(3aS,6aR,8S,9S,9aS,9bS)-8,9-dihydroxy-9-methyl-3,6-dimethylidene-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-2-one

Details

• Internal ID: 23682a26-a30f-484b-b4d0-94b76b103713
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: (3aS,6aR,8S,9S,9aS,9bS)-8,9-dihydroxy-9-methyl-3,6-dimethylidene-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-2-one
• SMILES (Canonical): CC1(C(CC2C1C3C(CCC2=C)C(=C)C(=O)O3)O)O
• SMILES (Isomeric): C[C@]1([C@H](C[C@@H]2[C@H]1[C@@H]3[C@@H](CCC2=C)C(=C)C(=O)O3)O)O
• InChI: InChI=1S/C15H20O4/c1-7-4-5-9-8(2)14(17)19-13(9)12-10(7)6-11(16)15(12,3)18/h9-13,16,18H,1-2,4-6H2,3H3/t9-,10-,11-,12-,13-,15+/m0/s1
• InChI Key: XPIJQWSXDNIFNJ-XTXFXJEVSA-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: 0.90
• 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	+	0.9579	95.79%
Caco-2	-	0.5692	56.92%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.6510	65.10%
OATP2B1 inhibitior	-	0.8543	85.43%
OATP1B1 inhibitior	+	0.8826	88.26%
OATP1B3 inhibitior	+	0.9462	94.62%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7071	70.71%
BSEP inhibitior	-	0.9744	97.44%
P-glycoprotein inhibitior	-	0.9135	91.35%
P-glycoprotein substrate	-	0.8449	84.49%
CYP3A4 substrate	+	0.6185	61.85%
CYP2C9 substrate	-	0.8087	80.87%
CYP2D6 substrate	-	0.8486	84.86%
CYP3A4 inhibition	-	0.8958	89.58%
CYP2C9 inhibition	-	0.8083	80.83%
CYP2C19 inhibition	-	0.6537	65.37%
CYP2D6 inhibition	-	0.9354	93.54%
CYP1A2 inhibition	+	0.5196	51.96%
CYP2C8 inhibition	-	0.7778	77.78%
CYP inhibitory promiscuity	-	0.9767	97.67%
UGT catelyzed	+	0.5362	53.62%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5283	52.83%
Eye corrosion	-	0.9807	98.07%
Eye irritation	-	0.7727	77.27%
Skin irritation	-	0.5182	51.82%
Skin corrosion	-	0.8832	88.32%
Ames mutagenesis	-	0.7500	75.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5628	56.28%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	+	0.9324	93.24%
skin sensitisation	-	0.7968	79.68%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	+	0.4941	49.41%
Acute Oral Toxicity (c)	IV	0.4160	41.60%
Estrogen receptor binding	+	0.6489	64.89%
Androgen receptor binding	+	0.6475	64.75%
Thyroid receptor binding	-	0.5474	54.74%
Glucocorticoid receptor binding	+	0.7662	76.62%
Aromatase binding	-	0.6838	68.38%
PPAR gamma	-	0.7253	72.53%
Honey bee toxicity	-	0.8408	84.08%
Biodegradation	-	0.5750	57.50%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.9601	96.01%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.36%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.19%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.11%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.59%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.81%	95.56%
CHEMBL241	Q14432	Phosphodiesterase 3A	88.35%	92.94%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.76%	100.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.91%	99.23%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.95%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.91%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.48%	95.89%

Plants that contains it

• Ajania fruticulosa

Cross-Links

• PubChem: 15690510
• LOTUS: LTS0129353
• wikiData: Q105338393