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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:25:28 UTC
Update Date2022-03-07 02:54:08 UTC
HMDB IDHMDB0034551
Secondary Accession Numbers
  • HMDB34551
Metabolite Identification
Common NameMedicagenic acid
DescriptionMedicagenic acid, also known as medicagenate, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Based on a literature review a small amount of articles have been published on Medicagenic acid.
Structure
Data?1563862580
Synonyms
ValueSource
MedicagenateGenerator
2-beta,3-beta-Dihydroxyolean-12-ene-23,28-dioic acidHMDB
CatsanogeninHMDB
Medicogenic acidHMDB
2,3-Dihydroxy-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicene-4,8a-dicarboxylateGenerator
Chemical FormulaC30H46O6
Average Molecular Weight502.6826
Monoisotopic Molecular Weight502.329439204
IUPAC Name2,3-dihydroxy-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicene-4,8a-dicarboxylic acid
Traditional Name2,3-dihydroxy-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-4,8a-dicarboxylic acid
CAS Registry Number599-07-5
SMILES
CC1(C)CCC2(CCC3(C)C(=CCC4C5(C)CC(O)C(O)C(C)(C5CCC34C)C(O)=O)C2C1)C(O)=O
InChI Identifier
InChI=1S/C30H46O6/c1-25(2)11-13-30(24(35)36)14-12-27(4)17(18(30)15-25)7-8-20-26(3)16-19(31)22(32)29(6,23(33)34)21(26)9-10-28(20,27)5/h7,18-22,31-32H,8-16H2,1-6H3,(H,33,34)(H,35,36)
InChI KeyIDGXIXSKISLYAC-UHFFFAOYSA-N
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
  • 12-hydroxysteroid
  • 15-hydroxysteroid
  • Hydroxysteroid
  • Steroid
  • Beta-hydroxy acid
  • Hydroxy acid
  • Dicarboxylic acid or derivatives
  • Cyclic alcohol
  • Secondary alcohol
  • 1,2-diol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point352 - 353 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.092 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0061 g/LALOGPS
logP4.15ALOGPS
logP4.71ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)4.28ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area115.06 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity136.7 m³·mol⁻¹ChemAxon
Polarizability56.78 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+212.68331661259
DarkChem[M-H]-207.70531661259
DeepCCS[M-2H]-252.68230932474
DeepCCS[M+Na]+228.10630932474
AllCCS[M+H]+219.632859911
AllCCS[M+H-H2O]+218.132859911
AllCCS[M+NH4]+220.932859911
AllCCS[M+Na]+221.332859911
AllCCS[M-H]-216.632859911
AllCCS[M+Na-2H]-218.832859911
AllCCS[M+HCOO]-221.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Medicagenic acidCC1(C)CCC2(CCC3(C)C(=CCC4C5(C)CC(O)C(O)C(C)(C5CCC34C)C(O)=O)C2C1)C(O)=O3528.1Standard polar33892256
Medicagenic acidCC1(C)CCC2(CCC3(C)C(=CCC4C5(C)CC(O)C(O)C(C)(C5CCC34C)C(O)=O)C2C1)C(O)=O3676.1Standard non polar33892256
Medicagenic acidCC1(C)CCC2(CCC3(C)C(=CCC4C5(C)CC(O)C(O)C(C)(C5CCC34C)C(O)=O)C2C1)C(O)=O4157.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Medicagenic acid,1TMS,isomer #1CC1(C)CCC2(C(=O)O)CCC3(C)C(=CCC4C5(C)CC(O[Si](C)(C)C)C(O)C(C)(C(=O)O)C5CCC43C)C2C14186.3Semi standard non polar33892256
Medicagenic acid,1TMS,isomer #2CC1(C)CCC2(C(=O)O)CCC3(C)C(=CCC4C5(C)CC(O)C(O[Si](C)(C)C)C(C)(C(=O)O)C5CCC43C)C2C14143.8Semi standard non polar33892256
Medicagenic acid,1TMS,isomer #3CC1(C)CCC2(C(=O)O)CCC3(C)C(=CCC4C5(C)CC(O)C(O)C(C)(C(=O)O[Si](C)(C)C)C5CCC43C)C2C14113.7Semi standard non polar33892256
Medicagenic acid,1TMS,isomer #4CC1(C)CCC2(C(=O)O[Si](C)(C)C)CCC3(C)C(=CCC4C5(C)CC(O)C(O)C(C)(C(=O)O)C5CCC43C)C2C14104.6Semi standard non polar33892256
Medicagenic acid,2TMS,isomer #1CC1(C)CCC2(C(=O)O[Si](C)(C)C)CCC3(C)C(=CCC4C5(C)CC(O[Si](C)(C)C)C(O)C(C)(C(=O)O)C5CCC43C)C2C13998.1Semi standard non polar33892256
