[(1S,5R,6R)-5-acetyloxy-3-(hydroxymethyl)-2-oxo-6-propan-2-ylcyclohex-3-en-1-yl] (E)-4-acetyloxy-2-methylbut-2-enoate

Details

• Internal ID: 0117afda-fd69-446a-9d92-5fefb393257c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Monoterpenoids > Menthane monoterpenoids
• IUPAC Name: [(1S,5R,6R)-5-acetyloxy-3-(hydroxymethyl)-2-oxo-6-propan-2-ylcyclohex-3-en-1-yl] (E)-4-acetyloxy-2-methylbut-2-enoate
• SMILES (Canonical): CC(C)C1C(C=C(C(=O)C1OC(=O)C(=CCOC(=O)C)C)CO)OC(=O)C
• SMILES (Isomeric): CC(C)[C@@H]1[C@@H](C=C(C(=O)[C@H]1OC(=O)/C(=C/COC(=O)C)/C)CO)OC(=O)C
• InChI: InChI=1S/C19H26O8/c1-10(2)16-15(26-13(5)22)8-14(9-20)17(23)18(16)27-19(24)11(3)6-7-25-12(4)21/h6,8,10,15-16,18,20H,7,9H2,1-5H3/b11-6+/t15-,16-,18+/m1/s1
• InChI Key: LRYKURPAEKHAKB-MSSGIYBDSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₆O₈
• Molecular Weight: 382.40 g/mol
• Exact Mass: 382.16276778 g/mol
• Topological Polar Surface Area (TPSA): 116.00 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 1.11
• H-Bond Acceptor: 8
• H-Bond Donor: 1
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9731	97.31%
Caco-2	-	0.5329	53.29%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.8742	87.42%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8907	89.07%
OATP1B3 inhibitior	+	0.9333	93.33%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.6535	65.35%
P-glycoprotein inhibitior	+	0.6174	61.74%
P-glycoprotein substrate	-	0.7616	76.16%
CYP3A4 substrate	+	0.5471	54.71%
CYP2C9 substrate	-	0.7980	79.80%
CYP2D6 substrate	-	0.9124	91.24%
CYP3A4 inhibition	-	0.9198	91.98%
CYP2C9 inhibition	-	0.7722	77.22%
CYP2C19 inhibition	-	0.7940	79.40%
CYP2D6 inhibition	-	0.7958	79.58%
CYP1A2 inhibition	-	0.8092	80.92%
CYP2C8 inhibition	-	0.8763	87.63%
CYP inhibitory promiscuity	-	0.9121	91.21%
UGT catelyzed	+	0.6362	63.62%
Carcinogenicity (binary)	-	0.6761	67.61%
Carcinogenicity (trinary)	Non-required	0.7133	71.33%
Eye corrosion	-	0.9662	96.62%
Eye irritation	-	0.8715	87.15%
Skin irritation	-	0.6773	67.73%
Skin corrosion	-	0.9622	96.22%
Ames mutagenesis	-	0.5000	50.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7915	79.15%
Micronuclear	-	0.7000	70.00%
Hepatotoxicity	+	0.6338	63.38%
skin sensitisation	+	0.4834	48.34%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.5111	51.11%
Mitochondrial toxicity	-	0.7875	78.75%
Nephrotoxicity	+	0.4728	47.28%
Acute Oral Toxicity (c)	III	0.6109	61.09%
Estrogen receptor binding	-	0.5525	55.25%
Androgen receptor binding	-	0.6381	63.81%
Thyroid receptor binding	-	0.6064	60.64%
Glucocorticoid receptor binding	+	0.6313	63.13%
Aromatase binding	-	0.7000	70.00%
PPAR gamma	-	0.5902	59.02%
Honey bee toxicity	-	0.8482	84.82%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.7800	78.00%
Fish aquatic toxicity	+	0.9459	94.59%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.49%	96.09%
CHEMBL2581	P07339	Cathepsin D	95.22%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.90%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.48%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.55%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.51%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.61%	99.17%
CHEMBL340	P08684	Cytochrome P450 3A4	82.52%	91.19%
CHEMBL3401	O75469	Pregnane X receptor	81.69%	94.73%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	80.51%	89.34%

Plants that contains it

• Sphaeranthus ukambensis

Cross-Links

• PubChem: 163188117
• LOTUS: LTS0220087
• wikiData: Q105156394