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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-08-13 23:06:49 UTC
Update Date2022-03-07 02:49:21 UTC
HMDB IDHMDB0004649
Secondary Accession Numbers
  • HMDB04649
Metabolite Identification
Common NameDemethylphylloquinone
DescriptionDemethylphylloquinone is a form of vitamin K that occurs in nature as part of a series of compounds with a common 2-methyl-1,4 naphthoquinone nucleus and differing isoprenoid side chains at the 3 position. Vitamin K forms comprise a single major plant form, phylloquinone with a phytyl side chain and a family of bacterially synthesized menaquinones (MKs) with multiprenyl side chains. Bacterially produced menaquinones are biologically active forms of vitamin K that are present in high concentrations in the human lower bowel. Both phylloquinone and menaquinones are bioactive in hepatic gamma-carboxylation but long-chain MKs are less well absorbed. Liver stores of vitamin K are relatively small. The hepatic reserves of phylloquinone (approximately 10% of the total) are labile and turn over at a faster rate than menaquinones. Vitamin K is recognised as a factor required for normal blood coagulation, and in relation to its role in bone metabolism. Vitamin K is a substrate for a liver microsomal enzyme that catalyzes the conversion of specific glutamyl residues to gamma-carboxyglutamyl residues in a limited number of proteins. These include the vitamin K-dependent clotting factors: prothrombin (factor II), factor VII, factor IX, and factor X. In the absence of vitamin K, nonfunctional clotting factors are synthesized and hemorrhage can result. Vitamin K is a coenzyme for glutamate carboxylase, which mediates the conversion of glutamate to gamma-carboxyglutamate (Gla). There are at least three Gla proteins associated with bone tissue, of which osteocalcin is the most abundant and best known. Trabecular and cortical bone appear to contain substantial concentrations of both phylloquinone and menaquinones. (PMID: 8642453 , 8527227 , 15018483 , 1573141 ).
Structure
Data?1599944340
Synonyms
ValueSource
PHNQ CPDHMDB
2-Phytyl-1,4-naphthoquinoneHMDB
2-[(2E,7R,11R)-3,7,11,15-Tetramethyl-2-hexadecenyl]-1,4-naphthalenedioneHMDB
Nor-alpha-phylloquinoneHMDB
Nor-α-phylloquinoneHMDB
Norvitamin KHMDB
DemethylphylloquinoneChEBI
Chemical FormulaC30H44O2
Average Molecular Weight436.68
Monoisotopic Molecular Weight436.334130657
IUPAC Name2-[(2E,7R,11R)-3,7,11,15-tetramethylhexadec-2-en-1-yl]-1,4-dihydronaphthalene-1,4-dione
Traditional Name2-phytyl-1,4-naphthoquinone
CAS Registry Number34625-86-0
SMILES
CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC\C(C)=C\CC1=CC(=O)C2=CC=CC=C2C1=O
InChI Identifier
InChI=1S/C30H44O2/c1-22(2)11-8-12-23(3)13-9-14-24(4)15-10-16-25(5)19-20-26-21-29(31)27-17-6-7-18-28(27)30(26)32/h6-7,17-19,21-24H,8-16,20H2,1-5H3/b25-19+/t23-,24-/m1/s1
InChI KeyUDYIPZFWVJJQJF-KQPZCCJBSA-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.
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
Disposition

Biological location

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP8.719Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility3.7e-05 g/LALOGPS
logP8.38ALOGPS
logP9.3ChemAxon
logS-7.1ALOGPS
pKa (Strongest Acidic)12.48ChemAxon
pKa (Strongest Basic)-7.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity138.6 m³·mol⁻¹ChemAxon
Polarizability54.23 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+212.31530932474
DeepCCS[M-H]-209.95730932474
DeepCCS[M-2H]-242.84130932474
DeepCCS[M+Na]+218.83230932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DemethylphylloquinoneCC(C)CCC[C@@H](C)CCC[C@@H](C)CCC\C(C)=C\CC1=CC(=O)C2=CC=CC=C2C1=O4267.0Standard polar33892256
DemethylphylloquinoneCC(C)CCC[C@@H](C)CCC[C@@H](C)CCC\C(C)=C\CC1=CC(=O)C2=CC=CC=C2C1=O3311.8Standard non polar33892256
DemethylphylloquinoneCC(C)CCC[C@@H](C)CCC[C@@H](C)CCC\C(C)=C\CC1=CC(=O)C2=CC=CC=C2C1=O3394.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Demethylphylloquinone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Demethylphylloquinone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Demethylphylloquinone 10V, Positive-QTOFsplash10-000i-0125900000-60ee1796aba3070aecfd2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Demethylphylloquinone 20V, Positive-QTOFsplash10-00di-4912000000-0c3cb0b67fd0cded41a82021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Demethylphylloquinone 40V, Positive-QTOFsplash10-05fr-2910000000-1f5a699bad595e9e17812021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Demethylphylloquinone 10V, Negative-QTOFsplash10-000i-0000900000-386f84e878751722959d2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Demethylphylloquinone 20V, Negative-QTOFsplash10-00dr-0900700000-4029e6872c46a289779a2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Demethylphylloquinone 40V, Negative-QTOFsplash10-0fl1-0968300000-5c6ffbc09a6370adf5ae2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023391
KNApSAcK IDNot Available
Chemspider ID26333244
KEGG Compound IDNot Available
BioCyc IDCPD-6947
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound56927684
PDB IDNot Available
ChEBI ID31087
Food Biomarker OntologyNot Available
VMH IDDMPHQNO
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Shearer MJ, Bach A, Kohlmeier M: Chemistry, nutritional sources, tissue distribution and metabolism of vitamin K with special reference to bone health. J Nutr. 1996 Apr;126(4 Suppl):1181S-6S. [PubMed:8642453 ]
  2. Suttie JW: The importance of menaquinones in human nutrition. Annu Rev Nutr. 1995;15:399-417. [PubMed:8527227 ]
  3. Bugel S: Vitamin K and bone health. Proc Nutr Soc. 2003 Nov;62(4):839-43. [PubMed:15018483 ]
  4. Suttie JW: Vitamin K and human nutrition. J Am Diet Assoc. 1992 May;92(5):585-90. [PubMed:1573141 ]