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Record Information
Version2.0
Created at2022-09-02 23:49:06 UTC
Updated at2022-09-02 23:49:06 UTC
NP-MRD IDNP0164855
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1e,3z)-3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)deca-1,3-dien-5-one
Description6-Dehydrogingerdione belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. (1e,3z)-3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)deca-1,3-dien-5-one is found in Zingiber officinale. (1e,3z)-3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)deca-1,3-dien-5-one was first documented in 2014 (PMID: 25162585). Based on a literature review a small amount of articles have been published on 6-Dehydrogingerdione (PMID: 28872603) (PMID: 24869427).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC17H22O4
Average Mass290.3590 Da
Monoisotopic Mass290.15181 Da
IUPAC Name(1E,3Z)-3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)deca-1,3-dien-5-one
Traditional Name(1E,3Z)-3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)deca-1,3-dien-5-one
CAS Registry NumberNot Available
SMILES
CCCCCC(=O)\C=C(/O)\C=C\C1=CC=C(O)C(OC)=C1
InChI Identifier
InChI=1S/C17H22O4/c1-3-4-5-6-14(18)12-15(19)9-7-13-8-10-16(20)17(11-13)21-2/h7-12,19-20H,3-6H2,1-2H3/b9-7+,15-12-
InChI KeyFZWNRFAUDBWSKY-QNQPVOBRSA-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
Zingiber officinaleLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassMethoxyphenols
Direct ParentMethoxyphenols
Alternative Parents
Substituents
  • Methoxyphenol
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Styrene
  • Phenol ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Acryloyl-group
  • Vinylogous acid
  • Alpha,beta-unsaturated ketone
  • Enone
  • Ketone
  • Ether
  • Enol
  • Organic oxygen compound
  • Carbonyl group
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic 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
logP3.8ALOGPS
logP3.9ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)9.21ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity85.7 m³·mol⁻¹ChemAxon
Polarizability32.85 ųChemAxon
Number of Rings1ChemAxon
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 IDC00047685
Chemspider ID11338321
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound22321203
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Liu CM, Kao CL, Tseng YT, Lo YC, Chen CY: Ginger Phytochemicals Inhibit Cell Growth and Modulate Drug Resistance Factors in Docetaxel Resistant Prostate Cancer Cell. Molecules. 2017 Sep 5;22(9). pii: molecules22091477. doi: 10.3390/molecules22091477. [PubMed:28872603 ]
  2. Huang SH, Lee CH, Wang HM, Chang YW, Lin CY, Chen CY, Chen YH: 6-Dehydrogingerdione restrains lipopolysaccharide-induced inflammatory responses in RAW 264.7 macrophages. J Agric Food Chem. 2014 Sep 17;62(37):9171-9. doi: 10.1021/jf501665v. Epub 2014 Sep 9. [PubMed:25162585 ]
  3. Yao J, Ge C, Duan D, Zhang B, Cui X, Peng S, Liu Y, Fang J: Activation of the phase II enzymes for neuroprotection by ginger active constituent 6-dehydrogingerdione in PC12 cells. J Agric Food Chem. 2014 Jun 18;62(24):5507-18. doi: 10.1021/jf405553v. Epub 2014 Jun 9. [PubMed:24869427 ]
  4. LOTUS database [Link]