye corrosion	-	0.9872	98.72%
Eye irritation	-	0.9384	93.84%
Skin irritation	-	0.7890	78.90%
Skin corrosion	-	0.9223	92.23%
Ames mutagenesis	-	0.5470	54.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.3684	36.84%
Micronuclear	+	0.5600	56.00%
Hepatotoxicity	-	0.6952	69.52%
skin sensitisation	-	0.8700	87.00%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.9500	95.00%
Nephrotoxicity	-	0.6867	68.67%
Acute Oral Toxicity (c)	III	0.5525	55.25%
Estrogen receptor binding	+	0.7401	74.01%
Androgen receptor binding	+	0.6869	68.69%
Thyroid receptor binding	+	0.7627	76.27%
Glucocorticoid receptor binding	+	0.6120	61.20%
Aromatase binding	+	0.6900	69.00%
PPAR gamma	+	0.6219	62.19%
Honey bee toxicity	-	0.7503	75.03%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	-	0.5582	55.82%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL204	P00734	Thrombin	99.06%	96.01%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.02%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.82%	97.25%
CHEMBL226	P30542	Adenosine A1 receptor	94.62%	95.93%
CHEMBL2730	P21980	Protein-glutamine gamma-glutamyltransferase	93.74%	92.38%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.27%	97.09%
CHEMBL1871	P10275	Androgen Receptor	90.96%	96.43%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.49%	100.00%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	90.39%	95.58%
CHEMBL221	P23219	Cyclooxygenase-1	88.63%	90.17%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	87.90%	97.50%
CHEMBL241	Q14432	Phosphodiesterase 3A	87.88%	92.94%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.83%	91.11%
CHEMBL4073	P09237	Matrix metalloproteinase 7	87.53%	97.56%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	87.13%	92.62%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	86.26%	100.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.99%	85.14%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	85.66%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.48%	86.33%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	84.90%	96.77%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	84.77%	82.38%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	84.35%	95.50%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	84.25%	82.69%
CHEMBL259	P32245	Melanocortin receptor 4	84.06%	95.38%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.16%	95.89%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	82.87%	89.05%
CHEMBL332	P03956	Matrix metalloproteinase-1	82.72%	94.50%
CHEMBL3922	P50579	Methionine aminopeptidase 2	81.90%	97.28%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	81.54%	95.17%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	81.02%	91.03%
CHEMBL3820	P35557	Hexokinase type IV	80.54%	91.96%
CHEMBL240	Q12809	HERG	80.29%	89.76%

Plants that contains it

• Aconitum karakolicum

Cross-Links

• PubChem: 162944645
• LOTUS: LTS0223689
• wikiData: Q105248139