(4R)-3-[(3,4-dihydroxyphenyl)methyl]-4-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-3-hydroxyhexanedioic 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	ecf48811-7d05-40b1-b44a-ad8874ed4134
Taxonomy	Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
IUPAC Name	(4R)-3-[(3,4-dihydroxyphenyl)methyl]-4-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-3-hydroxyhexanedioic acid
SMILES (Canonical)
SMILES (Isomeric)
InChI	InChI=1S/C22H22O11/c23-14-4-1-12(7-16(14)25)3-6-21(31)33-18(9-19(27)28)22(32,11-20(29)30)10-13-2-5-15(24)17(26)8-13/h1-8,18,23-26,32H,9-11H2,(H,27,28)(H,29,30)/b6-3+/t18-,22?/m1/s1
InChI Key	NIILTAHMGPDJNM-GSMBFNAYSA-N
Popularity	16 references in papers

Physical and Chemical Properties

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Molecular Formula	C₂₂H₂₂O₁₁
Molecular Weight	462.40 g/mol
Exact Mass	462.11621151 g/mol
Topological Polar Surface Area (TPSA)	202.00 Å²
XlogP	1.00
Atomic LogP (AlogP)	1.36
H-Bond Acceptor	9
H-Bond Donor	7
Rotatable Bonds	10

Synonyms

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There are no found synonyms.

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	+	0.7967	79.67%
Caco-2	-	0.9116	91.16%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.6940	69.40%
OATP2B1 inhibitior	+	0.5714	57.14%
OATP1B1 inhibitior	+	0.9206	92.06%
OATP1B3 inhibitior	+	0.9370	93.70%
MATE1 inhibitior	-	0.6600	66.00%
OCT2 inhibitior	-	0.8088	80.88%
BSEP inhibitior	+	0.9479	94.79%
P-glycoprotein inhibitior	+	0.5784	57.84%
P-glycoprotein substrate	-	0.7844	78.44%
CYP3A4 substrate	+	0.5376	53.76%
CYP2C9 substrate	-	0.5983	59.83%
CYP2D6 substrate	-	0.8633	86.33%
CYP3A4 inhibition	-	0.6990	69.90%
CYP2C9 inhibition	-	0.8983	89.83%
CYP2C19 inhibition	-	0.8963	89.63%
CYP2D6 inhibition	-	0.9238	92.38%
CYP1A2 inhibition	-	0.8929	89.29%
CYP2C8 inhibition	+	0.5000	50.00%
CYP inhibitory promiscuity	-	0.9320	93.20%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8675	86.75%
Carcinogenicity (trinary)	Non-required	0.6251	62.51%
Eye corrosion	-	0.9932	99.32%
Eye irritation	-	0.7324	73.24%
Skin irritation	-	0.7306	73.06%
Skin corrosion	-	0.9177	91.77%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8306	83.06%
Micronuclear	+	0.6218	62.18%
Hepatotoxicity	+	0.5375	53.75%
skin sensitisation	-	0.6120	61.20%
Respiratory toxicity	-	0.5556	55.56%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.7031	70.31%
Acute Oral Toxicity (c)	III	0.7999	79.99%
Estrogen receptor binding	+	0.8400	84.00%
Androgen receptor binding	+	0.7792	77.92%
Thyroid receptor binding	+	0.5375	53.75%
Glucocorticoid receptor binding	+	0.6744	67.44%
Aromatase binding	+	0.5513	55.13%
PPAR gamma	+	0.6855	68.55%
Honey bee toxicity	-	0.8050	80.50%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9946	99.46%

Targets

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Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	98.90%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.11%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.16%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.00%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	94.48%	99.17%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	92.29%	96.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.43%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	89.68%	94.73%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	89.47%	95.50%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	87.54%	99.15%
CHEMBL3194	P02766	Transthyretin	86.92%	90.71%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	84.46%	80.78%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.91%	89.00%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	82.51%	100.00%
CHEMBL221	P23219	Cyclooxygenase-1	82.06%	90.17%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	81.35%	96.95%
CHEMBL2535	P11166	Glucose transporter	80.61%	98.75%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
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