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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:33:00 UTC
Update Date2022-09-22 18:34:24 UTC
HMDB IDHMDB0029843
Secondary Accession Numbers
  • HMDB29843
Metabolite Identification
Common NameGlycyrrhizin
DescriptionGlycyrrhizin 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 small amount of articles have been published on Glycyrrhizin.
Structure
Data?1582753474
Synonyms
ValueSource
beta-GlycyrrhizinHMDB
DermacrinHMDB
GlycyramHMDB
GlycyronHMDB
Glycyrrhetic acid 3-O-[b-D-glucuronopyranosyl-(1->2)-a-D-glucuronopyranoside]HMDB
GlycyrrhitinHMDB
Glycyrrhizin, janHMDB
GlycyrrhizinateHMDB
Glycyrrhizinic acidHMDB, MeSH
GlycyrrizinHMDB
Glycyrrhizate, zincMeSH, HMDB
Acid, glycyrrhizinicMeSH, HMDB
Dipotassium glycyrrhizinateMeSH, HMDB
Glycyrrhizinate, diammoniumMeSH, HMDB
Glycyrrhizinate, dipotassiumMeSH, HMDB
Zinc glycyrrhizateMeSH, HMDB
Acid, glycyrrhizicMeSH, HMDB
Glycyrrhizic acidMeSH, HMDB
Diammonium glycyrrhizinateMeSH, HMDB
6-({6-carboxy-2-[(11-carboxy-4,4,6a,6b,8a,11,14b-heptamethyl-14-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yl)oxy]-4,5-dihydroxyoxan-3-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylateGenerator
GlycyrrhizinMeSH
Chemical FormulaC42H62O16
Average Molecular Weight822.9321
Monoisotopic Molecular Weight822.403785936
IUPAC Name5-[(6-carboxy-3,4,5-trihydroxyoxan-2-yl)oxy]-6-[(11-carboxy-4,4,6a,6b,8a,11,14b-heptamethyl-14-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yl)oxy]-3,4-dihydroxyoxane-2-carboxylic acid
Traditional Nameammonium glycyrrhizate
CAS Registry Number1405-86-3
SMILES
CC1(C)C(CCC2(C)C1CCC1(C)C2C(=O)C=C2C3CC(C)(CCC3(C)CCC12C)C(O)=O)OC1OC(C(O)C(O)C1OC1OC(C(O)C(O)C1O)C(O)=O)C(O)=O
InChI Identifier
InChI=1S/C42H62O16/c1-37(2)21-8-11-42(7)31(20(43)16-18-19-17-39(4,36(53)54)13-12-38(19,3)14-15-41(18,42)6)40(21,5)10-9-22(37)55-35-30(26(47)25(46)29(57-35)33(51)52)58-34-27(48)23(44)24(45)28(56-34)32(49)50/h16,19,21-31,34-35,44-48H,8-15,17H2,1-7H3,(H,49,50)(H,51,52)(H,53,54)
InChI KeyLPLVUJXQOOQHMX-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
  • 1-o-glucuronide
  • O-glucuronide
  • Glucuronic acid or derivatives
  • Disaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Tricarboxylic acid or derivatives
  • Beta-hydroxy acid
  • Cyclohexenone
  • Pyran
  • Oxane
  • Hydroxy acid
  • Secondary alcohol
  • Ketone
  • Organoheterocyclic compound
  • Oxacycle
  • Polyol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Acetal
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Alcohol
  • Organooxygen compound
  • Organic oxide
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point220 °CNot Available
Boiling Point970.00 to 972.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility0.053 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP2.80Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.054 g/LALOGPS
