apocynin (CHEBI:2781)

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CHEBI:2781 - apocynin

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ChEBI Name	apocynin

ChEBI ID	CHEBI:2781

Definition	An aromatic ketone that is 1-phenylethanone substituted by a hydroxy group at position 4 and a methoxy group at position 3.

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information	eMolecules:520664, Selleckchem:apocynin-acetovanillone, ZINC000000162515

Download	Molfile XML SDF

more structures >>

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The Resolver thinks Mol

I75 - Ideal conformer

Mrv1927 05282116503D

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Time for openFile(I75 - Ideal conformer

Mrv1927 05282116503D

22 22 0 0 0 0 999 V2000

-1.9800 2.5450 0.0010 C 0 0 0 0 0 0 0 0 0 0 0 0

3.6270 -0.6530 0.0030 C 0 0 0 0 0 0 0 0 0 0 0 0

2.7020 1.5180 0.0140 O 0 0 0 0 0 0 0 0 0 0 0 0

-2.7950 -1.5530 -0.0250 O 0 0 0 0 0 0 0 0 0 0 0 0

-0.4590 -1.9980 -0.0120 C 0 0 0 0 0 0 0 0 0 0 0 0

0.8400 -1.5410 -0.0090 C 0 0 0 0 0 0 0 0 0 0 0 0

0.0310 0.7430 -0.0030 C 0 0 0 0 0 0 0 0 0 0 0 0

-2.3060 1.1540 -0.0100 O 0 0 0 0 0 0 0 0 0 0 0 0

2.4810 0.3260 0.0050 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.5160 -1.0970 -0.0160 C 0 0 0 0 0 0 0 0 0 0 0 0

1.0970 -0.1640 -0.0040 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.2680 0.2760 -0.0110 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.3920 2.7870 -0.8850 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.8970 3.1340 0.0010 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.4000 2.7760 0.8950 H 0 0 0 0 0 0 0 0 0 0 0 0

4.5710 -0.1070 0.0110 H 0 0 0 0 0 0 0 0 0 0 0 0

3.5660 -1.2850 0.8890 H 0 0 0 0 0 0 0 0 0 0 0 0

3.5740 -1.2730 -0.8910 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.1700 -1.6880 0.8560 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.6560 -3.0600 -0.0150 H 0 0 0 0 0 0 0 0 0 0 0 0

1.6600 -2.2440 -0.0090 H 0 0 0 0 0 0 0 0 0 0 0 0

0.2240 1.8060 0.0060 H 0 0 0 0 0 0 0 0 0 0 0 0

1 8 1 0 0 0 0

1 13 1 0 0 0 0

1 14 1 0 0 0 0

1 15 1 0 0 0 0

2 9 1 0 0 0 0

2 16 1 0 0 0 0

2 17 1 0 0 0 0

2 18 1 0 0 0 0

9 3 2 0 0 0 0

10 4 1 0 0 0 0

4 19 1 0 0 0 0

6 5 2 0 0 0 0

10 5 1 0 0 0 0

5 20 1 0 0 0 0

11 6 1 0 0 0 0

6 21 1 0 0 0 0

7 11 2 0 0 0 0

7 12 1 0 0 0 0

7 22 1 0 0 0 0

8 12 1 0 0 0 0

9 11 1 0 0 0 0

12 10 2 0 0 0 0

M END): 20 ms

reading 22 atoms

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22 atoms created

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Wikipedia	License
Apocynin, also known as acetovanillone, is a natural organic compound structurally related to vanillin. It has been isolated from a variety of plant sources and is being studied for its variety of pharmacological properties.
Read full article at Wikipedia

Formula

C9H10O3

Net Charge

Average Mass

166.176

Monoisotopic Mass

166.06299

InChI

InChI=1S/C9H10O3/c1-6(10)7-3-4-8(11)9(5-7)12-2/h3-5,11H,1-2H3

InChIKey

DFYRUELUNQRZTB-UHFFFAOYSA-N

SMILES

COC1=C(O)C=CC(=C1)C(C)=O

Metabolite of Species	Details
Paeonia rockii subsp. rockii (NCBI:txid459179)	Found in root (BTO:0001188). Isolated from chloroform soluble extract of air-dried and powdered roots See: PubMed
Cordyceps sinensis (NCBI:txid72228)	Found in mycelium (BTO:0001436). Ethanolic extract of dried mycelia See: PubMed

