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Showing Compound Phytomenadione (FDB012357)

Record Information
Version1.0
Creation date2010-04-08 22:10:07 UTC
Update date2019-11-26 03:06:37 UTC
Primary IDFDB012357
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePhytomenadione
DescriptionVitamin K1, also known as phytonadione or mephyton, 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. Vitamin K1 is an extremely weak basic (essentially neutral) compound (based on its pKa).
CAS Number12001-79-5
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
PhytonadioneKegg
2-Methyl-3-phytyl-1,4-naphthoquinoneKegg
PhytomenadioneKegg
MephytonKegg
2',3'-trans-Vitamin K1HMDB
2-Methyl-3-phythyl-1,4-naphthochinonHMDB
2-Methyl-3-phytyl-1,4-naphthochinonHMDB
2-Methyl-3-phytyl-1,4-napthoquinoneHMDB
2-Methyl-3-[(2E,7R,11R)-3,7,11,15-tetramethylhexadec-2-en-1-yl]naphthalene-1,4-dioneHMDB
3-PhytylmenadioneHMDB
a-PhylloquinoneHMDB
alpha-PhylloquinoneHMDB
Antihemorrhagic vitaminHMDB
Aqua mephytonHMDB
Aqua-mephytinHMDB
AquamephytonHMDB, MeSH
Combinal K1HMDB
FitomenadionaHMDB
FitomenadioneHMDB
K-JectHMDB
Kativ NHMDB
KephtonHMDB
KinadionHMDB
KonakionHMDB, MeSH
mono-KayHMDB
MonodionHMDB
PhyllochinonHMDB
PhyllochinonumHMDB
PhylloquinoneHMDB
Phythyl-menadionHMDB
PhytomenadionumHMDB
PhytonadionumHMDB
PhytylmenadioneHMDB
Synthex PHMDB
trans-PhylloquinoneHMDB
Vitamin K 1MeSH, HMDB
PhyllohydroquinoneMeSH, HMDB
Vitamin K1KEGG
Vitamin KMeSH, HMDB
α-phylloquinonebiospider
1,4-Naphthoquinone, 2-methyl-3-phytyl-biospider
2-Methyl-3-(3,7,11,15-tetramethyl-2-hexadecenyl)-1,4-naphthalenedione, 9CIdb_source
2-Methyl-3-[(2e,7R,11R)-3,7,11,15-tetramethylhexadec-2-en-1-yl]naphthalene-1,4-dioneHMDB
A-phylloquinonebiospider
a-Phyllostindb_source
Alpha-phylloquinonebiospider
K-jectbiospider
Kaywandb_source
Konakimdb_source
Mono-kaybiospider
Phytomenadione, BAN, INNdb_source
Phytonadione, USANdb_source
Synthex pbiospider
Trans-phylloquinonebiospider
Vitamin kbiospider
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
Polarizability56.8 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC31H46O2
IUPAC name2-methyl-3-[(2E)-3,7,11,15-tetramethylhexadec-2-en-1-yl]-1,4-dihydronaphthalene-1,4-dione
InChI IdentifierInChI=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+
InChI KeyMBWXNTAXLNYFJB-LKUDQCMESA-N
Isomeric SMILESCC(C)CCCC(C)CCCC(C)CCC\C(C)=C\CC1=C(C)C(=O)C2=CC=CC=C2C1=O
Average Molecular Weight450.6957
Monoisotopic Molecular Weight450.349780716
Classification
Description 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
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 82.61%; H 10.29%; O 7.10%DFC
Melting PointMp -4°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data328 () (MeOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0ug0-9860500000-a5cd1646f1fc838bc7d72014-09-20View Spectrum
Predicted GC-MSPhytomenadione, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000i-6895400000-254b168b019b1fc92c97Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0121900000-22d50aa41f7e3fa9b9da2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0apr-1679100000-60b28d715716b428496d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4j-6592000000-1898f88b8876c5be2ea32016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000900000-20c987b9d7c887aaedea2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0101900000-ad51a9cf10696cc2c1cc2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0089-2924500000-7863f3ba8e25eb26d7e02016-08-03View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Spectrum
ChemSpider ID4444124
ChEMBL IDCHEMBL520156
KEGG Compound IDC02059
Pubchem Compound ID5280483
Pubchem Substance IDNot Available
ChEBI ID18067
Phenol-Explorer IDNot Available
DrugBank IDDB01022
HMDB IDHMDB03555
CRC / DFC (Dictionary of Food Compounds) IDHGN34-M:HGN34-M
EAFUS ID3864
Dr. Duke IDVIT-K|VITAMIN-K-1|VIT-K-1|PHYLLOQUINONE|VITAMIN-K
BIGG ID39000
KNApSAcK IDC00002868
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDVitamin K
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
Anti-hemorrhagic50248 An agent that stops or prevents bleeding, promoting blood clotting and tissue repair. It plays a biological role in maintaining vascular integrity and is therapeutically used to treat bleeding disorders, injuries, and surgical wounds, with key medical applications in trauma care, surgery, and hemophilia management.DUKE
CoagulantAn agent that causes blood or another liquid to coagulate, playing a crucial biological role in wound healing and hemostasis. Therapeutically, coagulants are used to treat bleeding disorders, such as hemophilia, and to prevent excessive bleeding during surgery, with key medical uses including trauma treatment and transfusion medicine.DUKE
Fungicide24127 An agent that kills or inhibits the growth of fungi, playing a biological role in preventing fungal infections. Therapeutically, it is used to treat fungal diseases, with key medical applications including athlete's foot, ringworm, and candidiasis, as well as agricultural uses to protect crops from fungal damage.DUKE
HypotensiveAn agent that lowers blood pressure, playing a biological role in regulating cardiovascular function. Therapeutically, it's used to manage hypertension, heart failure, and angina, with key medical applications in preventing stroke, kidney disease, and cardiac complications.DUKE
Pesticide25944 An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.DUKE
Toxic52209 A substance that can harm or poison living organisms. Biologically, it can disrupt cellular functions and cause damage. Therapeutically, toxins are used in small, controlled doses for applications such as cancer treatment and immunosuppression. Key medical uses include chemotherapy and immunotherapy, where toxins are used to target and destroy diseased cells.DUKE
Enzymes
NameGene NameUniProt ID
Vitamin K epoxide reductase complex subunit 1VKORC1Q9BQB6
Pathways
NameSMPDB LinkKEGG Link
Vitamin K MetabolismSMP00464 Not Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Saxholt, E., et al. 'Danish food composition databank, revision 7.' Department of Nutrition, National Food Institute, Technical University of Denmark (2008).
— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.