6-(1-hydroxy-3-oxobutyl)-7-methyl-3-methylidene-4,5,6,7,8,8a-hexahydro-3aH-cyclohepta[b]furan-2-one

Details

• Internal ID: 5743b7a8-f646-42eb-8be2-ca2d8762a9f1
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Xanthanolides
• IUPAC Name: 6-(1-hydroxy-3-oxobutyl)-7-methyl-3-methylidene-4,5,6,7,8,8a-hexahydro-3aH-cyclohepta[b]furan-2-one
• SMILES (Canonical): CC1CC2C(CCC1C(CC(=O)C)O)C(=C)C(=O)O2
• SMILES (Isomeric): CC1CC2C(CCC1C(CC(=O)C)O)C(=C)C(=O)O2
• InChI: InChI=1S/C15H22O4/c1-8-6-14-12(10(3)15(18)19-14)5-4-11(8)13(17)7-9(2)16/h8,11-14,17H,3-7H2,1-2H3
• InChI Key: ZZURGMOHXZITJV-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₄
• Molecular Weight: 266.33 g/mol
• Exact Mass: 266.15180918 g/mol
• Topological Polar Surface Area (TPSA): 63.60 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 1.86
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9790	97.90%
Caco-2	+	0.6355	63.55%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.6542	65.42%
OATP2B1 inhibitior	-	0.8541	85.41%
OATP1B1 inhibitior	+	0.9089	90.89%
OATP1B3 inhibitior	+	0.9246	92.46%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7820	78.20%
BSEP inhibitior	-	0.8977	89.77%
P-glycoprotein inhibitior	-	0.8285	82.85%
P-glycoprotein substrate	-	0.7419	74.19%
CYP3A4 substrate	+	0.5415	54.15%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8706	87.06%
CYP3A4 inhibition	-	0.5875	58.75%
CYP2C9 inhibition	-	0.8558	85.58%
CYP2C19 inhibition	-	0.8139	81.39%
CYP2D6 inhibition	-	0.9401	94.01%
CYP1A2 inhibition	-	0.5514	55.14%
CYP2C8 inhibition	-	0.8347	83.47%
CYP inhibitory promiscuity	-	0.9516	95.16%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6689	66.89%
Eye corrosion	-	0.9785	97.85%
Eye irritation	-	0.5500	55.00%
Skin irritation	-	0.5193	51.93%
Skin corrosion	-	0.9108	91.08%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5835	58.35%
Micronuclear	-	0.8500	85.00%
Hepatotoxicity	+	0.7681	76.81%
skin sensitisation	-	0.8054	80.54%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	+	0.6446	64.46%
Acute Oral Toxicity (c)	II	0.5180	51.80%
Estrogen receptor binding	-	0.5573	55.73%
Androgen receptor binding	+	0.5311	53.11%
Thyroid receptor binding	-	0.5675	56.75%
Glucocorticoid receptor binding	+	0.6484	64.84%
Aromatase binding	-	0.8047	80.47%
PPAR gamma	-	0.7621	76.21%
Honey bee toxicity	-	0.9008	90.08%
Biodegradation	-	0.5000	50.00%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.9919	99.19%

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	97.75%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.98%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.44%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.79%	91.11%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	87.64%	94.80%
CHEMBL2581	P07339	Cathepsin D	87.38%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.46%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.79%	95.56%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.81%	95.89%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.26%	99.23%

Plants that contains it

• Dittrichia graveolens

Cross-Links

• PubChem: 162993680
• LOTUS: LTS0246389
• wikiData: Q105387094