[(1S,2R,3S,4R,7S,8Z,12R,13S,14S)-2,14-diacetyloxy-3-hydroxy-4,9,13,17-tetramethyl-5-oxo-6-oxatricyclo[11.4.0.03,7]heptadeca-8,16-dien-12-yl] butanoate

Details

• Internal ID: ca8b8b90-678b-4ac8-a9d7-a54c988fbdf4
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
• IUPAC Name: [(1S,2R,3S,4R,7S,8Z,12R,13S,14S)-2,14-diacetyloxy-3-hydroxy-4,9,13,17-tetramethyl-5-oxo-6-oxatricyclo[11.4.0.03,7]heptadeca-8,16-dien-12-yl] butanoate
• SMILES (Canonical): CCCC(=O)OC1CCC(=CC2C(C(C(=O)O2)C)(C(C3C1(C(CC=C3C)OC(=O)C)C)OC(=O)C)O)C
• SMILES (Isomeric): CCCC(=O)O[C@@H]1CC/C(=C\[C@H]2[C@@]([C@H](C(=O)O2)C)([C@@H]([C@@H]3[C@@]1([C@H](CC=C3C)OC(=O)C)C)OC(=O)C)O)/C
• InChI: InChI=1S/C28H40O9/c1-8-9-23(31)36-21-12-10-15(2)14-22-28(33,17(4)26(32)37-22)25(35-19(6)30)24-16(3)11-13-20(27(21,24)7)34-18(5)29/h11,14,17,20-22,24-25,33H,8-10,12-13H2,1-7H3/b15-14-/t17-,20-,21+,22-,24+,25+,27+,28-/m0/s1
• InChI Key: WUAAFCGTSYYMLQ-LOIFNGLMSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₄₀O₉
• Molecular Weight: 520.60 g/mol
• Exact Mass: 520.26723285 g/mol
• Topological Polar Surface Area (TPSA): 125.00 Ų
• XlogP: 2.80
• Atomic LogP (AlogP): 3.57
• H-Bond Acceptor: 9
• H-Bond Donor: 1
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9907	99.07%
Caco-2	-	0.6284	62.84%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.6184	61.84%
OATP2B1 inhibitior	-	0.8613	86.13%
OATP1B1 inhibitior	+	0.8581	85.81%
OATP1B3 inhibitior	+	0.8405	84.05%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	+	0.9802	98.02%
P-glycoprotein inhibitior	+	0.8582	85.82%
P-glycoprotein substrate	-	0.5209	52.09%
CYP3A4 substrate	+	0.6986	69.86%
CYP2C9 substrate	-	0.8135	81.35%
CYP2D6 substrate	-	0.8794	87.94%
CYP3A4 inhibition	-	0.5970	59.70%
CYP2C9 inhibition	-	0.8520	85.20%
CYP2C19 inhibition	-	0.7930	79.30%
CYP2D6 inhibition	-	0.9410	94.10%
CYP1A2 inhibition	-	0.5858	58.58%
CYP2C8 inhibition	+	0.4756	47.56%
CYP inhibitory promiscuity	-	0.8590	85.90%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5534	55.34%
Eye corrosion	-	0.9873	98.73%
Eye irritation	-	0.8850	88.50%
Skin irritation	+	0.6098	60.98%
Skin corrosion	-	0.8677	86.77%
Ames mutagenesis	-	0.5970	59.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.4274	42.74%
Micronuclear	-	0.8100	81.00%
Hepatotoxicity	-	0.5375	53.75%
skin sensitisation	-	0.7840	78.40%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	-	0.6954	69.54%
Acute Oral Toxicity (c)	III	0.4956	49.56%
Estrogen receptor binding	+	0.7864	78.64%
Androgen receptor binding	+	0.6510	65.10%
Thyroid receptor binding	-	0.5369	53.69%
Glucocorticoid receptor binding	+	0.8214	82.14%
Aromatase binding	+	0.6806	68.06%
PPAR gamma	+	0.7671	76.71%
Honey bee toxicity	-	0.7754	77.54%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.6000	60.00%
Fish aquatic toxicity	+	0.9781	97.81%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.32%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.26%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.62%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.03%	97.25%
CHEMBL2581	P07339	Cathepsin D	92.86%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.48%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.99%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	91.02%	99.23%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.59%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.49%	95.56%
CHEMBL230	P35354	Cyclooxygenase-2	89.97%	89.63%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	87.00%	92.62%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.99%	97.09%
CHEMBL1871	P10275	Androgen Receptor	86.71%	96.43%
CHEMBL241	Q14432	Phosphodiesterase 3A	86.47%	92.94%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	84.44%	94.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.41%	100.00%
CHEMBL340	P08684	Cytochrome P450 3A4	84.09%	91.19%
CHEMBL5255	O00206	Toll-like receptor 4	83.87%	92.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.75%	95.89%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.74%	94.00%
CHEMBL221	P23219	Cyclooxygenase-1	83.70%	90.17%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.13%	99.17%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	80.82%	89.05%
CHEMBL3359	P21462	Formyl peptide receptor 1	80.21%	93.56%

Plants that contains it

• Piper retrofractum

Cross-Links

• PubChem: 21778081
• LOTUS: LTS0210104
• wikiData: Q105193292