Avenanthramide B

Details

• Internal ID: 4f905d16-a39b-44da-8db5-5e36d8ef4a42
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Hydroxycinnamic acids > Avenanthramides
• IUPAC Name: 5-hydroxy-2-[[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]amino]benzoic acid
• SMILES (Canonical): COC1=C(C=CC(=C1)C=CC(=O)NC2=C(C=C(C=C2)O)C(=O)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)/C=C/C(=O)NC2=C(C=C(C=C2)O)C(=O)O)O
• InChI: InChI=1S/C17H15NO6/c1-24-15-8-10(2-6-14(15)20)3-7-16(21)18-13-5-4-11(19)9-12(13)17(22)23/h2-9,19-20H,1H3,(H,18,21)(H,22,23)/b7-3+
• InChI Key: JXFZHMCSCYADIX-XVNBXDOJSA-N
• Popularity: 10 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₁₅NO₆
• Molecular Weight: 329.30 g/mol
• Exact Mass: 329.08993720 g/mol
• Topological Polar Surface Area (TPSA): 116.00 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 2.46
• H-Bond Acceptor: 5
• H-Bond Donor: 4
• Rotatable Bonds: 5

Synonyms

• 108605-69-2
• Avenanthramide 1
• Avenanthramide 2F
• Avenanthramide BF
• F8BQ5730IL
• N-feruloyl-5-hydroxyanthranilic acid
• Benzoic acid, 5-hydroxy-2-(((2E)-3-(4-hydroxy-3-methoxyphenyl)-1-oxo-2-propen-1-yl)amino)-
• CHEBI:167489
• DTXSID50148603
• 5-hydroxy-2-[[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]amino]benzoic acid
• Benzoic acid, 5-hydroxy-2-[[(2E)-3-(4-hydroxy-3-methoxyphenyl)-1-oxo-2-propen-1-yl]amino]-
• N-(4'-hydroxy-3'-methoxy-(E)-cinnamoyl)-5-hydroxyanthranilic acid
• N-[4'-hydroxy-3'-methoxy-(E)-cinnamoyl]-5-hydroxyanthranilic acid
• 5-hydroxy-2-(((E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl)amino)benzoic acid
• RefChem:560398
• DTXCID5071094
• UNII-F8BQ5730IL
• (Z)-N-Feruloyl-5-hydroxyanthranilic acid
• 5-hydroxy-2-[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamido]benzoic acid
• 5-Hydroxy-2-(((2E)-3-(4-hydroxy-3-methoxyphenyl)-2-propenoyl)amino)benzoic acid
• (E)-5-Hydroxy-2-(3-(4-hydroxy-3-methoxyphenyl)acrylamido)benzoic acid
• orb2893539
• SCHEMBL4671925
• SCHEMBL29375351
• Avenanthramide B, analytical standard
• TN8487
• Q27277808
• N-(4'-hydroxy-3'methoxy-(e)-cinnamoyl)-5-hydroxyanthranilic acid
• 5-hydroxy-2-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)-1-oxo-2-propenyl]amino}benzoic acid
• 5-hydroxy-2-{[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]amino}benzoic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7866	78.66%
Caco-2	-	0.7257	72.57%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	+	0.6286	62.86%
Subcellular localzation	Mitochondria	0.6281	62.81%
OATP2B1 inhibitior	-	0.5764	57.64%
OATP1B1 inhibitior	+	0.9242	92.42%
OATP1B3 inhibitior	+	0.9538	95.38%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9838	98.38%
BSEP inhibitior	+	0.5600	56.00%
P-glycoprotein inhibitior	-	0.9086	90.86%
P-glycoprotein substrate	-	0.8226	82.26%
CYP3A4 substrate	-	0.5711	57.11%
CYP2C9 substrate	-	0.8008	80.08%
CYP2D6 substrate	-	0.8695	86.95%
CYP3A4 inhibition	-	0.8057	80.57%
CYP2C9 inhibition	-	0.8924	89.24%
CYP2C19 inhibition	-	0.8955	89.55%
CYP2D6 inhibition	-	0.9567	95.67%
CYP1A2 inhibition	-	0.8910	89.10%
CYP2C8 inhibition	+	0.8374	83.74%
CYP inhibitory promiscuity	-	0.7685	76.85%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.7584	75.84%
Carcinogenicity (trinary)	Non-required	0.4833	48.33%
Eye corrosion	-	0.9936	99.36%
Eye irritation	-	0.7310	73.10%
Skin irritation	-	0.8453	84.53%
Skin corrosion	-	0.9742	97.42%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7010	70.10%
Micronuclear	+	0.7000	70.00%
Hepatotoxicity	+	0.5249	52.49%
skin sensitisation	-	0.9351	93.51%
Respiratory toxicity	-	0.6778	67.78%
Reproductive toxicity	+	0.6111	61.11%
Mitochondrial toxicity	-	0.6125	61.25%
Nephrotoxicity	+	0.4931	49.31%
Acute Oral Toxicity (c)	III	0.7539	75.39%
Estrogen receptor binding	+	0.8347	83.47%
Androgen receptor binding	+	0.8155	81.55%
Thyroid receptor binding	+	0.5185	51.85%
Glucocorticoid receptor binding	+	0.7223	72.23%
Aromatase binding	+	0.5690	56.90%
PPAR gamma	+	0.7067	70.67%
Honey bee toxicity	-	0.9000	90.00%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.7400	74.00%
Fish aquatic toxicity	+	0.9772	97.72%

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	97.12%	91.11%
CHEMBL3194	P02766	Transthyretin	95.91%	90.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.09%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.21%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	92.21%	96.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.97%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.59%	99.17%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	89.90%	95.50%
CHEMBL2535	P11166	Glucose transporter	88.42%	98.75%
CHEMBL1255126	O15151	Protein Mdm4	88.20%	90.20%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.69%	94.45%
CHEMBL4208	P20618	Proteasome component C5	84.44%	90.00%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	84.17%	89.62%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.80%	99.15%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	83.78%	81.11%
CHEMBL3714130	P46095	G-protein coupled receptor 6	83.27%	97.36%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	83.11%	94.42%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.62%	89.00%
CHEMBL340	P08684	Cytochrome P450 3A4	81.12%	91.19%
CHEMBL2413	P32246	C-C chemokine receptor type 1	81.09%	89.50%

Plants that contains it

• Avena sativa

Cross-Links

• PubChem: 10087955
• LOTUS: LTS0174884
• wikiData: Q104981394