Np mrd loader

You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on NP-MRD.
Record Information
Version1.0
Created at2021-06-19 23:56:43 UTC
Updated at2021-06-30 00:03:07 UTC
NP-MRD IDNP0033383
Secondary Accession NumbersNone
Natural Product Identification
Common Name3,23-disulfate ester of 29-hydroxyhederagenin
Provided ByJEOL DatabaseJEOL Logo
Description29-Hydroxy-3beta,23-bis(sulfooxy)oleana-12-ene-28-oic acid belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. 3,23-disulfate ester of 29-hydroxyhederagenin is found in Melissa officinalis. It was first documented in 2007 (Mencherini, T., et al.). Based on a literature review very few articles have been published on 29-Hydroxy-3beta,23-bis(sulfooxy)oleana-12-ene-28-oic acid.
Structure
Thumb
Synonyms
ValueSource
29-Hydroxy-3b,23-bis(sulfooxy)oleana-12-ene-28-OateGenerator
29-Hydroxy-3b,23-bis(sulfooxy)oleana-12-ene-28-Oic acidGenerator
29-Hydroxy-3b,23-bis(sulphooxy)oleana-12-ene-28-OateGenerator
29-Hydroxy-3b,23-bis(sulphooxy)oleana-12-ene-28-Oic acidGenerator
29-Hydroxy-3beta,23-bis(sulfooxy)oleana-12-ene-28-OateGenerator
29-Hydroxy-3beta,23-bis(sulphooxy)oleana-12-ene-28-OateGenerator
29-Hydroxy-3beta,23-bis(sulphooxy)oleana-12-ene-28-Oic acidGenerator
29-Hydroxy-3β,23-bis(sulfooxy)oleana-12-ene-28-OateGenerator
29-Hydroxy-3β,23-bis(sulfooxy)oleana-12-ene-28-Oic acidGenerator
29-Hydroxy-3β,23-bis(sulphooxy)oleana-12-ene-28-OateGenerator
29-Hydroxy-3β,23-bis(sulphooxy)oleana-12-ene-28-Oic acidGenerator
Chemical FormulaC30H48O11S2
Average Mass648.8200 Da
Monoisotopic Mass648.26380 Da
IUPAC Name(2R,4aR,6aS,6bR,8aR,9R,10S,12aR,12bR,14bS)-2-(hydroxymethyl)-2,6a,6b,9,12a-pentamethyl-10-(sulfooxy)-9-[(sulfooxy)methyl]-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid
Traditional Name(2R,4aR,6aS,6bR,8aR,9R,10S,12aR,12bR,14bS)-2-(hydroxymethyl)-2,6a,6b,9,12a-pentamethyl-10-(sulfooxy)-9-[(sulfooxy)methyl]-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylic acid
CAS Registry NumberNot Available
SMILES
[H]OC(=O)[C@@]12C([H])([H])C([H])([H])[C@@]3(C(=C([H])C([H])([H])[C@]4([H])[C@@]5(C([H])([H])[H])C([H])([H])C([H])([H])[C@]([H])(O[S](=O)(=O)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@@]34C([H])([H])[H])[C@]1([H])C([H])([H])[C@](C([H])([H])[H])(C([H])([H])O[H])C([H])([H])C2([H])[H])C([H])([H])[H]
InChI Identifier
InChI=1S/C30H48O11S2/c1-25(17-31)12-14-30(24(32)33)15-13-28(4)19(20(30)16-25)6-7-22-26(2)10-9-23(41-43(37,38)39)27(3,18-40-42(34,35)36)21(26)8-11-29(22,28)5/h6,20-23,31H,7-18H2,1-5H3,(H,32,33)(H,34,35,36)(H,37,38,39)/t20-,21+,22+,23-,25+,26-,27-,28+,29+,30-/m0/s1
InChI KeyXQMVPBYOHLDJAR-LYABJINESA-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. 70, 1889 (2007)
Chemical Taxonomy
Description Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTriterpenoids
Direct ParentTriterpenoids
Alternative Parents
Substituents
  • Triterpenoid
  • Sulfated steroid skeleton
  • Steroid
  • Sulfuric acid ester
  • Alkyl sulfate
  • Sulfate-ester
  • Sulfuric acid monoester
  • Organic sulfuric acid or derivatives
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic 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
logP-0.22ALOGPS
logP1.03ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)-2ChemAxon
pKa (Strongest Basic)-1ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area184.73 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity157.16 m³·mol⁻¹ChemAxon
Polarizability66.45 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
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 IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound24763403
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Mencherini, T., et al. (2007). Mencherini, T., et al, J. Nat. Prod. 70, 1889 (2007). J. Nat. Prod..