logP2.78ALOGPS
logP3.13ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)2.96ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area267.04 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity198.83 m³·mol⁻¹ChemAxon
Polarizability86.97 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]-298.76430932474
DeepCCS[M+Na]+272.57430932474
AllCCS[M+H]+276.032859911
AllCCS[M+H-H2O]+276.032859911
AllCCS[M+NH4]+276.032859911
AllCCS[M+Na]+276.032859911
AllCCS[M-H]-244.132859911
AllCCS[M+Na-2H]-249.532859911
AllCCS[M+HCOO]-255.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
GlycyrrhizinCC1(C)C(CCC2(C)C1CCC1(C)C2C(=O)C=C2C3CC(C)(CCC3(C)CCC12C)C(O)=O)OC1OC(C(O)C(O)C1OC1OC(C(O)C(O)C1O)C(O)=O)C(O)=O4554.1Standard polar33892256
GlycyrrhizinCC1(C)C(CCC2(C)C1CCC1(C)C2C(=O)C=C2C3CC(C)(CCC3(C)CCC12C)C(O)=O)OC1OC(C(O)C(O)C1OC1OC(C(O)C(O)C1O)C(O)=O)C(O)=O5112.9Standard non polar33892256
GlycyrrhizinCC1(C)C(CCC2(C)C1CCC1(C)C2C(=O)C=C2C3CC(C)(CCC3(C)CCC12C)C(O)=O)OC1OC(C(O)C(O)C1OC1OC(C(O)C(O)C1O)C(O)=O)C(O)=O6398.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Glycyrrhizin,1TMS,isomer #1CC1(C(=O)O[Si](C)(C)C)CCC2(C)CCC3(C)C(=CC(=O)C4C5(C)CCC(OC6OC(C(=O)O)C(O)C(O)C6OC6OC(C(=O)O)C(O)C(O)C6O)C(C)(C)C5CCC43C)C2C16336.7Semi standard non polar33892256
Glycyrrhizin,1TMS,isomer #1CC1(C(=O)O[Si](C)(C)C)CCC2(C)CCC3(C)C(=CC(=O)C4C5(C)CCC(OC6OC(C(=O)O)C(O)C(O)C6OC6OC(C(=O)O)C(O)C(O)C6O)C(C)(C)C5CCC43C)C2C15555.8Standard non polar33892256
Glycyrrhizin,1TMS,isomer #2CC1(C(=O)O)CCC2(C)CCC3(C)C(=CC(=O)C4C5(C)CCC(OC6OC(C(=O)O)C(O[Si](C)(C)C)C(O)C6OC6OC(C(=O)O)C(O)C(O)C6O)C(C)(C)C5CCC43C)C2C16426.0Semi standard non polar33892256
Glycyrrhizin,1TMS,isomer #2CC1(C(=O)O)CCC2(C)CCC3(C)C(=CC(=O)C4C5(C)CCC(OC6OC(C(=O)O)C(O[Si](C)(C)C)C(O)C6OC6OC(C(=O)O)C(O)C(O)C6O)C(C)(C)C5CCC43C)C2C15581.4Standard non polar33892256
Glycyrrhizin,1TMS,isomer #3CC1(C(=O)O)CCC2(C)CCC3(C)C(=CC(=O)C4C5(C)CCC(OC6OC(C(=O)O)C(O)C(O[Si](C)(C)C)C6OC6OC(C(=O)O)C(O)C(O)C6O)C(C)(C)C5CCC43C)C2C16428.2Semi standard non polar33892256
Glycyrrhizin,1TMS,isomer #3CC1(C(=O)O)CCC2(C)CCC3(C)C(=CC(=O)C4C5(C)CCC(OC6OC(C(=O)O)C(O)C(O[Si](C)(C)C)C6OC6OC(C(=O)O)C(O)C(O)C6O)C(C)(C)C5CCC43C)C2C15563.9Standard non polar33892256
Glycyrrhizin,1TMS,isomer #4CC1(C(=O)O)CCC2(C)CCC3(C)C(=CC(=O)C4C5(C)CCC(OC6OC(C(=O)O)C(O)C(O)C6OC6OC(C(=O)O)C(O[Si](C)(C)C)C(O)C6O)C(C)(C)C5CCC43C)C2C16407.2Semi standard non polar33892256
Glycyrrhizin,1TMS,isomer #4CC1(C(=O)O)CCC2(C)CCC3(C)C(=CC(=O)C4C5(C)CCC(OC6OC(C(=O)O)C(O)C(O)C6OC6OC(C(=O)O)C(O[Si](C)(C)C)C(O)C6O)C(C)(C)C5CCC43C)C2C15568.5Standard non polar33892256
Glycyrrhizin,1TMS,isomer #5CC1(C(=O)O)CCC2(C)CCC3(C)C(=CC(=O)C4C5(C)CCC(OC6OC(C(=O)O)C(O)C(O)C6OC6OC(C(=O)O)C(O)C(O[Si](C)(C)C)C6O)C(C)(C)C5CCC43C)C2C16417.9Semi standard non polar33892256
