[(3aS,4R,6E,10R,11aR)-6,10-dimethyl-3-methylidene-2,9-dioxo-4,5,8,10,11,11a-hexahydro-3aH-cyclodeca[b]furan-4-yl] (Z)-2-hydroxybut-2-enoate

Details

• Internal ID: 75482775-575b-4172-8f64-360eccc94842
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: [(3aS,4R,6E,10R,11aR)-6,10-dimethyl-3-methylidene-2,9-dioxo-4,5,8,10,11,11a-hexahydro-3aH-cyclodeca[b]furan-4-yl] (Z)-2-hydroxybut-2-enoate
• SMILES (Canonical): CC=C(C(=O)OC1CC(=CCC(=O)C(CC2C1C(=C)C(=O)O2)C)C)O
• SMILES (Isomeric): C/C=C(/C(=O)O[C@@H]1C/C(=C/CC(=O)[C@@H](C[C@@H]2[C@@H]1C(=C)C(=O)O2)C)/C)\O
• InChI: InChI=1S/C19H24O6/c1-5-13(20)19(23)25-15-8-10(2)6-7-14(21)11(3)9-16-17(15)12(4)18(22)24-16/h5-6,11,15-17,20H,4,7-9H2,1-3H3/b10-6+,13-5-/t11-,15-,16-,17-/m1/s1
• InChI Key: XQJVXOHRRMMPED-IXQVSDGSSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₄O₆
• Molecular Weight: 348.40 g/mol
• Exact Mass: 348.15728848 g/mol
• Topological Polar Surface Area (TPSA): 89.90 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 2.79
• H-Bond Acceptor: 6
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9871	98.71%
Caco-2	+	0.6633	66.33%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.5798	57.98%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8851	88.51%
OATP1B3 inhibitior	+	0.8767	87.67%
MATE1 inhibitior	-	0.7400	74.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.6482	64.82%
P-glycoprotein inhibitior	-	0.5193	51.93%
P-glycoprotein substrate	-	0.7957	79.57%
CYP3A4 substrate	+	0.6177	61.77%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9019	90.19%
CYP3A4 inhibition	-	0.7545	75.45%
CYP2C9 inhibition	-	0.9122	91.22%
CYP2C19 inhibition	-	0.8227	82.27%
CYP2D6 inhibition	-	0.9526	95.26%
CYP1A2 inhibition	-	0.5715	57.15%
CYP2C8 inhibition	-	0.6274	62.74%
CYP inhibitory promiscuity	-	0.9518	95.18%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.5932	59.32%
Eye corrosion	-	0.9528	95.28%
Eye irritation	-	0.8899	88.99%
Skin irritation	-	0.6111	61.11%
Skin corrosion	-	0.9484	94.84%
Ames mutagenesis	-	0.6754	67.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.4921	49.21%
Micronuclear	-	0.6800	68.00%
Hepatotoxicity	+	0.8293	82.93%
skin sensitisation	-	0.7441	74.41%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.5333	53.33%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	+	0.8137	81.37%
Acute Oral Toxicity (c)	III	0.3239	32.39%
Estrogen receptor binding	-	0.5179	51.79%
Androgen receptor binding	+	0.5912	59.12%
Thyroid receptor binding	-	0.6284	62.84%
Glucocorticoid receptor binding	+	0.6764	67.64%
Aromatase binding	-	0.6064	60.64%
PPAR gamma	-	0.6153	61.53%
Honey bee toxicity	-	0.7239	72.39%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9926	99.26%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.62%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.66%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.08%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.93%	99.23%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	87.30%	95.50%
CHEMBL3401	O75469	Pregnane X receptor	85.25%	94.73%
CHEMBL221	P23219	Cyclooxygenase-1	84.17%	90.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.46%	94.45%
CHEMBL3359	P21462	Formyl peptide receptor 1	81.48%	93.56%

Plants that contains it

• Stevia jujuyensis

Cross-Links

• PubChem: 162896022
• LOTUS: LTS0252070
• wikiData: Q105339783