3-(3,4-Dihydroxyphenyl)-2-[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]propanoic 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	d96e32f3-007d-4899-9cdc-eedf53fdce18
Taxonomy	Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
IUPAC Name	3-(3,4-dihydroxyphenyl)-2-[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]propanoic acid
SMILES (Canonical)	C1=CC(=C(C=C1CC(C(=O)O)OC(=O)C=CC2=CC(=C(C=C2)O)O)O)O
SMILES (Isomeric)	C1=CC(=C(C=C1CC(C(=O)O)OC(=O)C=CC2=CC(=C(C=C2)O)O)O)O
InChI	InChI=1S/C18H16O8/c19-12-4-1-10(7-14(12)21)3-6-17(23)26-16(18(24)25)9-11-2-5-13(20)15(22)8-11/h1-8,16,19-22H,9H2,(H,24,25)
InChI Key	DOUMFZQKYFQNTF-UHFFFAOYSA-N
Popularity	1,611 references in papers

Physical and Chemical Properties

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Molecular Formula	C₁₈H₁₆O₈
Molecular Weight	360.30 g/mol
Exact Mass	360.08451746 g/mol
Topological Polar Surface Area (TPSA)	145.00 Å²
XlogP	2.40
Atomic LogP (AlogP)	1.76
H-Bond Acceptor	7
H-Bond Donor	5
Rotatable Bonds	6

Synonyms

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Spectrum_001930

SpecPlus_000702

Spectrum3_001995

(R)-(+)-Rosmarinic Acid

KBioSS_002472

DivK1c_006798

KBio1_001742

KBio2_002465

KBio2_005033

KBio2_007601

There are more than 10 synonyms. If you wish to see them all click here.

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	+	0.8756	87.56%
Caco-2	-	0.9373	93.73%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.8306	83.06%
OATP2B1 inhibitior	-	0.5749	57.49%
OATP1B1 inhibitior	+	0.9413	94.13%
OATP1B3 inhibitior	+	0.9479	94.79%
MATE1 inhibitior	+	0.5200	52.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.6882	68.82%
P-glycoprotein inhibitior	-	0.8529	85.29%
P-glycoprotein substrate	-	0.9340	93.40%
CYP3A4 substrate	-	0.5802	58.02%
CYP2C9 substrate	-	0.5979	59.79%
CYP2D6 substrate	-	0.8612	86.12%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	-	0.8754	87.54%
CYP2C19 inhibition	-	0.9026	90.26%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.6279	62.79%
CYP2C8 inhibition	+	0.5112	51.12%
CYP inhibitory promiscuity	-	0.8300	83.00%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8141	81.41%
Carcinogenicity (trinary)	Non-required	0.6152	61.52%
Eye corrosion	-	0.9895	98.95%
Eye irritation	+	0.5264	52.64%
Skin irritation	-	0.7211	72.11%
Skin corrosion	-	0.9416	94.16%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4806	48.06%
Micronuclear	+	0.7159	71.59%
Hepatotoxicity	-	0.6250	62.50%
skin sensitisation	-	0.5655	56.55%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	-	0.8974	89.74%
Acute Oral Toxicity (c)	III	0.7720	77.20%
Estrogen receptor binding	+	0.8228	82.28%
Androgen receptor binding	+	0.8585	85.85%
Thyroid receptor binding	+	0.5265	52.65%
Glucocorticoid receptor binding	+	0.6399	63.99%
Aromatase binding	-	0.5927	59.27%
PPAR gamma	+	0.5798	57.98%
Honey bee toxicity	-	0.7466	74.66%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9952	99.52%

Targets

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Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL2392	P06746	DNA polymerase beta	223.9 nM	Potency	via Super-PRED
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	631 nM	Potency	via Super-PRED
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	25.1 nM	Potency	via Super-PRED
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	891.3 nM 223.9 nM	Potency Potency	via Super-PRED via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	98.69%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.94%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	93.33%	96.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.20%	94.45%
CHEMBL3060	Q9Y345	Glycine transporter 2	93.01%	99.17%
CHEMBL3194	P02766	Transthyretin	92.66%	90.71%
CHEMBL4040	P28482	MAP kinase ERK2	92.41%	83.82%
CHEMBL2581	P07339	Cathepsin D	91.23%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.96%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.95%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	88.66%	90.17%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	88.08%	99.15%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	87.53%	95.50%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	87.43%	91.71%
CHEMBL1255126	O15151	Protein Mdm4	81.75%	90.20%

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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