[(1S,4S,5R,6S,8R,9S,13S,16S)-11-ethyl-8,9-dihydroxy-4,6,16,18-tetramethoxy-11-azahexacyclo[7.7.2.12,5.01,10.03,8.013,17]nonadecan-13-yl]methyl 2-(3-methyl-2,5-dioxopyrrolidin-1-yl)benzoate

Details

• Internal ID: 086d39b8-3023-4307-b9a1-056e4e798948
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Aconitane-type diterpenoid alkaloids
• IUPAC Name: [(1S,4S,5R,6S,8R,9S,13S,16S)-11-ethyl-8,9-dihydroxy-4,6,16,18-tetramethoxy-11-azahexacyclo[7.7.2.12,5.01,10.03,8.013,17]nonadecan-13-yl]methyl 2-(3-methyl-2,5-dioxopyrrolidin-1-yl)benzoate
• SMILES (Canonical): CCN1CC2(CCC(C34C2C(C(C31)(C5(CC(C6CC4C5C6OC)OC)O)O)OC)OC)COC(=O)C7=CC=CC=C7N8C(=O)CC(C8=O)C
• SMILES (Isomeric): CCN1C[C@@]2(CC[C@@H]([C@@]34C2C([C@@](C31)([C@]5(C[C@@H]([C@H]6CC4C5[C@H]6OC)OC)O)O)OC)OC)COC(=O)C7=CC=CC=C7N8C(=O)CC(C8=O)C
• InChI: InChI=1S/C37H50N2O10/c1-7-38-17-34(18-49-32(42)20-10-8-9-11-23(20)39-26(40)14-19(2)31(39)41)13-12-25(46-4)36-22-15-21-24(45-3)16-35(43,27(22)28(21)47-5)37(44,33(36)38)30(48-6)29(34)36/h8-11,19,21-22,24-25,27-30,33,43-44H,7,12-18H2,1-6H3/t19?,21-,22?,24+,25+,27?,28+,29?,30?,33?,34+,35-,36+,37-/m1/s1
• InChI Key: XLTANAWLDBYGFU-OQXBGOKZSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₇H₅₀N₂O₁₀
• Molecular Weight: 682.80 g/mol
• Exact Mass: 682.34654580 g/mol
• Topological Polar Surface Area (TPSA): 144.00 Ų
• XlogP: 1.00
• Atomic LogP (AlogP): 2.04
• H-Bond Acceptor: 11
• H-Bond Donor: 2
• Rotatable Bonds: 9

Synonyms

• 21019-30-7

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7378	73.78%
Caco-2	-	0.8196	81.96%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.6126	61.26%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8433	84.33%
OATP1B3 inhibitior	+	0.9294	92.94%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.9896	98.96%
P-glycoprotein inhibitior	+	0.7745	77.45%
P-glycoprotein substrate	+	0.7467	74.67%
CYP3A4 substrate	+	0.7383	73.83%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7782	77.82%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.9387	93.87%
CYP2C8 inhibition	+	0.7671	76.71%
CYP inhibitory promiscuity	-	0.9484	94.84%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.6126	61.26%
Eye corrosion	-	0.9883	98.83%
Eye irritation	-	0.9248	92.48%
Skin irritation	-	0.7895	78.95%
Skin corrosion	-	0.9390	93.90%
Ames mutagenesis	-	0.6840	68.40%
Human Ether-a-go-go-Related Gene inhibition	+	0.7328	73.28%
Micronuclear	+	0.7600	76.00%
Hepatotoxicity	-	0.6642	66.42%
skin sensitisation	-	0.8849	88.49%
Respiratory toxicity	+	0.8778	87.78%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	-	0.8963	89.63%
Acute Oral Toxicity (c)	III	0.5759	57.59%
Estrogen receptor binding	+	0.8134	81.34%
Androgen receptor binding	+	0.7704	77.04%
Thyroid receptor binding	-	0.4890	48.90%
Glucocorticoid receptor binding	+	0.6625	66.25%
Aromatase binding	+	0.7036	70.36%
PPAR gamma	+	0.7520	75.20%
Honey bee toxicity	-	0.7207	72.07%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.9332	93.32%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL2492	P36544	Neuronal acetylcholine receptor protein alpha-7 subunit	1 nM	Ki	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.35%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.41%	97.25%
CHEMBL2581	P07339	Cathepsin D	94.94%	98.95%
CHEMBL221	P23219	Cyclooxygenase-1	94.74%	90.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.73%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.55%	86.33%
CHEMBL2095172	P14867	GABA-A receptor; alpha-1/beta-2/gamma-2	92.11%	92.67%
CHEMBL299	P17252	Protein kinase C alpha	91.14%	98.03%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.59%	91.11%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	89.19%	97.14%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	88.31%	82.69%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.12%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.62%	85.14%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	85.34%	93.03%
CHEMBL1902	P62942	FK506-binding protein 1A	85.04%	97.05%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	83.74%	91.07%
CHEMBL340	P08684	Cytochrome P450 3A4	82.74%	91.19%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.46%	99.23%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	80.90%	97.33%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	80.55%	93.00%

Plants that contains it

• Aconitum orientale
• Delphinium andersonii
• Delphinium barbeyi
• Delphinium bicolor
• Delphinium brunonianum
• Delphinium cheilanthum
• Delphinium delavayi
• Delphinium dictyocarpum
• Delphinium dissectum
• Delphinium elatum
• Delphinium iliense
• Delphinium majus
• Delphinium menziesii
• Delphinium nudicaule
• Delphinium nuttallianum
• Delphinium oreophilum
• Delphinium potaninii
• Delphinium retropilosum
• Delphinium schmalhausenii
• Delphinium semibarbatum
• Delphinium speciosum
• Delphinium taliense
• Delphinium thamarae
• Delphinium winklerianum

Cross-Links

• PubChem: 139292146
• LOTUS: LTS0054381
• wikiData: Q104252958