2H-12,3,6a-Ethanylylidene-7,9-methanonaphth[2,3-b]azocine, aconitane-3,8,13,14,15-pentol deriv.

Details

• Internal ID: 27d45930-f5c8-4f69-9c53-7760a46dc044
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Aconitane-type diterpenoid alkaloids
• IUPAC Name: [8-acetyloxy-11-ethyl-5,7,14-trihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.12,5.01,10.03,8.013,17]nonadecan-4-yl] benzoate
• SMILES (Canonical): CCN1CC2(C(CC(C34C2C(C(C31)C5(C6C4CC(C6OC(=O)C7=CC=CC=C7)(C(C5O)OC)O)OC(=O)C)OC)OC)O)COC
• SMILES (Isomeric): CCN1CC2(C(CC(C34C2C(C(C31)C5(C6C4CC(C6OC(=O)C7=CC=CC=C7)(C(C5O)OC)O)OC(=O)C)OC)OC)O)COC
• InChI: InChI=1S/C34H47NO11/c1-7-35-15-31(16-41-3)20(37)13-21(42-4)33-19-14-32(40)28(45-30(39)18-11-9-8-10-12-18)22(19)34(46-17(2)36,27(38)29(32)44-6)23(26(33)35)24(43-5)25(31)33/h8-12,19-29,37-38,40H,7,13-16H2,1-6H3
• InChI Key: XFSBVAOIAHNAPC-UHFFFAOYSA-N
• Popularity: 1,635 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₄H₄₇NO₁₁
• Molecular Weight: 645.70 g/mol
• Exact Mass: 645.31491132 g/mol
• Topological Polar Surface Area (TPSA): 153.00 Ų
• XlogP: 0.30
• Atomic LogP (AlogP): 0.65
• H-Bond Acceptor: 12
• H-Bond Donor: 3
• Rotatable Bonds: 9

Synonyms

• Aconitin cristallisat
• Aconitinum
• 302-27-2
• Aconitysat
• Aconitin
• Akonitin
• UNII-X8YN71D5WC
• Aconitin cristallisat [German]
• EINECS 206-121-7
• NSC 56464
• C34-H47-N-O11
• SCHEMBL15681737
• CHEBI:181261
• XFSBVAOIAHNAPC-UHFFFAOYSA-N
• [8-acetyloxy-11-ethyl-5,7,14-trihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.12,5.01,10.03,8.013,17]nonadecan-4-yl] benzoate
• 2H-12,3,6a-Ethanylylidene-7,9-methanonaphth[2,3-b]azocine, aconitane-3,8,13,14,15-pentol deriv.
• 8-(Acetyloxy)-20-ethyl-3,13,15-trihydroxy-1,6,16-trimethoxy-4-(methoxymethyl)aconitan-14-yl benzoate #
• Aconitane-3,8,13,14,15-pentol, 20-ethyl-1,6,16-trimethoxy-4-(methoxymethyl)-, 8-acetate 14-benzoate, (1.alpha.,3.alpha.,6.alpha.,14.alpha.,15.alpha.,16.beta.)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7333	73.33%
Caco-2	-	0.8135	81.35%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Lysosomes	0.5905	59.05%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9414	94.14%
OATP1B3 inhibitior	+	0.9479	94.79%
MATE1 inhibitior	-	0.9220	92.20%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.8957	89.57%
P-glycoprotein inhibitior	+	0.6545	65.45%
P-glycoprotein substrate	+	0.7095	70.95%
CYP3A4 substrate	+	0.7147	71.47%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7414	74.14%
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	-	0.9045	90.45%
CYP2C8 inhibition	+	0.7636	76.36%
CYP inhibitory promiscuity	-	0.9299	92.99%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5722	57.22%
Eye corrosion	-	0.9898	98.98%
Eye irritation	-	0.9142	91.42%
Skin irritation	-	0.7771	77.71%
Skin corrosion	-	0.9411	94.11%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7089	70.89%
Micronuclear	+	0.5600	56.00%
Hepatotoxicity	+	0.8804	88.04%
skin sensitisation	-	0.8786	87.86%
Respiratory toxicity	+	0.9556	95.56%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	-	0.9243	92.43%
Acute Oral Toxicity (c)	I	0.7618	76.18%
Estrogen receptor binding	+	0.8173	81.73%
Androgen receptor binding	+	0.6788	67.88%
Thyroid receptor binding	+	0.5595	55.95%
Glucocorticoid receptor binding	-	0.8662	86.62%
Aromatase binding	+	0.7033	70.33%
PPAR gamma	+	0.7727	77.27%
Honey bee toxicity	-	0.7690	76.90%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.5145	51.45%
Fish aquatic toxicity	+	0.8712	87.12%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293235	P02545	Prelamin-A/C	63.1 nM	Potency	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	99.41%	96.09%
CHEMBL4040	P28482	MAP kinase ERK2	98.49%	83.82%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.33%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.74%	86.33%
CHEMBL2581	P07339	Cathepsin D	96.33%	98.95%
CHEMBL221	P23219	Cyclooxygenase-1	95.61%	90.17%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	93.55%	94.08%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	92.51%	99.23%
CHEMBL5028	O14672	ADAM10	86.12%	97.50%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	86.08%	96.00%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	84.82%	94.62%
CHEMBL2535	P11166	Glucose transporter	84.79%	98.75%
CHEMBL2815	P04629	Nerve growth factor receptor Trk-A	84.78%	87.16%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.11%	94.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.57%	92.62%
CHEMBL340	P08684	Cytochrome P450 3A4	83.44%	91.19%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	82.05%	81.11%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.81%	95.89%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	81.61%	95.50%
CHEMBL4208	P20618	Proteasome component C5	81.43%	90.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.83%	95.56%

Plants that contains it

• Aconitum brachypodum
• Aconitum brunneum
• Aconitum carmichaelii
• Aconitum chasmanthum
• Aconitum jaluense
• Aconitum japonicum
• Aconitum karakolicum
• Aconitum kusnezoffii
• Aconitum napellus
• Aconitum polyschistum
• Aconitum volubile var. pubescens
• Thalictrum minus

Cross-Links

• PubChem: 2012
• NPASS: NPC87288
• LOTUS: LTS0139961
• wikiData: Q105327247