Medicagenic acid,2TMS,isomer #2CC1(C)CCC2(C(=O)O)CCC3(C)C(=CCC4C5(C)CC(O[Si](C)(C)C)C(O[Si](C)(C)C)C(C)(C(=O)O)C5CCC43C)C2C14116.0Semi standard non polar33892256
Medicagenic acid,2TMS,isomer #3CC1(C)CCC2(C(=O)O)CCC3(C)C(=CCC4C5(C)CC(O[Si](C)(C)C)C(O)C(C)(C(=O)O[Si](C)(C)C)C5CCC43C)C2C14045.7Semi standard non polar33892256
Medicagenic acid,2TMS,isomer #4CC1(C)CCC2(C(=O)O[Si](C)(C)C)CCC3(C)C(=CCC4C5(C)CC(O)C(O[Si](C)(C)C)C(C)(C(=O)O)C5CCC43C)C2C13957.6Semi standard non polar33892256
Medicagenic acid,2TMS,isomer #5CC1(C)CCC2(C(=O)O)CCC3(C)C(=CCC4C5(C)CC(O)C(O[Si](C)(C)C)C(C)(C(=O)O[Si](C)(C)C)C5CCC43C)C2C14005.7Semi standard non polar33892256
Medicagenic acid,2TMS,isomer #6CC1(C)CCC2(C(=O)O[Si](C)(C)C)CCC3(C)C(=CCC4C5(C)CC(O)C(O)C(C)(C(=O)O[Si](C)(C)C)C5CCC43C)C2C13971.0Semi standard non polar33892256
Medicagenic acid,3TMS,isomer #1CC1(C)CCC2(C(=O)O[Si](C)(C)C)CCC3(C)C(=CCC4C5(C)CC(O[Si](C)(C)C)C(O[Si](C)(C)C)C(C)(C(=O)O)C5CCC43C)C2C13926.1Semi standard non polar33892256
Medicagenic acid,3TMS,isomer #2CC1(C)CCC2(C(=O)O[Si](C)(C)C)CCC3(C)C(=CCC4C5(C)CC(O[Si](C)(C)C)C(O)C(C)(C(=O)O[Si](C)(C)C)C5CCC43C)C2C13886.2Semi standard non polar33892256
Medicagenic acid,3TMS,isomer #3CC1(C)CCC2(C(=O)O)CCC3(C)C(=CCC4C5(C)CC(O[Si](C)(C)C)C(O[Si](C)(C)C)C(C)(C(=O)O[Si](C)(C)C)C5CCC43C)C2C13985.3Semi standard non polar33892256
Medicagenic acid,3TMS,isomer #4CC1(C)CCC2(C(=O)O[Si](C)(C)C)CCC3(C)C(=CCC4C5(C)CC(O)C(O[Si](C)(C)C)C(C)(C(=O)O[Si](C)(C)C)C5CCC43C)C2C13859.2Semi standard non polar33892256
Medicagenic acid,4TMS,isomer #1CC1(C)CCC2(C(=O)O[Si](C)(C)C)CCC3(C)C(=CCC4C5(C)CC(O[Si](C)(C)C)C(O[Si](C)(C)C)C(C)(C(=O)O[Si](C)(C)C)C5CCC43C)C2C13806.8Semi standard non polar33892256
Medicagenic acid,1TBDMS,isomer #1CC1(C)CCC2(C(=O)O)CCC3(C)C(=CCC4C5(C)CC(O[Si](C)(C)C(C)(C)C)C(O)C(C)(C(=O)O)C5CCC43C)C2C14392.6Semi standard non polar33892256
Medicagenic acid,1TBDMS,isomer #2CC1(C)CCC2(C(=O)O)CCC3(C)C(=CCC4C5(C)CC(O)C(O[Si](C)(C)C(C)(C)C)C(C)(C(=O)O)C5CCC43C)C2C14346.8Semi standard non polar33892256
Medicagenic acid,1TBDMS,isomer #3CC1(C)CCC2(C(=O)O)CCC3(C)C(=CCC4C5(C)CC(O)C(O)C(C)(C(=O)O[Si](C)(C)C(C)(C)C)C5CCC43C)C2C14341.6Semi standard non polar33892256
Medicagenic acid,1TBDMS,isomer #4CC1(C)CCC2(C(=O)O[Si](C)(C)C(C)(C)C)CCC3(C)C(=CCC4C5(C)CC(O)C(O)C(C)(C(=O)O)C5CCC43C)C2C14335.5Semi standard non polar33892256
Medicagenic acid,2TBDMS,isomer #1CC1(C)CCC2(C(=O)O[Si](C)(C)C(C)(C)C)CCC3(C)C(=CCC4C5(C)CC(O[Si](C)(C)C(C)(C)C)C(O)C(C)(C(=O)O)C5CCC43C)C2C14442.9Semi standard non polar33892256
Medicagenic acid,2TBDMS,isomer #2CC1(C)CCC2(C(=O)O)CCC3(C)C(=CCC4C5(C)CC(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(C)(C(=O)O)C5CCC43C)C2C14537.6Semi standard non polar33892256
Medicagenic acid,2TBDMS,isomer #3CC1(C)CCC2(C(=O)O)CCC3(C)C(=CCC4C5(C)CC(O[Si](C)(C)C(C)(C)C)C(O)C(C)(C(=O)O[Si](C)(C)C(C)(C)C)C5CCC43C)C2C14469.0Semi standard non polar33892256
Medicagenic acid,2TBDMS,isomer #4CC1(C)CCC2(C(=O)O[Si](C)(C)C(C)(C)C)CCC3(C)C(=CCC4C5(C)CC(O)C(O[Si](C)(C)C(C)(C)C)C(C)(C(=O)O)C5CCC43C)C2C14406.3Semi standard non polar33892256
Medicagenic acid,2TBDMS,isomer #5CC1(C)CCC2(C(=O)O)CCC3(C)C(=CCC4C5(C)CC(O)C(O[Si](C)(C)C(C)(C)C)C(C)(C(=O)O[Si](C)(C)C(C)(C)C)C5CCC43C)C2C14446.8Semi standard non polar33892256
Medicagenic acid,2TBDMS,isomer #6CC1(C)CCC2(C(=O)O[Si](C)(C)C(C)(C)C)CCC3(C)C(=CCC4C5(C)CC(O)C(O)C(C)(C(=O)O[Si](C)(C)C(C)(C)C)C5CCC43C)C2C14430.0Semi standard non polar33892256
Medicagenic acid,3TBDMS,isomer #1CC1(C)CCC2(C(=O)O[Si](C)(C)C(C)(C)C)CCC3(C)C(=CCC4C5(C)CC(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(C)(C(=O)O)C5CCC43C)C2C14566.1Semi standard non polar33892256
