(3R,3aS,5S,7R,8aR,9aR)-3,7-dihydroxy-3,5,8a-trimethyl-5,6,7,8,9,9a-hexahydro-3aH-benzo[f][1]benzofuran-2-one

Details

• Internal ID: dc84f4e1-00cb-4cf5-9433-5429c8f62610
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: (3R,3aS,5S,7R,8aR,9aR)-3,7-dihydroxy-3,5,8a-trimethyl-5,6,7,8,9,9a-hexahydro-3aH-benzo[f][1]benzofuran-2-one
• InChI: InChI=1S/C15H22O4/c1-8-4-9(16)6-14(2)7-12-11(5-10(8)14)15(3,18)13(17)19-12/h5,8-9,11-12,16,18H,4,6-7H2,1-3H3/t8-,9+,11-,12+,14+,15+/m0/s1
• InChI Key: OQZGMELLQSHWQI-SOYOYJHUSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₄
• Molecular Weight: 266.33 g/mol
• Exact Mass: 266.15180918 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 1.20
• Atomic LogP (AlogP): 1.41
• 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	+	0.9869	98.69%
Caco-2	+	0.6587	65.87%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.5921	59.21%
OATP2B1 inhibitior	-	0.8541	85.41%
OATP1B1 inhibitior	+	0.9369	93.69%
OATP1B3 inhibitior	+	0.9582	95.82%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.9056	90.56%
P-glycoprotein inhibitior	-	0.9034	90.34%
P-glycoprotein substrate	-	0.8042	80.42%
CYP3A4 substrate	+	0.5877	58.77%
CYP2C9 substrate	-	0.5973	59.73%
CYP2D6 substrate	-	0.8243	82.43%
CYP3A4 inhibition	-	0.7590	75.90%
CYP2C9 inhibition	-	0.9018	90.18%
CYP2C19 inhibition	-	0.8789	87.89%
CYP2D6 inhibition	-	0.9455	94.55%
CYP1A2 inhibition	-	0.7639	76.39%
CYP2C8 inhibition	-	0.9004	90.04%
CYP inhibitory promiscuity	-	0.8270	82.70%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Danger	0.4185	41.85%
Eye corrosion	-	0.9901	99.01%
Eye irritation	-	0.9278	92.78%
Skin irritation	+	0.5821	58.21%
Skin corrosion	-	0.9212	92.12%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.9028	90.28%
Micronuclear	-	0.6200	62.00%
Hepatotoxicity	+	0.7493	74.93%
skin sensitisation	-	0.7585	75.85%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	+	0.5857	58.57%
Acute Oral Toxicity (c)	I	0.5128	51.28%
Estrogen receptor binding	+	0.6763	67.63%
Androgen receptor binding	-	0.5000	50.00%
Thyroid receptor binding	+	0.6376	63.76%
Glucocorticoid receptor binding	+	0.7314	73.14%
Aromatase binding	-	0.4900	49.00%
PPAR gamma	-	0.6001	60.01%
Honey bee toxicity	-	0.9018	90.18%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.6013	60.13%
Fish aquatic toxicity	+	0.9600	96.00%

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	92.58%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.24%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.70%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.42%	85.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.02%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.62%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.31%	86.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.58%	100.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.63%	99.23%

Plants that contains it

• Inula helenium

Cross-Links

• PubChem: 163004189
• LOTUS: LTS0251412
• wikiData: Q105197331