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	ChemicalBook:CB1271654, ZINC000002123545

Download	Molfile XML SDF

more structures >>

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Marvin 02060821293D

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Marvin 02060821293D

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): 17 ms

reading 21 atoms

ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false

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21 atoms created

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Molfile expand

Wikipedia	License
Uridine monophosphate (UMP), also known as 5′-uridylic acid (conjugate base uridylate), is a nucleotide that is used as a monomer in RNA. It is an ester of phosphoric acid with the nucleoside uridine. UMP consists of the phosphate group, the pentose sugar ribose, and the nucleobase uracil; hence, it is a ribonucleotide monophosphate. As a substituent or radical its name takes the form of the prefix uridylyl-. The deoxy form is abbreviated dUMP. Covalent attachment of UMP (e.g., to a protein such as adenylyltransferase) is called uridylylation (or sometimes uridylation).
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	Types	Sources
10433694	PubMed citation	Europe PMC
11372776	PubMed citation	Europe PMC
12665684	PubMed citation	Europe PMC
12895502	PubMed citation	Europe PMC
13779073	PubMed citation	Europe PMC
15052609	PubMed citation	Europe PMC
15265851	PubMed citation	Europe PMC
15613473	PubMed citation	Europe PMC
15722567	PubMed citation	Europe PMC
16109308	PubMed citation	Europe PMC
16140270	PubMed citation	Europe PMC
16469140	PubMed citation	Europe PMC
1650428	PubMed citation	Europe PMC
1697141	PubMed citation	Europe PMC
1857739	PubMed citation	Europe PMC
18698499	PubMed citation	Europe PMC
19593550	PubMed citation	Europe PMC
19766112	PubMed citation	Europe PMC
2064595	PubMed citation	Europe PMC
2333843	PubMed citation	Europe PMC
28166217	PubMed citation	Europe PMC
30119016	PubMed citation	Europe PMC
30609653	PubMed citation	Europe PMC
3083821	PubMed citation	Europe PMC
31238027	PubMed citation	Europe PMC
31520616	PubMed citation	Europe PMC
31701430	PubMed citation	Europe PMC
32630491	PubMed citation	Europe PMC
32798378	PubMed citation	Europe PMC
33227312	PubMed citation	Europe PMC
33800926	PubMed citation	Europe PMC
33901557	PubMed citation	Europe PMC
33945810	PubMed citation	Europe PMC
34040527	PubMed citation	Europe PMC
8785182	PubMed citation	Europe PMC
9010592	PubMed citation	Europe PMC
9380028	PubMed citation	Europe PMC

Last Modified

26 July 2021

CHEBI:28869 - menadione

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