Medicagenic acid,3TBDMS,isomer #2CC1(C)CCC2(C(=O)O[Si](C)(C)C(C)(C)C)CCC3(C)C(=CCC4C5(C)CC(O[Si](C)(C)C(C)(C)C)C(O)C(C)(C(=O)O[Si](C)(C)C(C)(C)C)C5CCC43C)C2C14516.7Semi standard non polar33892256
Medicagenic acid,3TBDMS,isomer #3CC1(C)CCC2(C(=O)O)CCC3(C)C(=CCC4C5(C)CC(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(C)(C(=O)O[Si](C)(C)C(C)(C)C)C5CCC43C)C2C14621.8Semi standard non polar33892256
Medicagenic acid,3TBDMS,isomer #4CC1(C)CCC2(C(=O)O[Si](C)(C)C(C)(C)C)CCC3(C)C(=CCC4C5(C)CC(O)C(O[Si](C)(C)C(C)(C)C)C(C)(C(=O)O[Si](C)(C)C(C)(C)C)C5CCC43C)C2C14507.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Medicagenic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-052k-0005900000-a33a4002b4c1302b46592017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Medicagenic acid GC-MS (2 TMS) - 70eV, Positivesplash10-001l-2101389000-80d5ef655500a2fa81b42017-10-06Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Medicagenic acid 10V, Positive-QTOFsplash10-000i-0000920000-30633985c2f723b613552015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Medicagenic acid 20V, Positive-QTOFsplash10-00kr-0000900000-f1a091624fb93c8c2bf32015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Medicagenic acid 40V, Positive-QTOFsplash10-002r-2102900000-3ba43c8639c393ea5a8e2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Medicagenic acid 10V, Positive-QTOFsplash10-000i-0000920000-30633985c2f723b613552015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Medicagenic acid 20V, Positive-QTOFsplash10-00kr-0000900000-f1a091624fb93c8c2bf32015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Medicagenic acid 40V, Positive-QTOFsplash10-002r-2102900000-3ba43c8639c393ea5a8e2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Medicagenic acid 10V, Negative-QTOFsplash10-0zfr-0000950000-2d372344b7ee50149bd82015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Medicagenic acid 20V, Negative-QTOFsplash10-0bti-0000910000-822a4dadf0d1c6d0888a2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Medicagenic acid 40V, Negative-QTOFsplash10-03du-1000900000-d35362f51385858e08292015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Medicagenic acid 10V, Negative-QTOFsplash10-0zfr-0000950000-2d372344b7ee50149bd82015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Medicagenic acid 20V, Negative-QTOFsplash10-0bti-0000910000-822a4dadf0d1c6d0888a2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Medicagenic acid 40V, Negative-QTOFsplash10-03du-1000900000-d35362f51385858e08292015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Medicagenic acid 10V, Positive-QTOFsplash10-0udr-0000970000-da2e1350b2e61bed82522021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Medicagenic acid 20V, Positive-QTOFsplash10-0k9i-7179820000-e7d2649b952f39e765de2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Medicagenic acid 40V, Positive-QTOFsplash10-015i-2904300000-03b1e4013a12d03a5d972021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Medicagenic acid 10V, Negative-QTOFsplash10-0udi-0000090000-f78590c58887ccbd2f8b2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Medicagenic acid 20V, Negative-QTOFsplash10-0zfr-0000980000-9e6f6272b2f6f1bbd2ca2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Medicagenic acid 40V, Negative-QTOFsplash10-0kmi-9000630000-5bf2173b3a4bc34a1e6b2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • 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 IDFDB013057
KNApSAcK IDC00053464
Chemspider ID385658
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound436072
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1843981
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.