Record Information
Version2.0
Creation Date2012-05-31 14:45:05 -0600
Update Date2015-06-03 17:20:01 -0600
Secondary Accession Numbers
  • ECMDB20441
Identification
Name:Menaquinone-1
Description:Menaquinone-1 is a menaquinone with 1 isoprenyl group. Menaquinones and demethylmenaquinones are isoprenoid quinones of the naphthalene series, and are constituents of bacterial plasma membranes, where they play important roles in electron transfer and oxidative phosphorylation. Menaquinones or Vitamin K2 homologs are characterized by the number of isoprenoid residues in their side chain. Menaquinones are abbreviated MK-n, where n represents the number of isoprenoid side chain residues. For example, menaquinone-4 (abbreviated MK-4), has four isoprene residues in its side chain. The most common length of the side chain in bacteria is 8, although minor amounts of MK-1 through MK-14 have been found
Structure
Thumb
Synonyms:
  • 2-Methyl-3-(3-methyl-2-butenyl)naphthoquinone
  • Lepachol acetate
  • Lepachol acetic acid
  • Vitamin MK 1
Chemical Formula:C16H18O2
Weight:Average: 242.3129
Monoisotopic: 242.13067982
InChI Key:PXIPYHVOWDEAMD-UHFFFAOYSA-N
InChI:InChI=1S/C16H18O2/c1-10(2)8-9-12-11(3)15(17)13-6-4-5-7-14(13)16(12)18/h4-8,15,17H,9H2,1-3H3
CAS number:Not Available
IUPAC Name:4-hydroxy-3-methyl-2-(3-methylbut-2-en-1-yl)-1,4-dihydronaphthalen-1-one
Traditional IUPAC Name:4-hydroxy-3-methyl-2-(3-methylbut-2-en-1-yl)-4H-naphthalen-1-one
SMILES:CC(C)=CCC1=C(C)C(O)C2=CC=CC=C2C1=O
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as naphthalenes. These are compounds containing a naphthalene moiety, which consists of two fused benzene rings.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassNaphthalenes
Direct ParentNaphthalenes
Alternative Parents
Substituents
  • Naphthalene
  • Monoterpenoid
  • Bicyclic monoterpenoid
  • Aromatic monoterpenoid
  • Aryl ketone
  • Secondary alcohol
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External DescriptorsNot Available
Physical Properties
State:Not Available
Charge:0
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.1 g/LALOGPS
logP2.97ALOGPS
logP3.06ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)13.62ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity74.62 m³·mol⁻¹ChemAxon
Polarizability27.77 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
SMPDB Pathways:Not Available
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0290000000-9412e6aa8f1e678dfbcfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001r-2920000000-2f314d5e57827a6e9d01View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00lr-9300000000-448505caf980069124adView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0090000000-3f2e1fb1f169cc664277View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0290000000-8fd814b11ad7484faf16View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0adr-3920000000-fc0560088e01277a00fdView in MoNA
References
References:
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDNot Available
Pubchem Compound ID25200371
Kegg IDNot Available
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDCPD0-1367
EcoCyc IDCPD0-1367

Enzymes

General function:
Involved in FMN binding
Specific function:
Catalyzes the 6-electron oxidation of protoporphyrinogen-IX to form protoporphyrin-IX. Does not use oxygen directly. Is coupled to the respiratory chain
Gene Name:
hemG
Uniprot ID:
P0ACB4
Molecular weight:
21226
Reactions
Protoporphyrinogen IX + 3 menaquinone = protoporphyrin IX + 3 menaquinol.