Avenanthramide C

Details

• Internal ID: 74d4a95c-5a76-4f20-9bd7-4247f83821d6
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Hydroxycinnamic acids > Avenanthramides
• IUPAC Name: 2-[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]amino]-5-hydroxybenzoic acid
• InChI: InChI=1S/C16H13NO6/c18-10-3-4-12(11(8-10)16(22)23)17-15(21)6-2-9-1-5-13(19)14(20)7-9/h1-8,18-20H,(H,17,21)(H,22,23)/b6-2+
• InChI Key: IDUUXROOZBOOPH-QHHAFSJGSA-N
• Popularity: 100 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₃NO₆
• Molecular Weight: 315.28 g/mol
• Exact Mass: 315.07428713 g/mol
• Topological Polar Surface Area (TPSA): 127.00 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 2.15
• H-Bond Acceptor: 5
• H-Bond Donor: 5
• Rotatable Bonds: 4

Synonyms

• 116764-15-9
• Avenanthramide BC
• Benzoic acid, 2-(((2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl)amino)-5-hydroxy-
• 2-[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]amino]-5-hydroxybenzoic acid
• DTXSID60151507
• 2-[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enamido]-5-hydroxybenzoic acid
• 2-(((E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl)amino)-5-hydroxybenzoic acid
• 2-((2E)-3-(3,4-dihydroxyphenyl)prop-2-enamido)-5-hydroxybenzoic acid
• Benzoic acid, 2-[[(2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl]amino]-5-hydroxy-
• RefChem:560399
• DTXCID6073998
• Avenanthramide 2C
• Avenanthramide
• 5FRF61BOYU
• (E)-2-(3-(3,4-Dihydroxyphenyl)acrylamido)-5-hydroxybenzoic acid
• N-(3',4'-dihydroxycinnamoyl)-5-hydroxyanthranilic acid
• AVENANTHRAMIDEC
• UNII-5FRF61BOYU
• Avenanthramide-c
• 2-[[(2E)-3-(3,4-Dihydroxyphenyl)-1-oxo-2-propen-1-yl]amino]-5-hydroxybenzoic Acid; Avenanthramide 2c; Avenanthramide Bc
• orb2802060
• SCHEMBL4199523
• SCHEMBL29403984
• CHEBI:185306
• Avenanthramide C, analytical standard
• 2-[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]amino]-5-hydroxy-benzoic Acid
• FA59483
• CS-0086258
• C22372
• G63315
• N-(3,4-Dihydroxycinnamoyl)-5-hydroxyanthranilic acid
• Q27262004
• N-(3,4-dihydroxy)-(e)-cinnamoyl-5-hydroxyanthranilic acid
• 2-[(2E)-3-(3,4-Dihydroxyphenyl)prop-2-enamido]-5-hydroxybenzoate
• 2-{[(2E)-3-(3,4-dihydroxyphenyl)-1-hydroxyprop-2-en-1-ylidene]amino}-5-hydroxybenzoic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6693	66.93%
Caco-2	-	0.5867	58.67%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.5784	57.84%
OATP2B1 inhibitior	-	0.7063	70.63%
OATP1B1 inhibitior	+	0.9386	93.86%
OATP1B3 inhibitior	+	0.9494	94.94%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9088	90.88%
BSEP inhibitior	-	0.5000	50.00%
P-glycoprotein inhibitior	-	0.9528	95.28%
P-glycoprotein substrate	-	0.8923	89.23%
CYP3A4 substrate	-	0.6520	65.20%
CYP2C9 substrate	-	0.6068	60.68%
CYP2D6 substrate	-	0.8796	87.96%
CYP3A4 inhibition	-	0.7770	77.70%
CYP2C9 inhibition	-	0.9222	92.22%
CYP2C19 inhibition	-	0.9149	91.49%
CYP2D6 inhibition	-	0.9553	95.53%
CYP1A2 inhibition	-	0.8444	84.44%
CYP2C8 inhibition	+	0.6705	67.05%
CYP inhibitory promiscuity	-	0.9004	90.04%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.7884	78.84%
Carcinogenicity (trinary)	Non-required	0.6257	62.57%
Eye corrosion	-	0.9954	99.54%
Eye irritation	+	0.5462	54.62%
Skin irritation	-	0.7605	76.05%
Skin corrosion	-	0.9755	97.55%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7597	75.97%
Micronuclear	+	0.7400	74.00%
Hepatotoxicity	-	0.5125	51.25%
skin sensitisation	-	0.7641	76.41%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	+	0.4849	48.49%
Acute Oral Toxicity (c)	III	0.5727	57.27%
Estrogen receptor binding	+	0.8781	87.81%
Androgen receptor binding	+	0.9154	91.54%
Thyroid receptor binding	-	0.5173	51.73%
Glucocorticoid receptor binding	+	0.8000	80.00%
Aromatase binding	+	0.6296	62.96%
PPAR gamma	+	0.7919	79.19%
Honey bee toxicity	-	0.9009	90.09%
Biodegradation	-	0.9750	97.50%
Crustacea aquatic toxicity	-	0.8000	80.00%
Fish aquatic toxicity	+	0.9887	98.87%

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	97.98%	91.11%
CHEMBL3194	P02766	Transthyretin	95.56%	90.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.84%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.88%	86.33%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	86.69%	81.11%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	86.46%	99.15%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	85.40%	95.50%
CHEMBL1929	P47989	Xanthine dehydrogenase	85.22%	96.12%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.07%	99.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.10%	89.00%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	83.50%	94.42%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.40%	96.00%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	81.37%	94.62%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.15%	94.45%
CHEMBL4208	P20618	Proteasome component C5	80.46%	90.00%
CHEMBL2964	P36507	Dual specificity mitogen-activated protein kinase kinase 2	80.43%	80.00%

Plants that contains it

• Avena sativa

Cross-Links

• PubChem: 11723200
• LOTUS: LTS0081548
• wikiData: Q27262004