Phytonadione

Basic Info

Common NamePhytonadione(F04775)
2D Structure
Description

Phylloquinone 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.

FRCD IDF04775
CAS Number84-80-0
PubChem CID5284607
FormulaC31H46O2
IUPAC Name

2-methyl-3-[(E,7R,11R)-3,7,11,15-tetramethylhexadec-2-enyl]naphthalene-1,4-dione

InChI Key

MBWXNTAXLNYFJB-NKFFZRIASA-N

InChI

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

Canonical SMILES

CC1=C(C(=O)C2=CC=CC=C2C1=O)CC=C(C)CCCC(C)CCCC(C)CCCC(C)C

Isomeric SMILES

CC1=C(C(=O)C2=CC=CC=C2C1=O)C/C=C(\C)/CCC[C@H](C)CCC[C@H](C)CCCC(C)C

WikipediaPhytonadione
Synonyms
        
            Phytylmenadione
        
            VITAMIN K1
        
            phytonadione
        
            84-80-0
        
            Phylloquinone
        
            Phyllochinon
        
            Phytomenadione
        
            alpha-Phylloquinone
        
            3-Phytylmenadione
        
            Konakion
Classifies
                

                  
                    Predicted: Pollutant
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassLipids and lipid-like molecules
ClassPrenol lipids
SubclassQuinone and hydroquinone lipids
Intermediate Tree NodesNot available
Direct ParentVitamin K compounds
Alternative Parents
Molecular FrameworkAromatic homopolycyclic compounds
SubstituentsDiterpenoid - Naphthoquinone - Naphthalene - Aryl ketone - Quinone - Benzenoid - Ketone - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Aromatic homopolycyclic compound
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.

Properties

Property NameProperty Value
Molecular Weight450.707
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count2
Rotatable Bond Count14
Complexity696
Monoisotopic Mass450.35
Exact Mass450.35
XLogP10.9
Formal Charge0
Heavy Atom Count33
Defined Atom Stereocenter Count2
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.8941
Human Intestinal AbsorptionHIA+1.0000
Caco-2 PermeabilityCaco2+0.7993
P-glycoprotein SubstrateSubstrate0.6643
P-glycoprotein InhibitorInhibitor0.8581
Inhibitor0.9503
Renal Organic Cation TransporterNon-inhibitor0.7232
Distribution
Subcellular localizationMitochondria0.7617
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7852
CYP450 2D6 SubstrateNon-substrate0.8270
CYP450 3A4 SubstrateSubstrate0.6854
CYP450 1A2 InhibitorInhibitor0.9107
CYP450 2C9 InhibitorInhibitor0.8949
CYP450 2D6 InhibitorNon-inhibitor0.9231
CYP450 2C19 InhibitorInhibitor0.8994
CYP450 3A4 InhibitorNon-inhibitor0.8309
CYP Inhibitory PromiscuityHigh CYP Inhibitory Promiscuity0.7542
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.5675
Inhibitor0.5000
AMES ToxicityNon AMES toxic0.8945
CarcinogensNon-carcinogens0.9183
Fish ToxicityHigh FHMT0.9977
Tetrahymena Pyriformis ToxicityHigh TPT0.9987
Honey Bee ToxicityHigh HBT0.7758
BiodegradationNot ready biodegradable0.9051
Acute Oral ToxicityIV0.6192
Carcinogenicity (Three-class)Non-required0.6185
Model Value Unit
Absorption
Aqueous solubility-5.1702LogS
Caco-2 Permeability1.8116LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity1.1603LD50, mol/kg
Fish Toxicity-0.9294pLC50, mg/L
Tetrahymena Pyriformis Toxicity1.6894pIGC50, ug/L

References

TitleJournalDatePubmed ID
In vitro characterization and in vivo toxicity, antioxidant and immunomodulatory effect of fermented foods; Xeniji™.BMC Complement Altern Med2017 Jun 3028666436
[ANTIHEMOPHILIC GLOBULIN CONSUMPTION DURING BLOOD COAGULATION].Nihon Naika Gakkai Zasshi1963 Nov 1014156201

Targets

Target Details

Vitamin K-dependent gamma-carboxylase

General Function:
Gamma-glutamyl carboxylase activity
Specific Function:
Mediates the vitamin K-dependent carboxylation of glutamate residues to calcium-binding gamma-carboxyglutamate (Gla) residues with the concomitant conversion of the reduced hydroquinone form of vitamin K to vitamin K epoxide.
Gene Name:
GGCX
Uniprot ID:
P38435
Molecular Weight:
87560.065 Da
Mechanism of Action:
Vitamin K is an essential cofactor for the gamma-carboxylase enzymes which catalyze the posttranslational gamma-carboxylation of glutamic acid residues in inactive hepatic precursors of coagulation factors II, VII, IX and X. Gamma-carboxylation converts these inactive precursors into active coagulation factors which are secreted by hepatocytes into the blood. Supplementing with Phytonadione results in a relief of vitamin K deficiency symptoms which include easy bruisability, epistaxis, gastrointestinal bleeding, menorrhagia and hematuria.
References
  1. Morris DP, Soute BA, Vermeer C, Stafford DW: Characterization of the purified vitamin K-dependent gamma-glutamyl carboxylase. J Biol Chem. 1993 Apr 25;268(12):8735-42. [8473318 ]
Target Details

Osteocalcin

General Function:
Structural molecule activity
Specific Function:
Constitutes 1-2% of the total bone protein. It binds strongly to apatite and calcium.
Gene Name:
BGLAP
Uniprot ID:
P02818
Molecular Weight:
10962.445 Da
Mechanism of Action:
Vitamin K is an essential cofactor for the gamma-carboxylase enzymes which catalyze the posttranslational gamma-carboxylation of glutamic acid residues in inactive hepatic precursors of coagulation factors II, VII, IX and X. Gamma-carboxylation converts these inactive precursors into active coagulation factors which are secreted by hepatocytes into the blood. Supplementing with Phytonadione results in a relief of vitamin K deficiency symptoms which include easy bruisability, epistaxis, gastrointestinal bleeding, menorrhagia and hematuria.
References
  1. Sato Y, Tsuru T, Oizumi K, Kaji M: Vitamin K deficiency and osteopenia in disuse-affected limbs of vitamin D-deficient elderly stroke patients. Am J Phys Med Rehabil. 1999 Jul-Aug;78(4):317-22. [10418836 ]