menadione (CHEBI:28869)

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CHEBI:28869 - menadione

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ChEBI Name	menadione

ChEBI ID	CHEBI:28869

Definition	A member of the class of 1,4-naphthoquinones that is 1,4-naphthoquinone which is substituted at position 2 by a methyl group. It is used as a nutritional supplement and for the treatment of hypoprothrombinemia.

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

Secondary ChEBI IDs	CHEBI:46306, CHEBI:6747, CHEBI:27304

Supplier Information	ZINC000001532902

Download	Molfile XML SDF

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21 22 0 0 0 0 999 V2000

0.5614 1.8131 -1.0401 C 0 0 0 0 0 0 0 0 0 0 0 0

2.2747 -0.4028 -0.8135 C 0 0 0 0 0 0 0 0 0 0 0 0

2.6967 0.7462 -1.5015 C 0 0 0 0 0 0 0 0 0 0 0 0

1.8412 1.8537 -1.6151 C 0 0 0 0 0 0 0 0 0 0 0 0

0.9891 -0.4628 -0.2275 C 0 0 0 0 0 0 0 0 0 0 0 0

0.1166 0.6642 -0.3423 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.7081 -1.6070 1.0135 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.1560 0.5871 0.2456 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.9183 1.5452 0.1570 O 0 0 0 0 0 0 0 0 0 0 0 0

0.5405 -1.5960 0.4652 C 0 0 0 0 0 0 0 0 0 0 0 0

1.2394 -2.5943 0.5990 O 0 0 0 0 0 0 0 0 0 0 0 0

-1.5537 -0.5526 0.9189 C 0 0 0 0 0 0 0 0 0 0 0 0

-2.8783 -0.6171 1.5239 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.0368 2.6380 -1.1418 H 0 0 0 0 0 0 0 0 0 0 0 0

2.9218 -1.1929 -0.7485 H 0 0 0 0 0 0 0 0 0 0 0 0

3.6284 0.7738 -1.9192 H 0 0 0 0 0 0 0 0 0 0 0 0

2.1467 2.6906 -2.1154 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.9943 -2.4290 1.4989 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.0976 -1.5580 2.0323 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.6360 -0.4817 0.7489 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.9774 0.1822 2.2616 H 0 0 0 0 0 0 0 0 0 0 0 0

1 6 4 0 0 0 0

1 4 4 0 0 0 0

5 2 4 0 0 0 0

2 3 4 0 0 0 0

3 4 4 0 0 0 0

10 5 1 0 0 0 0

6 5 4 0 0 0 0

8 6 1 0 0 0 0

8 12 1 0 0 0 0

12 7 2 0 0 0 0

7 10 1 0 0 0 0

8 9 2 0 0 0 0

10 11 2 0 0 0 0

12 13 1 0 0 0 0

1 14 1 0 0 0 0

2 15 1 0 0 0 0

3 16 1 0 0 0 0

4 17 1 0 0 0 0

7 18 1 0 0 0 0

13 19 1 0 0 0 0

13 20 1 0 0 0 0

13 21 1 0 0 0 0

M END): 20 ms

reading 21 atoms

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Wikipedia	License
Ammonia is an inorganic chemical compound of nitrogen and hydrogen with the formula NH3. A stable binary hydride and the simplest pnictogen hydride, ammonia is a colourless gas with a distinctive pungent smell. Biologically, it is a common nitrogenous waste, and it contributes significantly to the nutritional needs of terrestrial organisms by serving as a precursor to fertilisers. Around 70% of ammonia produced industrially is used to make fertilisers in various forms and composition, such as urea and diammonium phosphate. Ammonia in pure form is also applied directly into the soil. Ammonia, either directly or indirectly, is also a building block for the synthesis of many chemicals. Ammonia occurs in nature and has been detected in the interstellar medium. In many countries, it is classified as an extremely hazardous substance. Ammonia is produced biologically in a process called nitrogen fixation, but even more is generated industrially by the Haber process. The process helped revolutionize agriculture by providing cheap fertilizers. The global industrial production of ammonia in 2021 was 235 million tonnes. Industrial ammonia is transported by road in tankers, by rail in tank wagons, by sea in gas carriers, or in cylinders. Ammonia boils at −33.34 °C (−28.012 °F) at a pressure of one atmosphere, but the liquid can often be handled in the laboratory without external cooling. Household ammonia or ammonium hydroxide is a solution of ammonia in water.
Read full article at Wikipedia

