2,3-bis[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-2,3-dihydroxybutanedioic acid

Details

• Internal ID: b135f686-d07f-4da4-a6bf-8e3ae0432747
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives
• IUPAC Name: 2,3-bis[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-2,3-dihydroxybutanedioic acid
• SMILES (Canonical): C1=CC(=C(C=C1C=CC(=O)C(C(=O)O)(C(C(=O)C=CC2=CC(=C(C=C2)O)O)(C(=O)O)O)O)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1/C=C/C(=O)C(O)(C(O)(C(=O)O)C(=O)/C=C/C2=CC(=C(C=C2)O)O)C(=O)O)O)O
• InChI: InChI=1S/C22H18O12/c23-13-5-1-11(9-15(13)25)3-7-17(27)21(33,19(29)30)22(34,20(31)32)18(28)8-4-12-2-6-14(24)16(26)10-12/h1-10,23-26,33-34H,(H,29,30)(H,31,32)/b7-3+,8-4+
• InChI Key: IHFPHNHRXPJFAJ-FCXRPNKRSA-N
• Popularity: 52 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₁₈O₁₂
• Molecular Weight: 474.40 g/mol
• Exact Mass: 474.07982601 g/mol
• Topological Polar Surface Area (TPSA): 230.00 Ų
• XlogP: 0.30
• Atomic LogP (AlogP): 0.01
• H-Bond Acceptor: 10
• H-Bond Donor: 8
• Rotatable Bonds: 9

Synonyms

• SCHEMBL23854648

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9051	90.51%
Caco-2	-	0.9050	90.50%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.7096	70.96%
OATP2B1 inhibitior	-	0.5633	56.33%
OATP1B1 inhibitior	+	0.9603	96.03%
OATP1B3 inhibitior	+	0.9475	94.75%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8088	80.88%
BSEP inhibitior	+	0.7669	76.69%
P-glycoprotein inhibitior	-	0.6301	63.01%
P-glycoprotein substrate	-	0.9765	97.65%
CYP3A4 substrate	-	0.6516	65.16%
CYP2C9 substrate	-	0.6038	60.38%
CYP2D6 substrate	-	0.8659	86.59%
CYP3A4 inhibition	-	0.7117	71.17%
CYP2C9 inhibition	-	0.6810	68.10%
CYP2C19 inhibition	-	0.9394	93.94%
CYP2D6 inhibition	-	0.9409	94.09%
CYP1A2 inhibition	-	0.8642	86.42%
CYP2C8 inhibition	-	0.7853	78.53%
CYP inhibitory promiscuity	-	0.8773	87.73%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.7797	77.97%
Carcinogenicity (trinary)	Non-required	0.6266	62.66%
Eye corrosion	-	0.9928	99.28%
Eye irritation	-	0.6180	61.80%
Skin irritation	+	0.5000	50.00%
Skin corrosion	-	0.8372	83.72%
Ames mutagenesis	-	0.8300	83.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5557	55.57%
Micronuclear	+	0.7400	74.00%
Hepatotoxicity	-	0.5351	53.51%
skin sensitisation	+	0.6764	67.64%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	-	0.5444	54.44%
Mitochondrial toxicity	-	0.5375	53.75%
Nephrotoxicity	-	0.8422	84.22%
Acute Oral Toxicity (c)	III	0.7010	70.10%
Estrogen receptor binding	+	0.6592	65.92%
Androgen receptor binding	+	0.8539	85.39%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.6062	60.62%
Aromatase binding	+	0.5341	53.41%
PPAR gamma	+	0.7298	72.98%
Honey bee toxicity	-	0.9333	93.33%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.7200	72.00%
Fish aquatic toxicity	+	0.9951	99.51%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	98.09%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.80%	91.11%
CHEMBL3194	P02766	Transthyretin	92.66%	90.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.75%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.02%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.73%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	86.50%	99.15%
CHEMBL2581	P07339	Cathepsin D	84.75%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	83.06%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.60%	99.17%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	81.34%	80.78%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.93%	96.00%

Plants that contains it

• Cichorium intybus
• Isodon rubescens

Cross-Links

• PubChem: 23131559
• LOTUS: LTS0254897
• wikiData: Q105113003