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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:35:11 UTC
Update Date2022-03-07 02:52:27 UTC
HMDB IDHMDB0030163
Secondary Accession Numbers
  • HMDB30163
Metabolite Identification
Common NameGalbanic acid
DescriptionGalbanic acid, also known as galbanate or asacoumarin b, belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. Based on a literature review a significant number of articles have been published on Galbanic acid.
Structure
Data?1563861947
Synonyms
ValueSource
GalbanateGenerator
2,3-Dimethyl-6-(dimethylethylidene)-2-[[(2-oxo-2H-1-benzopyran-7-yl)oxy]methyl]cyclohexanepropanoic acidHMDB
Asacoumarin bHMDB
3-(2,3-Dimethyl-2-{[(2-oxo-2H-chromen-7-yl)oxy]methyl}-6-(propan-2-ylidene)cyclohexyl)propanoateHMDB
Galbanic acidMeSH
Chemical FormulaC24H30O5
Average Molecular Weight398.492
Monoisotopic Molecular Weight398.20932407
IUPAC Name3-(2,3-dimethyl-2-{[(2-oxo-2H-chromen-7-yl)oxy]methyl}-6-(propan-2-ylidene)cyclohexyl)propanoic acid
Traditional Name3-(2,3-dimethyl-2-{[(2-oxochromen-7-yl)oxy]methyl}-6-(propan-2-ylidene)cyclohexyl)propanoic acid
CAS Registry Number3566-55-0
SMILES
CC1CCC(C(CCC(O)=O)C1(C)COC1=CC2=C(C=CC(=O)O2)C=C1)=C(C)C
InChI Identifier
InChI=1S/C24H30O5/c1-15(2)19-9-5-16(3)24(4,20(19)10-11-22(25)26)14-28-18-8-6-17-7-12-23(27)29-21(17)13-18/h6-8,12-13,16,20H,5,9-11,14H2,1-4H3,(H,25,26)
InChI KeyCVWWNYPTZYQCSE-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene lactones
Direct ParentTerpene lactones
Alternative Parents
Substituents
  • Terpene lactone
  • Coumarin
  • Aromatic monoterpenoid
  • Benzopyran
  • Bicyclic monoterpenoid
  • P-menthane monoterpenoid
  • 1-benzopyran
  • Monoterpenoid
  • Carbocyclic fatty acid
  • Alkyl aryl ether
  • Pyranone
  • Fatty acyl
  • Benzenoid
  • Pyran
  • Heteroaromatic compound
  • Lactone
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Carboxylic acid
  • Ether
  • Monocarboxylic acid or derivatives
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point92 - 93 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.013 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0017 g/LALOGPS
logP4.71ALOGPS
logP4.83ChemAxon
logS-5.4ALOGPS
pKa (Strongest Acidic)4.49ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area72.83 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity112.4 m³·mol⁻¹ChemAxon
Polarizability44.28 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+190.46131661259
DarkChem[M-H]-186.2531661259
DeepCCS[M+H]+200.59430932474
DeepCCS[M-H]-198.23630932474
DeepCCS[M-2H]-232.45430932474
DeepCCS[M+Na]+208.53730932474
AllCCS[M+H]+197.932859911
AllCCS[M+H-H2O]+195.432859911
AllCCS[M+NH4]+200.232859911
AllCCS[M+Na]+200.832859911
AllCCS[M-H]-200.632859911
AllCCS[M+Na-2H]-200.832859911
AllCCS[M+HCOO]-201.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Galbanic acidCC1CCC(C(CCC(O)=O)C1(C)COC1=CC2=C(C=CC(=O)O2)C=C1)=C(C)C4360.7Standard polar33892256
Galbanic acidCC1CCC(C(CCC(O)=O)C1(C)COC1=CC2=C(C=CC(=O)O2)C=C1)=C(C)C3227.5Standard non polar33892256
Galbanic acidCC1CCC(C(CCC(O)=O)C1(C)COC1=CC2=C(C=CC(=O)O2)C=C1)=C(C)C3493.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Galbanic acid,1TMS,isomer #1CC(C)=C1CCC(C)C(C)(COC2=CC=C3C=CC(=O)OC3=C2)C1CCC(=O)O[Si](C)(C)C3416.6Semi standard non polar33892256
Galbanic acid,1TBDMS,isomer #1CC(C)=C1CCC(C)C(C)(COC2=CC=C3C=CC(=O)OC3=C2)C1CCC(=O)O[Si](C)(C)C(C)(C)C3659.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Galbanic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-01yo-4439000000-54b630ef65ede4ce48ab2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Galbanic acid GC-MS (1 TMS) - 70eV, Positivesplash10-0ads-9265600000-a4478a969eab6e6fc6702017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Galbanic 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 - Galbanic acid 10V, Positive-QTOFsplash10-001i-0019000000-2d14baaf79872f93d8a62015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Galbanic acid 20V, Positive-QTOFsplash10-0il9-1109000000-3754585c82931d6260ff2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Galbanic acid 40V, Positive-QTOFsplash10-01tc-4910000000-e0a82639e92fa4ce85fa2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Galbanic acid 10V, Negative-QTOFsplash10-0002-0209000000-430aa3b453dea69741432015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Galbanic acid 20V, Negative-QTOFsplash10-0imj-1409000000-df81baf042b82c34e97c2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Galbanic acid 40V, Negative-QTOFsplash10-014i-2900000000-0983cc899ba690c128c42015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Galbanic acid 10V, Negative-QTOFsplash10-0gxt-0109000000-17eb426f8e4b62d0d6222021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Galbanic acid 20V, Negative-QTOFsplash10-03di-0907000000-1512d57c74d63c602b032021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Galbanic acid 40V, Negative-QTOFsplash10-07w9-1904000000-9cdb9c02b16e7705d8972021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Galbanic acid 10V, Positive-QTOFsplash10-03dr-0629000000-6e84f8d3739abfa477f52021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Galbanic acid 20V, Positive-QTOFsplash10-03di-0956000000-012fad4276144be73c062021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Galbanic acid 40V, Positive-QTOFsplash10-03dl-2900000000-01238689b5ae29e5defc2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • 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 IDFDB001972
KNApSAcK IDC00034520
Chemspider ID3430215
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound4220856
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1817541
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.