9-Hydroxy-9-(hydroxymethyl)-3-methyl-6-methylidene-3,3a,4,5,6a,7,9a,9b-octahydroazuleno[4,5-b]furan-2,8-dione

Details

• Internal ID: cf635280-c6ca-4358-8bce-f5f7c094a116
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: 9-hydroxy-9-(hydroxymethyl)-3-methyl-6-methylidene-3,3a,4,5,6a,7,9a,9b-octahydroazuleno[4,5-b]furan-2,8-dione
• SMILES (Canonical): CC1C2CCC(=C)C3CC(=O)C(C3C2OC1=O)(CO)O
• SMILES (Isomeric): CC1C2CCC(=C)C3CC(=O)C(C3C2OC1=O)(CO)O
• InChI: InChI=1S/C15H20O5/c1-7-3-4-9-8(2)14(18)20-13(9)12-10(7)5-11(17)15(12,19)6-16/h8-10,12-13,16,19H,1,3-6H2,2H3
• InChI Key: YXNSRUQZUQFDQO-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: 0.50
• 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	+	0.9242	92.42%
Caco-2	-	0.6270	62.70%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7358	73.58%
OATP2B1 inhibitior	-	0.8582	85.82%
OATP1B1 inhibitior	+	0.8874	88.74%
OATP1B3 inhibitior	+	0.9626	96.26%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6814	68.14%
BSEP inhibitior	-	0.9105	91.05%
P-glycoprotein inhibitior	-	0.9223	92.23%
P-glycoprotein substrate	-	0.7608	76.08%
CYP3A4 substrate	+	0.5804	58.04%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8673	86.73%
CYP3A4 inhibition	-	0.8439	84.39%
CYP2C9 inhibition	-	0.7858	78.58%
CYP2C19 inhibition	-	0.8229	82.29%
CYP2D6 inhibition	-	0.9339	93.39%
CYP1A2 inhibition	-	0.7444	74.44%
CYP2C8 inhibition	-	0.8472	84.72%
CYP inhibitory promiscuity	-	0.9779	97.79%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5942	59.42%
Eye corrosion	-	0.9850	98.50%
Eye irritation	-	0.8706	87.06%
Skin irritation	-	0.5410	54.10%
Skin corrosion	-	0.9189	91.89%
Ames mutagenesis	-	0.7278	72.78%
Human Ether-a-go-go-Related Gene inhibition	-	0.7272	72.72%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	+	0.6000	60.00%
skin sensitisation	-	0.8799	87.99%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	+	0.6465	64.65%
Acute Oral Toxicity (c)	III	0.4665	46.65%
Estrogen receptor binding	-	0.4911	49.11%
Androgen receptor binding	+	0.6744	67.44%
Thyroid receptor binding	+	0.5309	53.09%
Glucocorticoid receptor binding	+	0.6691	66.91%
Aromatase binding	-	0.7673	76.73%
PPAR gamma	-	0.8071	80.71%
Honey bee toxicity	-	0.8651	86.51%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9475	94.75%

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	95.92%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.62%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.67%	97.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.83%	85.14%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.41%	100.00%
CHEMBL2581	P07339	Cathepsin D	86.07%	98.95%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	85.38%	85.11%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.92%	90.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.89%	95.56%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	82.14%	93.04%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	81.61%	96.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	81.41%	92.94%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.25%	99.23%

Plants that contains it

• Centaurea musimonum

Cross-Links

• PubChem: 162902316
• LOTUS: LTS0093854
• wikiData: Q105367931