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Showing metabocard for Vitamin K1 (HMDB0003555)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (4) Show 4 proteinsXML
enzymes (4) Show 4 proteins
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-08-12 23:40:55 UTC
Update Date2022-03-07 02:49:19 UTC
HMDB IDHMDB0003555
Secondary Accession Numbers
  • HMDB0003596
  • HMDB0015157
  • HMDB03555
  • HMDB03596
  • HMDB15157
Metabolite Identification
Common NameVitamin K1
DescriptionVitamin 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
Thumb
MOLSDFPDBSMILESInChI

MOL for HMDB0003555 (Vitamin K1)

Not Available

3D MOL for HMDB0003555 (Vitamin K1)

Not Available

3D SDF for HMDB0003555 (Vitamin K1)

Not Available

3D-SDF for HMDB0003555 (Vitamin K1)

Not Available

PDB for HMDB0003555 (Vitamin K1)

Not Available

3D PDB for HMDB0003555 (Vitamin K1)

Not Available

SMILES for HMDB0003555 (Vitamin K1)

Not Available

INCHI for HMDB0003555 (Vitamin K1)

Not Available
View in JSmolView Stereo Labels
SynonymsNot Available
Chemical FormulaC31H46O2
Average Molecular Weight450.6957
Monoisotopic Molecular Weight450.349780716
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry Number84-80-0
SMILESNot 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 KeyMBWXNTAXLNYFJB-NKFFZRIASA-N
Chemical Taxonomy
ClassificationNot classified
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
Process
Naturally occurring process
Role
Industrial applicationBiological role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties
Predicted Molecular PropertiesNot Available
Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Vitamin K1CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC\C(C)=C\CC1=C(C)C(=O)C2=C(C=CC=C2)C1=O4253.4Standard polar33892256
Vitamin K1CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC\C(C)=C\CC1=C(C)C(=O)C2=C(C=CC=C2)C1=O3339.7Standard non polar33892256
Vitamin K1CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC\C(C)=C\CC1=C(C)C(=O)C2=C(C=CC=C2)C1=O3414.8Semi standard non polar33892256
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.00049 (0.00009-0.0022) uMAdolescent (13-18 years old)BothNormal details
BloodDetected and Quantified0.0011 +/- 0.0042 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.000540 +/- 0.000560 uMAdult (>18 years old)Both
Normal		 details
BloodDetected and Quantified0.000560 +/- 0.000580 uMAdult (>18 years old)Female
Normal		 details
BloodDetected and Quantified0.000500 +/- 0.000520 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.00164 +/- 0.00215 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.00102 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.00147 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.00150 +/- 0.00219 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.00106 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.00143 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.00180 +/- 0.00209 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.0058 (0.0020-0.017) uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
 details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
External LinksNot Available
References
Synthesis ReferenceAraki, Shin; Murasawa, Hisashi; Tamura, Masanori. Manufacture of vitamin K with Bacillus natto and liquid media for it. Jpn. Kokai Tokkyo Koho (2002), 5 pp.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. [PubMed:2851012 ]
  2. 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 ]
  3. 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. [PubMed:10701947 ]
  4. 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. [PubMed:10893417 ]
  5. 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 ]
  6. 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. [PubMed:1009028 ]
  7. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  8. 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. Epub 2006 Aug 10. [PubMed:16902246 ]
  9. 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. Epub 2007 Mar 20. [PubMed:17374880 ]
  10. 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 ]
  11. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

Enzyme Details
1. NAD(P)H dehydrogenase [quinone] 1
General function:
Involved in electron carrier activity
Specific function:
The enzyme apparently serves as a quinone reductase in connection with conjugation reactions of hydroquinons involved in detoxification pathways as well as in biosynthetic processes such as the vitamin K-dependent gamma-carboxylation of glutamate residues in prothrombin synthesis.
Gene Name:
NQO1
Uniprot ID:
P15559
Molecular weight:
30867.405
Reactions
Vitamin K1 + NADH + Hydrogen Ion → Phylloquinol + NADdetails
Enzyme Details
2. Vitamin K-dependent gamma-carboxylase
General function:
Involved in 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
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. [PubMed:8473318 ]
  2. Tuan RS: Vitamin K-dependent gamma-glutamyl carboxylase activity in the chick embryonic chorioallantoic membrane. J Biol Chem. 1979 Feb 25;254(4):1356-64. [PubMed:105006 ]
  3. Reedstrom CK, Suttie JW: Comparative distribution, metabolism, and utilization of phylloquinone and menaquinone-9 in rat liver. Proc Soc Exp Biol Med. 1995 Sep;209(4):403-9. [PubMed:7638250 ]
  4. Tasatargil A, Cadir B, Dalaklioglu S, Yurdakonar E, Caglar S, Turkay C: Effects of vitamin K1 supplementation on vascular responsiveness and oxidative stress in a rat femoral osteotomy model. Cell Biochem Funct. 2007 Sep-Oct;25(5):485-90. [PubMed:16929463 ]
  5. Olson RE: The function and metabolism of vitamin K. Annu Rev Nutr. 1984;4:281-337. [PubMed:6380538 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Enzyme Details
3. Osteocalcin
General function:
Involved in regulation of bone mineralization
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:
10962.4
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. [PubMed:10418836 ]
  2. Schurgers LJ, Dissel PE, Spronk HM, Soute BA, Dhore CR, Cleutjens JP, Vermeer C: Role of vitamin K and vitamin K-dependent proteins in vascular calcification. Z Kardiol. 2001;90 Suppl 3:57-63. [PubMed:11374034 ]
  3. Vermeer C, Wolf J, Craciun AM, Knapen MH: Bone markers during a 6-month space flight: effects of vitamin K supplementation. J Gravit Physiol. 1998 Oct;5(2):65-9. [PubMed:11541904 ]
  4. Askim M: [Vitamin K in the Norwegian diet and osteoporosis]. Tidsskr Nor Laegeforen. 2001 Sep 20;121(22):2614-6. [PubMed:11668761 ]
  5. Kawana K, Takahashi M, Hoshino H, Kushida K: Circulating levels of vitamin K1, menaquinone-4, and menaquinone-7 in healthy elderly Japanese women and patients with vertebral fractures and patients with hip fractures. Endocr Res. 2001 Aug;27(3):337-43. [PubMed:11678581 ]
Enzyme Details
4. Vitamin K epoxide reductase complex subunit 1
General function:
Involved in vitamin-K-epoxide reductase (warfarin-sensi
Specific function:
Involved in vitamin K metabolism. Catalytic subunit of the vitamin K epoxide reductase (VKOR) complex which reduces inactive vitamin K 2,3-epoxide to active vitamin K.
Gene Name:
VKORC1
Uniprot ID:
Q9BQB6
Molecular weight:
18234.3
Reactions
Vitamin K1 + Oxidized dithiothreitol + Water → Vitamin K1 2,3-epoxide + 1,4-Dithiothreitoldetails