3a,7-Dihydroxy-5a,9-dimethyl-3-methylidene-4,5,6,7,8,9b-hexahydrobenzo[g][1]benzofuran-2-one

Details

• Internal ID: 56c88964-b0a9-474c-803e-2664f07363f5
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: 3a,7-dihydroxy-5a,9-dimethyl-3-methylidene-4,5,6,7,8,9b-hexahydrobenzo[g][1]benzofuran-2-one
• SMILES (Canonical): CC1=C2C3C(CCC2(CC(C1)O)C)(C(=C)C(=O)O3)O
• SMILES (Isomeric): CC1=C2C3C(CCC2(CC(C1)O)C)(C(=C)C(=O)O3)O
• InChI: InChI=1S/C15H20O4/c1-8-6-10(16)7-14(3)4-5-15(18)9(2)13(17)19-12(15)11(8)14/h10,12,16,18H,2,4-7H2,1,3H3
• InChI Key: QMDOXPAVXVTWGC-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₄
• Molecular Weight: 264.32 g/mol
• Exact Mass: 264.13615911 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 0.50
• Atomic LogP (AlogP): 1.47
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9900	99.00%
Caco-2	+	0.6605	66.05%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.6286	62.86%
Subcellular localzation	Mitochondria	0.7369	73.69%
OATP2B1 inhibitior	-	0.8522	85.22%
OATP1B1 inhibitior	+	0.8902	89.02%
OATP1B3 inhibitior	+	0.9008	90.08%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.5420	54.20%
BSEP inhibitior	-	0.9354	93.54%
P-glycoprotein inhibitior	-	0.8814	88.14%
P-glycoprotein substrate	-	0.8660	86.60%
CYP3A4 substrate	+	0.6093	60.93%
CYP2C9 substrate	-	0.8028	80.28%
CYP2D6 substrate	-	0.8494	84.94%
CYP3A4 inhibition	-	0.6339	63.39%
CYP2C9 inhibition	-	0.8973	89.73%
CYP2C19 inhibition	-	0.8566	85.66%
CYP2D6 inhibition	-	0.9380	93.80%
CYP1A2 inhibition	-	0.6261	62.61%
CYP2C8 inhibition	-	0.9115	91.15%
CYP inhibitory promiscuity	-	0.9267	92.67%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.4495	44.95%
Eye corrosion	-	0.9908	99.08%
Eye irritation	-	0.5246	52.46%
Skin irritation	+	0.6622	66.22%
Skin corrosion	-	0.8981	89.81%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6497	64.97%
Micronuclear	-	0.8100	81.00%
Hepatotoxicity	+	0.5087	50.87%
skin sensitisation	-	0.8226	82.26%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	+	0.5941	59.41%
Acute Oral Toxicity (c)	I	0.3419	34.19%
Estrogen receptor binding	-	0.4823	48.23%
Androgen receptor binding	-	0.5572	55.72%
Thyroid receptor binding	-	0.5335	53.35%
Glucocorticoid receptor binding	-	0.5545	55.45%
Aromatase binding	+	0.5608	56.08%
PPAR gamma	-	0.6198	61.98%
Honey bee toxicity	-	0.8250	82.50%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9943	99.43%

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	92.04%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.90%	95.56%
CHEMBL221	P23219	Cyclooxygenase-1	89.21%	90.17%
CHEMBL2581	P07339	Cathepsin D	87.65%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.83%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.76%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.97%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	81.74%	96.09%
CHEMBL1937	Q92769	Histone deacetylase 2	80.85%	94.75%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.73%	97.09%

Plants that contains it

• Sphaeranthus suaveolens

Cross-Links

• PubChem: 14589095
• LOTUS: LTS0158639
• wikiData: Q105223916