MiMeDB: Showing metabocard for Vitamin K1 (MMDBc0000248)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-10-27 23:41:16 UTC

Update Date

2024-10-09 22:46:10 UTC

Metabolite ID

MMDBc0000248

Metabolite Identification

Common Name

Vitamin K1

Description

Vitamin K1, also known as phylloquinone or phytonadione, is a polycyclic aromatic ketone, based on 1,4-naphthoquinone, with 2-methyl and 3-phytyl substituents. Vitamin K is a family of phylloquinones that contain a ring of 2-methyl-1,4-naphthoquinone and an isoprenoid side chain. Several forms of vitamin K have been identified: vitamin K1 derived from plants, vitamin K2 (menaquinone) from bacteria and synthetic naphthoquinone provitamins, and vitamin K3 (menadione). Vitamin K1 has only one double bond on the proximal isoprene unit. Vitamin K1 possesses the same type and degree of activity as does naturally-occurring vitamin K, which is necessary for the production via the liver of active prothrombin (factor II), proconvertin (factor VII), plasma thromboplastin component (factor IX), and Stuart factor (factor X). Rich sources of vitamin K1 include green plants, algae, and photosynthetic bacteria. Vitamin K1 has antihemorrhagic and prothrombogenic activity. Vitamin K1 is a fat-soluble vitamin that is stable to air and moisture but decomposes in sunlight. Vitamin K1 is an antidote for coumatetralyl.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-Methyl-3-(3,7,11,15-tetramethyl-2-hexadecenyl)-1,4-naphthalenedione	ChEBI
2-Methyl-3-[(2E)-3,7,11,15-tetramethyl-2-hexadecenyl]naphthoquinone	ChEBI
2-Methyl-3-phytyl-1,4-naphthochinon	ChEBI
2-Methyl-3-phytyl-1,4-naphthoquinone	ChEBI
3-Phytylmenadione	ChEBI
alpha-Phylloquinone	ChEBI
Fitomenadiona	ChEBI
Phyllochinon	ChEBI
Phyllochinonum	ChEBI
Phytomenadione	ChEBI
Phytomenadionum	ChEBI
Phytonadione	ChEBI
Phytonadionum	ChEBI
Phytylmenadione	ChEBI
trans-Phylloquinone	ChEBI
a-Phylloquinone	Generator
Α-phylloquinone	Generator
Vitamin K hydroquinone (phylloquinone)	HMDB
Phyllohydroquinone	HMDB
Phylloquinone	HMDB
Aquamephyton	HMDB
Konakion	HMDB
Vitamin K 1	HMDB
2',3'-trans-Vitamin K1	HMDB
2’,3’-trans-vitamin K1	HMDB
Vitamin K1	ChEBI

Molecular Formula

C₃₁H₄₆O₂

Average Mass

450.6957

Monoisotopic Mass

450.349780716

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

84-80-0

SMILES

Not Available

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

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

phylloquinones (CHEBI:18067 )
Vitamin K (LMPR02030028 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Not Available

Spectra

Not Available

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Blood
Feces
Liver
Urine

Tissue Locations

Liver

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0193201	NAD(P)H dehydrogenase [quinone] 1	Unknown	P15559	Homo sapiens
MMDBp0193203	Vitamin K-dependent gamma-carboxylase	Unknown	P38435	Homo sapiens
MMDBp0193374	Osteocalcin	Unknown	P02818	Homo sapiens
MMDBp0193465	Vitamin K epoxide reductase complex subunit 1	Enzyme	Q9BQB6	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0007527	S-Adenosylmethionine	S-Adenosylhomocysteine	Not Available		VMH	30371894
MMDBr0010754	Vitamin K1	Phylloquinol	NAD(P)H dehydrogenase, quinone 1		VMH; KEGG	30371894

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	144	Human feces; Human sputum; Human unknown; Pig ; Human ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human stool; Human feces; pleural fluid plaque; bal	Metabolic reconstruction
Bacteria	Actinobacteria	44	Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque; Human ; Human supragingival plaque; Human mucosa; Human saliva; Human subgingival plaque	Metabolic reconstruction
Bacteria	Verrucomicrobia	1	Human ; Human feces	Metabolic reconstruction
Bacteria	Bacteroidetes	91	Human feces; Human ; Human stool; Human saliva; Human gastric fluid; Human urine; Human subgingival plaque	Metabolic reconstruction
Bacteria	Firmicutes	148	Human feces; Human ; Human subgingival plaque; Human saliva	Metabolic reconstruction
Archaea	Thaumarchaeota	1		Metabolic reconstruction
Bacteria	Fusobacteria	13	Human feces	Metabolic reconstruction
Bacteria	Synergistetes	1	Human feces	Metabolic reconstruction
Archaea	Euryarchaeota	3		Metabolic reconstruction
Bacteria	Candidatus melainabacteria	1	Human feces	Metabolic reconstruction
Bacteria	Planctomycetes	1	Human feces	Metabolic reconstruction

