(2E)-2-[(3,4-dihydroxyphenyl)methylidene]-4-methoxy-4-oxobutanoic acid

Details

• Internal ID: 2c825f53-3106-4033-9ef6-1e35c31ec8bb
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Hydroxycinnamic acids
• IUPAC Name: (2E)-2-[(3,4-dihydroxyphenyl)methylidene]-4-methoxy-4-oxobutanoic acid
• SMILES (Canonical): COC(=O)CC(=CC1=CC(=C(C=C1)O)O)C(=O)O
• SMILES (Isomeric): COC(=O)C/C(=C\C1=CC(=C(C=C1)O)O)/C(=O)O
• InChI: InChI=1S/C12H12O6/c1-18-11(15)6-8(12(16)17)4-7-2-3-9(13)10(14)5-7/h2-5,13-14H,6H2,1H3,(H,16,17)/b8-4+
• InChI Key: GRXZRSFMMJBTSZ-XBXARRHUSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₂H₁₂O₆
• Molecular Weight: 252.22 g/mol
• Exact Mass: 252.06338810 g/mol
• Topological Polar Surface Area (TPSA): 104.00 Ų
• XlogP: 1.00
• Atomic LogP (AlogP): 1.13
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9742	97.42%
Caco-2	-	0.5805	58.05%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.7952	79.52%
OATP2B1 inhibitior	-	0.8616	86.16%
OATP1B1 inhibitior	+	0.9418	94.18%
OATP1B3 inhibitior	+	0.9507	95.07%
MATE1 inhibitior	-	0.6200	62.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.8176	81.76%
P-glycoprotein inhibitior	-	0.9780	97.80%
P-glycoprotein substrate	-	0.9421	94.21%
CYP3A4 substrate	-	0.6356	63.56%
CYP2C9 substrate	-	0.5872	58.72%
CYP2D6 substrate	-	0.8647	86.47%
CYP3A4 inhibition	-	0.9592	95.92%
CYP2C9 inhibition	-	0.6459	64.59%
CYP2C19 inhibition	-	0.7396	73.96%
CYP2D6 inhibition	-	0.8478	84.78%
CYP1A2 inhibition	-	0.6173	61.73%
CYP2C8 inhibition	-	0.6697	66.97%
CYP inhibitory promiscuity	-	0.8977	89.77%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.7804	78.04%
Carcinogenicity (trinary)	Non-required	0.6971	69.71%
Eye corrosion	-	0.9606	96.06%
Eye irritation	+	0.9484	94.84%
Skin irritation	-	0.6038	60.38%
Skin corrosion	-	0.9157	91.57%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7585	75.85%
Micronuclear	+	0.6318	63.18%
Hepatotoxicity	-	0.6125	61.25%
skin sensitisation	-	0.5430	54.30%
Respiratory toxicity	-	0.6333	63.33%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	-	0.7250	72.50%
Nephrotoxicity	-	0.7465	74.65%
Acute Oral Toxicity (c)	III	0.5230	52.30%
Estrogen receptor binding	-	0.5705	57.05%
Androgen receptor binding	+	0.7630	76.30%
Thyroid receptor binding	-	0.5865	58.65%
Glucocorticoid receptor binding	+	0.6460	64.60%
Aromatase binding	-	0.6670	66.70%
PPAR gamma	-	0.5080	50.80%
Honey bee toxicity	-	0.9626	96.26%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.7000	70.00%
Fish aquatic toxicity	+	0.9837	98.37%

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	98.68%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	96.88%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.54%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.33%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.83%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.11%	86.33%
CHEMBL4208	P20618	Proteasome component C5	88.19%	90.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.26%	94.45%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.95%	96.00%
CHEMBL3401	O75469	Pregnane X receptor	85.29%	94.73%
CHEMBL2581	P07339	Cathepsin D	83.01%	98.95%
CHEMBL3194	P02766	Transthyretin	82.88%	90.71%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	82.27%	99.15%

Plants that contains it

• Dalbergia sissoo

Cross-Links

• PubChem: 57390741
• NPASS: NPC247412
• LOTUS: LTS0062950
• wikiData: Q105016833