Ketcher 07262113142D 1   1.00000     0.00000     0

 13 14  0     0  0            999 V2000
   -1.7320   -0.6538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7320    0.3462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8661    0.8462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8661   -1.1538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.6538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.3462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7320   -0.6538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8661    0.8462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8661   -1.1538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7320    0.3462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8661    1.8462    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8661   -2.1538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5982    0.8462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0     0  0
  3  2  2  0     0  0
  4  1  2  0     0  0
  5  4  1  0     0  0
  6  5  2  0     0  0
  3  6  1  0     0  0
  8  6  1  0     0  0
  8 11  2  0     0  0
  7  9  1  0     0  0
  9  5  1  0     0  0
  9 12  2  0     0  0
 10  7  2  0     0  0
  8 10  1  0     0  0
 10 13  1  0     0  0
M  END
> <ID>
CHEBI:28869

> <NAME>
menadione

> <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.

> <STAR>
3

> <SECONDARY_ID>
CHEBI:46306; CHEBI:6747; CHEBI:27304

> <SYNONYM>
vitamin K3; vitamin K3; menaquinone 0; menaquinone; menaphthone; menaphthon; menadione; MENADIONE; Menadione; menadion; 3-methyl-1,4-naphthoquinone; 2-methylnaphthoquinone; 2-methyl-1,4-naphthoquinone; 2-Methyl-1,4-naphthochinon; 2-methyl-1,4-naphthalenedione

> <IUPAC_NAME>
2-methylnaphthalene-1,4-dione

> <BRAND_NAME>
Kappaxin; Hemodal; Aquinone; Aquakay

> <FORMULA>
C11H8O2

> <MASS>
172.183

> <MONOISOTOPIC_MASS>
172.05243

> <CHARGE>
0

> <SMILES>
CC1=CC(=O)C2=C(C=CC=C2)C1=O

> <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

> <CAS_REGISTRY_NUMBER>
58-27-5

> <REAXYS_REGISTRY_NUMBER>
1908453

> <CHEMIDPLUS>
58-27-5

> <DRUGBANK_ACCESSION>
DB00170

> <KEGG_COMPOUND_ACCESSION>
C05377

> <KEGG_DRUG_ACCESSION>
D02335

> <LINCS_ACCESSION>
LSM-3755

> <METACYC_ACCESSION>
CPD-3766

> <NIST_CHEMISTRY_WEBBOOK>
58-27-5

> <PDBECHEM_ACCESSION>
VK3

> <WIKIPEDIA_ACCESSION>
Menadione

> <PUBMED_CITATION>
10433694; 11372776; 12665684; 12895502; 13779073; 15052609; 15265851; 15613473; 15722567; 16109308; 16140270; 16469140; 1650428; 1697141; 1857739; 18698499; 19593550; 19766112; 2064595; 2333843; 28166217; 30119016; 30609653; 3083821; 31238027; 31520616; 31701430; 32630491; 32798378; 33227312; 33800926; 33901557; 33945810; 34040527; 8785182; 9010592; 9380028

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