(1S,3R,4R,5R)-3,4-Bis[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-1,5-dihydroxycyclohexane-1-carboxylic acid

Details

Physical and Chemical Properties

Synonyms

2D Structure

3D Structure

ADMET Properties

Targets (proven and/or predicted)

Plants that contains it

Cross-Links

Details

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Internal ID	636b2f7a-6060-492d-ada5-ceb88156e748
Taxonomy	Organic oxygen compounds > Organooxygen compounds > Alcohols and polyols > Cyclitols and derivatives > Quinic acids and derivatives
IUPAC Name	(1S,3R,4R,5R)-3,4-bis[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-1,5-dihydroxycyclohexane-1-carboxylic acid
SMILES (Canonical)	C1C(C(C(CC1(C(=O)O)O)OC(=O)C=CC2=CC(=C(C=C2)O)O)OC(=O)C=CC3=CC(=C(C=C3)O)O)O
SMILES (Isomeric)	C1[C@H]([C@H]([C@@H](C[C@@]1(C(=O)O)O)OC(=O)C=CC2=CC(=C(C=C2)O)O)OC(=O)C=CC3=CC(=C(C=C3)O)O)O
InChI	InChI=1S/C25H24O12/c26-15-5-1-13(9-17(15)28)3-7-21(31)36-20-12-25(35,24(33)34)11-19(30)23(20)37-22(32)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-30,35H,11-12H2,(H,33,34)/t19-,20-,23-,25+/m1/s1
InChI Key	UFCLZKMFXSILNL-BBLPPJRLSA-N
Popularity	39 references in papers

Physical and Chemical Properties

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Molecular Formula	C₂₅H₂₄O₁₂
Molecular Weight	516.40 g/mol
Exact Mass	516.12677620 g/mol
Topological Polar Surface Area (TPSA)	211.00 Å²
XlogP	1.50
Atomic LogP (AlogP)	1.03
H-Bond Acceptor	11
H-Bond Donor	7
Rotatable Bonds	7

Synonyms

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14534-61-3

(1S,3R,4R,5R)-3,4-Bis[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-1,5-dihydroxycyclohexane-1-carboxylic acid

102851-07-0

SCHEMBL18317178

DTXSID101025840

DTXSID901106525

AKOS030230742

CID 153946

rel-(1R,3S,4S,5S)-3,4-Bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]-1,5-dihydroxycyclohexanecarboxylic acid

2D Structure

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3D Structure

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ADMET Properties (via admetSAR 2)

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Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8460	84.60%
Caco-2	-	0.9181	91.81%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.6770	67.70%
OATP2B1 inhibitior	-	0.7111	71.11%
OATP1B1 inhibitior	+	0.9543	95.43%
OATP1B3 inhibitior	+	0.9424	94.24%
MATE1 inhibitior	-	0.7400	74.00%
OCT2 inhibitior	-	0.8338	83.38%
BSEP inhibitior	+	0.8783	87.83%
P-glycoprotein inhibitior	+	0.6172	61.72%
P-glycoprotein substrate	-	0.8199	81.99%
CYP3A4 substrate	+	0.5534	55.34%
CYP2C9 substrate	-	0.5941	59.41%
CYP2D6 substrate	-	0.8566	85.66%
CYP3A4 inhibition	-	0.8744	87.44%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9069	90.69%
CYP2D6 inhibition	-	0.9388	93.88%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	-	0.6804	68.04%
CYP inhibitory promiscuity	-	0.9686	96.86%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.8864	88.64%
Carcinogenicity (trinary)	Non-required	0.6128	61.28%
Eye corrosion	-	0.9932	99.32%
Eye irritation	-	0.8935	89.35%
Skin irritation	-	0.6985	69.85%
Skin corrosion	-	0.9034	90.34%
Ames mutagenesis	-	0.9200	92.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7429	74.29%
Micronuclear	+	0.5800	58.00%
Hepatotoxicity	+	0.7125	71.25%
skin sensitisation	-	0.6266	62.66%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.8939	89.39%
Acute Oral Toxicity (c)	III	0.7775	77.75%
Estrogen receptor binding	+	0.7453	74.53%
Androgen receptor binding	+	0.7561	75.61%
Thyroid receptor binding	+	0.5602	56.02%
Glucocorticoid receptor binding	+	0.6464	64.64%
Aromatase binding	-	0.5999	59.99%
PPAR gamma	+	0.6222	62.22%
Honey bee toxicity	-	0.8332	83.32%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6055	60.55%
Fish aquatic toxicity	+	0.9928	99.28%

Targets

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Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL5983	O60218	Aldo-keto reductase family 1 member B10	240 nM	IC50	via Super-PRED
CHEMBL1900	P15121	Aldose reductase	78 nM	IC50	via Super-PRED
CHEMBL2487	P05067	Beta amyloid A4 protein	100 nM	IC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.69%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	94.32%	91.49%
CHEMBL221	P23219	Cyclooxygenase-1	93.56%	90.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.96%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.27%	95.56%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	92.17%	94.62%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.01%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.22%	86.33%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	91.06%	94.08%
CHEMBL3194	P02766	Transthyretin	90.55%	90.71%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	89.93%	99.15%
CHEMBL4208	P20618	Proteasome component C5	89.85%	90.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.60%	89.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	88.69%	96.00%
CHEMBL2179	P04062	Beta-glucocerebrosidase	88.00%	85.31%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.18%	97.09%
CHEMBL245	P20309	Muscarinic acetylcholine receptor M3	83.95%	97.53%
CHEMBL340	P08684	Cytochrome P450 3A4	83.66%	91.19%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.42%	95.50%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	81.79%	94.23%
CHEMBL211	P08172	Muscarinic acetylcholine receptor M2	80.31%	94.97%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.

Astragalus bisulcatus

Baccharoides lasiopus

Bhesa nitidissima

Bidens pilosa

Boenninghausenia albiflora

Bothriocline ripensis

Brachyglottis bidwillii