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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 21:59:14 UTC
Update Date2022-03-07 02:55:04 UTC
HMDB IDHMDB0036811
Secondary Accession Numbers
  • HMDB36811
Metabolite Identification
Common NameIsopimaric acid
DescriptionIsopimaric acid, also known as 4-epi-isopimarate, belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. Based on a literature review a significant number of articles have been published on Isopimaric acid.
Structure
Data?1601225629
Synonyms
ValueSource
(1R,4AR,4BS,7S,10ar)-7-ethenyl-1,4a,7-trimethyl-3,4,4b,5,6,8,10,10a-octahydro-2H-phenanthrene-1-carboxylic acidChEBI
4-Epi-isopimaric acidChEBI
(1R,4AR,4BS,7S,10ar)-7-ethenyl-1,4a,7-trimethyl-3,4,4b,5,6,8,10,10a-octahydro-2H-phenanthrene-1-carboxylateGenerator
4-Epi-isopimarateGenerator
IsopimarateGenerator
13beta-Methyl-13-vinylpodocarp-7-en-15-Oic acidHMDB
13Β-methyl-13-vinylpodocarp-7-en-15-Oic acidHMDB
(-)-13beta-Methyl-13-vinylpodocarp-7-en-15-Oic acidHMDB
(-)-13Β-methyl-13-vinylpodocarp-7-en-15-Oic acidHMDB
(+)-Isopimaric acidHMDB
7,15-Isopimaradien-18-Oic acidHMDB
Isopimaric acid aHMDB
delta7,15-Isopimaric acidHMDB
Δ7,15-isopimaric acidHMDB
Chemical FormulaC20H30O2
Average Molecular Weight302.458
Monoisotopic Molecular Weight302.224580206
IUPAC Name(1R,4aR,4bS,7S,10aR)-7-ethenyl-1,4a,7-trimethyl-1,2,3,4,4a,4b,5,6,7,8,10,10a-dodecahydrophenanthrene-1-carboxylic acid
Traditional Nameisopimaric acid
CAS Registry Number5835-26-7
SMILES
[H][C@]12CC[C@@](C)(CC1=CC[C@@]1([H])[C@@](C)(CCC[C@]21C)C(O)=O)C=C
InChI Identifier
InChI=1S/C20H30O2/c1-5-18(2)12-9-15-14(13-18)7-8-16-19(15,3)10-6-11-20(16,4)17(21)22/h5,7,15-16H,1,6,8-13H2,2-4H3,(H,21,22)/t15-,16+,18-,19+,20+/m0/s1
InChI KeyMXYATHGRPJZBNA-KRFUXDQASA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassDiterpenoids
Direct ParentDiterpenoids
Alternative Parents
Substituents
  • Pimarane diterpenoid
  • Diterpenoid
  • Phenanthrene
  • Hydrophenanthrene
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point162 - 164 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00065 g/LALOGPS
logP5.28ALOGPS
logP5.07ChemAxon
logS-5.7ALOGPS
pKa (Strongest Acidic)4.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity90.33 m³·mol⁻¹ChemAxon
Polarizability35.97 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-202.95930932474
DeepCCS[M+Na]+178.26230932474
AllCCS[M+H]+177.032859911
AllCCS[M+H-H2O]+173.932859911
AllCCS[M+NH4]+179.832859911
AllCCS[M+Na]+180.732859911
AllCCS[M-H]-183.232859911
AllCCS[M+Na-2H]-183.632859911
AllCCS[M+HCOO]-184.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Isopimaric acid[H][C@]12CC[C@@](C)(CC1=CC[C@@]1([H])[C@@](C)(CCC[C@]21C)C(O)=O)C=C2972.0Standard polar33892256
Isopimaric acid[H][C@]12CC[C@@](C)(CC1=CC[C@@]1([H])[C@@](C)(CCC[C@]21C)C(O)=O)C=C2239.4Standard non polar33892256
Isopimaric acid[H][C@]12CC[C@@](C)(CC1=CC[C@@]1([H])[C@@](C)(CCC[C@]21C)C(O)=O)C=C2361.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Isopimaric acid,1TMS,isomer #1C=C[C@@]1(C)CC[C@H]2C(=CC[C@H]3[C@](C)(C(=O)O[Si](C)(C)C)CCC[C@]23C)C12367.3Semi standard non polar33892256
Isopimaric acid,1TBDMS,isomer #1C=C[C@@]1(C)CC[C@H]2C(=CC[C@H]3[C@](C)(C(=O)O[Si](C)(C)C(C)(C)C)CCC[C@]23C)C12656.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Isopimaric 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 - Isopimaric acid 10V, Positive-QTOFsplash10-0zfr-0194000000-6accdee6fd7ecb3aaf3d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isopimaric acid 20V, Positive-QTOFsplash10-005i-0490000000-975cf74c21d7d3ce91742021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isopimaric acid 40V, Positive-QTOFsplash10-014i-8930000000-2d7a80b65b8b2f09efa12021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isopimaric acid 10V, Negative-QTOFsplash10-0udi-0009000000-16d58525184e918518fa2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isopimaric acid 20V, Negative-QTOFsplash10-0udi-0009000000-16d58525184e918518fa2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isopimaric acid 40V, Negative-QTOFsplash10-0udj-1095000000-dd8fb46ea5f348ad26ff2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
    • Zerihun T. Dame, ...
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDC00003444
Chemspider ID390596
KEGG Compound IDC09118
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkIsopimaric acid
METLIN IDNot Available
PubChem Compound442048
PDB IDNot Available
ChEBI ID6039
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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.