3a-hydroxy-5a,9-dimethyl-3-methylidene-5,6,7,9b-tetrahydro-4H-benzo[g][1]benzofuran-2,8-dione

Details

• Internal ID: 3adcca66-09ab-40ca-811e-40fe69757c18
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: 3a-hydroxy-5a,9-dimethyl-3-methylidene-5,6,7,9b-tetrahydro-4H-benzo[g][1]benzofuran-2,8-dione
• SMILES (Canonical): CC1=C2C3C(CCC2(CCC1=O)C)(C(=C)C(=O)O3)O
• SMILES (Isomeric): CC1=C2C3C(CCC2(CCC1=O)C)(C(=C)C(=O)O3)O
• InChI: InChI=1S/C15H18O4/c1-8-10(16)4-5-14(3)6-7-15(18)9(2)13(17)19-12(15)11(8)14/h12,18H,2,4-7H2,1,3H3
• InChI Key: JJQNORUJCLAZCD-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₈O₄
• Molecular Weight: 262.30 g/mol
• Exact Mass: 262.12050905 g/mol
• Topological Polar Surface Area (TPSA): 63.60 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): 1.68
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9936	99.36%
Caco-2	+	0.7640	76.40%
Blood Brain Barrier	+	0.8500	85.00%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.7703	77.03%
OATP2B1 inhibitior	-	0.8507	85.07%
OATP1B1 inhibitior	+	0.9110	91.10%
OATP1B3 inhibitior	+	0.8780	87.80%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	+	0.5348	53.48%
BSEP inhibitior	-	0.9542	95.42%
P-glycoprotein inhibitior	-	0.8781	87.81%
P-glycoprotein substrate	-	0.9320	93.20%
CYP3A4 substrate	+	0.5783	57.83%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9007	90.07%
CYP3A4 inhibition	-	0.5994	59.94%
CYP2C9 inhibition	-	0.8980	89.80%
CYP2C19 inhibition	-	0.9143	91.43%
CYP2D6 inhibition	-	0.9485	94.85%
CYP1A2 inhibition	-	0.7158	71.58%
CYP2C8 inhibition	-	0.9280	92.80%
CYP inhibitory promiscuity	-	0.9715	97.15%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5077	50.77%
Eye corrosion	-	0.9884	98.84%
Eye irritation	+	0.7225	72.25%
Skin irritation	+	0.6407	64.07%
Skin corrosion	-	0.8665	86.65%
Ames mutagenesis	-	0.6782	67.82%
Human Ether-a-go-go-Related Gene inhibition	-	0.6082	60.82%
Micronuclear	-	0.7100	71.00%
Hepatotoxicity	+	0.5171	51.71%
skin sensitisation	-	0.8149	81.49%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.9750	97.50%
Nephrotoxicity	-	0.5774	57.74%
Acute Oral Toxicity (c)	IV	0.4401	44.01%
Estrogen receptor binding	-	0.5889	58.89%
Androgen receptor binding	+	0.5269	52.69%
Thyroid receptor binding	-	0.5875	58.75%
Glucocorticoid receptor binding	-	0.5930	59.30%
Aromatase binding	-	0.6542	65.42%
PPAR gamma	-	0.5243	52.43%
Honey bee toxicity	-	0.8717	87.17%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.9953	99.53%

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	93.91%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.20%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.93%	99.23%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.55%	100.00%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	82.31%	93.04%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.88%	86.33%
CHEMBL230	P35354	Cyclooxygenase-2	81.40%	89.63%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.82%	89.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	80.62%	97.25%

Plants that contains it

• Sphaeranthus indicus

Cross-Links

• PubChem: 77175428
• LOTUS: LTS0156597
• wikiData: Q105129824