[(3aR,4R,6aR,9aR,9bR)-9-methyl-3,6-dimethylidene-2-oxo-4,5,6a,7,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-4-yl] (Z)-2,4-dihydroxybut-2-enoate

Details

• Internal ID: 9ccfe526-d2da-4142-a414-aa14199fc99a
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: [(3aR,4R,6aR,9aR,9bR)-9-methyl-3,6-dimethylidene-2-oxo-4,5,6a,7,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-4-yl] (Z)-2,4-dihydroxybut-2-enoate
• InChI: InChI=1S/C19H22O6/c1-9-4-5-12-10(2)8-14(24-19(23)13(21)6-7-20)16-11(3)18(22)25-17(16)15(9)12/h4,6,12,14-17,20-21H,2-3,5,7-8H2,1H3/b13-6-/t12-,14+,15-,16+,17+/m0/s1
• InChI Key: LLEISBHTKVIJHY-OGAYMVAHSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₂O₆
• Molecular Weight: 346.40 g/mol
• Exact Mass: 346.14163842 g/mol
• Topological Polar Surface Area (TPSA): 93.10 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): 1.97
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9437	94.37%
Caco-2	-	0.6367	63.67%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.6403	64.03%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8987	89.87%
OATP1B3 inhibitior	+	0.9553	95.53%
MATE1 inhibitior	-	0.8412	84.12%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.8264	82.64%
P-glycoprotein inhibitior	-	0.6976	69.76%
P-glycoprotein substrate	-	0.7448	74.48%
CYP3A4 substrate	+	0.6125	61.25%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9032	90.32%
CYP3A4 inhibition	-	0.8571	85.71%
CYP2C9 inhibition	-	0.8279	82.79%
CYP2C19 inhibition	-	0.8389	83.89%
CYP2D6 inhibition	-	0.9365	93.65%
CYP1A2 inhibition	-	0.7407	74.07%
CYP2C8 inhibition	-	0.6396	63.96%
CYP inhibitory promiscuity	-	0.8388	83.88%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6948	69.48%
Eye corrosion	-	0.9769	97.69%
Eye irritation	-	0.7533	75.33%
Skin irritation	-	0.6797	67.97%
Skin corrosion	-	0.9098	90.98%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4892	48.92%
Micronuclear	-	0.7100	71.00%
Hepatotoxicity	-	0.5500	55.00%
skin sensitisation	-	0.8309	83.09%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	+	0.5330	53.30%
Acute Oral Toxicity (c)	III	0.4652	46.52%
Estrogen receptor binding	+	0.7412	74.12%
Androgen receptor binding	+	0.5955	59.55%
Thyroid receptor binding	+	0.5950	59.50%
Glucocorticoid receptor binding	+	0.5902	59.02%
Aromatase binding	+	0.5362	53.62%
PPAR gamma	-	0.4853	48.53%
Honey bee toxicity	-	0.7902	79.02%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.9437	94.37%

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	93.46%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.34%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.14%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	87.32%	94.73%
CHEMBL221	P23219	Cyclooxygenase-1	87.05%	90.17%
CHEMBL3359	P21462	Formyl peptide receptor 1	86.46%	93.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.04%	99.17%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.85%	99.23%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	83.48%	95.50%
CHEMBL2581	P07339	Cathepsin D	83.37%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.83%	94.45%

Plants that contains it

• Eupatorium chinense

Cross-Links

• PubChem: 162845320
• LOTUS: LTS0188019
• wikiData: Q105153435