(6beta,8betaOH)-6,8-Dihydroxy-7(11)-eremophilen-12,8-olide

Details

• Internal ID: 8fb30439-eb75-42b3-b2cf-c345d78e7eb9
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: 4,9a-dihydroxy-3,4a,5-trimethyl-5,6,7,8,8a,9-hexahydro-4H-benzo[f][1]benzofuran-2-one
• SMILES (Canonical): CC1CCCC2C1(C(C3=C(C(=O)OC3(C2)O)C)O)C
• SMILES (Isomeric): CC1CCCC2C1(C(C3=C(C(=O)OC3(C2)O)C)O)C
• InChI: InChI=1S/C15H22O4/c1-8-5-4-6-10-7-15(18)11(9(2)13(17)19-15)12(16)14(8,10)3/h8,10,12,16,18H,4-7H2,1-3H3
• InChI Key: HOZOKRDCQVUMIA-UHFFFAOYSA-N
• Popularity: 4 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): 66.80 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 1.76
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

• 6beta,8beta-Dihydroxyeremophilenolide
• 6beta,8beta-Dihydroxyeremophil-7(11)-en-12,8alpha-olide
• CHEBI:174497
• 4,9a-dihydroxy-3,4a,5-trimethyl-5,6,7,8,8a,9-hexahydro-4H-benzo[][1]benzouran-2-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9836	98.36%
Caco-2	+	0.8611	86.11%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.6857	68.57%
Subcellular localzation	Mitochondria	0.6190	61.90%
OATP2B1 inhibitior	-	0.8547	85.47%
OATP1B1 inhibitior	+	0.9289	92.89%
OATP1B3 inhibitior	+	0.9572	95.72%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.5000	50.00%
BSEP inhibitior	-	0.8165	81.65%
P-glycoprotein inhibitior	-	0.9252	92.52%
P-glycoprotein substrate	-	0.8744	87.44%
CYP3A4 substrate	+	0.5902	59.02%
CYP2C9 substrate	-	0.7943	79.43%
CYP2D6 substrate	-	0.8686	86.86%
CYP3A4 inhibition	-	0.6327	63.27%
CYP2C9 inhibition	-	0.9154	91.54%
CYP2C19 inhibition	-	0.9353	93.53%
CYP2D6 inhibition	-	0.9489	94.89%
CYP1A2 inhibition	-	0.6099	60.99%
CYP2C8 inhibition	-	0.8667	86.67%
CYP inhibitory promiscuity	-	0.8696	86.96%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.4304	43.04%
Eye corrosion	-	0.9920	99.20%
Eye irritation	-	0.9341	93.41%
Skin irritation	+	0.7052	70.52%
Skin corrosion	-	0.9076	90.76%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6261	62.61%
Micronuclear	-	0.8200	82.00%
Hepatotoxicity	+	0.5524	55.24%
skin sensitisation	-	0.8135	81.35%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	+	0.6011	60.11%
Acute Oral Toxicity (c)	I	0.4947	49.47%
Estrogen receptor binding	-	0.5309	53.09%
Androgen receptor binding	-	0.5156	51.56%
Thyroid receptor binding	+	0.6504	65.04%
Glucocorticoid receptor binding	+	0.5674	56.74%
Aromatase binding	-	0.6415	64.15%
PPAR gamma	-	0.5709	57.09%
Honey bee toxicity	-	0.9242	92.42%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.6000	60.00%
Fish aquatic toxicity	+	0.9869	98.69%

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	96.00%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.87%	91.11%
CHEMBL2581	P07339	Cathepsin D	89.25%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.94%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.26%	97.09%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	84.65%	93.03%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.19%	100.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.72%	97.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.16%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.50%	89.00%

Plants that contains it

• Ligularia fauriei
• Ligularia fischeri
• Ligularia lamarum
• Ligularia muliensis
• Ligularia virgaurea
• Petasites japonicus

Cross-Links

• PubChem: 78173026
• LOTUS: LTS0035553
• wikiData: Q105031601