Glycyrrhizin,1TMS,isomer #5CC1(C(=O)O)CCC2(C)CCC3(C)C(=CC(=O)C4C5(C)CCC(OC6OC(C(=O)O)C(O)C(O)C6OC6OC(C(=O)O)C(O)C(O[Si](C)(C)C)C6O)C(C)(C)C5CCC43C)C2C15568.2Standard non polar33892256
Glycyrrhizin,1TMS,isomer #6CC1(C(=O)O)CCC2(C)CCC3(C)C(=CC(=O)C4C5(C)CCC(OC6OC(C(=O)O)C(O)C(O)C6OC6OC(C(=O)O)C(O)C(O)C6O[Si](C)(C)C)C(C)(C)C5CCC43C)C2C16401.9Semi standard non polar33892256
Glycyrrhizin,1TMS,isomer #6CC1(C(=O)O)CCC2(C)CCC3(C)C(=CC(=O)C4C5(C)CCC(OC6OC(C(=O)O)C(O)C(O)C6OC6OC(C(=O)O)C(O)C(O)C6O[Si](C)(C)C)C(C)(C)C5CCC43C)C2C15560.8Standard non polar33892256
Glycyrrhizin,1TMS,isomer #7CC1(C(=O)O)CCC2(C)CCC3(C)C(=CC(=O)C4C5(C)CCC(OC6OC(C(=O)O)C(O)C(O)C6OC6OC(C(=O)O[Si](C)(C)C)C(O)C(O)C6O)C(C)(C)C5CCC43C)C2C16364.8Semi standard non polar33892256
Glycyrrhizin,1TMS,isomer #7CC1(C(=O)O)CCC2(C)CCC3(C)C(=CC(=O)C4C5(C)CCC(OC6OC(C(=O)O)C(O)C(O)C6OC6OC(C(=O)O[Si](C)(C)C)C(O)C(O)C6O)C(C)(C)C5CCC43C)C2C15600.8Standard non polar33892256
Glycyrrhizin,1TMS,isomer #8CC1(C(=O)O)CCC2(C)CCC3(C)C(=CC(=O)C4C5(C)CCC(OC6OC(C(=O)O[Si](C)(C)C)C(O)C(O)C6OC6OC(C(=O)O)C(O)C(O)C6O)C(C)(C)C5CCC43C)C2C16369.1Semi standard non polar33892256
Glycyrrhizin,1TMS,isomer #8CC1(C(=O)O)CCC2(C)CCC3(C)C(=CC(=O)C4C5(C)CCC(OC6OC(C(=O)O[Si](C)(C)C)C(O)C(O)C6OC6OC(C(=O)O)C(O)C(O)C6O)C(C)(C)C5CCC43C)C2C15600.2Standard non polar33892256
Glycyrrhizin,1TMS,isomer #9CC1(C(=O)O)CCC2(C)CCC3(C)C(=CC(O[Si](C)(C)C)=C4C5(C)CCC(OC6OC(C(=O)O)C(O)C(O)C6OC6OC(C(=O)O)C(O)C(O)C6O)C(C)(C)C5CCC43C)C2C16167.4Semi standard non polar33892256
Glycyrrhizin,1TMS,isomer #9CC1(C(=O)O)CCC2(C)CCC3(C)C(=CC(O[Si](C)(C)C)=C4C5(C)CCC(OC6OC(C(=O)O)C(O)C(O)C6OC6OC(C(=O)O)C(O)C(O)C6O)C(C)(C)C5CCC43C)C2C15523.4Standard non polar33892256
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Glycyrrhizin Linear Ion Trap , negative-QTOFsplash10-0udi-0009001000-76ff4bd04d18861bcec12017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Glycyrrhizin Linear Ion Trap , negative-QTOFsplash10-0udi-0009000000-ad9d816c97b0b6260b222017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Glycyrrhizin Linear Ion Trap , positive-QTOFsplash10-0002-0000509430-04def68d9fdc818580402017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Glycyrrhizin Linear Ion Trap , positive-QTOFsplash10-00kr-0000902000-ed61a3fba8a67934b5b42017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Glycyrrhizin Linear Ion Trap , positive-QTOFsplash10-00kr-0000902000-0bd1a08a534d106c473d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Glycyrrhizin Linear Ion Trap , positive-QTOFsplash10-014i-0000109000-9621e9e32834e62d1b982017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Glycyrrhizin Linear Ion Trap , positive-QTOFsplash10-000i-0000039000-8ffe627b0abc1703ebf92017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Glycyrrhizin