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

Details

• Internal ID: d14f0e86-0e29-480c-9ce4-6c81b2ae4160
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: 3a,9a-dihydroxy-5a-methyl-3,9-dimethylidene-4,5,6,7,8,9b-hexahydrobenzo[g][1]benzofuran-2-one
• SMILES (Canonical): CC12CCCC(=C)C1(C3C(CC2)(C(=C)C(=O)O3)O)O
• SMILES (Isomeric): CC12CCCC(=C)C1(C3C(CC2)(C(=C)C(=O)O3)O)O
• InChI: InChI=1S/C15H20O4/c1-9-5-4-6-13(3)7-8-14(17)10(2)11(16)19-12(14)15(9,13)18/h12,17-18H,1-2,4-8H2,3H3
• InChI Key: MWZZGEICVXRRSD-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: 1.00
• 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	+	0.9758	97.58%
Caco-2	+	0.7023	70.23%
Blood Brain Barrier	-	0.5973	59.73%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.6455	64.55%
OATP2B1 inhibitior	-	0.8537	85.37%
OATP1B1 inhibitior	+	0.8959	89.59%
OATP1B3 inhibitior	+	0.9024	90.24%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.6071	60.71%
BSEP inhibitior	-	0.9868	98.68%
P-glycoprotein inhibitior	-	0.9357	93.57%
P-glycoprotein substrate	-	0.9450	94.50%
CYP3A4 substrate	+	0.5552	55.52%
CYP2C9 substrate	-	0.5997	59.97%
CYP2D6 substrate	-	0.8580	85.80%
CYP3A4 inhibition	-	0.7813	78.13%
CYP2C9 inhibition	-	0.9042	90.42%
CYP2C19 inhibition	-	0.8210	82.10%
CYP2D6 inhibition	-	0.9402	94.02%
CYP1A2 inhibition	-	0.6577	65.77%
CYP2C8 inhibition	-	0.9169	91.69%
CYP inhibitory promiscuity	-	0.9107	91.07%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.4893	48.93%
Eye corrosion	-	0.9897	98.97%
Eye irritation	+	0.5960	59.60%
Skin irritation	+	0.5965	59.65%
Skin corrosion	-	0.8904	89.04%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7338	73.38%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	+	0.5898	58.98%
skin sensitisation	-	0.8109	81.09%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	-	0.5947	59.47%
Acute Oral Toxicity (c)	IV	0.3249	32.49%
Estrogen receptor binding	-	0.4927	49.27%
Androgen receptor binding	+	0.5690	56.90%
Thyroid receptor binding	-	0.6432	64.32%
Glucocorticoid receptor binding	+	0.5810	58.10%
Aromatase binding	+	0.5832	58.32%
PPAR gamma	-	0.5769	57.69%
Honey bee toxicity	-	0.9274	92.74%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.9904	99.04%

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	95.30%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.99%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.78%	97.25%
CHEMBL230	P35354	Cyclooxygenase-2	90.24%	89.63%
CHEMBL2581	P07339	Cathepsin D	85.84%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.31%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.23%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.21%	100.00%

Plants that contains it

• Sphaeranthus indicus

Cross-Links

• PubChem: 85447409
• LOTUS: LTS0132684
• wikiData: Q105173932