Exposure Sources

Source Type	Activity	Data Source	Reference
General Exposome	Not Available	U.S. Environmental Protection Agency	CompTox
Drugs	Not Available	U.S. Environmental Protection Agency	CompTox
Drugs	Antimicrobial	U.S. Environmental Protection Agency	CompTox
Cosmetics	Not Available	U.S. Environmental Protection Agency	CompTox
Domestics	Not Available	U.S. Environmental Protection Agency	CompTox
Domestics	Not Available	U.S. Environmental Protection Agency	CompTox
Cosmetics	Not Available	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB
Human Blood	Detected and Quantified	0.00102				uM	Adult (>18 years old)	Female	Normal	HMDB	9109609
Human Blood	Detected and Quantified	0.00106				uM	Adult (>18 years old)	Male	Normal	HMDB	9109609
Human Blood	Detected and Quantified	0.00143				uM	Adult (>18 years old)	Male	Normal	HMDB	9109609
Human Blood	Detected and Quantified	0.00147				uM	Adult (>18 years old)	Female	Normal	HMDB	9109609
Human Blood	Detected and Quantified	0.00049		0.00009	0.0022	uM	Adolescent (13-18 years old)	Both	Normal	HMDB	7657478
Human Blood	Detected and Quantified	0.000500	0.000520			uM	Adult (>18 years old)	Male	Normal	HMDB	12067432
Human Blood	Detected and Quantified	0.000540	0.000560			uM	Adult (>18 years old)	Both	Normal	HMDB	12067432
Human Blood	Detected and Quantified	0.000560	0.000580			uM	Adult (>18 years old)	Female	Normal	HMDB	12067432
Human Blood	Detected and Quantified	0.0011	0.0042			uM	Adult (>18 years old)	Female	Normal	HMDB	15340366
Human Blood	Detected and Quantified	0.00150	0.00219			uM	Adult (>18 years old)	Female	Normal	HMDB	17181887
Human Blood	Detected and Quantified	0.00164	0.00215			uM	Adult (>18 years old)	Both	Normal	HMDB	17181887
Human Blood	Detected and Quantified	0.00180	0.00209			uM	Adult (>18 years old)	Male	Normal	HMDB	17181887
Human Blood	Detected and Quantified	0.0058		0.0020	0.017	uM	Adult (>18 years old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Liver	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0003555

DrugBank ID

DB01022

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Phytonadione

METLIN ID

7027

PubChem Compound

5284607

PDB ID

Not Available

ChEBI ID

18067

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Gover PA, Ingram GI, Cork MS, Holland L, Hopkins RP, Callaghan P, Barkhan P, Shearer MJ: Bleeding from self-administration of phenindione: a detailed case study. Br J Haematol. 1976 Aug;33(4):551-64. doi: 10.1111/j.1365-2141.1976.tb03574.x. [PubMed:1009028 ]
Hirauchi K, Sakano T, Nagaoka T, Morimoto A: Simultaneous determination of vitamin K1, vitamin K1 2,3-epoxide and menaquinone-4 in human plasma by high-performance liquid chromatography with fluorimetric detection. J Chromatogr. 1988 Aug 19;430(1):21-9. doi: 10.1016/s0378-4347(00)83130-8. [PubMed:2851012 ]
Shearer MJ, Mallinson CN, Webster GR, Barkhan P: Absorption of tritiated vitamin K1 in patients with fat malabsorption. Gut. 1970 Dec;11(12):1063-4. [PubMed:5511811 ]
Huang Y, Zhang C, Zhang X, Zhang Z: Chemiluminescence analysis of menadione sodium bisulfite and analgin in pharmaceutical preparations and biological fluids. J Pharm Biomed Anal. 1999 Dec;21(4):817-25. doi: 10.1016/s0731-7085(99)00191-0. [PubMed:10701947 ]
Begley GS, Furie BC, Czerwiec E, Taylor KL, Furie GL, Bronstein L, Stenflo J, Furie B: A conserved motif within the vitamin K-dependent carboxylase gene is widely distributed across animal phyla. J Biol Chem. 2000 Nov 17;275(46):36245-9. doi: 10.1074/jbc.M003944200. [PubMed:10893417 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. doi: 10.1038/35036052. [PubMed:11413487 ]
de Moerloose P, Boehlen F: [Haemostasis. A search for an ideal antithrombotics agent]. Rev Med Suisse. 2005 Jan 5;1(1):35-8. [PubMed:15773196 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. doi: 10.1194/jlr.R600022-JLR200. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. doi: 10.1194/jlr.R700005-JLR200. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Vitamin K1 (MMDBc0000248)

MOL for #<Metabolite:0x00007fdb24b5e3a0>

3D MOL for #<Metabolite:0x00007fdb24b5e3a0>

3D SDF for #<Metabolite:0x00007fdb24b5e3a0>

3D-SDF for #<Metabolite:0x00007fdb24b5e3a0>

PDB for #<Metabolite:0x00007fdb24b5e3a0>

3D PDB for #<Metabolite:0x00007fdb24b5e3a0>

SMILES for #<Metabolite:0x00007fdb24b5e3a0>

INCHI for #<Metabolite:0x00007fdb24b5e3a0>

Structure for #<Metabolite:0x00007fdb24b5e3a0>

3D Structure for #<Metabolite:0x00007fdb24b5e3a0>