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Record Information
Version2.0
Created at2022-09-06 00:21:49 UTC
Updated at2022-09-06 00:21:49 UTC
NP-MRD IDNP0222504
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1r)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-en-1-yl propanoate
DescriptionPropionylshikonin 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). (1r)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-en-1-yl propanoate is found in Lithospermum erythrorhizon. (1r)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-en-1-yl propanoate was first documented in 2009 (PMID: 19233376). Based on a literature review a small amount of articles have been published on Propionylshikonin (PMID: 29758466) (PMID: 27554028).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC19H20O6
Average Mass344.3630 Da
Monoisotopic Mass344.12599 Da
IUPAC Name(1R)-1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl propanoate
Traditional Name(1R)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-en-1-yl propanoate
CAS Registry NumberNot Available
SMILES
CCC(=O)O[C@H](CC=C(C)C)C1=CC(=O)C2=C(O)C=CC(O)=C2C1=O
InChI Identifier
InChI=1S/C19H20O6/c1-4-16(23)25-15(8-5-10(2)3)11-9-14(22)17-12(20)6-7-13(21)18(17)19(11)24/h5-7,9,15,20-21H,4,8H2,1-3H3/t15-/m1/s1
InChI KeyDLBQFLWCDFTEQG-OAHLLOKOSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Lithospermum erythrorhizonLOTUS Database
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
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External DescriptorsNot Available
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
logP4.15ChemAxon
pKa (Strongest Acidic)8.49ChemAxon
pKa (Strongest Basic)-5.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area100.9 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity93.6 m³·mol⁻¹ChemAxon
Polarizability35.97 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID135714
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound153984
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Mitra S, Dash R: Structural dynamics and quantum mechanical aspects of shikonin derivatives as CREBBP bromodomain inhibitors. J Mol Graph Model. 2018 Aug;83:42-52. doi: 10.1016/j.jmgm.2018.04.014. Epub 2018 May 4. [PubMed:29758466 ]
  2. He JM, Zhang SY, Mu Q: Online-storage recycling counter-current chromatography for preparative isolation of naphthaquinones from Arnebia euchroma (Royle) Johnst. J Chromatogr A. 2016 Sep 16;1464:79-86. doi: 10.1016/j.chroma.2016.08.022. Epub 2016 Aug 10. [PubMed:27554028 ]
  3. Albreht A, Vovk I, Simonovska B, Srbinoska M: Identification of shikonin and its ester derivatives from the roots of Echium italicum L. J Chromatogr A. 2009 Apr 10;1216(15):3156-62. doi: 10.1016/j.chroma.2009.01.098. Epub 2009 Feb 5. [PubMed:19233376 ]
  4. LOTUS database [Link]