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

Details

• Internal ID: 49918dce-43ae-46a0-965c-9f716ecce5e0
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Monoterpenoids > Bicyclic monoterpenoids
• IUPAC Name: (2S,3aS)-3a-[(2E)-3,7-dimethylocta-2,6-dienyl]-6-hydroxy-2-(2-hydroxypropan-2-yl)-5-methyl-7-[(2R)-2-methylbutanoyl]-2,3-dihydro-1-benzofuran-4-one
• SMILES (Canonical): CCC(C)C(=O)C1=C2C(CC(O2)C(C)(C)O)(C(=O)C(=C1O)C)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(=C1O)C)C/C=C(\C)/CCC=C(C)C
• InChI: InChI=1S/C27H40O5/c1-9-18(5)22(28)21-23(29)19(6)24(30)27(14-13-17(4)12-10-11-16(2)3)15-20(26(7,8)31)32-25(21)27/h11,13,18,20,29,31H,9-10,12,14-15H2,1-8H3/b17-13+/t18-,20+,27-/m1/s1
• InChI Key: RAZPLVILXFNLJF-NMWAPBGFSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₄₀O₅
• Molecular Weight: 444.60 g/mol
• Exact Mass: 444.28757437 g/mol
• Topological Polar Surface Area (TPSA): 83.80 Ų
• XlogP: 5.60
• Atomic LogP (AlogP): 5.90
• H-Bond Acceptor: 5
• 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	+	0.9958	99.58%
Caco-2	+	0.6345	63.45%
Blood Brain Barrier	+	0.8500	85.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7812	78.12%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8292	82.92%
OATP1B3 inhibitior	+	0.9294	92.94%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	+	0.5186	51.86%
BSEP inhibitior	+	0.8103	81.03%
P-glycoprotein inhibitior	+	0.5914	59.14%
P-glycoprotein substrate	-	0.5390	53.90%
CYP3A4 substrate	+	0.6368	63.68%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8851	88.51%
CYP3A4 inhibition	+	0.5585	55.85%
CYP2C9 inhibition	-	0.7014	70.14%
CYP2C19 inhibition	-	0.8077	80.77%
CYP2D6 inhibition	-	0.9284	92.84%
CYP1A2 inhibition	-	0.6647	66.47%
CYP2C8 inhibition	-	0.6390	63.90%
CYP inhibitory promiscuity	-	0.7947	79.47%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5425	54.25%
Eye corrosion	-	0.9877	98.77%
Eye irritation	-	0.9088	90.88%
Skin irritation	+	0.5426	54.26%
Skin corrosion	-	0.9130	91.30%
Ames mutagenesis	-	0.6878	68.78%
Human Ether-a-go-go-Related Gene inhibition	-	0.5842	58.42%
Micronuclear	-	0.8400	84.00%
Hepatotoxicity	+	0.5625	56.25%
skin sensitisation	-	0.7608	76.08%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	-	0.5759	57.59%
Acute Oral Toxicity (c)	III	0.4130	41.30%
Estrogen receptor binding	+	0.6612	66.12%
Androgen receptor binding	+	0.6253	62.53%
Thyroid receptor binding	+	0.6383	63.83%
Glucocorticoid receptor binding	+	0.7315	73.15%
Aromatase binding	+	0.6504	65.04%
PPAR gamma	+	0.8074	80.74%
Honey bee toxicity	-	0.8588	85.88%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9905	99.05%

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	96.52%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.45%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.61%	94.45%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	94.05%	89.34%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.96%	97.25%
CHEMBL3401	O75469	Pregnane X receptor	93.69%	94.73%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.19%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.42%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.49%	99.23%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	87.61%	97.21%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	87.03%	96.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.97%	96.09%
CHEMBL236	P41143	Delta opioid receptor	86.94%	99.35%
CHEMBL3359	P21462	Formyl peptide receptor 1	86.57%	93.56%
CHEMBL5103	Q969S8	Histone deacetylase 10	85.73%	90.08%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.96%	97.09%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	84.95%	96.90%
CHEMBL2964	P36507	Dual specificity mitogen-activated protein kinase kinase 2	83.93%	80.00%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	83.70%	90.93%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.61%	95.56%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	81.52%	96.47%
CHEMBL2413	P32246	C-C chemokine receptor type 1	80.35%	89.50%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	80.17%	93.00%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	80.07%	95.71%

Plants that contains it

• Hypericum yojiroanum

Cross-Links

• PubChem: 163189237
• LOTUS: LTS0014777
• wikiData: Q105232989