(4aR,5S,8aR)-5-hydroxy-3,5,8a-trimethyl-4a,6,7,9-tetrahydrobenzo[f][1]benzofuran-4,8-dione

Details

• Internal ID: f66373ed-1f5c-45be-bf61-871b6209df98
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids
• IUPAC Name: (4aR,5S,8aR)-5-hydroxy-3,5,8a-trimethyl-4a,6,7,9-tetrahydrobenzo[f][1]benzofuran-4,8-dione
• SMILES (Canonical): CC1=COC2=C1C(=O)C3C(CCC(=O)C3(C2)C)(C)O
• SMILES (Isomeric): CC1=COC2=C1C(=O)[C@H]3[C@@](CCC(=O)[C@@]3(C2)C)(C)O
• InChI: InChI=1S/C15H18O4/c1-8-7-19-9-6-14(2)10(16)4-5-15(3,18)13(14)12(17)11(8)9/h7,13,18H,4-6H2,1-3H3/t13-,14+,15+/m1/s1
• InChI Key: JSTVAWBAYPLCTK-ILXRZTDVSA-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): 67.50 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): 2.06
• 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	+	0.9943	99.43%
Caco-2	+	0.5369	53.69%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7661	76.61%
OATP2B1 inhibitior	-	0.8528	85.28%
OATP1B1 inhibitior	+	0.9212	92.12%
OATP1B3 inhibitior	+	0.8867	88.67%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.6321	63.21%
BSEP inhibitior	-	0.8924	89.24%
P-glycoprotein inhibitior	-	0.9210	92.10%
P-glycoprotein substrate	-	0.8839	88.39%
CYP3A4 substrate	+	0.6005	60.05%
CYP2C9 substrate	-	0.7977	79.77%
CYP2D6 substrate	-	0.8431	84.31%
CYP3A4 inhibition	-	0.7264	72.64%
CYP2C9 inhibition	-	0.7831	78.31%
CYP2C19 inhibition	-	0.8550	85.50%
CYP2D6 inhibition	-	0.9631	96.31%
CYP1A2 inhibition	-	0.5419	54.19%
CYP2C8 inhibition	-	0.7782	77.82%
CYP inhibitory promiscuity	-	0.9596	95.96%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8800	88.00%
Carcinogenicity (trinary)	Non-required	0.5869	58.69%
Eye corrosion	-	0.9934	99.34%
Eye irritation	-	0.6412	64.12%
Skin irritation	-	0.5270	52.70%
Skin corrosion	-	0.8756	87.56%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7918	79.18%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	+	0.5450	54.50%
skin sensitisation	-	0.8947	89.47%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	-	0.6294	62.94%
Acute Oral Toxicity (c)	II	0.3589	35.89%
Estrogen receptor binding	-	0.6794	67.94%
Androgen receptor binding	+	0.6482	64.82%
Thyroid receptor binding	-	0.5919	59.19%
Glucocorticoid receptor binding	-	0.5255	52.55%
Aromatase binding	-	0.5636	56.36%
PPAR gamma	+	0.6848	68.48%
Honey bee toxicity	-	0.9407	94.07%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.9878	98.78%

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	93.59%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.21%	95.56%
CHEMBL2581	P07339	Cathepsin D	90.67%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.11%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.88%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.33%	100.00%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	83.02%	96.38%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.61%	97.09%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	82.48%	93.03%
CHEMBL2996	Q05655	Protein kinase C delta	82.34%	97.79%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.31%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.23%	86.33%

Plants that contains it

• Chloranthus multistachys
• Chloranthus serratus

Cross-Links

• PubChem: 102279301
• LOTUS: LTS0274157
• wikiData: Q105134565