Linear Ion Trap , positive-QTOFsplash10-0w9a-0001906310-070e8a42beae3e32b9ee2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Glycyrrhizin Linear Ion Trap , positive-QTOFsplash10-00kr-0000902000-b15e55841197b74676f32017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Glycyrrhizin Linear Ion Trap , positive-QTOFsplash10-014i-0000109000-d1f369e2c1009923d6022017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Glycyrrhizin Linear Ion Trap , positive-QTOFsplash10-000i-0000039000-ff48b9c18064290532df2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Glycyrrhizin 6V, Positive-QTOFsplash10-0ikc-2902000000-399923f2f0b32e08f2122021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Glycyrrhizin 6V, Positive-QTOFsplash10-0udi-0000900000-8aab5d58fbdb2b9cd0b12021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Glycyrrhizin 6V, Positive-QTOFsplash10-0ikc-2902000000-233d95340032c864fb3b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Glycyrrhizin 10V, Positive-QTOFsplash10-0udi-0000902020-217813344bd06b8780802021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Glycyrrhizin 6V, Positive-QTOFsplash10-00di-0001000090-061037d23e7a7de1013f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Glycyrrhizin 6V, Positive-QTOFsplash10-00di-0000000090-a45ac1fef7312591606f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Glycyrrhizin 6V, Positive-QTOFsplash10-0ur0-0000902080-cace6a504d72d3e68c212021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Glycyrrhizin 20V, Positive-QTOFsplash10-0udi-0000901000-73210eda76448fb2f3332021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycyrrhizin 10V, Positive-QTOFsplash10-0pk9-0100906250-8be353527a95cffaba8a2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycyrrhizin 20V, Positive-QTOFsplash10-0fmi-0100904000-f24b016e7c30fe1397182015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycyrrhizin 40V, Positive-QTOFsplash10-00fr-0302901000-8eb7f40c63ac563121732015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycyrrhizin 10V, Negative-QTOFsplash10-0g29-1500827970-ab2b4b8ca046fbd429d62015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycyrrhizin 20V, Negative-QTOFsplash10-016s-1700914310-0fc211d45115fc0c16e52015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycyrrhizin 40V, Negative-QTOFsplash10-00kb-3700911000-213b48473924464dafcc2015-04-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB001060
KNApSAcK IDC00003522
Chemspider ID3375
KEGG Compound IDC02284
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkGlycyrrhizin
METLIN IDNot Available
PubChem Compound3495
PDB IDNot Available
ChEBI ID15939
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1032161
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.