methyl (3R,4S,5R)-4-hydroxy-3,5-bis[[(E)-3-methylpent-2-enoyl]oxy]cyclohexene-1-carboxylate

Details

• Internal ID: 2f10edd5-348b-469a-b309-fa47ab38ef83
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Tricarboxylic acids and derivatives
• IUPAC Name: methyl (3R,4S,5R)-4-hydroxy-3,5-bis[[(E)-3-methylpent-2-enoyl]oxy]cyclohexene-1-carboxylate
• InChI: InChI=1S/C20H28O7/c1-6-12(3)8-17(21)26-15-10-14(20(24)25-5)11-16(19(15)23)27-18(22)9-13(4)7-2/h8-10,15-16,19,23H,6-7,11H2,1-5H3/b12-8+,13-9+/t15-,16-,19-/m1/s1
• InChI Key: DNOICGYKMBYMBW-VVIKSDSVSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₈O₇
• Molecular Weight: 380.40 g/mol
• Exact Mass: 380.18350323 g/mol
• Topological Polar Surface Area (TPSA): 99.10 Ų
• XlogP: 3.50
• Atomic LogP (AlogP): 2.39
• H-Bond Acceptor: 7
• 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	+	0.9802	98.02%
Caco-2	+	0.5673	56.73%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.7935	79.35%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9194	91.94%
OATP1B3 inhibitior	+	0.9446	94.46%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.7535	75.35%
P-glycoprotein inhibitior	+	0.7798	77.98%
P-glycoprotein substrate	-	0.5661	56.61%
CYP3A4 substrate	+	0.5765	57.65%
CYP2C9 substrate	+	0.6079	60.79%
CYP2D6 substrate	-	0.8926	89.26%
CYP3A4 inhibition	-	0.9022	90.22%
CYP2C9 inhibition	-	0.9125	91.25%
CYP2C19 inhibition	-	0.8340	83.40%
CYP2D6 inhibition	-	0.9004	90.04%
CYP1A2 inhibition	-	0.9454	94.54%
CYP2C8 inhibition	-	0.6882	68.82%
CYP inhibitory promiscuity	-	0.9231	92.31%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.7745	77.45%
Carcinogenicity (trinary)	Non-required	0.6122	61.22%
Eye corrosion	-	0.9718	97.18%
Eye irritation	-	0.8550	85.50%
Skin irritation	-	0.7839	78.39%
Skin corrosion	-	0.9759	97.59%
Ames mutagenesis	-	0.6754	67.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.5525	55.25%
Micronuclear	-	0.5700	57.00%
Hepatotoxicity	+	0.5734	57.34%
skin sensitisation	-	0.6218	62.18%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.6111	61.11%
Mitochondrial toxicity	-	0.7875	78.75%
Nephrotoxicity	-	0.6673	66.73%
Acute Oral Toxicity (c)	III	0.5182	51.82%
Estrogen receptor binding	+	0.6446	64.46%
Androgen receptor binding	-	0.5971	59.71%
Thyroid receptor binding	+	0.6204	62.04%
Glucocorticoid receptor binding	+	0.7059	70.59%
Aromatase binding	-	0.6406	64.06%
PPAR gamma	-	0.7162	71.62%
Honey bee toxicity	-	0.8102	81.02%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.9330	93.30%

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	99.04%	96.09%
CHEMBL2581	P07339	Cathepsin D	95.55%	98.95%
CHEMBL4040	P28482	MAP kinase ERK2	94.11%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.61%	91.11%
CHEMBL221	P23219	Cyclooxygenase-1	88.63%	90.17%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.05%	99.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.85%	94.45%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	82.92%	94.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.27%	96.00%

Plants that contains it

• Senecio squalidus

Cross-Links

• PubChem: 14034006
• LOTUS: LTS0028002
• wikiData: Q104985660