Yunaconitine

Details

• Internal ID: 7568e276-aad5-4576-8c8a-d977dfdbe9e3
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Aconitane-type diterpenoid alkaloids
• IUPAC Name: [8-acetyloxy-11-ethyl-5,14-dihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.12,5.01,10.03,8.013,17]nonadecan-4-yl] 4-methoxybenzoate
• SMILES (Canonical): CCN1CC2(C(CC(C34C2C(C(C31)C5(CC(C6(CC4C5C6OC(=O)C7=CC=C(C=C7)OC)O)OC)OC(=O)C)OC)OC)O)COC
• SMILES (Isomeric): CCN1CC2(C(CC(C34C2C(C(C31)C5(CC(C6(CC4C5C6OC(=O)C7=CC=C(C=C7)OC)O)OC)OC(=O)C)OC)OC)O)COC
• InChI: InChI=1S/C35H49NO11/c1-8-36-16-32(17-41-3)22(38)13-23(43-5)35-21-14-33(40)24(44-6)15-34(47-18(2)37,26(29(35)36)27(45-7)28(32)35)25(21)30(33)46-31(39)19-9-11-20(42-4)12-10-19/h9-12,21-30,38,40H,8,13-17H2,1-7H3
• InChI Key: LLEMSCWAKNQHHA-UHFFFAOYSA-N
• Popularity: 19 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₅H₄₉NO₁₁
• Molecular Weight: 659.80 g/mol
• Exact Mass: 659.33056138 g/mol
• Topological Polar Surface Area (TPSA): 142.00 Ų
• XlogP: 1.20
• Atomic LogP (AlogP): 1.69
• H-Bond Acceptor: 12
• H-Bond Donor: 2
• Rotatable Bonds: 10

Synonyms

• Guayewuanine B
• Isoaconitine
• 70578-24-4
• Vilmorrianine B
• 3-alpha,13-Dihydroxyforesaconitine
• YunaconitineGuayewuanine B
• [8-acetyloxy-11-ethyl-5,14-dihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.12,5.01,10.03,8.013,17]nonadecan-4-yl] 4-methoxybenzoate
• Isoaconitine (6CI)
• Aconitane-3,8,13,14-tetrol, 20-ethyl-4-(methoxymethyl)-1,6,16-trimethoxy-, 8-acetate 14-(4-methoxybenzoate), (1-alpha,3-alpha,6-alpha,14-alpha,16-beta)-
• C35H49NO11
• C35-H49-N-O11
• DTXSID90990805
• BCP25728
• 8-(Acetyloxy)-20-ethyl-3,13-dihydroxy-1,6,16-trimethoxy-4-(methoxymethyl)aconitan-14-yl 4-methoxybenzoate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9196	91.96%
Caco-2	-	0.8056	80.56%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Lysosomes	0.4580	45.80%
OATP2B1 inhibitior	-	0.8588	85.88%
OATP1B1 inhibitior	+	0.9113	91.13%
OATP1B3 inhibitior	+	0.9378	93.78%
MATE1 inhibitior	-	0.9620	96.20%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.9529	95.29%
P-glycoprotein inhibitior	+	0.7573	75.73%
P-glycoprotein substrate	+	0.7365	73.65%
CYP3A4 substrate	+	0.7167	71.67%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7152	71.52%
CYP3A4 inhibition	-	0.7691	76.91%
CYP2C9 inhibition	-	0.8971	89.71%
CYP2C19 inhibition	-	0.8788	87.88%
CYP2D6 inhibition	-	0.8967	89.67%
CYP1A2 inhibition	-	0.8787	87.87%
CYP2C8 inhibition	+	0.7481	74.81%
CYP inhibitory promiscuity	-	0.9377	93.77%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5474	54.74%
Eye corrosion	-	0.9907	99.07%
Eye irritation	-	0.9171	91.71%
Skin irritation	-	0.7932	79.32%
Skin corrosion	-	0.9452	94.52%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7930	79.30%
Micronuclear	+	0.5600	56.00%
Hepatotoxicity	+	0.6375	63.75%
skin sensitisation	-	0.8728	87.28%
Respiratory toxicity	+	0.7889	78.89%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	-	0.7882	78.82%
Acute Oral Toxicity (c)	I	0.5552	55.52%
Estrogen receptor binding	+	0.7929	79.29%
Androgen receptor binding	+	0.7283	72.83%
Thyroid receptor binding	+	0.5214	52.14%
Glucocorticoid receptor binding	-	0.5613	56.13%
Aromatase binding	+	0.7119	71.19%
PPAR gamma	+	0.7543	75.43%
Honey bee toxicity	-	0.7898	78.98%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5363	53.63%
Fish aquatic toxicity	+	0.9107	91.07%

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	99.64%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	97.80%	90.17%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.80%	85.14%
CHEMBL4208	P20618	Proteasome component C5	96.30%	90.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.81%	86.33%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	93.10%	81.11%
CHEMBL2581	P07339	Cathepsin D	90.62%	98.95%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	89.37%	96.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.32%	94.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.89%	97.09%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	87.96%	94.08%
CHEMBL340	P08684	Cytochrome P450 3A4	87.89%	91.19%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.57%	95.89%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	86.85%	92.62%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	86.66%	87.67%
CHEMBL3922	P50579	Methionine aminopeptidase 2	84.61%	97.28%
CHEMBL211	P08172	Muscarinic acetylcholine receptor M2	83.47%	94.97%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.98%	92.94%
CHEMBL3492	P49721	Proteasome Macropain subunit	81.60%	90.24%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	81.39%	96.90%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	80.88%	91.11%

Plants that contains it

• Aconitum carmichaelii
• Aconitum forrestii
• Aconitum hemsleyanum
• Aconitum jaluense
• Aconitum japonicum
• Aconitum kusnezoffii
• Aconitum nagarum
• Aconitum sinomontanum
• Aconitum transsectum
• Aconitum vilmorinianum
• Aconitum volubile var. pubescens

Cross-Links

• PubChem: 155569
• NPASS: NPC260441
• LOTUS: LTS0119887
• wikiData: Q72516798