(2,3,4,5,6-Pentahydroxycyclohexyl) 3-(4-hydroxyphenyl)prop-2-enoate

Details

• Internal ID: 21a73a05-b6f4-44ae-ba19-56ab03f8c189
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Hydroxycinnamic acid esters > Coumaric acid esters
• IUPAC Name: (2,3,4,5,6-pentahydroxycyclohexyl) 3-(4-hydroxyphenyl)prop-2-enoate
• SMILES (Canonical): C1=CC(=CC=C1C=CC(=O)OC2C(C(C(C(C2O)O)O)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1C=CC(=O)OC2C(C(C(C(C2O)O)O)O)O)O
• InChI: InChI=1S/C15H18O8/c16-8-4-1-7(2-5-8)3-6-9(17)23-15-13(21)11(19)10(18)12(20)14(15)22/h1-6,10-16,18-22H
• InChI Key: BLAKLJDVFMLDKM-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₈O₈
• Molecular Weight: 326.30 g/mol
• Exact Mass: 326.10016753 g/mol
• Topological Polar Surface Area (TPSA): 148.00 Ų
• XlogP: -1.40
• Atomic LogP (AlogP): -1.86
• H-Bond Acceptor: 8
• H-Bond Donor: 6
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9233	92.33%
Caco-2	-	0.7709	77.09%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.6736	67.36%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9309	93.09%
OATP1B3 inhibitior	+	0.9601	96.01%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	-	0.9588	95.88%
BSEP inhibitior	-	0.9043	90.43%
P-glycoprotein inhibitior	-	0.9238	92.38%
P-glycoprotein substrate	-	0.9586	95.86%
CYP3A4 substrate	-	0.5567	55.67%
CYP2C9 substrate	-	0.8000	80.00%
CYP2D6 substrate	-	0.8489	84.89%
CYP3A4 inhibition	-	0.6586	65.86%
CYP2C9 inhibition	-	0.7716	77.16%
CYP2C19 inhibition	-	0.9167	91.67%
CYP2D6 inhibition	-	0.9694	96.94%
CYP1A2 inhibition	-	0.6370	63.70%
CYP2C8 inhibition	+	0.5153	51.53%
CYP inhibitory promiscuity	-	0.5875	58.75%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8166	81.66%
Carcinogenicity (trinary)	Non-required	0.5742	57.42%
Eye corrosion	-	0.9803	98.03%
Eye irritation	-	0.7439	74.39%
Skin irritation	+	0.5533	55.33%
Skin corrosion	-	0.9417	94.17%
Ames mutagenesis	-	0.8200	82.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7251	72.51%
Micronuclear	+	0.7300	73.00%
Hepatotoxicity	-	0.7003	70.03%
skin sensitisation	+	0.7376	73.76%
Respiratory toxicity	-	0.6444	64.44%
Reproductive toxicity	-	0.5333	53.33%
Mitochondrial toxicity	-	0.7250	72.50%
Nephrotoxicity	-	0.7304	73.04%
Acute Oral Toxicity (c)	III	0.7432	74.32%
Estrogen receptor binding	-	0.7116	71.16%
Androgen receptor binding	-	0.5937	59.37%
Thyroid receptor binding	-	0.5507	55.07%
Glucocorticoid receptor binding	-	0.5087	50.87%
Aromatase binding	-	0.6872	68.72%
PPAR gamma	-	0.5128	51.28%
Honey bee toxicity	-	0.7853	78.53%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6355	63.55%
Fish aquatic toxicity	+	0.9830	98.30%

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	95.96%	91.11%
CHEMBL3194	P02766	Transthyretin	91.91%	90.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.70%	95.56%
CHEMBL4040	P28482	MAP kinase ERK2	88.77%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.33%	96.09%
CHEMBL245	P20309	Muscarinic acetylcholine receptor M3	86.16%	97.53%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.55%	96.00%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	85.37%	89.67%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.20%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.18%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.47%	99.17%
CHEMBL1951	P21397	Monoamine oxidase A	82.09%	91.49%

Plants that contains it

• Taxus baccata
• Taxus mairei

Cross-Links

• PubChem: 76060023
• LOTUS: LTS0275281
• wikiData: Q104937865