(3aR,5aR,6R,9aS,9bS)-6-hydroxy-5a,9-dimethyl-3-methylidene-3a,4,5,6,9a,9b-hexahydrobenzo[g][1]benzofuran-2,7-dione

Details

• Internal ID: f87ea8e6-f2b4-4607-8521-21c11e962ff4
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: (3aR,5aR,6R,9aS,9bS)-6-hydroxy-5a,9-dimethyl-3-methylidene-3a,4,5,6,9a,9b-hexahydrobenzo[g][1]benzofuran-2,7-dione
• SMILES (Canonical): CC1=CC(=O)C(C2(C1C3C(CC2)C(=C)C(=O)O3)C)O
• SMILES (Isomeric): CC1=CC(=O)[C@@H]([C@]2([C@H]1[C@@H]3[C@H](CC2)C(=C)C(=O)O3)C)O
• InChI: InChI=1S/C15H18O4/c1-7-6-10(16)13(17)15(3)5-4-9-8(2)14(18)19-12(9)11(7)15/h6,9,11-13,17H,2,4-5H2,1,3H3/t9-,11-,12+,13+,15-/m1/s1
• InChI Key: OUPKJRAFJRTDMN-GOGITYCRSA-N
• Popularity: 1 reference 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: 1.20
• Atomic LogP (AlogP): 1.39
• 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	+	0.9824	98.24%
Caco-2	+	0.6307	63.07%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	+	0.6429	64.29%
Subcellular localzation	Mitochondria	0.7435	74.35%
OATP2B1 inhibitior	-	0.8576	85.76%
OATP1B1 inhibitior	+	0.8266	82.66%
OATP1B3 inhibitior	+	0.8425	84.25%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.5874	58.74%
BSEP inhibitior	-	0.9871	98.71%
P-glycoprotein inhibitior	-	0.9243	92.43%
P-glycoprotein substrate	-	0.8233	82.33%
CYP3A4 substrate	+	0.6479	64.79%
CYP2C9 substrate	-	0.7829	78.29%
CYP2D6 substrate	-	0.8959	89.59%
CYP3A4 inhibition	-	0.6127	61.27%
CYP2C9 inhibition	-	0.8457	84.57%
CYP2C19 inhibition	-	0.8636	86.36%
CYP2D6 inhibition	-	0.8861	88.61%
CYP1A2 inhibition	+	0.5598	55.98%
CYP2C8 inhibition	-	0.7641	76.41%
CYP inhibitory promiscuity	-	0.8213	82.13%
UGT catelyzed	-	0.5638	56.38%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5044	50.44%
Eye corrosion	-	0.9855	98.55%
Eye irritation	-	0.8020	80.20%
Skin irritation	+	0.5498	54.98%
Skin corrosion	-	0.7755	77.55%
Ames mutagenesis	-	0.8000	80.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5727	57.27%
Micronuclear	-	0.7000	70.00%
Hepatotoxicity	+	0.8283	82.83%
skin sensitisation	-	0.6597	65.97%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	-	0.6416	64.16%
Acute Oral Toxicity (c)	III	0.5642	56.42%
Estrogen receptor binding	+	0.6925	69.25%
Androgen receptor binding	+	0.6854	68.54%
Thyroid receptor binding	-	0.5224	52.24%
Glucocorticoid receptor binding	-	0.5000	50.00%
Aromatase binding	-	0.7667	76.67%
PPAR gamma	-	0.5725	57.25%
Honey bee toxicity	-	0.8372	83.72%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9939	99.39%

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	94.83%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.59%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.89%	99.23%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.63%	100.00%
CHEMBL221	P23219	Cyclooxygenase-1	86.96%	90.17%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.88%	97.25%
CHEMBL4530	P00488	Coagulation factor XIII	85.63%	96.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.21%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.31%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.77%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.10%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.50%	86.33%

Plants that contains it

• Chloranthus henryi

Cross-Links

• PubChem: 162911591
• LOTUS: LTS0027539
• wikiData: Q105200338