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Record Information
Version1.0
Created at2021-06-22 16:57:25 UTC
Updated at2021-06-22 16:57:25 UTC
NP-MRD IDNP0043770
Secondary Accession NumbersNone
Natural Product Identification
Common NameBurttinone
DescriptionBurttinone belongs to the class of organic compounds known as 3'-prenylated flavanones. These are flavanones that features a C5-isoprenoid substituent at the 3'-position. Thus, burttinone is considered to be a flavonoid. Burttinone is found in Erythrina abyssinica, Erythrina burttii and Erythrina lysistemon . It was first documented in 1997 (PMID: 9366096). Based on a literature review a small amount of articles have been published on Burttinone (PMID: 24665834) (PMID: 20623615) (PMID: 12150799).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC26H30O6
Average Mass438.5200 Da
Monoisotopic Mass438.20424 Da
IUPAC Name(2S)-5,7-dihydroxy-2-{3-[(1E)-3-hydroxy-3-methylbut-1-en-1-yl]-4-methoxy-5-(3-methylbut-2-en-1-yl)phenyl}-3,4-dihydro-2H-1-benzopyran-4-one
Traditional Nameburttinone
CAS Registry NumberNot Available
SMILES
COC1=C(CC=C(C)C)C=C(C=C1\C=C\C(C)(C)O)[C@@H]1CC(=O)C2=C(O)C=C(O)C=C2O1
InChI Identifier
InChI=1S/C26H30O6/c1-15(2)6-7-16-10-18(11-17(25(16)31-5)8-9-26(3,4)30)22-14-21(29)24-20(28)12-19(27)13-23(24)32-22/h6,8-13,22,27-28,30H,7,14H2,1-5H3/b9-8+/t22-/m0/s1
InChI KeyBOBWTYODGOYWRC-UVIRAJKCSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 75 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 150 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 250 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 175 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 225 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 125 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 25 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Erythrina abyssinicaLOTUS Database
Erythrina burttiiLinigton's dataset
Erythrina lysistemonPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 3'-prenylated flavanones. These are flavanones that features a C5-isoprenoid substituent at the 3'-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavans
Direct Parent3'-prenylated flavanones
Alternative Parents
Substituents
  • 3'-prenylated flavanone
  • 4p-methoxyflavonoid-skeleton
  • Hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Flavanone
  • Chromone
  • Cinnamyl alcohol
  • Chromane
  • 1-benzopyran
  • Benzopyran
  • Methoxybenzene
  • Phenol ether
  • Aryl alkyl ketone
  • Aryl ketone
  • Anisole
  • Phenoxy compound
  • Styrene
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Vinylogous acid
  • Tertiary alcohol
  • Ketone
  • Ether
  • Organoheterocyclic compound
  • Oxacycle
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic 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
logP4.33ALOGPS
logP5.25ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)7.87ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area96.22 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity126.21 m³·mol⁻¹ChemAxon
Polarizability49.3 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00014174
Chemspider ID24716962
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound42607959
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Tabata N, Ito M, Tomoda H, Omura S: Xanthohumols, diacylglycerol acyltransferase inhibitors, from Humulus lupulus. Phytochemistry. 1997 Oct;46(4):683-7. doi: 10.1016/s0031-9422(97)00157-x. [PubMed:9366096 ]
  2. Desta ZY, Sewald N, Majinda RR: New flavonoids from the stem bark of Erythrina caffra Thunb. Nat Prod Res. 2014;28(9):667-73. doi: 10.1080/14786419.2014.895726. Epub 2014 Mar 25. [PubMed:24665834 ]
  3. Chukwujekwu JC, Van Heerden FR, Van Staden J: Antibacterial activity of flavonoids from the stem bark of Erythrina caffra thunb. Phytother Res. 2011 Jan;25(1):46-8. doi: 10.1002/ptr.3159. [PubMed:20623615 ]
  4. el-Masry S, Amer ME, Abdel-Kader MS, Zaatout HH: Prenylated flavonoids of Erythrina lysistemon grown in Egypt. Phytochemistry. 2002 Aug;60(8):783-7. doi: 10.1016/s0031-9422(02)00202-9. [PubMed:12150799 ]