(3R,3aR,6S,6aS,9aR,9bR)-3-hydroxy-9-(hydroxymethyl)-3,6-dimethyl-4,5,6,6a,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-2,7-dione

Details

• Internal ID: d07938b8-3774-4149-9b9b-b0ba9716bdd6
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: (3R,3aR,6S,6aS,9aR,9bR)-3-hydroxy-9-(hydroxymethyl)-3,6-dimethyl-4,5,6,6a,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-2,7-dione
• InChI: InChI=1S/C15H20O5/c1-7-3-4-9-13(20-14(18)15(9,2)19)12-8(6-16)5-10(17)11(7)12/h5,7,9,11-13,16,19H,3-4,6H2,1-2H3/t7-,9+,11+,12-,13-,15+/m0/s1
• InChI Key: FJZPPCNENYYPMA-BBVKGEMHSA-N
• Popularity: 2 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: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9529	95.29%
Caco-2	+	0.5000	50.00%
Blood Brain Barrier	+	0.6428	64.28%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.6657	66.57%
OATP2B1 inhibitior	-	0.8588	85.88%
OATP1B1 inhibitior	+	0.8773	87.73%
OATP1B3 inhibitior	+	0.9297	92.97%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.6761	67.61%
BSEP inhibitior	-	0.9573	95.73%
P-glycoprotein inhibitior	-	0.9365	93.65%
P-glycoprotein substrate	-	0.7350	73.50%
CYP3A4 substrate	+	0.5990	59.90%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9056	90.56%
CYP3A4 inhibition	-	0.7724	77.24%
CYP2C9 inhibition	-	0.6995	69.95%
CYP2C19 inhibition	-	0.8530	85.30%
CYP2D6 inhibition	-	0.9111	91.11%
CYP1A2 inhibition	-	0.5789	57.89%
CYP2C8 inhibition	-	0.8533	85.33%
CYP inhibitory promiscuity	-	0.8662	86.62%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5521	55.21%
Eye corrosion	-	0.9825	98.25%
Eye irritation	-	0.9530	95.30%
Skin irritation	-	0.5486	54.86%
Skin corrosion	-	0.8774	87.74%
Ames mutagenesis	-	0.6261	62.61%
Human Ether-a-go-go-Related Gene inhibition	-	0.6702	67.02%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	+	0.7065	70.65%
skin sensitisation	-	0.8527	85.27%
Respiratory toxicity	+	0.7778	77.78%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	+	0.5121	51.21%
Acute Oral Toxicity (c)	III	0.4956	49.56%
Estrogen receptor binding	+	0.6173	61.73%
Androgen receptor binding	+	0.6265	62.65%
Thyroid receptor binding	+	0.6138	61.38%
Glucocorticoid receptor binding	+	0.7180	71.80%
Aromatase binding	-	0.7736	77.36%
PPAR gamma	-	0.6626	66.26%
Honey bee toxicity	-	0.9330	93.30%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5187	51.87%
Fish aquatic toxicity	+	0.9235	92.35%

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	95.75%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.34%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.66%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.55%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.43%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.61%	100.00%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	87.92%	94.80%
CHEMBL226	P30542	Adenosine A1 receptor	87.84%	95.93%
CHEMBL2581	P07339	Cathepsin D	83.30%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.28%	95.89%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	82.67%	86.92%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	81.51%	86.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.21%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.10%	85.14%

Plants that contains it

• Parasenecio petasitoides

Cross-Links

• PubChem: 12111491
• LOTUS: LTS0001180
• wikiData: Q104996435