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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 01:39:42 UTC
Update Date2022-03-07 02:56:28 UTC
HMDB IDHMDB0040123
Secondary Accession Numbers
  • HMDB40123
Metabolite Identification
Common NameCentellasaponin B
DescriptionCentellasaponin B 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. Based on a literature review a significant number of articles have been published on Centellasaponin B.
Structure
Data?1563863493
Synonyms
ValueSource
(+)-Centellasaponin bHMDB
3,4,5-Trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl 8,10,11-trihydroxy-9-(hydroxymethyl)-1,2,6a,6b,9,12a-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acidGenerator
Centellasaponin bMeSH
Chemical FormulaC42H68O16
Average Molecular Weight828.9797
Monoisotopic Molecular Weight828.450736128
IUPAC Name3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl 8,10,11-trihydroxy-9-(hydroxymethyl)-1,2,6a,6b,9,12a-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylate
Traditional Name3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl 8,10,11-trihydroxy-9-(hydroxymethyl)-1,2,6a,6b,9,12a-hexamethyl-2,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydro-1H-picene-4a-carboxylate
CAS Registry Number386223-75-2
SMILES
CC1CCC2(CCC3(C)C(=CCC4C5(C)CC(O)C(O)C(C)(CO)C5C(O)CC34C)C2C1C)C(=O)OC1OC(COC2OC(CO)C(O)C(O)C2O)C(O)C(O)C1O
InChI Identifier
InChI=1S/C42H68O16/c1-18-9-10-42(37(54)58-36-32(52)30(50)28(48)24(57-36)16-55-35-31(51)29(49)27(47)23(15-43)56-35)12-11-40(5)20(26(42)19(18)2)7-8-25-38(3)13-22(46)34(53)39(4,17-44)33(38)21(45)14-41(25,40)6/h7,18-19,21-36,43-53H,8-17H2,1-6H3
InChI KeyJSQCMNXZFPMWES-UHFFFAOYSA-N
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
  • 7-hydroxysteroid
  • Steroid
  • Disaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Oxane
  • Cyclic alcohol
  • Secondary alcohol
  • Carboxylic acid ester
  • Polyol
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Acetal
  • Carboxylic acid derivative
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Alcohol
  • Primary alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point223 - 224 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.12 g/LALOGPS
logP0.17ALOGPS
logP-1.1ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)11.89ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area276.52 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity203.27 m³·mol⁻¹ChemAxon
Polarizability88.68 ųChemAxon
Number of Rings7ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-308.32830932474
DeepCCS[M+Na]+282.21730932474
AllCCS[M+H]+274.732859911
AllCCS[M+H-H2O]+274.832859911
AllCCS[M+NH4]+274.632859911
AllCCS[M+Na]+274.532859911
AllCCS[M-H]-257.732859911
AllCCS[M+Na-2H]-263.232859911
AllCCS[M+HCOO]-269.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Centellasaponin BCC1CCC2(CCC3(C)C(=CCC4C5(C)CC(O)C(O)C(C)(CO)C5C(O)CC34C)C2C1C)C(=O)OC1OC(COC2OC(CO)C(O)C(O)C2O)C(O)C(O)C1O3770.2Standard polar33892256
Centellasaponin BCC1CCC2(CCC3(C)C(=CCC4C5(C)CC(O)C(O)C(C)(CO)C5C(O)CC34C)C2C1C)C(=O)OC1OC(COC2OC(CO)C(O)C(O)C2O)C(O)C(O)C1O5465.2Standard non polar33892256
Centellasaponin BCC1CCC2(CCC3(C)C(=CCC4C5(C)CC(O)C(O)C(C)(CO)C5C(O)CC34C)C2C1C)C(=O)OC1OC(COC2OC(CO)C(O)C(O)C2O)C(O)C(O)C1O6473.3Semi standard non polar33892256
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Centellasaponin B 10V, Positive-QTOFsplash10-01p9-0002921250-202aada2cb2ea8faa4562017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Centellasaponin B 20V, Positive-QTOFsplash10-000i-0201913110-6fe4aa883cdb3687b42d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Centellasaponin B 40V, Positive-QTOFsplash10-01p9-3502910110-352023114e6c5975fc112017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Centellasaponin B 10V, Negative-QTOFsplash10-0kbr-1411942380-3623c772742cd8d844692017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Centellasaponin B 20V, Negative-QTOFsplash10-0mdr-4712951340-83c5cd09e4acabf863ee2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Centellasaponin B 40V, Negative-QTOFsplash10-0udl-8620690100-9d729fe3a77386427a1b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Centellasaponin B 10V, Negative-QTOFsplash10-004i-0001110190-142c9e4a62e3f39baf502021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Centellasaponin B 20V, Negative-QTOFsplash10-0a6r-2000103940-8dc45c75a0b8eca16f822021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Centellasaponin B 40V, Negative-QTOFsplash10-05g0-4000900100-9315f2015d8ff5081b8a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Centellasaponin B 10V, Positive-QTOFsplash10-004i-0000313290-86e0352cbec16e2242b12021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Centellasaponin B 20V, Positive-QTOFsplash10-0554-1410937680-3ea96172f9489653cb1f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Centellasaponin B 40V, Positive-QTOFsplash10-0a4i-8942471110-b7913c4c1989c77c8bcb2021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB019816
KNApSAcK IDC00032805
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound85411973
PDB IDNot Available
ChEBI ID176324
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1881971
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.