(3S,3aR,5S,7S,8aR,9aR)-7-hydroxy-3,3a,5,8a,9a-pentamethyl-3,5,6,7,8,9-hexahydrobenzo[f][1]benzofuran-2-one

Details

• Internal ID: 7c697d47-8271-4c37-afe6-06cd386f84ea
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: (3S,3aR,5S,7S,8aR,9aR)-7-hydroxy-3,3a,5,8a,9a-pentamethyl-3,5,6,7,8,9-hexahydrobenzo[f][1]benzofuran-2-one
• SMILES (Canonical): CC1CC(CC2(C1=CC3(C(C(=O)OC3(C2)C)C)C)C)O
• SMILES (Isomeric): C[C@H]1C[C@@H](C[C@]2(C1=C[C@@]3([C@@H](C(=O)O[C@@]3(C2)C)C)C)C)O
• InChI: InChI=1S/C17H26O3/c1-10-6-12(18)7-15(3)9-17(5)16(4,8-13(10)15)11(2)14(19)20-17/h8,10-12,18H,6-7,9H2,1-5H3/t10-,11+,12-,15+,16+,17+/m0/s1
• InChI Key: FGGHJSQRWLAAQR-WMDYZLQMSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₆O₃
• Molecular Weight: 278.40 g/mol
• Exact Mass: 278.18819469 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 2.80
• Atomic LogP (AlogP): 3.07
• H-Bond Acceptor: 3
• 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	+	0.9973	99.73%
Caco-2	+	0.8367	83.67%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	+	0.7857	78.57%
Subcellular localzation	Mitochondria	0.6086	60.86%
OATP2B1 inhibitior	-	0.8518	85.18%
OATP1B1 inhibitior	+	0.9264	92.64%
OATP1B3 inhibitior	+	0.9730	97.30%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.7305	73.05%
P-glycoprotein inhibitior	-	0.8905	89.05%
P-glycoprotein substrate	-	0.7575	75.75%
CYP3A4 substrate	+	0.6101	61.01%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8383	83.83%
CYP3A4 inhibition	-	0.7453	74.53%
CYP2C9 inhibition	-	0.9040	90.40%
CYP2C19 inhibition	-	0.8374	83.74%
CYP2D6 inhibition	-	0.9457	94.57%
CYP1A2 inhibition	-	0.6665	66.65%
CYP2C8 inhibition	-	0.8634	86.34%
CYP inhibitory promiscuity	-	0.8123	81.23%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.4223	42.23%
Eye corrosion	-	0.9921	99.21%
Eye irritation	-	0.7873	78.73%
Skin irritation	+	0.6281	62.81%
Skin corrosion	-	0.9080	90.80%
Ames mutagenesis	+	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6847	68.47%
Micronuclear	-	0.7200	72.00%
Hepatotoxicity	-	0.5382	53.82%
skin sensitisation	-	0.6307	63.07%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	+	0.5273	52.73%
Acute Oral Toxicity (c)	III	0.6246	62.46%
Estrogen receptor binding	+	0.6584	65.84%
Androgen receptor binding	+	0.6710	67.10%
Thyroid receptor binding	+	0.6642	66.42%
Glucocorticoid receptor binding	+	0.5882	58.82%
Aromatase binding	+	0.7841	78.41%
PPAR gamma	-	0.6541	65.41%
Honey bee toxicity	-	0.8652	86.52%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.5700	57.00%
Fish aquatic toxicity	+	0.9816	98.16%

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	95.11%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.34%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.34%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.50%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.86%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.46%	89.00%
CHEMBL2581	P07339	Cathepsin D	82.09%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.65%	99.23%
CHEMBL299	P17252	Protein kinase C alpha	81.42%	98.03%

Plants that contains it

• Inula racemosa

Cross-Links

• PubChem: 162937864
• LOTUS: LTS0145969
• wikiData: Q104994877