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Record Information
Version1.0
Created at2021-06-19 20:03:33 UTC
Updated at2021-06-29 23:54:37 UTC
NP-MRD IDNP0028071
Secondary Accession NumbersNone
Natural Product Identification
Common Name1beta-furanoyl-2beta,3alpha,7alpha,8beta,11-pentaacetoxy-4alpha,5alpha-di+
Provided ByJEOL DatabaseJEOL Logo
Description 1beta-furanoyl-2beta,3alpha,7alpha,8beta,11-pentaacetoxy-4alpha,5alpha-di+ is found in Tripterygium wilfordii. It was first documented in 2005 (Wang, X., et al.). Based on a literature review a significant number of articles have been published on 3-Furancarboxylic acid (3S,10R)-2,2,9beta-trimethyl-4alpha,5beta,7beta,8alpha-tetraacetoxy-5abeta-(acetoxymethyl)-9,10-dihydroxy-3,4,5,5a,6,7,8,9-octahydro-2H-3beta,9abeta-methano-1-benzoxepin-6beta-yl ester.
Structure
Thumb
Synonyms
ValueSource
3-Furancarboxylate (3S,10R)-2,2,9b-trimethyl-4a,5b,7b,8a-tetraacetoxy-5abeta-(acetoxymethyl)-9,10-dihydroxy-3,4,5,5a,6,7,8,9-octahydro-2H-3b,9abeta-methano-1-benzoxepin-6b-yl esterGenerator
3-Furancarboxylate (3S,10R)-2,2,9beta-trimethyl-4alpha,5beta,7beta,8alpha-tetraacetoxy-5abeta-(acetoxymethyl)-9,10-dihydroxy-3,4,5,5a,6,7,8,9-octahydro-2H-3beta,9abeta-methano-1-benzoxepin-6beta-yl esterGenerator
3-Furancarboxylate (3S,10R)-2,2,9β-trimethyl-4α,5β,7β,8α-tetraacetoxy-5abeta-(acetoxymethyl)-9,10-dihydroxy-3,4,5,5a,6,7,8,9-octahydro-2H-3β,9abeta-methano-1-benzoxepin-6β-yl esterGenerator
3-Furancarboxylic acid (3S,10R)-2,2,9b-trimethyl-4a,5b,7b,8a-tetraacetoxy-5abeta-(acetoxymethyl)-9,10-dihydroxy-3,4,5,5a,6,7,8,9-octahydro-2H-3b,9abeta-methano-1-benzoxepin-6b-yl esterGenerator
3-Furancarboxylic acid (3S,10R)-2,2,9β-trimethyl-4α,5β,7β,8α-tetraacetoxy-5abeta-(acetoxymethyl)-9,10-dihydroxy-3,4,5,5a,6,7,8,9-octahydro-2H-3β,9abeta-methano-1-benzoxepin-6β-yl esterGenerator
Chemical FormulaC30H38O16
Average Mass654.6180 Da
Monoisotopic Mass654.21599 Da
IUPAC Name(1S,2S,3S,4R,5R,6R,7S,8S,9S,12R)-3,4,7,8-tetrakis(acetyloxy)-6-[(acetyloxy)methyl]-2,12-dihydroxy-2,10,10-trimethyl-11-oxatricyclo[7.2.1.0^{1,6}]dodecan-5-yl furan-3-carboxylate
Traditional Name(1S,2S,3S,4R,5R,6R,7S,8S,9S,12R)-3,4,7,8-tetrakis(acetyloxy)-6-[(acetyloxy)methyl]-2,12-dihydroxy-2,10,10-trimethyl-11-oxatricyclo[7.2.1.0^{1,6}]dodecan-5-yl furan-3-carboxylate
CAS Registry NumberNot Available
SMILES
[H]O[C@]1([H])[C@@]2([H])[C@]([H])(OC(=O)C([H])([H])[H])[C@@]([H])(OC(=O)C([H])([H])[H])[C@]3(C([H])([H])OC(=O)C([H])([H])[H])[C@@]([H])(OC(=O)C4=C([H])OC([H])=C4[H])[C@@]([H])(OC(=O)C([H])([H])[H])[C@]([H])(OC(=O)C([H])([H])[H])[C@@](O[H])(C([H])([H])[H])[C@@]13OC2(C([H])([H])[H])C([H])([H])[H]
InChI Identifier
InChI=1S/C30H38O16/c1-13(31)40-12-29-24(44-17(5)35)20(41-14(2)32)19-22(36)30(29,46-27(19,6)7)28(8,38)23(43-16(4)34)21(42-15(3)33)25(29)45-26(37)18-9-10-39-11-18/h9-11,19-25,36,38H,12H2,1-8H3/t19-,20+,21+,22-,23+,24-,25+,28+,29-,30+/m1/s1
InChI KeyFELPYEJQNHFWHQ-ZSEVBWKXSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 300 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Tripterygium wilfordiiJEOL database
    • Wang, X., et al, Chem. Pharm. Bull. 53, 607 (2005)
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hexacarboxylic acids and derivatives. These are carboxylic acids containing exactly six carboxyl groups.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassHexacarboxylic acids and derivatives
Direct ParentHexacarboxylic acids and derivatives
Alternative Parents
Substituents
  • Hexacarboxylic acid or derivatives
  • Agarofuran
  • Sesquiterpenoid
  • Furoic acid ester
  • Furoic acid or derivatives
  • Furan-3-carboxylic acid ester
  • Furan-3-carboxylic acid or derivatives
  • Oxepane
  • Cyclitol or derivatives
  • Cyclic alcohol
  • Furan
  • Heteroaromatic compound
  • Tertiary alcohol
  • Tetrahydrofuran
  • Carboxylic acid ester
  • Secondary alcohol
  • Ether
  • Dialkyl ether
  • Oxacycle
  • Organoheterocyclic compound
  • Organic oxide
  • Organooxygen compound
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxygen compound
  • Carbonyl group
  • 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
logP1.68ALOGPS
logP-0.79ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)12.67ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area220.63 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity145.63 m³·mol⁻¹ChemAxon
Polarizability62.13 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID9344843
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11169748
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Wang, X., et al. (2005). Wang, X., et al, Chem. Pharm. Bull. 53, 607 (2005). Chem. Pharm. Bull..