Showing Compound Card for Phylloquinol (CDB005220)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (3) Show 3 proteinsXML
Record Information
Version1.0
Created at2020-04-17 19:21:22 UTC
Updated at2020-12-07 19:11:47 UTC
CannabisDB IDCDB005220
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NamePhylloquinol
DescriptionPhylloquinol, also known as phytonadiol or dihydrovitamin K1, belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. Thus, phylloquinol is considered to be a quinone lipid molecule. Phylloquinol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Phylloquinol is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
PhytonadiolChEBI
Vitamin K hydroquinoneChEBI
Vitamin K1 hydroquinoneChEBI
Reduced vitamin K1HMDB
Dihydrovitamin K1HMDB
Dihydroxyvitamin KHMDB
Reduced vitamin KHMDB
[R-[R*,r*-(e)]]-2-methyl-3-(3,7,11,15-tetramethyl-2-hexadecenyl)-1,4-naphthalenediolHMDB
2-Methyl-3-[(2E,7R,11R)-3,7,11,15-tetramethyl-2-hexadecenyl]-1,4-naphthalenediolHMDB
(e)-2-Methyl-3-phytyl-1,4-naphthalenediolHMDB
2-Methyl-3-[(2E,7R,11R)-3,7,11,15-tetramethyl-2-hexadecen-1-yl]-1,4-naphthalenediolHMDB
2-Methyl-3-phytyl-1,4-naphthohydroquinoneHMDB
Dihydro-phylloquinoneHMDB
Reduced phylloquinoneHMDB
Α-phyllohydroquinoneHMDB
alpha-PhyllohydroquinoneHMDB
PhylloquinolHMDB
Chemical FormulaC31H48O2
Average Molecular Weight452.71
Monoisotopic Molecular Weight452.3654
IUPAC Name2-methyl-3-[(2E,7R,11R)-3,7,11,15-tetramethylhexadec-2-en-1-yl]naphthalene-1,4-diol
Traditional Namevitamin K hydroquinone
CAS Registry Number572-96-3
SMILES
CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC\C(C)=C\CC1=C(O)C2=C(C=CC=C2)C(O)=C1C
InChI Identifier
InChI=1S/C31H48O2/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/h7-8,18-20,22-24,32-33H,9-17,21H2,1-6H3/b25-20+/t23-,24-/m1/s1
InChI KeyBUFJIHPUGZHTHL-NKFFZRIASA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassDiterpenoids
Direct ParentDiterpenoids
Alternative Parents
Substituents
  • Diterpenoid
  • Prenylbenzoquinol
  • 1-naphthol
  • Naphthalene
  • Hydroquinone
  • Benzenoid
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP9ALOGPS
logP10.79ChemAxon
logS-7ALOGPS
pKa (Strongest Acidic)9.38ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity144.61 m³·mol⁻¹ChemAxon
Polarizability56.91 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSPhylloquinol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000l-7985400000-4cfe604c94178a729cf3Spectrum
Predicted GC-MSPhylloquinol, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-001i-3202290000-25d2205e065a0bc3f3c6Spectrum
Predicted GC-MSPhylloquinol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0231900000-da7eef794d2e18b29e5e2017-10-06View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05ra-4894400000-0c348ad8b15b7a4285702017-10-06View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9772200000-7096132ee959664099b92017-10-06View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000900000-dddf4ff7cce1cd10e63d2017-10-06View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0000900000-0e62002f1cd3fa58a8762017-10-06View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-1922500000-1cdb8ac94dc6ec135bc12017-10-06View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0213900000-8b373faac5ad9f297e5b2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4s-9606200000-8fc6ca059ad0776f02f12021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-053b-9640000000-1310e158a977feb080ac2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000900000-ce8af0c741feb6e6a8a12021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udr-0510900000-67cf209cf7be0a03a70a2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-02tj-0629300000-4674747e6c430d2d5c932021-09-24View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
NAD(P)H dehydrogenase [quinone] 1NQO116q22.1P15559 details
Vitamin K-dependent gamma-carboxylaseGGCX2p12P38435 details
Vitamin K epoxide reductase complex subunit 1VKORC116p11.2Q9BQB6 details
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0004198
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB031116
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC03313
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5280585
PDB IDNot Available
ChEBI ID28433
References
General ReferencesNot Available

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
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
Enzyme Details
3. 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