(2R,3R,4S,5S,6S,8R,13S,16S,17R,18R)-11-ethyl-6,18-dimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.12,5.01,10.03,8.013,17]nonadecane-4,8,16-triol

Details

• Internal ID: ea7322a0-b454-4988-9e0d-45a17a16e3ba
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Aconitane-type diterpenoid alkaloids
• IUPAC Name: (2R,3R,4S,5S,6S,8R,13S,16S,17R,18R)-11-ethyl-6,18-dimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.12,5.01,10.03,8.013,17]nonadecane-4,8,16-triol
• SMILES (Canonical): CCN1CC2(CCC(C34C2C(C(C31)C5(CC(C6CC4C5C6O)OC)O)OC)O)COC
• SMILES (Isomeric): CCN1C[C@@]2(CC[C@@H](C34[C@@H]2[C@H](C(C31)[C@]5(C[C@@H]([C@H]6C[C@@H]4[C@@H]5[C@H]6O)OC)O)OC)O)COC
• InChI: InChI=1S/C24H39NO6/c1-5-25-10-22(11-29-2)7-6-15(26)24-13-8-12-14(30-3)9-23(28,16(13)18(12)27)17(21(24)25)19(31-4)20(22)24/h12-21,26-28H,5-11H2,1-4H3/t12-,13-,14+,15+,16-,17?,18+,19+,20-,21?,22+,23-,24?/m1/s1
• InChI Key: XRARAKHBJHWUHW-XPGJPNGISA-N
• Popularity: 12 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₃₉NO₆
• Molecular Weight: 437.60 g/mol
• Exact Mass: 437.27773796 g/mol
• Topological Polar Surface Area (TPSA): 91.60 Ų
• XlogP: -0.10
• Atomic LogP (AlogP): 0.50
• H-Bond Acceptor: 7
• H-Bond Donor: 3
• Rotatable Bonds: 5

Synonyms

• HY-N0478
• CS-0008999

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8399	83.99%
Caco-2	-	0.6106	61.06%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Lysosomes	0.7408	74.08%
OATP2B1 inhibitior	-	0.8585	85.85%
OATP1B1 inhibitior	+	0.9245	92.45%
OATP1B3 inhibitior	+	0.9434	94.34%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	-	0.4705	47.05%
P-glycoprotein inhibitior	-	0.9036	90.36%
P-glycoprotein substrate	+	0.6597	65.97%
CYP3A4 substrate	+	0.6939	69.39%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.4514	45.14%
CYP3A4 inhibition	-	0.9356	93.56%
CYP2C9 inhibition	-	0.8984	89.84%
CYP2C19 inhibition	-	0.8889	88.89%
CYP2D6 inhibition	-	0.9224	92.24%
CYP1A2 inhibition	-	0.9230	92.30%
CYP2C8 inhibition	+	0.4864	48.64%
CYP inhibitory promiscuity	-	0.9489	94.89%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6314	63.14%
Eye corrosion	-	0.9871	98.71%
Eye irritation	-	0.9246	92.46%
Skin irritation	-	0.7772	77.72%
Skin corrosion	-	0.9284	92.84%
Ames mutagenesis	-	0.5970	59.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.3778	37.78%
Micronuclear	-	0.5300	53.00%
Hepatotoxicity	-	0.5764	57.64%
skin sensitisation	-	0.8608	86.08%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	-	0.8168	81.68%
Acute Oral Toxicity (c)	III	0.4756	47.56%
Estrogen receptor binding	+	0.6826	68.26%
Androgen receptor binding	+	0.6433	64.33%
Thyroid receptor binding	+	0.6596	65.96%
Glucocorticoid receptor binding	-	0.5000	50.00%
Aromatase binding	+	0.6124	61.24%
PPAR gamma	+	0.5624	56.24%
Honey bee toxicity	-	0.7507	75.07%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	-	0.6766	67.66%

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	99.28%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.73%	97.25%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	97.48%	96.38%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	96.64%	95.58%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.11%	85.14%
CHEMBL226	P30542	Adenosine A1 receptor	94.61%	95.93%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.18%	97.09%
CHEMBL221	P23219	Cyclooxygenase-1	93.54%	90.17%
CHEMBL1871	P10275	Androgen Receptor	92.59%	96.43%
CHEMBL241	Q14432	Phosphodiesterase 3A	89.95%	92.94%
CHEMBL1907601	P11802	Cyclin-dependent kinase 4/cyclin D1	89.02%	98.99%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.60%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.55%	95.89%
CHEMBL204	P00734	Thrombin	88.53%	96.01%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	88.39%	91.03%
CHEMBL2581	P07339	Cathepsin D	85.42%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.88%	94.45%
CHEMBL3922	P50579	Methionine aminopeptidase 2	84.85%	97.28%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	83.49%	95.50%
CHEMBL2815	P04629	Nerve growth factor receptor Trk-A	83.18%	87.16%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	82.29%	97.50%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	82.26%	90.24%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	82.13%	92.86%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	81.75%	100.00%
CHEMBL2835	P23458	Tyrosine-protein kinase JAK1	81.65%	98.79%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.55%	95.89%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	81.41%	100.00%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	80.92%	95.17%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	80.30%	82.38%
CHEMBL1991	O14920	Inhibitor of nuclear factor kappa B kinase beta subunit	80.22%	97.15%

Plants that contains it

• Aconitum burnatii
• Aconitum carmichaelii
• Aconitum ferox
• Aconitum firmum
• Aconitum flavum
• Aconitum fukutomei
• Aconitum jaluense
• Aconitum japonicum
• Aconitum japonicum subsp. ibukiense
• Aconitum japonicum subsp. subcuneatum
• Aconitum karakolicum
• Aconitum kusnezoffii
• Aconitum liangshanicum
• Aconitum napellus
• Aconitum nemorum
• Aconitum soongaricum
• Aconitum tauricum
• Aconitum volubile
• Delphinium pictum
• Delphinium staphisagria
• Nepeta menthoides

Cross-Links

• PubChem: 146014456
• LOTUS: LTS0135571
• wikiData: Q105351350