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Record Information
Version3.6
Creation Date2012-09-06 15:16:51 UTC
Update Date2016-02-11 01:31:41 UTC
HMDB IDHMDB15157
Secondary Accession NumbersNone
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
PhytonadioneChEBI
PhytonadionumChEBI
PhytylmenadioneChEBI
trans-PhylloquinoneChEBI
Vitamin K1ChEBI
Vitamin K hydroquinone (phylloquinone)HMDB
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 KeyInChIKey=MBWXNTAXLNYFJB-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
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Drug
Biofunction
  • Antifibrinolytic Agents
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
  • Vitamins
  • Vitamins (Vitamin K)
Application
  • Nutrients
  • Pharmaceutical
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-20 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility5.92e-05 g/LNot Available
LogP9.3Not Available
Predicted Properties
PropertyValueSource
Water Solubility5.92e-05 mg/mLALOGPS
logP8.48ALOGPS
logP9.7ChemAxon
logS-6.9ALOGPS
pKa (Strongest Basic)-7.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 Å2ChemAxon
Rotatable Bond Count14ChemAxon
Refractivity142.96 m3·mol-1ChemAxon
Polarizability55.92 Å3ChemAxon
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
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Acenocoumarol PathwaySMP00269Not Available
Alteplase PathwaySMP00280Not Available
Aminocaproic Acid PathwaySMP00286Not Available
Anistreplase PathwaySMP00281Not Available
Aprotinin PathwaySMP00288Not Available
Ardeparin PathwaySMP00275Not Available
Argatroban PathwaySMP00276Not Available
Bivalirudin PathwaySMP00277Not Available
Coagulation SMP00586Not Available
Dicoumarol Action PathwaySMP00656Not Available
Dicumarol PathwaySMP00270Not Available
Enoxaparin PathwaySMP00272Not Available
Fondaparinux PathwaySMP00273Not Available
Heparin PathwaySMP00274Not Available
Lepirudin PathwaySMP00278Not Available
Phenindione Action PathwaySMP00655Not Available
Phenprocoumon PathwaySMP00271Not Available
Reteplase PathwaySMP00285Not Available
Streptokinase PathwaySMP00282Not Available
Tenecteplase PathwaySMP00283Not Available
Tranexamic Acid PathwaySMP00287Not Available
Urokinase PathwaySMP00284Not Available
Vitamin K MetabolismSMP00464Not Available
Warfarin PathwaySMP00268Not Available
Ximelagatran PathwaySMP00279Not Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01022
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01022
  • Not Applicable
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
NuGOwiki LinkHMDB15157
Metagene LinkHMDB15157
METLIN IDNot Available
PubChem Compound5284607
PDB IDPQN
ChEBI ID18067
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available