Formula

C11H8O2

Net Charge

Average Mass

172.183

Monoisotopic Mass

172.05243

InChI

InChI=1S/C11H8O2/c1-7-6-10(12)8-4-2-3-5-9(8)11(7)13/h2-6H,1H3

InChIKey

MJVAVZPDRWSRRC-UHFFFAOYSA-N

SMILES

CC1=CC(=O)C2=C(C=CC=C2)C1=O

Metabolite of Species	Details
Homo sapiens (NCBI:txid9606)	Found in urine (BTO:0001419). See: PubMed

Roles Classification
Biological Role(s):	human urinary metabolite Any metabolite (endogenous or exogenous) found in human urine samples. EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor An EC 3.4.22.* (cysteine endopeptidase) inhibitor that interferes with the action of SARS coronavirus main proteinase (EC 3.4.22.69). mouse metabolite Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus). (via vitamin K ) fat-soluble vitamin (role) Any vitamin that dissolves in fats and are stored in body tissues. Unlike the water-soluble vitamins, they are stored in the body for long periods of time and generally pose a greater risk for toxicity when consumed in excess. (via vitamin K )

Application(s):	angiogenesis inhibitor An agent and endogenous substances that antagonize or inhibit the development of new blood vessels. antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms. nutraceutical A product in capsule, tablet or liquid form that provide essential nutrients, such as a vitamin, an essential mineral, a protein, an herb, or similar nutritional substance.

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	menadione (CHEBI:28869) has role angiogenesis inhibitor (CHEBI:48422) menadione (CHEBI:28869) has role antineoplastic agent (CHEBI:35610) menadione (CHEBI:28869) has role EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor (CHEBI:147285) menadione (CHEBI:28869) has role human urinary metabolite (CHEBI:84087) menadione (CHEBI:28869) has role nutraceutical (CHEBI:50733) menadione (CHEBI:28869) is a 1,4-naphthoquinones (CHEBI:132142) menadione (CHEBI:28869) is a vitamin K (CHEBI:28384)

Incoming	menadione sodium sulfonate (CHEBI:63928) has functional parent menadione (CHEBI:28869) menadione sulfonic acid (CHEBI:63930) has functional parent menadione (CHEBI:28869)

IUPAC Name

2-methylnaphthalene-1,4-dione

Synonyms	Sources
2-methyl-1,4-naphthalenedione	ChemIDplus
2-Methyl-1,4-naphthochinon	ChemIDplus
2-methyl-1,4-naphthoquinone	KEGG COMPOUND
2-methylnaphthoquinone	ChemIDplus
3-methyl-1,4-naphthoquinone	ChemIDplus
menadion	ChemIDplus
Menadione	KEGG COMPOUND
MENADIONE	PDBeChem
menadione	UniProt
menaphthon	ChemIDplus
menaphthone	ChemIDplus
menaquinone	ChemIDplus
menaquinone 0	ChemIDplus
vitamin K3	ChemIDplus
vitamin K₃	ChEBI

Brand Names	Sources
Aquakay	ChemIDplus
Aquinone	ChemIDplus
Hemodal	ChemIDplus
Kappaxin	KEGG DRUG

Manual Xrefs	Databases
1683	DrugCentral
3915	ChemSpider
C05377	KEGG COMPOUND
CPD-3766	MetaCyc
D02335	KEGG DRUG
DB00170	DrugBank
FDB000953	FooDB
HMDB0001892	HMDB
LSM-3755	LINCS
Menadione	Wikipedia
VK3	PDBeChem
View more database links

Registry Numbers	Types	Sources
1908453	Reaxys Registry Number	Reaxys
58-27-5	CAS Registry Number	KEGG COMPOUND
58-27-5	CAS Registry Number	ChemIDplus
58-27-5	CAS Registry Number	NIST Chemistry WebBook

Citations

Last Modified

26 July 2021

CHEBI:28869 - menadione

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