(3R,3aS,5aR,8R,9R,9aR,9bR)-8,9-dihydroxy-3,5a,9-trimethyl-3a,4,5,6,7,8,9a,9b-octahydro-3H-benzo[g][1]benzofuran-2-one

Details

• Internal ID: e7e95ec5-4392-49e6-bf9e-cf32e8db162a
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: (3R,3aS,5aR,8R,9R,9aR,9bR)-8,9-dihydroxy-3,5a,9-trimethyl-3a,4,5,6,7,8,9a,9b-octahydro-3H-benzo[g][1]benzofuran-2-one
• SMILES (Canonical): CC1C2CCC3(CCC(C(C3C2OC1=O)(C)O)O)C
• SMILES (Isomeric): C[C@@H]1[C@@H]2CC[C@@]3(CC[C@H]([C@]([C@H]3[C@@H]2OC1=O)(C)O)O)C
• InChI: InChI=1S/C15H24O4/c1-8-9-4-6-14(2)7-5-10(16)15(3,18)12(14)11(9)19-13(8)17/h8-12,16,18H,4-7H2,1-3H3/t8-,9+,10-,11-,12+,14-,15+/m1/s1
• InChI Key: YNTYCWJZUUWXLK-CBIBUMFVSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₄O₄
• Molecular Weight: 268.35 g/mol
• Exact Mass: 268.16745924 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 1.49
• 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	+	0.9566	95.66%
Caco-2	-	0.5485	54.85%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.6905	69.05%
OATP2B1 inhibitior	-	0.8527	85.27%
OATP1B1 inhibitior	+	0.9361	93.61%
OATP1B3 inhibitior	+	0.9037	90.37%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7571	75.71%
BSEP inhibitior	-	0.9300	93.00%
P-glycoprotein inhibitior	-	0.9224	92.24%
P-glycoprotein substrate	-	0.8143	81.43%
CYP3A4 substrate	+	0.5895	58.95%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8471	84.71%
CYP3A4 inhibition	-	0.7221	72.21%
CYP2C9 inhibition	-	0.9018	90.18%
CYP2C19 inhibition	-	0.8080	80.80%
CYP2D6 inhibition	-	0.9709	97.09%
CYP1A2 inhibition	-	0.6394	63.94%
CYP2C8 inhibition	-	0.9558	95.58%
CYP inhibitory promiscuity	-	0.9849	98.49%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5749	57.49%
Eye corrosion	-	0.9923	99.23%
Eye irritation	-	0.9636	96.36%
Skin irritation	+	0.6380	63.80%
Skin corrosion	-	0.8621	86.21%
Ames mutagenesis	-	0.7500	75.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7244	72.44%
Micronuclear	-	0.9000	90.00%
Hepatotoxicity	+	0.7074	70.74%
skin sensitisation	-	0.8757	87.57%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.9500	95.00%
Nephrotoxicity	+	0.5681	56.81%
Acute Oral Toxicity (c)	III	0.3218	32.18%
Estrogen receptor binding	+	0.7179	71.79%
Androgen receptor binding	+	0.5642	56.42%
Thyroid receptor binding	+	0.6495	64.95%
Glucocorticoid receptor binding	+	0.7018	70.18%
Aromatase binding	-	0.6329	63.29%
PPAR gamma	-	0.7466	74.66%
Honey bee toxicity	-	0.8488	84.88%
Biodegradation	-	0.5500	55.00%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.9620	96.20%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.55%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.67%	97.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.50%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.43%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.26%	100.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.58%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.40%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.15%	99.23%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	82.06%	96.77%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.02%	94.45%
CHEMBL4072	P07858	Cathepsin B	80.98%	93.67%

Plants that contains it

• Ferula sinaica

Cross-Links

• PubChem: 12016126
• LOTUS: LTS0019632
• wikiData: Q105351108