Showing Compound Card for Vitamin K (CDB000391)

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Record Information
Version1.0
Created at2020-03-19 00:34:35 UTC
Updated at2020-11-18 16:35:09 UTC
CannabisDB IDCDB000391
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameVitamin K
DescriptionVitamin K is often called vitamin K1, also known as Phylloquinone or Phytonadione. Vitamin K1 is a polycyclic aromatic ketone, based on 1,4-naphthoquinone, with 2-methyl and 3-phytyl substituents. Vitamin K belongs to a family of phylloquinones that contain a ring of 2-methyl-1,4-naphthoquinone and an isoprenoid side chain. Vitamin K1 has only one double bond on the proximal isoprene unit. Several forms of vitamin K have been identified: vitamin K1 derived from plants, vitamin K2 (menaquinone) from bacteria and vitamin K3, synthetic naphthoquinone provitamins such as menadione (PMID: 27337968 ). The synthetic Vitamin K, K3, is toxic to animals as it interferes with glutathione. Vitamin K1 is a fat-soluble vitamin that is stable to air and moisture but decomposes in sunlight. Rich sources of vitamin K1 include green plants, algae, and photosynthetic bacteria. It is found naturally in a wide variety of green plants including Cannabis sativa (PMID: 6991645 ). The plant derived Vitamin K1 is used by animals and is converted to the following coagulation factors in the liver: active prothrombin (factor II), proconvertin (factor VII), plasma thromboplastin component (factor IX), and Stuart factor (factor X). Vitamin K1 is concerted to Vitamin K2 by the gut microflora. Vitamin K1 is an antidote for coumatetralyl, the anti-coagulant rodent poison. Vitamin K1 has antihemorrhagic and prothrombogenic activity and is used to treat bleeding disorders which include in warfarin overdose, vitamin K deficiency, and obstructive jaundice ( Ref:DOI ).
Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC31H46O2
Average Molecular Weight450.71
Monoisotopic Molecular Weight450.3498
IUPAC Name2-methyl-3-[(7R,11S)-3,7,11,15-tetramethylhexadec-2-en-1-yl]-1,4-dihydronaphthalene-1,4-dione
Traditional Name2-methyl-3-[(7R,11S)-3,7,11,15-tetramethylhexadec-2-en-1-yl]naphthalene-1,4-dione
CAS Registry Number12001-79-5
SMILES
CC(C)CCC[C@H](C)CCC[C@@H](C)CCCC(C)=CCC1=C(C)C(=O)C2=CC=CC=C2C1=O
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/t23-,24+/m0/s1
InChI KeyMBWXNTAXLNYFJB-BJKOFHAPSA-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 DescriptorsNot Available
Ontology
Not Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Polarizability57.35 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available2020-06-30View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. Basset GJ, Latimer S, Fatihi A, Soubeyrand E, Block A: Phylloquinone (Vitamin K1): Occurrence, Biosynthesis and Functions. Mini Rev Med Chem. 2017;17(12):1028-1038. doi: 10.2174/1389557516666160623082714. [PubMed:27337968 ]
  2. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]