[(3aR,4R,6R,6aR,8S,10aR)-8-hydroxy-6,9-dimethyl-3-methylidene-2-oxo-4,5,6,6a,7,8-hexahydro-3aH-benzo[h][1]benzofuran-4-yl] (E)-2-[[(E)-2-(acetyloxymethyl)but-2-enoyl]oxymethyl]-4-hydroxybut-2-enoate

Details

• Internal ID: 9cb8bf15-c00d-48a7-93d7-dbc92dd80991
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: [(3aR,4R,6R,6aR,8S,10aR)-8-hydroxy-6,9-dimethyl-3-methylidene-2-oxo-4,5,6,6a,7,8-hexahydro-3aH-benzo[h][1]benzofuran-4-yl] (E)-2-[[(E)-2-(acetyloxymethyl)but-2-enoyl]oxymethyl]-4-hydroxybut-2-enoate
• SMILES (Canonical): CC=C(COC(=O)C)C(=O)OCC(=CCO)C(=O)OC1CC(C2CC(C(=CC23C1C(=C)C(=O)O3)C)O)C
• SMILES (Isomeric): C/C=C(\COC(=O)C)/C(=O)OC/C(=C\CO)/C(=O)O[C@@H]1C[C@H]([C@H]2C[C@@H](C(=C[C@@]23[C@@H]1C(=C)C(=O)O3)C)O)C
• InChI: InChI=1S/C27H34O10/c1-6-18(12-34-17(5)29)25(32)35-13-19(7-8-28)26(33)36-22-9-14(2)20-10-21(30)15(3)11-27(20)23(22)16(4)24(31)37-27/h6-7,11,14,20-23,28,30H,4,8-10,12-13H2,1-3,5H3/b18-6+,19-7+/t14-,20-,21+,22-,23-,27+/m1/s1
• InChI Key: DBHPVAXUHNRLFC-YFOQPESSSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₄O₁₀
• Molecular Weight: 518.60 g/mol
• Exact Mass: 518.21519728 g/mol
• Topological Polar Surface Area (TPSA): 146.00 Ų
• XlogP: 1.20
• Atomic LogP (AlogP): 1.70
• H-Bond Acceptor: 10
• H-Bond Donor: 2
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9705	97.05%
Caco-2	-	0.7880	78.80%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.6958	69.58%
OATP2B1 inhibitior	-	0.8616	86.16%
OATP1B1 inhibitior	+	0.8562	85.62%
OATP1B3 inhibitior	+	0.9464	94.64%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.8006	80.06%
P-glycoprotein inhibitior	+	0.7281	72.81%
P-glycoprotein substrate	+	0.5794	57.94%
CYP3A4 substrate	+	0.7007	70.07%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8955	89.55%
CYP3A4 inhibition	-	0.6673	66.73%
CYP2C9 inhibition	-	0.8952	89.52%
CYP2C19 inhibition	-	0.8533	85.33%
CYP2D6 inhibition	-	0.9416	94.16%
CYP1A2 inhibition	-	0.8276	82.76%
CYP2C8 inhibition	+	0.5513	55.13%
CYP inhibitory promiscuity	-	0.7854	78.54%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5534	55.34%
Eye corrosion	-	0.9869	98.69%
Eye irritation	-	0.9318	93.18%
Skin irritation	-	0.5465	54.65%
Skin corrosion	-	0.9438	94.38%
Ames mutagenesis	+	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4788	47.88%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	+	0.5178	51.78%
skin sensitisation	-	0.8432	84.32%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	+	0.6666	66.66%
Acute Oral Toxicity (c)	III	0.3961	39.61%
Estrogen receptor binding	+	0.7056	70.56%
Androgen receptor binding	+	0.7244	72.44%
Thyroid receptor binding	-	0.5130	51.30%
Glucocorticoid receptor binding	+	0.7714	77.14%
Aromatase binding	+	0.6250	62.50%
PPAR gamma	+	0.5338	53.38%
Honey bee toxicity	-	0.6722	67.22%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.9938	99.38%

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	97.98%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.26%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.52%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.70%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.46%	86.33%
CHEMBL2581	P07339	Cathepsin D	90.15%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.71%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.17%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.19%	89.00%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	86.28%	94.80%
CHEMBL3401	O75469	Pregnane X receptor	85.19%	94.73%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.15%	99.23%
CHEMBL5028	O14672	ADAM10	83.94%	97.50%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	83.84%	91.07%
CHEMBL1937	Q92769	Histone deacetylase 2	83.06%	94.75%
CHEMBL340	P08684	Cytochrome P450 3A4	82.07%	91.19%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.72%	96.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	80.17%	96.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.01%	100.00%

Plants that contains it

• Mikania haenkeana

Cross-Links

• PubChem: 101635459
• LOTUS: LTS0092450
• wikiData: Q104974399