Acetyldelcosine

Details

• Internal ID: 8b606730-b68c-43b7-a6ff-c0cb4fa27e11
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Aconitane-type diterpenoid alkaloids
• IUPAC Name: [(1S,2R,3R,4S,5R,6S,8R,9S,10R,13S,16S,17R,18S)-11-ethyl-8,9,16-trihydroxy-6,18-dimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.12,5.01,10.03,8.013,17]nonadecan-4-yl] acetate
• SMILES (Canonical): CCN1CC2(CCC(C34C2C(C(C31)(C5(CC(C6CC4C5C6OC(=O)C)OC)O)O)OC)O)COC
• SMILES (Isomeric): CCN1C[C@@]2(CC[C@@H]([C@@]34[C@@H]2[C@@H]([C@@]([C@@H]31)([C@]5(C[C@@H]([C@H]6C[C@@H]4[C@@H]5[C@H]6OC(=O)C)OC)O)O)OC)O)COC
• InChI: InChI=1S/C26H41NO8/c1-6-27-11-23(12-32-3)8-7-17(29)25-15-9-14-16(33-4)10-24(30,18(15)19(14)35-13(2)28)26(31,22(25)27)21(34-5)20(23)25/h14-22,29-31H,6-12H2,1-5H3/t14-,15-,16+,17+,18-,19+,20-,21+,22-,23+,24-,25+,26-/m1/s1
• InChI Key: TUFFXFNBZVRWRL-TULAMMLGSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₄₁NO₈
• Molecular Weight: 495.60 g/mol
• Exact Mass: 495.28321727 g/mol
• Topological Polar Surface Area (TPSA): 118.00 Ų
• XlogP: -0.50
• Atomic LogP (AlogP): 0.19
• H-Bond Acceptor: 9
• H-Bond Donor: 3
• Rotatable Bonds: 6

Synonyms

• 14-acetyldelcosine
• Lucaconine, acetyl-
• Delcosine 14-acetate
• 14-O-Acetyldelcosine
• JTG60VG6L0
• UNII-JTG60VG6L0
• 50676-21-6
• Aconitane-1,7,8,14-tetrol, 20-ethyl-6,16-dimethoxy-4-(methoxymethyl)-, 14-acetate, (1alpha,6beta,14alpha,16beta)-
• Aconitane-1,7,8,14-tetrol, 20-ethyl-6,16-dimethoxy-4-(methoxymethyl)-, 14-acetate, (1.alpha.,6.beta.,14.alpha.,16.beta.)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4761	47.61%
Caco-2	-	0.7219	72.19%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Lysosomes	0.4939	49.39%
OATP2B1 inhibitior	-	0.8623	86.23%
OATP1B1 inhibitior	+	0.8984	89.84%
OATP1B3 inhibitior	+	0.9319	93.19%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.5922	59.22%
P-glycoprotein inhibitior	-	0.7705	77.05%
P-glycoprotein substrate	+	0.6345	63.45%
CYP3A4 substrate	+	0.7253	72.53%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7620	76.20%
CYP3A4 inhibition	-	0.8167	81.67%
CYP2C9 inhibition	-	0.9145	91.45%
CYP2C19 inhibition	-	0.9204	92.04%
CYP2D6 inhibition	-	0.9387	93.87%
CYP1A2 inhibition	-	0.9264	92.64%
CYP2C8 inhibition	+	0.5425	54.25%
CYP inhibitory promiscuity	-	0.9647	96.47%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5751	57.51%
Eye corrosion	-	0.9891	98.91%
Eye irritation	-	0.9140	91.40%
Skin irritation	-	0.7590	75.90%
Skin corrosion	-	0.9398	93.98%
Ames mutagenesis	-	0.6834	68.34%
Human Ether-a-go-go-Related Gene inhibition	+	0.6454	64.54%
Micronuclear	+	0.5700	57.00%
Hepatotoxicity	-	0.6388	63.88%
skin sensitisation	-	0.8740	87.40%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.9500	95.00%
Nephrotoxicity	-	0.7806	78.06%
Acute Oral Toxicity (c)	I	0.3792	37.92%
Estrogen receptor binding	+	0.8294	82.94%
Androgen receptor binding	+	0.7228	72.28%
Thyroid receptor binding	+	0.5991	59.91%
Glucocorticoid receptor binding	-	0.5270	52.70%
Aromatase binding	+	0.6647	66.47%
PPAR gamma	+	0.6738	67.38%
Honey bee toxicity	-	0.6976	69.76%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5555	55.55%
Fish aquatic toxicity	-	0.3939	39.39%

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	99.30%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.52%	97.25%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.28%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.60%	94.45%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	93.73%	96.38%
CHEMBL279	P35968	Vascular endothelial growth factor receptor 2	93.60%	95.52%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	91.24%	97.21%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	90.86%	96.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.76%	97.09%
CHEMBL340	P08684	Cytochrome P450 3A4	89.60%	91.19%
CHEMBL218	P21554	Cannabinoid CB1 receptor	86.72%	96.61%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	86.69%	94.33%
CHEMBL1907601	P11802	Cyclin-dependent kinase 4/cyclin D1	86.26%	98.99%
CHEMBL3922	P50579	Methionine aminopeptidase 2	86.14%	97.28%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.64%	100.00%
CHEMBL226	P30542	Adenosine A1 receptor	85.39%	95.93%
CHEMBL204	P00734	Thrombin	85.19%	96.01%
CHEMBL2581	P07339	Cathepsin D	84.67%	98.95%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.53%	95.89%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	83.70%	95.58%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.49%	86.33%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	83.43%	97.50%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	83.05%	95.50%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.97%	92.62%
CHEMBL2534	O15530	3-phosphoinositide dependent protein kinase-1	82.82%	95.36%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	82.81%	96.77%
CHEMBL221	P23219	Cyclooxygenase-1	82.44%	90.17%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	81.32%	91.24%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	80.90%	93.03%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.66%	91.07%

Plants that contains it

• Aconitum barbatum
• Aconitum japonicum
• Aconitum japonicum subsp. subcuneatum
• Aconitum sachalinense subsp. yezoense
• Delphinium andersonii

Cross-Links

• PubChem: 137332012
• LOTUS: LTS0187760
• wikiData: Q104391806