(3aS,6aR,8S,9R,9aS,9bR)-8-hydroxy-9-(hydroxymethyl)-3,6-dimethylidene-4,5,6a,7,8,9,9a,9b-octahydro-3aH-azuleno[4,5-b]furan-2-one

Details

• Internal ID: 7227732b-b4b3-4289-9aad-df5733203e76
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: (3aS,6aR,8S,9R,9aS,9bR)-8-hydroxy-9-(hydroxymethyl)-3,6-dimethylidene-4,5,6a,7,8,9,9a,9b-octahydro-3aH-azuleno[4,5-b]furan-2-one
• SMILES (Canonical): C=C1CCC2C(C3C1CC(C3CO)O)OC(=O)C2=C
• SMILES (Isomeric): C=C1CC[C@@H]2[C@@H]([C@H]3[C@H]1C[C@@H]([C@H]3CO)O)OC(=O)C2=C
• InChI: InChI=1S/C15H20O4/c1-7-3-4-9-8(2)15(18)19-14(9)13-10(7)5-12(17)11(13)6-16/h9-14,16-17H,1-6H2/t9-,10-,11+,12-,13-,14-/m0/s1
• InChI Key: KFIKXYBWGMDXOP-XQZGEAEESA-N
• Popularity: 1 reference 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: 1.40
• Atomic LogP (AlogP): 1.04
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9314	93.14%
Caco-2	+	0.5000	50.00%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	+	0.7000	70.00%
Subcellular localzation	Mitochondria	0.5955	59.55%
OATP2B1 inhibitior	-	0.8559	85.59%
OATP1B1 inhibitior	+	0.8530	85.30%
OATP1B3 inhibitior	+	0.9597	95.97%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7113	71.13%
BSEP inhibitior	-	0.9332	93.32%
P-glycoprotein inhibitior	-	0.9384	93.84%
P-glycoprotein substrate	-	0.8872	88.72%
CYP3A4 substrate	+	0.5060	50.60%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8042	80.42%
CYP3A4 inhibition	-	0.9073	90.73%
CYP2C9 inhibition	-	0.9048	90.48%
CYP2C19 inhibition	-	0.8265	82.65%
CYP2D6 inhibition	-	0.8925	89.25%
CYP1A2 inhibition	-	0.7979	79.79%
CYP2C8 inhibition	-	0.8398	83.98%
CYP inhibitory promiscuity	-	0.9035	90.35%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.7270	72.70%
Eye corrosion	-	0.9697	96.97%
Eye irritation	+	0.5783	57.83%
Skin irritation	-	0.7407	74.07%
Skin corrosion	-	0.9385	93.85%
Ames mutagenesis	-	0.6940	69.40%
Human Ether-a-go-go-Related Gene inhibition	-	0.6943	69.43%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	+	0.6625	66.25%
skin sensitisation	-	0.8623	86.23%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.6333	63.33%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	+	0.4625	46.25%
Acute Oral Toxicity (c)	III	0.4870	48.70%
Estrogen receptor binding	-	0.5858	58.58%
Androgen receptor binding	+	0.6470	64.70%
Thyroid receptor binding	-	0.6091	60.91%
Glucocorticoid receptor binding	+	0.7145	71.45%
Aromatase binding	-	0.7946	79.46%
PPAR gamma	-	0.7216	72.16%
Honey bee toxicity	-	0.7877	78.77%
Biodegradation	-	0.5250	52.50%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	+	0.8247	82.47%

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	95.82%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.94%	97.09%
CHEMBL226	P30542	Adenosine A1 receptor	90.60%	95.93%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.38%	85.14%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.83%	100.00%
CHEMBL2581	P07339	Cathepsin D	83.78%	98.95%
CHEMBL2996	Q05655	Protein kinase C delta	83.62%	97.79%
CHEMBL253	P34972	Cannabinoid CB2 receptor	83.11%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.47%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.89%	95.56%

Plants that contains it

• Amphoricarpos neumayerianus

Cross-Links

• PubChem: 163004001
• LOTUS: LTS0145392
• wikiData: Q105140391