(2R,3R,6S,8R,12R,16S,20R,21S)-14-ethyl-6,21-dimethoxy-16-(methoxymethyl)-9,11-dioxa-14-azaheptacyclo[10.7.2.12,5.01,13.03,8.08,12.016,20]docosane-4,19-diol

Details

• Internal ID: 16f9a9d2-b44b-4810-b92d-77f5e9169068
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Aconitane-type diterpenoid alkaloids
• IUPAC Name: (2R,3R,6S,8R,12R,16S,20R,21S)-14-ethyl-6,21-dimethoxy-16-(methoxymethyl)-9,11-dioxa-14-azaheptacyclo[10.7.2.12,5.01,13.03,8.08,12.016,20]docosane-4,19-diol
• SMILES (Canonical): CCN1CC2(CCC(C34C2C(C5(C31)C6(CC(C7CC4C6C7O)OC)OCO5)OC)O)COC
• SMILES (Isomeric): CCN1C[C@@]2(CCC(C34[C@@H]2[C@@H]([C@]5(C31)[C@]6(C[C@@H](C7C[C@@H]4[C@@H]6C7O)OC)OCO5)OC)O)COC
• InChI: InChI=1S/C25H39NO7/c1-5-26-10-22(11-29-2)7-6-16(27)24-14-8-13-15(30-3)9-23(17(14)18(13)28)25(21(24)26,33-12-32-23)20(31-4)19(22)24/h13-21,27-28H,5-12H2,1-4H3/t13?,14-,15+,16?,17-,18?,19-,20+,21?,22+,23-,24?,25+/m1/s1
• InChI Key: MSIFWQXGXCPJTR-QSGOVJJOSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₃₉NO₇
• Molecular Weight: 465.60 g/mol
• Exact Mass: 465.27265258 g/mol
• Topological Polar Surface Area (TPSA): 89.80 Ų
• XlogP: -0.20
• Atomic LogP (AlogP): 0.64
• H-Bond Acceptor: 8
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6828	68.28%
Caco-2	-	0.6040	60.40%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Lysosomes	0.6960	69.60%
OATP2B1 inhibitior	-	0.8590	85.90%
OATP1B1 inhibitior	+	0.9049	90.49%
OATP1B3 inhibitior	+	0.9434	94.34%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	+	0.6850	68.50%
P-glycoprotein inhibitior	-	0.8989	89.89%
P-glycoprotein substrate	+	0.6153	61.53%
CYP3A4 substrate	+	0.7093	70.93%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.3849	38.49%
CYP3A4 inhibition	-	0.9020	90.20%
CYP2C9 inhibition	-	0.9087	90.87%
CYP2C19 inhibition	-	0.8949	89.49%
CYP2D6 inhibition	-	0.9354	93.54%
CYP1A2 inhibition	-	0.9296	92.96%
CYP2C8 inhibition	+	0.6251	62.51%
CYP inhibitory promiscuity	-	0.9358	93.58%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5492	54.92%
Eye corrosion	-	0.9861	98.61%
Eye irritation	-	0.9208	92.08%
Skin irritation	-	0.7934	79.34%
Skin corrosion	-	0.9371	93.71%
Ames mutagenesis	-	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6766	67.66%
Micronuclear	+	0.5200	52.00%
Hepatotoxicity	-	0.6159	61.59%
skin sensitisation	-	0.8615	86.15%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	-	0.6152	61.52%
Acute Oral Toxicity (c)	III	0.4324	43.24%
Estrogen receptor binding	+	0.7282	72.82%
Androgen receptor binding	+	0.7540	75.40%
Thyroid receptor binding	+	0.7023	70.23%
Glucocorticoid receptor binding	-	0.4638	46.38%
Aromatase binding	+	0.6770	67.70%
PPAR gamma	+	0.6331	63.31%
Honey bee toxicity	-	0.7345	73.45%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	-	0.5959	59.59%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.63%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.56%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.95%	85.14%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	96.86%	95.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.30%	97.09%
CHEMBL226	P30542	Adenosine A1 receptor	90.84%	95.93%
CHEMBL221	P23219	Cyclooxygenase-1	90.79%	90.17%
CHEMBL204	P00734	Thrombin	90.40%	96.01%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	88.16%	92.62%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	88.09%	95.58%
CHEMBL218	P21554	Cannabinoid CB1 receptor	86.64%	96.61%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.56%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.28%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.86%	100.00%
CHEMBL1871	P10275	Androgen Receptor	85.78%	96.43%
CHEMBL279	P35968	Vascular endothelial growth factor receptor 2	85.72%	95.52%
CHEMBL241	Q14432	Phosphodiesterase 3A	85.66%	92.94%
CHEMBL2996	Q05655	Protein kinase C delta	85.15%	97.79%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	84.57%	96.77%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	84.36%	91.11%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	83.77%	97.21%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	82.92%	95.50%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.25%	86.33%
CHEMBL3922	P50579	Methionine aminopeptidase 2	81.97%	97.28%
CHEMBL2581	P07339	Cathepsin D	81.70%	98.95%
CHEMBL259	P32245	Melanocortin receptor 4	81.10%	95.38%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	80.64%	100.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.45%	94.33%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	80.36%	82.38%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	80.35%	97.50%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.07%	97.14%

Plants that contains it

• Fritillaria delavayi
• Fritillaria przewalskii

Cross-Links

• PubChem: 5316481
• NPASS: NPC298279