VK3

MENADIONE

Created: 1999-07-08
Last modified:  2020-06-05

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Chemical Details

Formal Charge0
Atom Count21
Chiral Atom Count0
Bond Count22
Aromatic Bond Count6
2D diagram of VK3
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Chemical Component Summary

NameMENADIONE
SynonymsVITAMIN K3; 2-METHYL-1,4-NAPHTHALENEDIONE
Systematic Name (OpenEye OEToolkits)2-methylnaphthalene-1,4-dione
FormulaC11 H8 O2
Molecular Weight172.18
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs10.04O=C2c1c(cccc1)C(=O)C(=C2)C
SMILESCACTVS3.341CC1=CC(=O)c2ccccc2C1=O
SMILESOpenEye OEToolkits1.5.0CC1=CC(=O)c2ccccc2C1=O
Canonical SMILESCACTVS3.341 CC1=CC(=O)c2ccccc2C1=O
Canonical SMILESOpenEye OEToolkits1.5.0 CC1=CC(=O)c2ccccc2C1=O
InChIInChI1.03 InChI=1S/C11H8O2/c1-7-6-10(12)8-4-2-3-5-9(8)11(7)13/h2-6H,1H3
InChIKeyInChI1.03 MJVAVZPDRWSRRC-UHFFFAOYSA-N

Drug Info: DrugBank

DrugBank IDDB00170 
NameMenadione
Groups
  • approved
  • nutraceutical
DescriptionA synthetic naphthoquinone without the isoprenoid side chain and biological activity, but can be converted to active vitamin K2, menaquinone, after alkylation in vivo.
Synonyms
  • 2-Methyl-1,4-Naphthalenedione
  • 2-Methyl-1,4-naphthochinon
  • Vitamin K3
  • 2-Methyl-1,4-naphthoquinone
  • Menadione
IndicationThe primary known function of vitamin K is to assist in the normal clotting of blood, but it may also play a role in normal bone calcification.
Categories
  • Antifibrinolytic Agents
  • Blood and Blood Forming Organs
  • Coagulants
  • Cytochrome P-450 CYP1A2 Inducers
  • Cytochrome P-450 CYP1A2 Inducers (strength unknown)
ATC-CodeB02BA02
CAS number58-27-5

Drug Targets

NameTarget SequencePharmacological ActionActions
Vitamin K-dependent gamma-carboxylaseMAVSAGSARTSPSSDKVQKDKAELISGPRQDSRIGKLLGFEWTDLSSWRR...unknowncofactor
Vitamin K epoxide reductase complex subunit 1MGSTWGSPGWVRLALCLTGLVLSLYALHVKAARARDRDYRALCDVGTAIS...unknowncofactor
Vitamin K epoxide reductase complex subunit 1-like protein 1MAAPVLLRVSVPRWERVARYAVCAAGILLSIYAYHVEREKERDPEHRALC...unknowncofactor
ProthrombinMAHVRGLQLPGCLALAALCSLVHSQHVFLAPQQARSLLQRVRRANTFLEE...unknownactivator
Coagulation factor IXMQRVNMIMAESPGLITICLLGYLLSAECTVFLDHENANKILNRPKRYNSG...unknownactivator
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Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL590
PubChem 4055
ChEMBL CHEMBL590
ChEBI CHEBI:28869
CCDC/CSD IVEJUO, ORACUH, ORADAO, RUYZAO, IVEJUO04, RUYYUH, IVEJUO01
COD 7225840, 7050129, 7050130