| Common Name |
Phytonadione
| Description |
Phytonadione 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 coagliation.
| Structure |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
| Synonyms |
| Value |
Source |
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 Formlia |
C31H46O2
| Average Molecliar Weight |
450.6957
| Monoisotopic Molecliar Weight |
450.349780716
| IUPAC Name |
2-methyl-3-[(2E,7R,11R)-3,7,11,15-tetramethylhexadec-2-en-1-yl]-1,4-dihydronaphthalene-1,4-dione
| Traditional Name |
vitamin K
| CAS Registry Number |
84-80-0
| SMILES |
CC(C)CCC[C@@H](C)CCC[C@@H](C)CCCC(C)=CCC1=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 Key |
MBWXNTAXLNYFJB-NKFFZRIASA-N
| Chemical Taxonomy |
| Description |
This 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.
| Kingdom |
Organic compounds
| Super Class |
Lipids and lipid-like moleclies
| Class |
Prenol lipids
| Sub Class |
Quinone and hydroquinone lipids
| Direct Parent |
Vitamin K compounds
| Alternative Parents |
Diterpenoids
Naphthoquinones
Quinones
Aryl ketones
Organic oxides
Hydrocarbon derivatives
| Substituents |
Diterpenoid
Naphthoquinone
Naphthalene
Aryl ketone
Quinone
Benzenoid
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homopolycyclic compound
| Molecliar Framework |
Aromatic homopolycyclic compounds
| External Descriptors |
phylloquinones (CHEBI:18067 )
Vitamin K (LMPR02030028 )
| Ontology |
| Status |
Expected 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 Emlisifiers
| Cellliar locations |
Extracellliar
Membrane
| Physical Properties |
| State |
Liquid
| Experimental Properties |
| Property |
Value |
Reference |
Melting Point-20 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility5.92e-05 g/LNot Available
LogP9.3Not Available
| Predicted Properties |
| Property |
Value |
Source |
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
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
| Spectrum Type |
Description |
Splash Key |
|
| GC-MS |
GC-MS Spectrum – GC-MSsplash10-002r-2930000000-2b32596edebbe7e02cf7View in MoNA
| GC-MS |
GC-MS Spectrum – GC-MS (1 TMS)splash10-0002-1290000000-fa752c2db990f115c3c6View in MoNA
| GC-MS |
GC-MS Spectrum – GC-MS (2 TMS)splash10-0002-8269080000-4bdc9b3a41d7d08b7265View in MoNA
| GC-MS |
GC-MS Spectrum – GC-MS (2 TMS)splash10-0002-7379080000-ba90762b738ee84b3151View in MoNA
| GC-MS |
GC-MS Spectrum – GC-MS (2 TMS)splash10-014i-6749020000-c4e58ef0e538e224dad4View in MoNA
| GC-MS |
GC-MS Spectrum – GC-MS (2 TMS)splash10-0g4i-3149020000-ad93d4a26002eefa74ceView in MoNA
| GC-MS |
GC-MS Spectrum – GC-MS (2 TMS)splash10-00xr-5397040000-221a2f93d46494325e33View in MoNA
| GC-MS |
GC-MS Spectrum – EI-Bsplash10-0udl-9740400000-e47d11ed7b15a667d611View in MoNA
| GC-MS |
GC-MS Spectrum – EI-Bsplash10-0udi-2540900000-d08585615fbc2418786aView in MoNA
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available
| Biological Properties |
| Cellliar Locations |
Extracellliar
Membrane
| Biofluid Locations |
Blood
Urine
| Tissue Location |
Not Available
| Pathways |
| Name |
SMPDB Link |
KEGG 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
Coagliation 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 |
| Biofluid |
Status |
Age |
Condition |
Reference |
Details |
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01022
21059682
details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01022
21059682
details
|
| Abnormal Concentrations |
|
Not Available
| Predicted Concentrations |
|
| Biofluid |
Original age |
Original condition |
Blood0-2 uMAdlit (>18 years old)BothNormalPredicted based on drug qualities
Blood0-1 umol/mmol creatinineAdlit (>18 years old)BothNormalPredicted based on drug qualities
| Associated Disorders and Diseases |
| Disease References |
None
| Associated OMIM IDs |
None
| External Links |
| DrugBank ID |
DB01022
| DrugBank Metabolite ID |
Not Available
| Phenol Explorer Compound ID |
Not Available
| Phenol Explorer Metabolite ID |
Not Available
| FoodDB ID |
Not Available
| KNApSAcK ID |
Not Available
| Chemspider ID |
4447652
| KEGG Compound ID |
C02059
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Phytonadione
| NuGOwiki Link |
HMDB15157
| Metagene Link |
HMDB15157
| METLIN ID |
Not Available
| PubChem Compound |
5284607
| PDB ID |
PQN
| ChEBI ID |
18067
Product: AP1904
References |
| Synthesis Reference |
Not Available |
| Material Safety Data Sheet (MSDS) |
Download (PDF) |
| General References |
Not Available |
PMID: 21892191
