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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:21:00 UTC
Update Date2022-03-07 02:54:07 UTC
HMDB IDHMDB0034502
Secondary Accession Numbers
  • HMDB34502
Metabolite Identification
Common NameArjunolic acid
DescriptionArjunolic acid, also known as arjunolate, 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 Arjunolic acid.
Structure
Data?1563862571
Synonyms
ValueSource
ArjunolateGenerator
2,3,23-Trihydroxyolean-12-en-28-Oic acidHMDB
10,11-Dihydroxy-9-(hydroxymethyl)-2,2,6a,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-carboxylateGenerator
Arjunolic acidMeSH
Chemical FormulaC30H48O5
Average Molecular Weight488.6991
Monoisotopic Molecular Weight488.350174646
IUPAC Name10,11-dihydroxy-9-(hydroxymethyl)-2,2,6a,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 acid
Traditional Name10,11-dihydroxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylic acid
CAS Registry Number465-00-9
SMILES
CC1(C)CCC2(CCC3(C)C(=CCC4C5(C)CC(O)C(O)C(C)(CO)C5CCC34C)C2C1)C(O)=O
InChI Identifier
InChI=1S/C30H48O5/c1-25(2)11-13-30(24(34)35)14-12-28(5)18(19(30)15-25)7-8-22-26(3)16-20(32)23(33)27(4,17-31)21(26)9-10-29(22,28)6/h7,19-23,31-33H,8-17H2,1-6H3,(H,34,35)
InChI KeyRWNHLTKFBKYDOJ-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
  • Hydroxysteroid
  • Steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Carbonyl group
  • Organooxygen compound
  • Primary alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point337 - 340 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.056 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0097 g/LALOGPS
logP5.13ALOGPS
logP4.24ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)4.74ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity136.76 m³·mol⁻¹ChemAxon
Polarizability57.09 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+212.43631661259
DarkChem[M-H]-202.03431661259
DeepCCS[M-2H]-250.01730932474
DeepCCS[M+Na]+225.53830932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Arjunolic acidCC1(C)CCC2(CCC3(C)C(=CCC4C5(C)CC(O)C(O)C(C)(CO)C5CCC34C)C2C1)C(O)=O3029.1Standard polar33892256
Arjunolic acidCC1(C)CCC2(CCC3(C)C(=CCC4C5(C)CC(O)C(O)C(C)(CO)C5CCC34C)C2C1)C(O)=O3645.8Standard non polar33892256
Arjunolic acidCC1(C)CCC2(CCC3(C)C(=CCC4C5(C)CC(O)C(O)C(C)(CO)C5CCC34C)C2C1)C(O)=O4178.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Arjunolic acid,1TMS,isomer #1CC1(C)CCC2(C(=O)O)CCC3(C)C(=CCC4C5(C)CC(O[Si](C)(C)C)C(O)C(C)(CO)C5CCC43C)C2C14121.6Semi standard non polar33892256
Arjunolic acid,1TMS,isomer #2CC1(C)CCC2(C(=O)O)CCC3(C)C(=CCC4C5(C)CC(O)C(O[Si](C)(C)C)C(C)(CO)C5CCC43C)C2C14117.9Semi standard non polar33892256
Arjunolic acid,1TMS,isomer #3CC1(C)CCC2(C(=O)O)CCC3(C)C(=CCC4C5(C)CC(O)C(O)C(C)(CO[Si](C)(C)C)C5CCC43C)C2C14128.1Semi standard non polar33892256
Arjunolic acid,1TMS,isomer #4CC1(C)CCC2(C(=O)O[Si](C)(C)C)CCC3(C)C(=CCC4C5(C)CC(O)C(O)C(C)(CO)C5CCC43C)C2C14038.9Semi standard non polar33892256
Arjunolic 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)(CO)C5CCC43C)C2C13949.8Semi standard non polar33892256
Arjunolic 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)(CO)C5CCC43C)C2C14077.9Semi standard non polar33892256
Arjunolic acid,2TMS,isomer #3CC1(C)CCC2(C(=O)O)CCC3(C)C(=CCC4C5(C)CC(O[Si](C)(C)C)C(O)C(C)(CO[Si](C)(C)C)C5CCC43C)C2C14080.8Semi standard non polar33892256
Arjunolic 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)(CO)C5CCC43C)C2C13945.1Semi standard non polar33892256
Arjunolic acid,2TMS,isomer #5CC1(C)CCC2(C(=O)O)CCC3(C)C(=CCC4C5(C)CC(O)C(O[Si](C)(C)C)C(C)(CO[Si](C)(C)C)C5CCC43C)C2C14075.8Semi standard non polar33892256
Arjunolic acid,2TMS,isomer #6CC1(C)CCC2(C(=O)O[Si](C)(C)C)CCC3(C)C(=CCC4C5(C)CC(O)C(O)C(C)(CO[Si](C)(C)C)C5CCC43C)C2C14007.4Semi standard non polar33892256
Arjunolic 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)(CO)C5CCC43C)C2C13880.2Semi standard non polar33892256
Arjunolic 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)(CO[Si](C)(C)C)C5CCC43C)C2C13891.8Semi standard non polar33892256
Arjunolic 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)(CO[Si](C)(C)C)C5CCC43C)C2C14030.1Semi standard non polar33892256
Arjunolic 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)(CO[Si](C)(C)C)C5CCC43C)C2C13881.8Semi standard non polar33892256
Arjunolic 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)(CO[Si](C)(C)C)C5CCC43C)C2C13843.4Semi standard non polar33892256
Arjunolic 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)(CO)C5CCC43C)C2C14331.8Semi standard non polar33892256
Arjunolic 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)(CO)C5CCC43C)C2C14328.7Semi standard non polar33892256
Arjunolic acid,1TBDMS,isomer #3CC1(C)CCC2(C(=O)O)CCC3(C)C(=CCC4C5(C)CC(O)C(O)C(C)(CO[Si](C)(C)C(C)(C)C)C5CCC43C)C2C14358.7Semi standard non polar33892256
Arjunolic 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)(CO)C5CCC43C)C2C14282.9Semi standard non polar33892256
Arjunolic 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)(CO)C5CCC43C)C2C14393.9Semi standard non polar33892256
Arjunolic 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)(CO)C5CCC43C)C2C14497.3Semi standard non polar33892256
