4,5,6-trihydroxy-6,9-dimethyl-3-methylidene-4,5,6a,7,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-2-one

Details

• Internal ID: 01d6f9c8-1a15-45ac-91d3-beae7548ad92
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: 4,5,6-trihydroxy-6,9-dimethyl-3-methylidene-4,5,6a,7,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-2-one
• SMILES (Canonical): CC1=CCC2C1C3C(C(C(C2(C)O)O)O)C(=C)C(=O)O3
• SMILES (Isomeric): CC1=CCC2C1C3C(C(C(C2(C)O)O)O)C(=C)C(=O)O3
• InChI: InChI=1S/C15H20O5/c1-6-4-5-8-9(6)12-10(7(2)14(18)20-12)11(16)13(17)15(8,3)19/h4,8-13,16-17,19H,2,5H2,1,3H3
• InChI Key: LLYGEJGXQWZFGX-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₅
• Molecular Weight: 280.32 g/mol
• Exact Mass: 280.13107373 g/mol
• Topological Polar Surface Area (TPSA): 87.00 Ų
• XlogP: -0.20
• Atomic LogP (AlogP): 0.15
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9064	90.64%
Caco-2	-	0.7220	72.20%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	+	0.7000	70.00%
Subcellular localzation	Mitochondria	0.4705	47.05%
OATP2B1 inhibitior	-	0.8594	85.94%
OATP1B1 inhibitior	+	0.9219	92.19%
OATP1B3 inhibitior	+	0.9377	93.77%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.9767	97.67%
P-glycoprotein inhibitior	-	0.9035	90.35%
P-glycoprotein substrate	-	0.8542	85.42%
CYP3A4 substrate	+	0.5779	57.79%
CYP2C9 substrate	-	0.8087	80.87%
CYP2D6 substrate	-	0.8486	84.86%
CYP3A4 inhibition	-	0.7973	79.73%
CYP2C9 inhibition	-	0.8074	80.74%
CYP2C19 inhibition	-	0.7504	75.04%
CYP2D6 inhibition	-	0.9157	91.57%
CYP1A2 inhibition	-	0.6235	62.35%
CYP2C8 inhibition	-	0.8955	89.55%
CYP inhibitory promiscuity	-	0.8471	84.71%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5441	54.41%
Eye corrosion	-	0.9775	97.75%
Eye irritation	-	0.9241	92.41%
Skin irritation	-	0.5786	57.86%
Skin corrosion	-	0.8527	85.27%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5857	58.57%
Micronuclear	-	0.6200	62.00%
Hepatotoxicity	+	0.6658	66.58%
skin sensitisation	-	0.7304	73.04%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	+	0.5915	59.15%
Acute Oral Toxicity (c)	III	0.3746	37.46%
Estrogen receptor binding	+	0.6109	61.09%
Androgen receptor binding	-	0.4888	48.88%
Thyroid receptor binding	+	0.5636	56.36%
Glucocorticoid receptor binding	+	0.6272	62.72%
Aromatase binding	-	0.7159	71.59%
PPAR gamma	-	0.5348	53.48%
Honey bee toxicity	-	0.8051	80.51%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.9605	96.05%

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	93.18%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.82%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.15%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.34%	94.45%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.19%	100.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.72%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.60%	89.00%
CHEMBL221	P23219	Cyclooxygenase-1	85.59%	90.17%
CHEMBL3401	O75469	Pregnane X receptor	84.74%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.16%	86.33%
CHEMBL2581	P07339	Cathepsin D	81.51%	98.95%

Plants that contains it

• Anthemis plutonia

Cross-Links

• PubChem: 163045096
• LOTUS: LTS0257417
• wikiData: Q105153787