5C-aglycone (CHEM021844)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:13:50 UTC
Update Date2016-11-09 01:17:22 UTC
Accession NumberCHEM021844
Identification
Common Name5C-aglycone
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
2-Methyl-3-(3'-carboxy-3'-methylpropyl)-1,4-naphthoquinoneMeSH
Vitamin K1 aglycone IIMeSH
Phylloquinone aglycone IIMeSH
1,4-dihydro-a,3-Dimethyl-1,4-dioxo-2-naphthalenebutanoateHMDB
1,4-dihydro-a,3-Dimethyl-1,4-dioxo-2-naphthalenebutanoic acidHMDB
2-Methyl-3-(3'-3'-carboxymethylpropyl)-1,4-naphthoquinoneHMDB
2-Methyl-3-(3'-carboxybutyl)-1,4-naphthoquinoneHMDB
2-Methyl-3-(3-carboxybutyl)-1,4-naphthoquinoneHMDB
2-Methyl-4-(3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)butanoateGenerator, HMDB
Chemical FormulaC16H16O4
Average Molecular Mass272.296 g/mol
Monoisotopic Mass272.105 g/mol
CAS Registry Number34927-45-2
IUPAC Name2-methyl-4-(3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)butanoic acid
Traditional Name5c-aglycone
SMILESCC(CCC1=C(C)C(=O)C2=C(C=CC=C2)C1=O)C(O)=O
InChI IdentifierInChI=1S/C16H16O4/c1-9(16(19)20)7-8-11-10(2)14(17)12-5-3-4-6-13(12)15(11)18/h3-6,9H,7-8H2,1-2H3,(H,19,20)
InChI KeyALLYVKRLOHDVKI-UHFFFAOYSA-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
  • Naphthoquinone
  • Naphthalene
  • Aryl ketone
  • Quinone
  • Benzenoid
  • Ketone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.068 g/LALOGPS
logP2.38ALOGPS
logP2.84ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)3.91ChemAxon
pKa (Strongest Basic)-7.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area71.44 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity74.94 m³·mol⁻¹ChemAxon
Polarizability28.59 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-054o-4490000000-73cacce0d4ef97b05e92Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00bi-9544000000-3602db57cbb78741da08Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05fr-0190000000-463324fdd2c715fd816eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-3960000000-21c1791e79025a6764a8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-9200000000-e94f15ae4f0fb45668d5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090000000-902e52700c099a8e7343Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00fr-0190000000-a0b5e022e540719a24deSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9830000000-da8088aae199017aac7fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dr-0390000000-36945061956f0529d3abSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0910000000-e5944af6e9276ef24a04Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-3900000000-28c91d12c029a31ae909Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00b9-0090000000-774fb9d9aaa581701042Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00a9-0980000000-8fb2cf64ffa57ba6471aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000t-0900000000-27fa3802fe36aee8df09Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0004810
FooDB IDFDB023421
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID7074
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID2339843
ChEBI ID89486
PubChem Compound ID3082405
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Harrington DJ, Soper R, Edwards C, Savidge GF, Hodges SJ, Shearer MJ: Determination of the urinary aglycone metabolites of vitamin K by HPLC with redox-mode electrochemical detection. J Lipid Res. 2005 May;46(5):1053-60. Epub 2005 Feb 1.
2. Watanabe M, Toyoda M, Imada I, Morimoto H: Ubiquinone and related compounds. XXVI. The urinary metabolites of phylloquinone and alpha-tocopherol. Chem Pharm Bull (Tokyo). 1974 Jan;22(1):176-82.
3. McBurney A, Shearer MJ, Barkhan P: Preparative isolation and characterization of the urinary aglycones of vitamin K1 (phylloquinone in man. Biochem Med. 1980 Dec;24(3):250-67.