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Record Information
Version2.0
Created at2022-04-28 01:39:47 UTC
Updated at2022-04-28 01:39:48 UTC
NP-MRD IDNP0055680
Secondary Accession NumbersNone
Natural Product Identification
Common NameArtocarpanone
DescriptionArtocarpanone belongs to the class of organic compounds known as 7-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone. Artocarpanone is found in Artocarpus integrifolia , Artocarpus champeden Spreng., Artocarpus heterophyllus , Mimosa hostilis and Mimosa tenuiflora. Artocarpanone was first documented in 2016 (PMID: 26834825). Based on a literature review a small amount of articles have been published on artocarpanone (PMID: 35011235) (PMID: 29943393) (PMID: 28512600) (PMID: 26304444).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC16H14O6
Average Mass302.2820 Da
Monoisotopic Mass302.07904 Da
IUPAC Name(2S)-2-(2,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-3,4-dihydro-2H-1-benzopyran-4-one
Traditional Name(2S)-2-(2,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-2,3-dihydro-1-benzopyran-4-one
CAS Registry NumberNot Available
SMILES
COC1=CC(O)=C2C(=O)C[C@H](OC2=C1)C1=CC=C(O)C=C1O
InChI Identifier
InChI=1S/C16H14O6/c1-21-9-5-12(19)16-13(20)7-14(22-15(16)6-9)10-3-2-8(17)4-11(10)18/h2-6,14,17-19H,7H2,1H3/t14-/m0/s1
InChI KeyFQGBGNHGEUOZIW-AWEZNQCLSA-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
Artocarpus champedenPlant
Artocarpus champeden Spreng.Plant
Artocarpus heterophyllusPlant
Mimosa hostilisPlant
Mimosa tenuifloraLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 7-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassO-methylated flavonoids
Direct Parent7-O-methylated flavonoids
Alternative Parents
Substituents
  • 7-methoxyflavonoid-skeleton
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • Flavanone
  • Hydroxyflavonoid
  • Flavan
  • Chromone
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Anisole
  • Aryl alkyl ketone
  • Phenol ether
  • Resorcinol
  • Aryl ketone
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Benzenoid
  • Vinylogous acid
  • Ketone
  • Organoheterocyclic compound
  • Ether
  • Oxacycle
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic 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
logP2.49ALOGPS
logP2.68ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)8.51ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area96.22 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity77.75 m³·mol⁻¹ChemAxon
Polarizability29.59 ųChemAxon
Number of Rings3ChemAxon
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 IDC00008362
Chemspider ID23339705
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound15298902
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Dej-Adisai S, Parndaeng K, Wattanapiromsakul C, Hwang JS: Three New Isoprenylated Flavones from Artocarpus chama Stem and Their Bioactivities. Molecules. 2021 Dec 21;27(1):3. doi: 10.3390/molecules27010003. [PubMed:35011235 ]
  2. Septama AW, Jantan I, Panichayupakaranant P: Flavonoids of Artocarpus heterophyllus Lam. heartwood inhibit the innate immune responses of human phagocytes. J Pharm Pharmacol. 2018 Sep;70(9):1242-1252. doi: 10.1111/jphp.12952. Epub 2018 Jun 25. [PubMed:29943393 ]
  3. Septama AW, Xiao J, Panichayupakaranant P: A synergistic effect of artocarpanone from Artocarpus heterophyllus L. (Moraceae) on the antibacterial activity of selected antibiotics and cell membrane permeability. J Intercult Ethnopharmacol. 2017 Apr 3;6(2):186-191. doi: 10.5455/jice.20170327073745. eCollection 2017 Apr-Jun. [PubMed:28512600 ]
  4. Nguyen HX, Nguyen NT, Nguyen MH, Le TH, Van Do TN, Hung TM, Nguyen MT: Tyrosinase inhibitory activity of flavonoids from Artocarpus heterophyllous. Chem Cent J. 2016 Jan 29;10:2. doi: 10.1186/s13065-016-0150-7. eCollection 2016. [PubMed:26834825 ]
  5. Dong X, Zhu Q, Dai Y, He J, Pan H, Chen J, Zheng ZP: Encapsulation artocarpanone and ascorbic acid in O/W microemulsions: Preparation, characterization, and antibrowning effects in apple juice. Food Chem. 2016 Feb 1;192:1033-40. doi: 10.1016/j.foodchem.2015.07.124. Epub 2015 Jul 28. [PubMed:26304444 ]