[(3aS,4R,7R,9S,10Z,11aS)-7,9-dihydroxy-10-methyl-3,6-dimethylidene-2-oxo-4,5,7,8,9,11a-hexahydro-3aH-cyclodeca[b]furan-4-yl] (E)-2-methylbut-2-enoate

Details

• Internal ID: bc2d153c-d7a2-489d-a9bc-5a3248b7e302
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: [(3aS,4R,7R,9S,10Z,11aS)-7,9-dihydroxy-10-methyl-3,6-dimethylidene-2-oxo-4,5,7,8,9,11a-hexahydro-3aH-cyclodeca[b]furan-4-yl] (E)-2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1CC(=C)C(CC(C(=CC2C1C(=C)C(=O)O2)C)O)O
• SMILES (Isomeric): C/C=C(\C)/C(=O)O[C@@H]1CC(=C)[C@@H](C[C@@H](/C(=C\[C@H]2[C@H]1C(=C)C(=O)O2)/C)O)O
• InChI: InChI=1S/C20H26O6/c1-6-10(2)19(23)25-16-7-11(3)14(21)9-15(22)12(4)8-17-18(16)13(5)20(24)26-17/h6,8,14-18,21-22H,3,5,7,9H2,1-2,4H3/b10-6+,12-8-/t14-,15+,16-,17+,18+/m1/s1
• InChI Key: SDFKKMBWIQKUOQ-LRCRIKIPSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₆O₆
• Molecular Weight: 362.40 g/mol
• Exact Mass: 362.17293854 g/mol
• Topological Polar Surface Area (TPSA): 93.10 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 1.98
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9760	97.60%
Caco-2	-	0.5645	56.45%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.5866	58.66%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8817	88.17%
OATP1B3 inhibitior	+	0.9345	93.45%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.5960	59.60%
P-glycoprotein inhibitior	-	0.6640	66.40%
P-glycoprotein substrate	-	0.6886	68.86%
CYP3A4 substrate	+	0.6038	60.38%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8778	87.78%
CYP3A4 inhibition	-	0.7108	71.08%
CYP2C9 inhibition	-	0.8961	89.61%
CYP2C19 inhibition	-	0.8714	87.14%
CYP2D6 inhibition	-	0.9384	93.84%
CYP1A2 inhibition	-	0.7639	76.39%
CYP2C8 inhibition	-	0.7483	74.83%
CYP inhibitory promiscuity	-	0.9123	91.23%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9325	93.25%
Carcinogenicity (trinary)	Non-required	0.5586	55.86%
Eye corrosion	-	0.9618	96.18%
Eye irritation	-	0.9017	90.17%
Skin irritation	-	0.6348	63.48%
Skin corrosion	-	0.9223	92.23%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4811	48.11%
Micronuclear	-	0.6100	61.00%
Hepatotoxicity	+	0.7125	71.25%
skin sensitisation	-	0.7813	78.13%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	+	0.6987	69.87%
Acute Oral Toxicity (c)	III	0.3620	36.20%
Estrogen receptor binding	+	0.7096	70.96%
Androgen receptor binding	-	0.5937	59.37%
Thyroid receptor binding	+	0.5491	54.91%
Glucocorticoid receptor binding	+	0.6826	68.26%
Aromatase binding	-	0.6652	66.52%
PPAR gamma	-	0.5458	54.58%
Honey bee toxicity	-	0.6156	61.56%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5900	59.00%
Fish aquatic toxicity	+	0.9678	96.78%

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	93.23%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.54%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.02%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.50%	94.45%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.78%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.34%	89.00%
CHEMBL340	P08684	Cytochrome P450 3A4	82.41%	91.19%
CHEMBL3401	O75469	Pregnane X receptor	82.30%	94.73%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.89%	95.50%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.77%	97.09%
CHEMBL221	P23219	Cyclooxygenase-1	80.49%	90.17%

Plants that contains it

• Calea berteroana

Cross-Links

• PubChem: 162907375
• LOTUS: LTS0001558
• wikiData: Q105250609