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

Details

• Internal ID: fe9c2b1c-4e96-4586-846e-eb456410124a
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: 5,6-dihydroxy-6,9-dimethyl-3-methylidene-4,5,6a,7,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-2-one
• SMILES (Canonical): CC1=CCC2C1C3C(CC(C2(C)O)O)C(=C)C(=O)O3
• SMILES (Isomeric): CC1=CCC2C1C3C(CC(C2(C)O)O)C(=C)C(=O)O3
• InChI: InChI=1S/C15H20O4/c1-7-4-5-10-12(7)13-9(8(2)14(17)19-13)6-11(16)15(10,3)18/h4,9-13,16,18H,2,5-6H2,1,3H3
• InChI Key: DCVONVXPVPZIGR-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₄
• Molecular Weight: 264.32 g/mol
• Exact Mass: 264.13615911 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 0.80
• Atomic LogP (AlogP): 1.18
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9658	96.58%
Caco-2	-	0.5334	53.34%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.5868	58.68%
OATP2B1 inhibitior	-	0.8557	85.57%
OATP1B1 inhibitior	+	0.9011	90.11%
OATP1B3 inhibitior	+	0.9329	93.29%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.9700	97.00%
P-glycoprotein inhibitior	-	0.9355	93.55%
P-glycoprotein substrate	-	0.7921	79.21%
CYP3A4 substrate	+	0.6011	60.11%
CYP2C9 substrate	-	0.8087	80.87%
CYP2D6 substrate	-	0.8486	84.86%
CYP3A4 inhibition	-	0.8167	81.67%
CYP2C9 inhibition	-	0.8645	86.45%
CYP2C19 inhibition	-	0.7800	78.00%
CYP2D6 inhibition	-	0.9236	92.36%
CYP1A2 inhibition	-	0.7159	71.59%
CYP2C8 inhibition	-	0.8329	83.29%
CYP inhibitory promiscuity	-	0.9576	95.76%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5769	57.69%
Eye corrosion	-	0.9815	98.15%
Eye irritation	-	0.9429	94.29%
Skin irritation	-	0.5585	55.85%
Skin corrosion	-	0.8703	87.03%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5531	55.31%
Micronuclear	-	0.6400	64.00%
Hepatotoxicity	+	0.7875	78.75%
skin sensitisation	-	0.7120	71.20%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	+	0.4888	48.88%
Acute Oral Toxicity (c)	III	0.4105	41.05%
Estrogen receptor binding	+	0.6407	64.07%
Androgen receptor binding	+	0.6217	62.17%
Thyroid receptor binding	+	0.5362	53.62%
Glucocorticoid receptor binding	+	0.7000	70.00%
Aromatase binding	-	0.7262	72.62%
PPAR gamma	-	0.5810	58.10%
Honey bee toxicity	-	0.7404	74.04%
Biodegradation	-	0.5250	52.50%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.9545	95.45%

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	92.99%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.20%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.95%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.93%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.13%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.05%	99.23%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.81%	94.45%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.89%	100.00%
CHEMBL1871	P10275	Androgen Receptor	83.08%	96.43%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.26%	89.00%
CHEMBL2996	Q05655	Protein kinase C delta	81.12%	97.79%

Plants that contains it

• Ajania achilleoides

Cross-Links

• PubChem: 14543451
• LOTUS: LTS0029342
• wikiData: Q104975940