ALKANET ROOT, EXTRACT (ALKANNA TINCTORIA TAUSCH) (CHEM004634)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-19 01:53:05 UTC
Update Date2016-11-09 01:09:23 UTC
Accession NumberCHEM004634
Identification
Common NameALKANET ROOT, EXTRACT (ALKANNA TINCTORIA TAUSCH)
ClassSmall Molecule
DescriptionAlkannin is a natural dye that is obtained from the extracts of plants from the borage family Alkanna tinctoria that are found in the south of France. The dye is used as a food coloring and in cosmetics. It is used as a red-brown food additive in regions such as Australia, and is designated in Europe as the E number E103, but is no longer approved for use. Alkannin has a deep red color in a greasy or oily environment and a violet color in an alkaline environment.The chemical structure as a naphthoquinone derivative was first determined by Brockmann in 1936. The enantiomer of alkannin is known as shikonin, and the racemic mixture of the two is known as shikalkin.The enzyme 4-hydroxybenzoate geranyltransferase utilizes geranyl diphosphate and 4-hydroxybenzoate to produce 3-geranyl-4-hydroxybenzoate and diphosphate. These compounds are then used to form alkannin.Alkannin is an antioxidant and has an antimicrobial effect against Staphylococcus aureus and Staphylococcus epidermidis. It is also known to have wound healing, antitumor, and antithrombotic properties. Shikonin is also found in the Chinese herbal medicine plant Lithospermum erythrorhizon, the red-root gromwell, (紫草 zicao, Pinyin: zǐcǎo).
Contaminant Sources
  • EAFUS Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
e103ChEMBL
AlkanninMeSH
Chemical FormulaC16H16O5
Average Molecular Mass288.299 g/mol
Monoisotopic Mass288.100 g/mol
CAS Registry Number23444-65-7
IUPAC Name5,8-dihydroxy-2-[(1S)-1-hydroxy-4-methylpent-3-en-1-yl]-1,4-dihydronaphthalene-1,4-dione
Traditional Namealkannin
SMILES[H][C@](O)(CC=C(C)C)C1=CC(=O)C2=C(O)C=CC(O)=C2C1=O
InChI IdentifierInChI=1S/C16H16O5/c1-8(2)3-4-10(17)9-7-13(20)14-11(18)5-6-12(19)15(14)16(9)21/h3,5-7,10,17-19H,4H2,1-2H3/t10-/m0/s1
InChI KeyNEZONWMXZKDMKF-JTQLQIEISA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as naphthoquinones. Naphthoquinones are compounds containing a naphthohydroquinone moiety, which consists of a benzene ring linearly fused to a bezene-1,4-dione (quinone).
KingdomOrganic compounds
Super ClassBenzenoids
ClassNaphthalenes
Sub ClassNaphthoquinones
Direct ParentNaphthoquinones
Alternative Parents
Substituents
  • Naphthoquinone
  • Aromatic monoterpenoid
  • Bicyclic monoterpenoid
  • Monoterpenoid
  • Aryl ketone
  • Quinone
  • 1-hydroxy-2-unsubstituted benzenoid
  • Vinylogous acid
  • Ketone
  • Secondary alcohol
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
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 Solubility0.24 g/LALOGPS
logP2.19ALOGPS
logP3.01ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)8.49ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity79.82 m³·mol⁻¹ChemAxon
Polarizability29.8 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dr-0090000000-075012fc8e371dc2176eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fy9-3690000000-91f11e32821de969fc96Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gbc-9230000000-192f49a494c02eaf64b3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-d06cd6d33d99ce2f26d7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-2790000000-649136aee6eabbfaaf17Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-2900000000-bbd3966288658c0b712fSpectrum
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 IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDC00002787
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkAlkannin
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID72521
Kegg Compound IDC10292
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available