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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:04:43 UTC
Update Date2022-03-07 02:55:06 UTC
HMDB IDHMDB0036896
Secondary Accession Numbers
  • HMDB36896
Metabolite Identification
Common NameGibberellin A19
DescriptionGibberellin A19 (GA19) belongs to the class of organic compounds known as C20-gibberellin 6-carboxylic acids. These are C20-gibberellins with a carboxyl group at the 6-position. Thus, gibberellin A19 is considered to be an isoprenoid lipid molecule. Gibberellin A19 is found in apple. Gibberellin A19 is a constituent of moso bamboo shoots (Phyllostachys edulis).
Structure
Data?1595343433
Synonyms
ValueSource
GA19ChEBI
Gibberellin 19ChEBI
GA19 CPDMeSH
Gibberellin a(19)MeSH
(1alpha,4aalpha,4bbeta,10beta)-4a-Formyl-7-hydroxy-1-methyl-8-methylenegibbane-1,10-dicarboxylic acidHMDB
(1α,4aα,4bβ,10β)-4a-Formyl-7-hydroxy-1-methyl-8-methylenegibbane-1,10-dicarboxylic acidHMDB
Gibberellin A19HMDB
Gibberellin GA19HMDB
Chemical FormulaC20H26O6
Average Molecular Weight362.4168
Monoisotopic Molecular Weight362.172938564
IUPAC Name(1S,2S,3S,4R,8R,9R,12S)-8-formyl-12-hydroxy-4-methyl-13-methylidenetetracyclo[10.2.1.0^{1,9}.0^{3,8}]pentadecane-2,4-dicarboxylic acid
Traditional Name(1S,2S,3S,4R,8R,9R,12S)-8-formyl-12-hydroxy-4-methyl-13-methylidenetetracyclo[10.2.1.0^{1,9}.0^{3,8}]pentadecane-2,4-dicarboxylic acid
CAS Registry Number6980-44-5
SMILES
[H][C@@]12CC[C@]3(O)C[C@]1(CC3=C)[C@@H](C(O)=O)[C@@]1([H])[C@]2(CCC[C@@]1(C)C(O)=O)C=O
InChI Identifier
InChI=1S/C20H26O6/c1-11-8-19-9-20(11,26)7-4-12(19)18(10-21)6-3-5-17(2,16(24)25)14(18)13(19)15(22)23/h10,12-14,26H,1,3-9H2,2H3,(H,22,23)(H,24,25)/t12-,13+,14+,17+,18+,19-,20-/m0/s1
InChI KeyVNCQCPQAMDQEBY-YTJHIPEWSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as c20-gibberellin 6-carboxylic acids. These are c20-gibberellins with a carboxyl group at the 6-position.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassDiterpenoids
Direct ParentC20-gibberellin 6-carboxylic acids
Alternative Parents
Substituents
  • Gibberellane-6-carboxylic acid
  • Dicarboxylic acid or derivatives
  • Tertiary alcohol
  • Cyclic alcohol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aldehyde
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point236 - 237 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.88 g/LALOGPS
logP1.23ALOGPS
logP1.46ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)3.94ChemAxon
pKa (Strongest Basic)-0.9ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area111.9 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity91.32 m³·mol⁻¹ChemAxon
Polarizability37.11 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-213.43430932474
DeepCCS[M+Na]+188.78830932474
AllCCS[M+H]+183.032859911
AllCCS[M+H-H2O]+180.532859911
AllCCS[M+NH4]+185.432859911
AllCCS[M+Na]+186.032859911
AllCCS[M-H]-187.132859911
AllCCS[M+Na-2H]-187.132859911
AllCCS[M+HCOO]-187.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Gibberellin A19[H][C@@]12CC[C@]3(O)C[C@]1(CC3=C)[C@@H](C(O)=O)[C@@]1([H])[C@]2(CCC[C@@]1(C)C(O)=O)C=O3637.2Standard polar33892256
Gibberellin A19[H][C@@]12CC[C@]3(O)C[C@]1(CC3=C)[C@@H](C(O)=O)[C@@]1([H])[C@]2(CCC[C@@]1(C)C(O)=O)C=O2613.6Standard non polar33892256
Gibberellin A19[H][C@@]12CC[C@]3(O)C[C@]1(CC3=C)[C@@H](C(O)=O)[C@@]1([H])[C@]2(CCC[C@@]1(C)C(O)=O)C=O2894.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Gibberellin A19,1TMS,isomer #1C=C1C[C@]23C[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@]1(C=O)CCC[C@@](C)(C(=O)O)[C@H]1[C@@H]3C(=O)O2796.8Semi standard non polar33892256
Gibberellin A19,1TMS,isomer #2C=C1C[C@]23C[C@@]1(O)CC[C@H]2[C@]1(C=O)CCC[C@@](C)(C(=O)O)[C@H]1[C@@H]3C(=O)O[Si](C)(C)C2749.7Semi standard non polar33892256
Gibberellin A19,1TMS,isomer #3C=C1C[C@]23C[C@@]1(O)CC[C@H]2[C@]1(C=O)CCC[C@@](C)(C(=O)O[Si](C)(C)C)[C@H]1[C@@H]3C(=O)O2775.2Semi standard non polar33892256