Roles Classification
Biological Role(s):	non-narcotic analgesic A drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors. EC 1.6.3.1. [NAD(P)H oxidase (H2O2-forming)] inhibitor An EC 1.6.3.* (oxidoreductase acting on NADH or NADPH with oxygen as acceptor) inhibitor that interferes with the action of NAD(P)H oxidase (H2O2-forming), EC 1.6.3.1. plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.

Application(s):	non-narcotic analgesic A drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors. non-steroidal anti-inflammatory drug An anti-inflammatory drug that is not a steroid. In addition to anti-inflammatory actions, non-steroidal anti-inflammatory drugs have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. antirheumatic drug A drug used to treat rheumatoid arthritis. peripheral nervous system drug A drug that acts principally at one or more sites within the peripheral neuroeffector systems, the autonomic system, and motor nerve-skeletal system.

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	apocynin (CHEBI:2781) has role antirheumatic drug (CHEBI:35842) apocynin (CHEBI:2781) has role EC 1.6.3.1. [NAD(P)H oxidase (H₂O₂-forming)] inhibitor (CHEBI:50423) apocynin (CHEBI:2781) has role non-narcotic analgesic (CHEBI:35481) apocynin (CHEBI:2781) has role non-steroidal anti-inflammatory drug (CHEBI:35475) apocynin (CHEBI:2781) has role peripheral nervous system drug (CHEBI:49110) apocynin (CHEBI:2781) has role plant metabolite (CHEBI:76924) apocynin (CHEBI:2781) is a acetophenones (CHEBI:22187) apocynin (CHEBI:2781) is a aromatic ketone (CHEBI:76224) apocynin (CHEBI:2781) is a methyl ketone (CHEBI:51867)

IUPAC Name

1-(4-hydroxy-3-methoxyphenyl)ethan-1-one

Synonyms	Sources
1-(4-Hydroxy-3-methoxyphenyl)ethanone	ChEBI
4'-hydroxy-3'-methoxyacetophenone	ChemIDplus
4-Acetyl-2-methoxyphenol	ChemIDplus
4-Hydroxy-3-methoxyphenyl methyl ketone	ChemIDplus
Acetoguaiacon	ChEBI
Acetoguaiacone	ChemIDplus
Acetovanillone	KEGG COMPOUND
Apocynin	KEGG COMPOUND

Manual Xrefs	Databases
Apocynin	Wikipedia
C00002689	KNApSAcK
C11380	KEGG COMPOUND
I75	PDBeChem
View more database links

Registry Numbers	Types	Sources
498-02-2	CAS Registry Number	KEGG COMPOUND
498-02-2	CAS Registry Number	ChemIDplus
498-02-2	CAS Registry Number	NIST Chemistry WebBook
637373	Reaxys Registry Number	Reaxys

Citations

Majumdar S, Lukk T, Solbiati JO, Bauer S, Nair SK, Cronan JE, Gerlt JA (2014)
Roles of small laccases from Streptomyces in lignin degradation.
Biochemistry 53, 4047-4058 [PubMed:24870309]
[show Abstract]

Yang ML, Kuo PC, Hwang TL, Wu TS (2011)
Anti-inflammatory principles from Cordyceps sinensis.
Journal of natural products 74, 1996-2000 [PubMed:21848266]
[show Abstract]

Mencherini T, Picerno P, Festa M, Russo P, Capasso A, Aquino R (2011)
Triterpenoid constituents from the roots of Paeonia rockii ssp. rockii.
Journal of natural products 74, 2116-2121 [PubMed:21954959]
[show Abstract]

Last Modified

28 May 2021

CHEBI:2781 - apocynin

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