[(1S,2S,3R,5S,7R,8S,9S,10R,14S)-3,7-diacetyloxy-9-hydroxy-11,11-dimethyl-6-methylidene-17-oxo-16-oxapentacyclo[7.5.3.15,8.01,10.02,8]octadecan-14-yl] acetate

Details

• Internal ID: 4e66f605-a9b5-4106-ae60-4c692c266814
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
• IUPAC Name: [(1S,2S,3R,5S,7R,8S,9S,10R,14S)-3,7-diacetyloxy-9-hydroxy-11,11-dimethyl-6-methylidene-17-oxo-16-oxapentacyclo[7.5.3.15,8.01,10.02,8]octadecan-14-yl] acetate
• SMILES (Canonical): CC(=O)OC1CCC(C2C13COC(=O)C2(C45C3C(CC(C4)C(=C)C5OC(=O)C)OC(=O)C)O)(C)C
• SMILES (Isomeric): CC(=O)O[C@H]1CCC([C@@H]2[C@@]13COC(=O)[C@]2([C@]45[C@H]3[C@@H](C[C@H](C4)C(=C)[C@H]5OC(=O)C)OC(=O)C)O)(C)C
• InChI: InChI=1S/C26H34O9/c1-12-16-9-17(33-13(2)27)19-24-11-32-22(30)26(31,25(19,10-16)20(12)35-15(4)29)21(24)23(5,6)8-7-18(24)34-14(3)28/h16-21,31H,1,7-11H2,2-6H3/t16-,17-,18+,19+,20-,21-,24+,25+,26-/m1/s1
• InChI Key: XRSOCYVQCVMDLO-ATAQONTKSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₃₄O₉
• Molecular Weight: 490.50 g/mol
• Exact Mass: 490.22028266 g/mol
• Topological Polar Surface Area (TPSA): 125.00 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 2.09
• H-Bond Acceptor: 9
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9650	96.50%
Caco-2	-	0.6911	69.11%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.8420	84.20%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8770	87.70%
OATP1B3 inhibitior	+	0.8298	82.98%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.5173	51.73%
BSEP inhibitior	+	0.6220	62.20%
P-glycoprotein inhibitior	+	0.6426	64.26%
P-glycoprotein substrate	-	0.5641	56.41%
CYP3A4 substrate	+	0.6970	69.70%
CYP2C9 substrate	-	0.8119	81.19%
CYP2D6 substrate	-	0.8663	86.63%
CYP3A4 inhibition	-	0.8273	82.73%
CYP2C9 inhibition	-	0.6167	61.67%
CYP2C19 inhibition	-	0.7632	76.32%
CYP2D6 inhibition	-	0.9502	95.02%
CYP1A2 inhibition	-	0.5895	58.95%
CYP2C8 inhibition	+	0.4564	45.64%
CYP inhibitory promiscuity	-	0.9325	93.25%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6776	67.76%
Eye corrosion	-	0.9894	98.94%
Eye irritation	-	0.8481	84.81%
Skin irritation	-	0.5203	52.03%
Skin corrosion	-	0.9347	93.47%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4289	42.89%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	-	0.5875	58.75%
skin sensitisation	-	0.8491	84.91%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	+	0.7310	73.10%
Acute Oral Toxicity (c)	III	0.4541	45.41%
Estrogen receptor binding	+	0.8589	85.89%
Androgen receptor binding	+	0.7079	70.79%
Thyroid receptor binding	+	0.5532	55.32%
Glucocorticoid receptor binding	+	0.7325	73.25%
Aromatase binding	+	0.6972	69.72%
PPAR gamma	+	0.7304	73.04%
Honey bee toxicity	-	0.7669	76.69%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9954	99.54%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.52%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.74%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.86%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.00%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.88%	97.09%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	89.67%	82.69%
CHEMBL1937	Q92769	Histone deacetylase 2	89.37%	94.75%
CHEMBL340	P08684	Cytochrome P450 3A4	88.68%	91.19%
CHEMBL2581	P07339	Cathepsin D	87.80%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.66%	100.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	87.33%	97.14%
CHEMBL259	P32245	Melanocortin receptor 4	87.01%	95.38%
CHEMBL3922	P50579	Methionine aminopeptidase 2	85.19%	97.28%
CHEMBL2413	P32246	C-C chemokine receptor type 1	84.90%	89.50%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	84.77%	96.77%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.92%	99.23%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	82.91%	91.07%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.59%	89.00%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	81.94%	93.04%
CHEMBL5255	O00206	Toll-like receptor 4	81.42%	92.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.14%	95.89%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	80.73%	95.50%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.66%	92.94%

Plants that contains it

• Isodon shikokianus

Cross-Links

• PubChem: 162849983
• LOTUS: LTS0202182
• wikiData: Q105340723