AFCDB: Phytomenadione (FDB012357)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:07 UTC

Update date

2019-11-26 03:06:37 UTC

Primary ID

FDB012357

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Phytomenadione

Description

Vitamin 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 Number

12001-79-5

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	5.9e-05 g/L	ALOGPS
logP	8.48	ALOGPS
logP	9.7	ChemAxon
logS	-6.9	ALOGPS
pKa (Strongest Basic)	-7.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	34.14 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	142.96 m³·mol⁻¹	ChemAxon
Polarizability	56.8 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C31H46O2

IUPAC name

2-methyl-3-[(2E)-3,7,11,15-tetramethylhexadec-2-en-1-yl]-1,4-dihydronaphthalene-1,4-dione

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+

InChI Key

MBWXNTAXLNYFJB-LKUDQCMESA-N

Isomeric SMILES

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

Average Molecular Weight

450.6957

Monoisotopic Molecular Weight

450.349780716

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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Quinone and hydroquinone lipids

Direct Parent

Vitamin 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 Framework

Aromatic homopolycyclic compounds

External Descriptors

vitamin K (C02059 )
Fat-soluble vitamins (C02059 )

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 82.61%; H 10.29%; O 7.10%	DFC
Melting Point	Mp -4°	DFC
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	328 () (MeOH) (Berdy)	DFC
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0ug0-9860500000-a5cd1646f1fc838bc7d7	2014-09-20	View Spectrum
Predicted GC-MS	Phytomenadione, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-000i-6895400000-254b168b019b1fc92c97	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0121900000-22d50aa41f7e3fa9b9da	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0apr-1679100000-60b28d715716b428496d	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4j-6592000000-1898f88b8876c5be2ea3	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0000900000-20c987b9d7c887aaedea	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-0101900000-ad51a9cf10696cc2c1cc	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0089-2924500000-7863f3ba8e25eb26d7e0	2016-08-03	View Spectrum

NMR

Type	Description		View
1D NMR	¹H NMR Spectrum (1D, 90 MHz, CDCl₃, experimental)		Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

18067

Phenol-Explorer ID

Not Available

DrugBank ID

DB01022

HMDB ID

HMDB03555

CRC / DFC (Dictionary of Food Compounds) ID

HGN34-M:HGN34-M

EAFUS ID

3864

Dr. Duke ID

VIT-K|VITAMIN-K-1|VIT-K-1|PHYLLOQUINONE|VITAMIN-K

BIGG ID

39000

KNApSAcK ID

C00002868

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Vitamin K

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
anti hemorrhagic	50248	Drug that acts on blood and blood-forming organs and those that affect the hemostatic system.	DUKE
coagulant			DUKE
fungicide	24127	A substance used to destroy fungal pests.	DUKE
hypotensive			DUKE
pesticide	25944	Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.	DUKE
toxic	52209	A role played by the molecular entity or part thereof which causes the development of a pathological process.	DUKE

Enzymes

Name	Gene Name	UniProt ID
Vitamin K epoxide reductase complex subunit 1	VKORC1	Q9BQB6

Pathways

Name	SMPDB Link	KEGG Link
Vitamin K Metabolism	SMP00464	Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not 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.

Phytomenadione (FDB012357)

Structure for FDB012357 (Phytomenadione)