(2S,3aS,5S)-3a-(3,7-dimethylocta-2,6-dienyl)-5-hydroxy-2-(2-hydroxypropan-2-yl)-5-methyl-7-[(2R)-2-methylbutanoyl]-2,3-dihydro-1-benzofuran-4,6-dione

Details

• Internal ID: fc157122-6f72-44b7-8d44-e3e068a81450
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Monoterpenoids > Bicyclic monoterpenoids
• IUPAC Name: (2S,3aS,5S)-3a-(3,7-dimethylocta-2,6-dienyl)-5-hydroxy-2-(2-hydroxypropan-2-yl)-5-methyl-7-[(2R)-2-methylbutanoyl]-2,3-dihydro-1-benzofuran-4,6-dione
• SMILES (Canonical): CCC(C)C(=O)C1=C2C(CC(O2)C(C)(C)O)(C(=O)C(C1=O)(C)O)CC=C(C)CCC=C(C)C
• SMILES (Isomeric): CC[C@@H](C)C(=O)C1=C2[C@](C[C@H](O2)C(C)(C)O)(C(=O)[C@](C1=O)(C)O)CC=C(C)CCC=C(C)C
• InChI: InChI=1S/C27H40O6/c1-9-18(5)21(28)20-22(29)26(8,32)24(30)27(14-13-17(4)12-10-11-16(2)3)15-19(25(6,7)31)33-23(20)27/h11,13,18-19,31-32H,9-10,12,14-15H2,1-8H3/t18-,19+,26-,27+/m1/s1
• InChI Key: DTEYYPBVTTXAMS-LZGFQUKRSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₄₀O₆
• Molecular Weight: 460.60 g/mol
• Exact Mass: 460.28248899 g/mol
• Topological Polar Surface Area (TPSA): 101.00 Ų
• XlogP: 4.60
• Atomic LogP (AlogP): 4.39
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9936	99.36%
Caco-2	+	0.5162	51.62%
Blood Brain Barrier	+	0.8250	82.50%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.8008	80.08%
OATP2B1 inhibitior	-	0.8573	85.73%
OATP1B1 inhibitior	+	0.8436	84.36%
OATP1B3 inhibitior	+	0.9279	92.79%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	+	0.5186	51.86%
BSEP inhibitior	+	0.6978	69.78%
P-glycoprotein inhibitior	+	0.6245	62.45%
P-glycoprotein substrate	-	0.5413	54.13%
CYP3A4 substrate	+	0.6390	63.90%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8708	87.08%
CYP3A4 inhibition	+	0.6384	63.84%
CYP2C9 inhibition	-	0.6638	66.38%
CYP2C19 inhibition	-	0.6996	69.96%
CYP2D6 inhibition	-	0.9160	91.60%
CYP1A2 inhibition	-	0.6048	60.48%
CYP2C8 inhibition	-	0.6722	67.22%
CYP inhibitory promiscuity	-	0.7222	72.22%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5308	53.08%
Eye corrosion	-	0.9888	98.88%
Eye irritation	-	0.9233	92.33%
Skin irritation	+	0.5866	58.66%
Skin corrosion	-	0.9129	91.29%
Ames mutagenesis	-	0.6378	63.78%
Human Ether-a-go-go-Related Gene inhibition	-	0.4131	41.31%
Micronuclear	-	0.8400	84.00%
Hepatotoxicity	+	0.5750	57.50%
skin sensitisation	-	0.7874	78.74%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	+	0.4685	46.85%
Acute Oral Toxicity (c)	III	0.3887	38.87%
Estrogen receptor binding	+	0.6587	65.87%
Androgen receptor binding	+	0.5777	57.77%
Thyroid receptor binding	+	0.6663	66.63%
Glucocorticoid receptor binding	+	0.7432	74.32%
Aromatase binding	+	0.6670	66.70%
PPAR gamma	+	0.7449	74.49%
Honey bee toxicity	-	0.8627	86.27%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9917	99.17%

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	98.66%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.25%	94.45%
CHEMBL2581	P07339	Cathepsin D	96.46%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.44%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.20%	91.11%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	94.00%	89.34%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.80%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	89.85%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.20%	89.00%
CHEMBL2413	P32246	C-C chemokine receptor type 1	87.10%	89.50%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	86.82%	83.57%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	86.19%	95.71%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	84.97%	85.30%
CHEMBL3359	P21462	Formyl peptide receptor 1	84.97%	93.56%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	84.21%	96.90%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	84.09%	96.95%
CHEMBL230	P35354	Cyclooxygenase-2	83.99%	89.63%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.98%	97.09%
CHEMBL5103	Q969S8	Histone deacetylase 10	83.90%	90.08%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.44%	99.23%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	82.55%	82.69%
CHEMBL2964	P36507	Dual specificity mitogen-activated protein kinase kinase 2	82.05%	80.00%
CHEMBL221	P23219	Cyclooxygenase-1	81.75%	90.17%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.55%	100.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.17%	100.00%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	80.89%	95.71%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	80.57%	93.00%

Plants that contains it

• Hypericum yojiroanum

Cross-Links

• PubChem: 162913817
• LOTUS: LTS0265001
• wikiData: Q104988252