8a-Hydroxy-3,4a-dimethyl-4-(2-methylbut-2-enoyloxy)-4,5,6,7,8,9-hexahydrobenzo[f][1]benzofuran-5-carboxylic acid

Details

• Internal ID: b21d6096-616f-41e5-afe8-bd7a11b03b51
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids
• IUPAC Name: 8a-hydroxy-3,4a-dimethyl-4-(2-methylbut-2-enoyloxy)-4,5,6,7,8,9-hexahydrobenzo[f][1]benzofuran-5-carboxylic acid
• SMILES (Canonical): CC=C(C)C(=O)OC1C2=C(CC3(C1(C(CCC3)C(=O)O)C)O)OC=C2C
• SMILES (Isomeric): CC=C(C)C(=O)OC1C2=C(CC3(C1(C(CCC3)C(=O)O)C)O)OC=C2C
• InChI: InChI=1S/C20H26O6/c1-5-11(2)18(23)26-16-15-12(3)10-25-14(15)9-20(24)8-6-7-13(17(21)22)19(16,20)4/h5,10,13,16,24H,6-9H2,1-4H3,(H,21,22)
• InChI Key: XYVWVOQDJAKFEB-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₆O₆
• Molecular Weight: 362.40 g/mol
• Exact Mass: 362.17293854 g/mol
• Topological Polar Surface Area (TPSA): 97.00 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 3.32
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9915	99.15%
Caco-2	+	0.6624	66.24%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.8263	82.63%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8768	87.68%
OATP1B3 inhibitior	+	0.8344	83.44%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.7571	75.71%
BSEP inhibitior	+	0.7234	72.34%
P-glycoprotein inhibitior	-	0.7564	75.64%
P-glycoprotein substrate	-	0.8038	80.38%
CYP3A4 substrate	+	0.6497	64.97%
CYP2C9 substrate	-	0.7979	79.79%
CYP2D6 substrate	-	0.9074	90.74%
CYP3A4 inhibition	-	0.6224	62.24%
CYP2C9 inhibition	-	0.7695	76.95%
CYP2C19 inhibition	-	0.7957	79.57%
CYP2D6 inhibition	-	0.9255	92.55%
CYP1A2 inhibition	+	0.6559	65.59%
CYP2C8 inhibition	-	0.6079	60.79%
CYP inhibitory promiscuity	-	0.8171	81.71%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.5156	51.56%
Eye corrosion	-	0.9928	99.28%
Eye irritation	-	0.9213	92.13%
Skin irritation	-	0.5740	57.40%
Skin corrosion	-	0.9324	93.24%
Ames mutagenesis	-	0.6370	63.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.4037	40.37%
Micronuclear	-	0.6300	63.00%
Hepatotoxicity	+	0.6166	61.66%
skin sensitisation	-	0.8177	81.77%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.9875	98.75%
Nephrotoxicity	+	0.4658	46.58%
Acute Oral Toxicity (c)	I	0.4035	40.35%
Estrogen receptor binding	+	0.6980	69.80%
Androgen receptor binding	+	0.6553	65.53%
Thyroid receptor binding	+	0.5487	54.87%
Glucocorticoid receptor binding	+	0.6759	67.59%
Aromatase binding	+	0.6635	66.35%
PPAR gamma	+	0.7115	71.15%
Honey bee toxicity	-	0.7972	79.72%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9963	99.63%

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	96.04%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.41%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.21%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.10%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.37%	97.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.84%	92.94%
CHEMBL3359	P21462	Formyl peptide receptor 1	83.63%	93.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.16%	99.23%
CHEMBL5028	O14672	ADAM10	80.33%	97.50%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.26%	100.00%

Plants that contains it

• Ligularia thyrsoidea

Cross-Links

• PubChem: 163081379
• LOTUS: LTS0270372
• wikiData: Q105344698