(3aS,6R,6aR,9R,9aS,9bS)-6,6a,9-trihydroxy-6,9-dimethyl-3-methylidene-4,5,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-2-one

Details

• Internal ID: 87bce5c2-a82f-48aa-a027-430535a8588b
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: (3aS,6R,6aR,9R,9aS,9bS)-6,6a,9-trihydroxy-6,9-dimethyl-3-methylidene-4,5,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-2-one
• SMILES (Canonical): CC1(CCC2C(C3C1(C=CC3(C)O)O)OC(=O)C2=C)O
• SMILES (Isomeric): C[C@]1(CC[C@@H]2[C@@H]([C@@H]3[C@@]1(C=C[C@@]3(C)O)O)OC(=O)C2=C)O
• InChI: InChI=1S/C15H20O5/c1-8-9-4-5-14(3,18)15(19)7-6-13(2,17)11(15)10(9)20-12(8)16/h6-7,9-11,17-19H,1,4-5H2,2-3H3/t9-,10-,11-,13+,14+,15+/m0/s1
• InChI Key: SGHTVVJDLWGFLU-GPOOSLAASA-N
• Popularity: 1 reference 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: -0.10
• Atomic LogP (AlogP): 0.30
• 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	+	0.9221	92.21%
Caco-2	-	0.6277	62.77%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	+	0.6429	64.29%
Subcellular localzation	Mitochondria	0.4936	49.36%
OATP2B1 inhibitior	-	0.8529	85.29%
OATP1B1 inhibitior	+	0.8788	87.88%
OATP1B3 inhibitior	+	0.9447	94.47%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8071	80.71%
BSEP inhibitior	-	0.9814	98.14%
P-glycoprotein inhibitior	-	0.9035	90.35%
P-glycoprotein substrate	-	0.9018	90.18%
CYP3A4 substrate	+	0.5903	59.03%
CYP2C9 substrate	-	0.8200	82.00%
CYP2D6 substrate	-	0.8568	85.68%
CYP3A4 inhibition	-	0.7807	78.07%
CYP2C9 inhibition	-	0.8057	80.57%
CYP2C19 inhibition	-	0.7563	75.63%
CYP2D6 inhibition	-	0.9047	90.47%
CYP1A2 inhibition	-	0.6142	61.42%
CYP2C8 inhibition	-	0.6363	63.63%
CYP inhibitory promiscuity	-	0.9403	94.03%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.5629	56.29%
Eye corrosion	-	0.9813	98.13%
Eye irritation	-	0.9608	96.08%
Skin irritation	-	0.5439	54.39%
Skin corrosion	-	0.8348	83.48%
Ames mutagenesis	-	0.7570	75.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.4841	48.41%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	+	0.8379	83.79%
skin sensitisation	-	0.7714	77.14%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	+	0.6286	62.86%
Acute Oral Toxicity (c)	III	0.3352	33.52%
Estrogen receptor binding	+	0.7000	70.00%
Androgen receptor binding	+	0.6236	62.36%
Thyroid receptor binding	+	0.6055	60.55%
Glucocorticoid receptor binding	+	0.5913	59.13%
Aromatase binding	-	0.5629	56.29%
PPAR gamma	+	0.5303	53.03%
Honey bee toxicity	-	0.8944	89.44%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9056	90.56%

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	95.76%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.25%	97.25%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.18%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.11%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.91%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.57%	94.45%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.40%	99.23%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.42%	100.00%
CHEMBL218	P21554	Cannabinoid CB1 receptor	81.60%	96.61%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.18%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.29%	89.00%

Plants that contains it

• Artemisia gorgonum

Cross-Links

• PubChem: 162987168
• LOTUS: LTS0092188
• wikiData: Q105252325