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Record Information
Version1.0
Created at2021-06-20 18:21:06 UTC
Updated at2021-06-30 00:05:15 UTC
NP-MRD IDNP0034695
Secondary Accession NumbersNone
Natural Product Identification
Common Nameniga-ichigoside F1 23-sulfate ester
Provided ByJEOL DatabaseJEOL Logo
DescriptionCHEMBL1078217 belongs to the class of organic compounds known as triterpene saponins. These are glycosylated derivatives of triterpene sapogenins. The sapogenin moiety backbone is usually based on the oleanane, ursane, taraxastane, bauerane, lanostane, lupeol, lupane, dammarane, cycloartane, friedelane, hopane, 9b,19-cyclo-lanostane, cycloartane, or cycloartanol skeleton. niga-ichigoside F1 23-sulfate ester is found in Melissa officinalis. It was first documented in 2009 (Mencherini, T., et al.). Based on a literature review very few articles have been published on CHEMBL1078217.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC36H58O14S
Average Mass746.9100 Da
Monoisotopic Mass746.35473 Da
IUPAC Name{[(2R,3R,4R,4aR,6aR,6bS,8aS,11R,12R,12aS,14aR,14bR)-2,3,12-trihydroxy-4,6a,6b,11,12,14b-hexamethyl-8a-({[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}carbonyl)-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-4-yl]methoxy}sulfonic acid
Traditional Name[(2R,3R,4R,4aR,6aR,6bS,8aS,11R,12R,12aS,14aR,14bR)-2,3,12-trihydroxy-4,6a,6b,11,12,14b-hexamethyl-8a-({[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}carbonyl)-1,2,3,4a,5,6,7,8,9,10,11,12a,14,14a-tetradecahydropicen-4-yl]methoxysulfonic acid
CAS Registry NumberNot Available
SMILES
[H]OC([H])([H])[C@@]1([H])O[C@@]([H])(OC(=O)[C@]23C([H])([H])C([H])([H])[C@@]([H])(C([H])([H])[H])[C@](O[H])(C([H])([H])[H])[C@@]2([H])C2=C([H])C([H])([H])[C@]4([H])[C@@]5(C([H])([H])[H])C([H])([H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@@](C([H])([H])[H])(C([H])([H])O[S](=O)(=O)O[H])[C@]5([H])C([H])([H])C([H])([H])[C@@]4(C([H])([H])[H])[C@]2(C([H])([H])[H])C([H])([H])C3([H])[H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]1([H])O[H]
InChI Identifier
InChI=1S/C36H58O14S/c1-18-9-12-36(30(43)50-29-26(41)25(40)24(39)21(16-37)49-29)14-13-33(4)19(27(36)35(18,6)44)7-8-23-31(2)15-20(38)28(42)32(3,17-48-51(45,46)47)22(31)10-11-34(23,33)5/h7,18,20-29,37-42,44H,8-17H2,1-6H3,(H,45,46,47)/t18-,20-,21-,22-,23-,24-,25+,26-,27-,28+,29+,31+,32+,33-,34-,35-,36+/m1/s1
InChI KeyXBNZAVUJFGQQSI-JVJIQXRHSA-N
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR13C NMR Spectrum (1D, 600 MHz, CD3OD, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, CD3OD, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, CD3OD, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, CD3OD, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, CD3OD, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, CD3OD, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, CD3OD, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, CD3OD, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, CD3OD, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, CD3OD, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, CD3OD, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, CD3OD, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, CD3OD, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, CD3OD, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, CD3OD, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, CD3OD, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, CD3OD, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, CD3OD, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, CD3OD, simulated)Wishart Lab2021-06-20View Spectrum
Species
Species of Origin
Species NameSourceReference
Melissa officinalis L.
    • Mencherini, T., et al, J. Nat. Prod. 72, 1512 (2009)
Chemical Taxonomy
Description Belongs to the class of organic compounds known as triterpene saponins. These are glycosylated derivatives of triterpene sapogenins. The sapogenin moiety backbone is usually based on the oleanane, ursane, taraxastane, bauerane, lanostane, lupeol, lupane, dammarane, cycloartane, friedelane, hopane, 9b,19-cyclo-lanostane, cycloartane, or cycloartanol skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene glycosides
Direct ParentTriterpene saponins
Alternative Parents
Substituents
  • Triterpene saponin
  • Triterpenoid
  • 12-hydroxysteroid
  • Hydroxysteroid
  • 12-beta-hydroxysteroid
  • Steroid
  • Hexose monosaccharide
  • Sulfuric acid ester
  • Alkyl sulfate
  • Monosaccharide
  • Oxane
  • Sulfate-ester
  • Sulfuric acid monoester
  • Cyclic alcohol
  • Organic sulfuric acid or derivatives
  • Tertiary alcohol
  • Carboxylic acid ester
  • Secondary alcohol
  • Polyol
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Acetal
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organic oxide
  • Alcohol
  • Hydrocarbon derivative
  • Carbonyl group
  • Primary alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic 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
logP0.84ALOGPS
logP-0.58ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)-1.4ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area240.74 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity180.86 m³·mol⁻¹ChemAxon
Polarizability78.3 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
External Links
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID24655303
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound44254605
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Mencherini, T., et al. (2009). Mencherini, T., et al, J. Nat. Prod. 72, 1512 (2009). J. Nat. Prod..