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Record Information
Version2.0
Created at2022-04-28 01:00:14 UTC
Updated at2022-04-28 01:00:14 UTC
NP-MRD IDNP0054751
Secondary Accession NumbersNone
Natural Product Identification
Common NameDerricidin
DescriptionDerricidin belongs to the class of organic compounds known as 2'-hydroxychalcones. These are organic compounds containing chalcone skeleton that carries a hydroxyl group at the 2'-position. Thus, derricidin is considered to be a flavonoid. Derricidin is found in Derris floribunda , Derris sericea, Lonchocarpus guatemalensis, Lonchocarpus neuroscapha, Lonchocarpus sericeus, Lonchocarpus xuul and Millettia erythrocalyx. Derricidin was first documented in 2015 (PMID: 25973483). Based on a literature review a small amount of articles have been published on Derricidin (PMID: 32530447) (PMID: 25775405).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC20H20O3
Average Mass308.3770 Da
Monoisotopic Mass308.14124 Da
IUPAC Name(2E)-1-{2-hydroxy-4-[(3-methylbut-2-en-1-yl)oxy]phenyl}-3-phenylprop-2-en-1-one
Traditional Namederricidin
CAS Registry NumberNot Available
SMILES
CC(C)=CCOC1=CC(O)=C(C=C1)C(=O)\C=C\C1=CC=CC=C1
InChI Identifier
InChI=1S/C20H20O3/c1-15(2)12-13-23-17-9-10-18(20(22)14-17)19(21)11-8-16-6-4-3-5-7-16/h3-12,14,22H,13H2,1-2H3/b11-8+
InChI KeyDGUGLZYULGVSIZ-DHZHZOJOSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Derris floribundaPlant
Derris sericeaPlant
Lonchocarpus guatemalensisPlant
Lonchocarpus neuroscaphaPlant
Lonchocarpus sericeusLOTUS Database
Lonchocarpus xuulPlant
Millettia erythrocalyxPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 2'-hydroxychalcones. These are organic compounds containing chalcone skeleton that carries a hydroxyl group at the 2'-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassLinear 1,3-diarylpropanoids
Sub ClassChalcones and dihydrochalcones
Direct Parent2'-Hydroxychalcones
Alternative Parents
Substituents
  • 2'-hydroxychalcone
  • Cinnamylphenol
  • Phenoxy compound
  • Benzoyl
  • Phenol ether
  • Styrene
  • Aryl ketone
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Benzenoid
  • Acryloyl-group
  • Enone
  • Vinylogous acid
  • Alpha,beta-unsaturated ketone
  • Ketone
  • Ether
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
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
logP4.49ALOGPS
logP5.44ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)7.09ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity94.44 m³·mol⁻¹ChemAxon
Polarizability35.3 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00007053
Chemspider ID4763974
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5961410
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Nabekura T, Kawasaki T, Kato Y, Kawai K, Fiorito S, Epifano F, Genovese S, Uwai Y: Citrus auraptene induces drug efflux transporter P-glycoprotein expression in human intestinal cells. Food Funct. 2020 Jun 24;11(6):5017-5023. doi: 10.1039/d0fo00315h. [PubMed:32530447 ]
  2. Taddeo VA, Epifano F, Genovese S, Fiorito S: Inhibition of soybean 15-lipoxygenase by naturally occurring acetophenones and derricidin. Nat Prod Commun. 2015 Apr;10(4):589-90. [PubMed:25973483 ]
  3. Fonseca BF, Predes D, Cerqueira DM, Reis AH, Amado NG, Cayres MC, Kuster RM, Oliveira FL, Mendes FA, Abreu JG: Derricin and derricidin inhibit Wnt/beta-catenin signaling and suppress colon cancer cell growth in vitro. PLoS One. 2015 Mar 16;10(3):e0120919. doi: 10.1371/journal.pone.0120919. eCollection 2015. [PubMed:25775405 ]