Arjunolic 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)(CO[Si](C)(C)C(C)(C)C)C5CCC43C)C2C14502.6Semi standard non polar33892256
Arjunolic 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)(CO)C5CCC43C)C2C14394.3Semi standard non polar33892256
Arjunolic 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)(CO[Si](C)(C)C(C)(C)C)C5CCC43C)C2C14499.0Semi standard non polar33892256
Arjunolic 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)(CO[Si](C)(C)C(C)(C)C)C5CCC43C)C2C14455.3Semi standard non polar33892256
Arjunolic 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)(CO)C5CCC43C)C2C14509.2Semi standard non polar33892256
Arjunolic 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)(CO[Si](C)(C)C(C)(C)C)C5CCC43C)C2C14516.3Semi standard non polar33892256
Arjunolic 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)(CO[Si](C)(C)C(C)(C)C)C5CCC43C)C2C14653.5Semi standard non polar33892256
Arjunolic 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)(CO[Si](C)(C)C(C)(C)C)C5CCC43C)C2C14516.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Arjunolic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-05fr-1003900000-8a4110776752ebca7a1b2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Arjunolic acid GC-MS (2 TMS) - 70eV, Positivesplash10-014i-2001239000-223c9c19034fc554d41e2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Arjunolic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Arjunolic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Arjunolic acid 10V, Positive-QTOFsplash10-0fki-0000900000-5a7317ac59a52deffb3c2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Arjunolic acid 20V, Positive-QTOFsplash10-0umi-0000900000-59243cb1cd5d2f59e0922015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Arjunolic acid 40V, Positive-QTOFsplash10-004i-3523900000-8c12129ef99b3d47c06f2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Arjunolic acid 10V, Positive-QTOFsplash10-0fki-0000900000-5a7317ac59a52deffb3c2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Arjunolic acid 20V, Positive-QTOFsplash10-0umi-0000900000-59243cb1cd5d2f59e0922015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Arjunolic acid 40V, Positive-QTOFsplash10-004i-3523900000-8c12129ef99b3d47c06f2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Arjunolic acid 10V, Positive-QTOFsplash10-0fki-0000900000-5a7317ac59a52deffb3c2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Arjunolic acid 20V, Positive-QTOFsplash10-0umi-0000900000-59243cb1cd5d2f59e0922015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Arjunolic acid 40V, Positive-QTOFsplash10-004i-3523900000-8c12129ef99b3d47c06f2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Arjunolic acid 10V, Positive-QTOFsplash10-0fki-0000900000-5a7317ac59a52deffb3c2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Arjunolic acid 20V, Positive-QTOFsplash10-0umi-0000900000-59243cb1cd5d2f59e0922015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Arjunolic acid 40V, Positive-QTOFsplash10-004i-3523900000-8c12129ef99b3d47c06f2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Arjunolic acid 10V, Negative-QTOFsplash10-000i-0000900000-d752851b33f1a8c5e0202015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Arjunolic acid 20V, Negative-QTOFsplash10-02bu-0000900000-1c7dbae0b69f588ab6d12015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Arjunolic acid 40V, Negative-QTOFsplash10-03dl-1000900000-a882b64084f20ef67a3f2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Arjunolic acid 10V, Negative-QTOFsplash10-000i-0000900000-d752851b33f1a8c5e0202015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Arjunolic acid 20V, Negative-QTOFsplash10-02bu-0000900000-1c7dbae0b69f588ab6d12015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Arjunolic acid 40V, Negative-QTOFsplash10-03dl-1000900000-a882b64084f20ef67a3f2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Arjunolic acid 10V, Negative-QTOFsplash10-000i-0000900000-d752851b33f1a8c5e0202015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Arjunolic acid 20V, Negative-QTOFsplash10-02bu-0000900000-1c7dbae0b69f588ab6d12015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Arjunolic acid 40V, Negative-QTOFsplash10-03dl-1000900000-a882b64084f20ef67a3f2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Arjunolic acid 10V, Negative-QTOFsplash10-000i-0000900000-d752851b33f1a8c5e0202015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Arjunolic acid 20V, Negative-QTOFsplash10-02bu-0000900000-1c7dbae0b69f588ab6d12015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Arjunolic acid 40V, Negative-QTOFsplash10-03dl-1000900000-a882b64084f20ef67a3f2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Arjunolic acid 10V, Negative-QTOFsplash10-000i-0000900000-1341db9b6725761823dd2021-09-22Wishart 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 IDFDB012998
KNApSAcK IDC00029724
Chemspider ID4478298
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5320146
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1843511
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.