Gibberellin A19,2TMS,isomer #1C=C1C[C@]23C[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@]1(C=O)CCC[C@@](C)(C(=O)O[Si](C)(C)C)[C@H]1[C@@H]3C(=O)O2765.9Semi standard non polar33892256
Gibberellin A19,2TMS,isomer #2C=C1C[C@]23C[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@]1(C=O)CCC[C@@](C)(C(=O)O)[C@H]1[C@@H]3C(=O)O[Si](C)(C)C2751.7Semi standard non polar33892256
Gibberellin A19,2TMS,isomer #3C=C1C[C@]23C[C@@]1(O)CC[C@H]2[C@]1(C=O)CCC[C@@](C)(C(=O)O[Si](C)(C)C)[C@H]1[C@@H]3C(=O)O[Si](C)(C)C2755.6Semi standard non polar33892256
Gibberellin A19,3TMS,isomer #1C=C1C[C@]23C[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@]1(C=O)CCC[C@@](C)(C(=O)O[Si](C)(C)C)[C@H]1[C@@H]3C(=O)O[Si](C)(C)C2760.8Semi standard non polar33892256
Gibberellin A19,1TBDMS,isomer #1C=C1C[C@]23C[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@]1(C=O)CCC[C@@](C)(C(=O)O)[C@H]1[C@@H]3C(=O)O3005.8Semi standard non polar33892256
Gibberellin A19,1TBDMS,isomer #2C=C1C[C@]23C[C@@]1(O)CC[C@H]2[C@]1(C=O)CCC[C@@](C)(C(=O)O)[C@H]1[C@@H]3C(=O)O[Si](C)(C)C(C)(C)C2981.9Semi standard non polar33892256
Gibberellin A19,1TBDMS,isomer #3C=C1C[C@]23C[C@@]1(O)CC[C@H]2[C@]1(C=O)CCC[C@@](C)(C(=O)O[Si](C)(C)C(C)(C)C)[C@H]1[C@@H]3C(=O)O3012.1Semi standard non polar33892256
Gibberellin A19,2TBDMS,isomer #1C=C1C[C@]23C[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@]1(C=O)CCC[C@@](C)(C(=O)O[Si](C)(C)C(C)(C)C)[C@H]1[C@@H]3C(=O)O3236.1Semi standard non polar33892256
Gibberellin A19,2TBDMS,isomer #2C=C1C[C@]23C[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@]1(C=O)CCC[C@@](C)(C(=O)O)[C@H]1[C@@H]3C(=O)O[Si](C)(C)C(C)(C)C3210.2Semi standard non polar33892256
Gibberellin A19,2TBDMS,isomer #3C=C1C[C@]23C[C@@]1(O)CC[C@H]2[C@]1(C=O)CCC[C@@](C)(C(=O)O[Si](C)(C)C(C)(C)C)[C@H]1[C@@H]3C(=O)O[Si](C)(C)C(C)(C)C3224.3Semi standard non polar33892256
Gibberellin A19,3TBDMS,isomer #1C=C1C[C@]23C[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@]1(C=O)CCC[C@@](C)(C(=O)O[Si](C)(C)C(C)(C)C)[C@H]1[C@@H]3C(=O)O[Si](C)(C)C(C)(C)C3455.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Gibberellin A19 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 - Gibberellin A19 10V, Positive-QTOFsplash10-0002-0019000000-0bbedc4c2de3df5c1bcc2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gibberellin A19 20V, Positive-QTOFsplash10-0002-0259000000-6bca58b4f92953d1db792016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gibberellin A19 40V, Positive-QTOFsplash10-00ds-1393000000-49db9433e0f9857a4c5a2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gibberellin A19 10V, Negative-QTOFsplash10-03xr-0029000000-27da0d30be6432de85402016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gibberellin A19 20V, Negative-QTOFsplash10-0301-0079000000-b5329968ffa0686a30e02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gibberellin A19 40V, Negative-QTOFsplash10-00dj-1294000000-90604aa4c46280d20b892016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gibberellin A19 10V, Negative-QTOFsplash10-03di-0009000000-28a5e8ce01750244e0ba2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gibberellin A19 20V, Negative-QTOFsplash10-03di-0029000000-8ff4985f4e6d164861e22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gibberellin A19 40V, Negative-QTOFsplash10-03dl-4169000000-bf31f794b8d10fb178972021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gibberellin A19 10V, Positive-QTOFsplash10-03di-0019000000-8e7fc70193751d8ab4d02021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gibberellin A19 20V, Positive-QTOFsplash10-000i-0098000000-5e60aff95e04ea33822b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gibberellin A19 40V, Positive-QTOFsplash10-03k9-0039000000-65699716bf58d6b213c62021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • 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 IDFDB015856
KNApSAcK IDC00000019
Chemspider ID4573832
KEGG Compound IDC02034
BioCyc IDCPD1F-96
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5460209
PDB IDNot Available
ChEBI ID28731
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.