[(1S,1'R,3'S,5R,6S,7S,9S,10S)-3'-acetyloxy-7-hydroxy-10-(hydroxymethyl)-6',6'-dimethyl-2,11-dioxospiro[3-oxatricyclo[7.2.1.01,6]dodecane-5,2'-cyclohexane]-1'-yl]methyl acetate

Details

• Internal ID: d0706584-5839-45d9-bd5c-3106effd0186
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
• IUPAC Name: [(1S,1'R,3'S,5R,6S,7S,9S,10S)-3'-acetyloxy-7-hydroxy-10-(hydroxymethyl)-6',6'-dimethyl-2,11-dioxospiro[3-oxatricyclo[7.2.1.01,6]dodecane-5,2'-cyclohexane]-1'-yl]methyl acetate
• SMILES (Canonical): CC(=O)OCC1C(CCC(C12COC(=O)C34C2C(CC(C3)C(C4=O)CO)O)OC(=O)C)(C)C
• SMILES (Isomeric): CC(=O)OC[C@H]1[C@@]2(COC(=O)[C@]34[C@H]2[C@H](C[C@H](C3)[C@H](C4=O)CO)O)[C@H](CCC1(C)C)OC(=O)C
• InChI: InChI=1S/C24H34O9/c1-12(26)31-10-17-22(3,4)6-5-18(33-13(2)27)24(17)11-32-21(30)23-8-14(7-16(28)19(23)24)15(9-25)20(23)29/h14-19,25,28H,5-11H2,1-4H3/t14-,15-,16+,17-,18+,19-,23+,24+/m1/s1
• InChI Key: PYKFFBWRFGXAHK-CLVIQGOJSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₃₄O₉
• Molecular Weight: 466.50 g/mol
• Exact Mass: 466.22028266 g/mol
• Topological Polar Surface Area (TPSA): 136.00 Ų
• XlogP: 1.60
• Atomic LogP (AlogP): 1.03
• H-Bond Acceptor: 9
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8690	86.90%
Caco-2	-	0.6513	65.13%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.7271	72.71%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8303	83.03%
OATP1B3 inhibitior	+	0.9408	94.08%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	+	0.7754	77.54%
P-glycoprotein inhibitior	-	0.5695	56.95%
P-glycoprotein substrate	-	0.5654	56.54%
CYP3A4 substrate	+	0.6908	69.08%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8464	84.64%
CYP3A4 inhibition	-	0.8163	81.63%
CYP2C9 inhibition	-	0.8396	83.96%
CYP2C19 inhibition	-	0.8571	85.71%
CYP2D6 inhibition	-	0.9568	95.68%
CYP1A2 inhibition	-	0.8555	85.55%
CYP2C8 inhibition	-	0.6188	61.88%
CYP inhibitory promiscuity	-	0.9542	95.42%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.7061	70.61%
Eye corrosion	-	0.9897	98.97%
Eye irritation	-	0.9393	93.93%
Skin irritation	-	0.6649	66.49%
Skin corrosion	-	0.9465	94.65%
Ames mutagenesis	-	0.6370	63.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.5180	51.80%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	+	0.5497	54.97%
skin sensitisation	-	0.9200	92.00%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	+	0.8545	85.45%
Acute Oral Toxicity (c)	I	0.4017	40.17%
Estrogen receptor binding	+	0.8150	81.50%
Androgen receptor binding	+	0.7428	74.28%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.7292	72.92%
Aromatase binding	+	0.5215	52.15%
PPAR gamma	+	0.6491	64.91%
Honey bee toxicity	-	0.7955	79.55%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.6000	60.00%
Fish aquatic toxicity	+	0.9245	92.45%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.90%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.82%	96.09%
CHEMBL4040	P28482	MAP kinase ERK2	96.31%	83.82%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.28%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.28%	97.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.13%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.06%	97.25%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.22%	100.00%
CHEMBL240	Q12809	HERG	89.08%	89.76%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	88.65%	82.69%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	88.01%	91.07%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	87.60%	96.77%
CHEMBL5555	O00767	Acyl-CoA desaturase	87.04%	97.50%
CHEMBL340	P08684	Cytochrome P450 3A4	86.50%	91.19%
CHEMBL226	P30542	Adenosine A1 receptor	85.55%	95.93%
CHEMBL2996	Q05655	Protein kinase C delta	85.30%	97.79%
CHEMBL2581	P07339	Cathepsin D	84.89%	98.95%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	84.47%	95.50%
CHEMBL2413	P32246	C-C chemokine receptor type 1	83.33%	89.50%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	83.29%	93.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.00%	89.00%
CHEMBL1871	P10275	Androgen Receptor	82.46%	96.43%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.89%	99.23%
CHEMBL3922	P50579	Methionine aminopeptidase 2	81.26%	97.28%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.99%	92.62%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.99%	86.33%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.63%	97.14%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.38%	95.89%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	80.16%	93.04%
CHEMBL5255	O00206	Toll-like receptor 4	80.11%	92.50%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.03%	95.56%

Plants that contains it

• Isodon excisoides

Cross-Links

• PubChem: 163188259
• LOTUS: LTS0230614
• wikiData: Q105216628