4,6-dihydroxy-3,6,9-trimethyl-3a,4,5,6a,9a,9b-hexahydro-3H-azuleno[4,5-b]furan-2,7-dione

Details

• Internal ID: 953f65b4-f584-4bd1-88cd-de0ec876f32b
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: 4,6-dihydroxy-3,6,9-trimethyl-3a,4,5,6a,9a,9b-hexahydro-3H-azuleno[4,5-b]furan-2,7-dione
• SMILES (Canonical): CC1C2C(CC(C3C(C2OC1=O)C(=CC3=O)C)(C)O)O
• SMILES (Isomeric): CC1C2C(CC(C3C(C2OC1=O)C(=CC3=O)C)(C)O)O
• InChI: InChI=1S/C15H20O5/c1-6-4-8(16)12-10(6)13-11(7(2)14(18)20-13)9(17)5-15(12,3)19/h4,7,9-13,17,19H,5H2,1-3H3
• InChI Key: LBDJBOGRXNNNOJ-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): 83.80 Ų
• XlogP: -0.10
• Atomic LogP (AlogP): 0.44
• H-Bond Acceptor: 5
• 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	+	0.9624	96.24%
Caco-2	-	0.6192	61.92%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.4300	43.00%
OATP2B1 inhibitior	-	0.8576	85.76%
OATP1B1 inhibitior	+	0.9037	90.37%
OATP1B3 inhibitior	+	0.9584	95.84%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.9396	93.96%
P-glycoprotein inhibitior	-	0.9018	90.18%
P-glycoprotein substrate	-	0.6531	65.31%
CYP3A4 substrate	+	0.5893	58.93%
CYP2C9 substrate	-	0.7890	78.90%
CYP2D6 substrate	-	0.8977	89.77%
CYP3A4 inhibition	-	0.8475	84.75%
CYP2C9 inhibition	-	0.8898	88.98%
CYP2C19 inhibition	-	0.9357	93.57%
CYP2D6 inhibition	-	0.9636	96.36%
CYP1A2 inhibition	-	0.7888	78.88%
CYP2C8 inhibition	-	0.9371	93.71%
CYP inhibitory promiscuity	-	0.9349	93.49%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Danger	0.3820	38.20%
Eye corrosion	-	0.9756	97.56%
Eye irritation	-	0.8188	81.88%
Skin irritation	-	0.5263	52.63%
Skin corrosion	-	0.8500	85.00%
Ames mutagenesis	-	0.5437	54.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.6148	61.48%
Micronuclear	-	0.5600	56.00%
Hepatotoxicity	+	0.6402	64.02%
skin sensitisation	-	0.6988	69.88%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	+	0.5248	52.48%
Acute Oral Toxicity (c)	III	0.3699	36.99%
Estrogen receptor binding	-	0.5709	57.09%
Androgen receptor binding	+	0.5462	54.62%
Thyroid receptor binding	+	0.6207	62.07%
Glucocorticoid receptor binding	-	0.5979	59.79%
Aromatase binding	-	0.8695	86.95%
PPAR gamma	-	0.7718	77.18%
Honey bee toxicity	-	0.8517	85.17%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.8365	83.65%

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	91.59%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.89%	91.11%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.49%	99.23%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.57%	100.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.32%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.86%	89.00%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	84.52%	85.30%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	84.24%	86.00%
CHEMBL1871	P10275	Androgen Receptor	83.20%	96.43%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.15%	86.33%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	80.90%	94.80%
CHEMBL2581	P07339	Cathepsin D	80.68%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	80.65%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.16%	97.09%

Plants that contains it

• Seriphidium deserti

Cross-Links

• PubChem: 162916153
• LOTUS: LTS0034015
• wikiData: Q105149196