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Record Information
Version1.0
Created at2022-09-05 23:41:10 UTC
Updated at2022-09-05 23:41:10 UTC
NP-MRD IDNP0221969
Secondary Accession NumbersNone
Natural Product Identification
Common Name5,8,9-trihydroxy-2,2-dimethyl-12-(3-methylbut-2-en-1-yl)-1,11-dioxatetracen-6-one
Description1,6,7-Trihydroxy-6',6'-dimethyl-2H-pyrano(2',3':3,2)-4-(3-Methylbut-2-enyl)xanthone belongs to the class of organic compounds known as 4-prenylated xanthones. These are organic compounds containing a C5-isoprenoid group linked to a xanthone moiety at the 4-position. Xanthone is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring that carries a ketone group. 5,8,9-trihydroxy-2,2-dimethyl-12-(3-methylbut-2-en-1-yl)-1,11-dioxatetracen-6-one is found in Garcinia lancilimba. It was first documented in 2007 (PMID: 17541202). 1,6,7-Trihydroxy-6',6'-dimethyl-2H-pyrano(2',3':3,2)-4-(3-Methylbut-2-enyl)xanthone is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC23H22O6
Average Mass394.4230 Da
Monoisotopic Mass394.14164 Da
IUPAC Name5,8,9-trihydroxy-2,2-dimethyl-12-(3-methylbut-2-en-1-yl)-2,6-dihydro-1,11-dioxatetracen-6-one
Traditional Name5,8,9-trihydroxy-2,2-dimethyl-12-(3-methylbut-2-en-1-yl)-1,11-dioxatetracen-6-one
CAS Registry NumberNot Available
SMILES
CC(C)=CCC1=C2OC3=CC(O)=C(O)C=C3C(=O)C2=C(O)C2=C1OC(C)(C)C=C2
InChI Identifier
InChI=1S/C23H22O6/c1-11(2)5-6-13-21-12(7-8-23(3,4)29-21)19(26)18-20(27)14-9-15(24)16(25)10-17(14)28-22(13)18/h5,7-10,24-26H,6H2,1-4H3
InChI KeyPIGUNUPUFZDCAM-UHFFFAOYSA-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
Garcinia lancilimbaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 4-prenylated xanthones. These are organic compounds containing a C5-isoprenoid group linked to a xanthone moiety at the 4-position. Xanthone is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring that carries a ketone group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzopyrans
Sub Class1-benzopyrans
Direct Parent4-prenylated xanthones
Alternative Parents
Substituents
  • 4-prenylated xanthone
  • Pyranoxanthone
  • Pyranochromene
  • 2,2-dimethyl-1-benzopyran
  • Chromone
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Pyranone
  • Pyran
  • Benzenoid
  • Heteroaromatic compound
  • Vinylogous acid
  • Polyol
  • Ether
  • Oxacycle
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • 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
logP4.58ALOGPS
logP5.33ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)7.46ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area96.22 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity111.4 m³·mol⁻¹ChemAxon
Polarizability42.46 ųChemAxon
Number of Rings4ChemAxon
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 IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound16743993
PDB IDNot Available
ChEBI ID66793
Good Scents IDNot Available
References
General References
  1. Yang NY, Han QB, Cao XW, Qiao CF, Song JZ, Chen SL, Yang DJ, Yiu H, Xu HX: Two new xanthones isolated from the stem bark of Garcinia lancilimba. Chem Pharm Bull (Tokyo). 2007 Jun;55(6):950-2. doi: 10.1248/cpb.55.950. [PubMed:17541202 ]
  2. LOTUS database [Link]