(3aS,4S,6aS,9aR,9bS)-6a-hydroperoxy-4-hydroxy-6,9-dimethyl-3-methylidene-4,7,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-2-one

Details

• Internal ID: 30d91773-23c9-4bc7-803e-2fc2f589a46a
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: (3aS,4S,6aS,9aR,9bS)-6a-hydroperoxy-4-hydroxy-6,9-dimethyl-3-methylidene-4,7,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-2-one
• SMILES (Canonical): CC1=CCC2(C1C3C(C(C=C2C)O)C(=C)C(=O)O3)OO
• SMILES (Isomeric): CC1=CC[C@@]2([C@H]1[C@@H]3[C@H]([C@H](C=C2C)O)C(=C)C(=O)O3)OO
• InChI: InChI=1S/C15H18O5/c1-7-4-5-15(20-18)8(2)6-10(16)11-9(3)14(17)19-13(11)12(7)15/h4,6,10-13,16,18H,3,5H2,1-2H3/t10-,11-,12+,13-,15+/m0/s1
• InChI Key: FYRYMWMYRKGLMQ-DKBOKBLXSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₈O₅
• Molecular Weight: 278.30 g/mol
• Exact Mass: 278.11542367 g/mol
• Topological Polar Surface Area (TPSA): 76.00 Ų
• XlogP: 0.20
• Atomic LogP (AlogP): 1.60
• 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	+	0.9708	97.08%
Caco-2	-	0.6044	60.44%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.5465	54.65%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9188	91.88%
OATP1B3 inhibitior	+	0.9031	90.31%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.9244	92.44%
P-glycoprotein inhibitior	-	0.9183	91.83%
P-glycoprotein substrate	-	0.8344	83.44%
CYP3A4 substrate	+	0.6027	60.27%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8297	82.97%
CYP3A4 inhibition	-	0.7287	72.87%
CYP2C9 inhibition	-	0.8258	82.58%
CYP2C19 inhibition	-	0.7734	77.34%
CYP2D6 inhibition	-	0.9297	92.97%
CYP1A2 inhibition	-	0.6402	64.02%
CYP2C8 inhibition	-	0.7675	76.75%
CYP inhibitory promiscuity	-	0.8476	84.76%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8725	87.25%
Carcinogenicity (trinary)	Non-required	0.5282	52.82%
Eye corrosion	-	0.9617	96.17%
Eye irritation	-	0.8838	88.38%
Skin irritation	-	0.6396	63.96%
Skin corrosion	-	0.8432	84.32%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6011	60.11%
Micronuclear	-	0.5800	58.00%
Hepatotoxicity	+	0.7441	74.41%
skin sensitisation	-	0.6988	69.88%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	+	0.6888	68.88%
Acute Oral Toxicity (c)	III	0.4077	40.77%
Estrogen receptor binding	-	0.5427	54.27%
Androgen receptor binding	+	0.5401	54.01%
Thyroid receptor binding	+	0.5842	58.42%
Glucocorticoid receptor binding	+	0.5440	54.40%
Aromatase binding	-	0.5787	57.87%
PPAR gamma	+	0.5580	55.80%
Honey bee toxicity	-	0.7215	72.15%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.9546	95.46%

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	95.13%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.82%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.99%	97.25%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.86%	99.23%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.47%	94.45%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.14%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.29%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.24%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	81.83%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.95%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.79%	95.89%

Plants that contains it

• Artemisia ludoviciana

Cross-Links

• PubChem: 162989022
• LOTUS: LTS0023193
• wikiData: Q105004675