(4S,4aR,5S,8S,8aS)-4,8-dihydroxy-3,4a,5-trimethyl-4,5,6,7,8,8a-hexahydrobenzo[f][1]benzofuran-9-one

Details

• Internal ID: 875449dd-3ec0-40ce-af19-a2f47ba36682
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids
• IUPAC Name: (4S,4aR,5S,8S,8aS)-4,8-dihydroxy-3,4a,5-trimethyl-4,5,6,7,8,8a-hexahydrobenzo[f][1]benzofuran-9-one
• SMILES (Canonical): CC1CCC(C2C1(C(C3=C(C2=O)OC=C3C)O)C)O
• SMILES (Isomeric): C[C@H]1CC[C@@H]([C@@H]2[C@@]1([C@@H](C3=C(C2=O)OC=C3C)O)C)O
• InChI: InChI=1S/C15H20O4/c1-7-6-19-13-10(7)14(18)15(3)8(2)4-5-9(16)11(15)12(13)17/h6,8-9,11,14,16,18H,4-5H2,1-3H3/t8-,9-,11-,14+,15+/m0/s1
• InChI Key: IINQVPBERPRLGN-IOJWWUGISA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₄
• Molecular Weight: 264.32 g/mol
• Exact Mass: 264.13615911 g/mol
• Topological Polar Surface Area (TPSA): 70.70 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 2.23
• 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	+	0.9897	98.97%
Caco-2	+	0.5000	50.00%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.6436	64.36%
OATP2B1 inhibitior	-	0.8544	85.44%
OATP1B1 inhibitior	+	0.9262	92.62%
OATP1B3 inhibitior	+	0.9237	92.37%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.7571	75.71%
BSEP inhibitior	-	0.9292	92.92%
P-glycoprotein inhibitior	-	0.9081	90.81%
P-glycoprotein substrate	-	0.8529	85.29%
CYP3A4 substrate	+	0.5846	58.46%
CYP2C9 substrate	-	0.7735	77.35%
CYP2D6 substrate	-	0.8054	80.54%
CYP3A4 inhibition	-	0.7340	73.40%
CYP2C9 inhibition	-	0.8018	80.18%
CYP2C19 inhibition	-	0.8222	82.22%
CYP2D6 inhibition	-	0.9274	92.74%
CYP1A2 inhibition	+	0.7555	75.55%
CYP2C8 inhibition	-	0.8456	84.56%
CYP inhibitory promiscuity	-	0.8567	85.67%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.4631	46.31%
Eye corrosion	-	0.9929	99.29%
Eye irritation	-	0.9795	97.95%
Skin irritation	-	0.5181	51.81%
Skin corrosion	-	0.8384	83.84%
Ames mutagenesis	-	0.6564	65.64%
Human Ether-a-go-go-Related Gene inhibition	-	0.7242	72.42%
Micronuclear	-	0.8100	81.00%
Hepatotoxicity	-	0.5448	54.48%
skin sensitisation	-	0.8229	82.29%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	-	0.7609	76.09%
Acute Oral Toxicity (c)	III	0.5148	51.48%
Estrogen receptor binding	+	0.5553	55.53%
Androgen receptor binding	+	0.6060	60.60%
Thyroid receptor binding	+	0.6039	60.39%
Glucocorticoid receptor binding	-	0.5883	58.83%
Aromatase binding	-	0.7058	70.58%
PPAR gamma	+	0.6101	61.01%
Honey bee toxicity	-	0.9385	93.85%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5600	56.00%
Fish aquatic toxicity	+	0.9020	90.20%

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	95.61%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.32%	95.56%
CHEMBL2581	P07339	Cathepsin D	90.95%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.19%	97.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.37%	99.23%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.64%	90.71%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	83.90%	97.33%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.46%	86.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.99%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.83%	89.00%

Plants that contains it

• Senecio rosmarinifolius

Cross-Links

• PubChem: 15627965
• LOTUS: LTS0051456
• wikiData: Q105113644