You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
Creation Date2012-09-06 15:16:51 UTC
Update Date2017-09-27 08:27:50 UTC
HMDB IDHMDB0015157
Secondary Accession Numbers
  • HMDB15157
Metabolite Identification
Common NamePhytonadione
DescriptionPhytonadione is often called vitamin K1. It is a fat-soluble vitamin that is stable to air and moisture but decomposes in sunlight. It is found naturally in a wide variety of green plants. Phylloquinone is also an antidote for coumatetralyl. Vitamin K is needed for the posttranslational modification of certain proteins, mostly required for blood coagulation.
Structure
Thumb
Synonyms
ValueSource
2-Methyl-3-(3,7,11,15-tetramethyl-2-hexadecenyl)-1,4-naphthalenedioneChEBI
2-Methyl-3-[(2E)-3,7,11,15-tetramethyl-2-hexadecenyl]naphthoquinoneChEBI
2-Methyl-3-phytyl-1,4-naphthochinonChEBI
2-Methyl-3-phytyl-1,4-naphthoquinoneChEBI
3-PhytylmenadioneChEBI
alpha-PhylloquinoneChEBI
FitomenadionaChEBI
PhyllochinonChEBI
PhyllochinonumChEBI
PhytomenadioneChEBI
PhytomenadionumChEBI
PhytonadionumChEBI
PhytylmenadioneChEBI
trans-PhylloquinoneChEBI
Vitamin K1ChEBI
a-PhylloquinoneGenerator
α-phylloquinoneGenerator
Vitamin K hydroquinone (phylloquinone)HMDB
PhyllohydroquinoneMeSH
PhylloquinoneMeSH
AquamephytonMeSH
KonakionMeSH
Vitamin K 1MeSH
Chemical FormulaC31H46O2
Average Molecular Weight450.6957
Monoisotopic Molecular Weight450.349780716
IUPAC Name2-methyl-3-[(2E,7R,11R)-3,7,11,15-tetramethylhexadec-2-en-1-yl]-1,4-dihydronaphthalene-1,4-dione
Traditional Namevitamin K
CAS Registry Number84-80-0
SMILES
CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC\C(C)=C\CC1=C(C)C(=O)C2=C(C=CC=C2)C1=O
InChI Identifier
InChI=1S/C31H46O2/c1-22(2)12-9-13-23(3)14-10-15-24(4)16-11-17-25(5)20-21-27-26(6)30(32)28-18-7-8-19-29(28)31(27)33/h7-8,18-20,22-24H,9-17,21H2,1-6H3/b25-20+/t23-,24-/m1/s1
InChI KeyMBWXNTAXLNYFJB-NKFFZRIASA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as vitamin k compounds. These are quinone lipids containing a methylated naphthoquinone ring structure, and vary in the aliphatic side chain attached at the 3-position.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassQuinone and hydroquinone lipids
Direct ParentVitamin K compounds
Alternative Parents
Substituents
  • Diterpenoid
  • Naphthoquinone
  • Naphthalene
  • Aryl ketone
  • Quinone
  • Benzenoid
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Source:

Route of exposure:

  Enteral:

  Parenteral:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

    Cellular process:

Role

Industrial application:

  Food and nutrition:

  Pharmaceutical industry:

Biological role:

Indirect biological role:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-20 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility5.9e-05 g/LNot Available
LogP9.3Not Available
Predicted Properties
PropertyValueSource
Water Solubility5.9e-05 g/LALOGPS
logP8.48ALOGPS
logP9.7ChemAxon
logS-6.9ALOGPS
pKa (Strongest Basic)-7.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity142.96 m³·mol⁻¹ChemAxon
Polarizability55.92 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSsplash10-002r-2930000000-2b32596edebbe7e02cf7View in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0002-1290000000-fa752c2db990f115c3c6View in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0002-8269080000-4bdc9b3a41d7d08b7265View in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0002-7379080000-ba90762b738ee84b3151View in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-014i-6749020000-c4e58ef0e538e224dad4View in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0g4i-3149020000-ad93d4a26002eefa74ceView in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-00xr-5397040000-221a2f93d46494325e33View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
GC-MSGC-MS Spectrum - EI-Bsplash10-0udl-9740400000-e47d11ed7b15a667d611View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-0udi-2540900000-d08585615fbc2418786aView in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-002r-2930000000-2b32596edebbe7e02cf7View in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-0002-1290000000-fa752c2db990f115c3c6View in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-0002-8269080000-4bdc9b3a41d7d08b7265View in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-0002-7379080000-ba90762b738ee84b3151View in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-014i-6749020000-c4e58ef0e538e224dad4View in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-0g4i-3149020000-ad93d4a26002eefa74ceView in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-00xr-5397040000-221a2f93d46494325e33View in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-002r-2930000000-2b32596edebbe7e02cf7View in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-0002-1290000000-fa752c2db990f115c3c6View in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-0002-8269080000-4bdc9b3a41d7d08b7265View in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-0002-7379080000-ba90762b738ee84b3151View in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-014i-6749020000-c4e58ef0e538e224dad4View in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-0g4i-3149020000-ad93d4a26002eefa74ceView in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-00xr-5397040000-221a2f93d46494325e33View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
Acenocoumarol PathwayPw000312Pw000312 greyscalePw000312 simpleNot Available
Alteplase PathwayPw000302Pw000302 greyscalePw000302 simpleNot Available
Aminocaproic Acid PathwayPw000308Pw000308 greyscalePw000308 simpleNot Available
Anistreplase PathwayPw000303Pw000303 greyscalePw000303 simpleNot Available
Aprotinin PathwayPw000310Pw000310 greyscalePw000310 simpleNot Available
Displaying entries 1 - 5 of 25 in total
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01022 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01022 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiofluidValueOriginal ageOriginal sexOriginal conditionComments
Blood0-2 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0-1 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01022
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4447652
KEGG Compound IDC02059
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPhytonadione
METLIN IDNot Available
PubChem Compound5284607
PDB IDPQN
ChEBI ID18067
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]