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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-08-12 23:44:01 UTC
Update Date2021-09-14 15:19:07 UTC
HMDB IDHMDB0003559
Secondary Accession Numbers
  • HMDB03559
Metabolite Identification
Common NameGibberellin A3
DescriptionGibberellic acid, also known as gibberellin A3, GA, or GA3, is a very potent hormone whose natural occurrence in plants controls their development. Since GA regulates growth, applications of very low concentrations can have a profound effect while too much will have the opposite effect. Gibberellic acid is a hormone found in plants. Gibberellic acid is a simple gibberellin promoting the growth and elongation of cells. It affects the decomposition of plants. It also helps plants grow if used in small amounts but eventually, plants grow a tolerance for it. Gibberellic acid stimulates the cells of germinating seeds to produce mRNA molecules that code for hydrolytic enzymes.
Structure
Data?1595349476
Synonyms
ValueSource
(+)-Gibberellic acidChEBI
GA3ChEBI
Gibberellic acidChEBI
Gibberellic acid ga3ChEBI
GibberellinChEBI
Gibberellin 3ChEBI
GibberellinsaeureChEBI
(+)-GibberellateGenerator
GibberellateGenerator
Gibberellate ga3Generator
GA(3) gibberellinMeSH
GA3 gibberellinMeSH
GibberelateHMDB
Gibberelic acidHMDB
GibberelinHMDB
GibberellinsHMDB
GibberillateHMDB
Gibberillic acidHMDB
Gibberellin A3MeSH
(+)-Gibberellin A3HMDB
GAHMDB
Gibberellin GA3HMDB
Chemical FormulaC19H22O6
Average Molecular Weight346.3744
Monoisotopic Molecular Weight346.141638436
IUPAC Name(1R,2R,5S,8S,9S,10R,11R,12S)-5,12-dihydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1^{5,8}.0^{1,10}.0^{2,8}]heptadec-13-ene-9-carboxylic acid
Traditional Name(1R,2R,5S,8S,9S,10R,11R,12S)-5,12-dihydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1^{5,8}.0^{1,10}.0^{2,8}]heptadec-13-ene-9-carboxylic acid
CAS Registry Number77-06-5
SMILES
[H][C@@]12CC[C@]3(O)C[C@]1(CC3=C)[C@@H](C(O)=O)[C@]1([H])[C@@]3(C)[C@@H](O)C=C[C@@]21OC3=O
InChI Identifier
InChI=1S/C19H22O6/c1-9-7-17-8-18(9,24)5-3-10(17)19-6-4-11(20)16(2,15(23)25-19)13(19)12(17)14(21)22/h4,6,10-13,20,24H,1,3,5,7-8H2,2H3,(H,21,22)/t10-,11+,12-,13-,16-,17+,18+,19-/m1/s1
InChI KeyIXORZMNAPKEEDV-OBDJNFEBSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as c19-gibberellin 6-carboxylic acids. These are c19-gibberellins with a carboxyl group at the 6-position.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassDiterpenoids
Direct ParentC19-gibberellin 6-carboxylic acids
Alternative Parents
Substituents
  • 20-norgibberellane-6-carboxylic acid
  • Diterpene lactone
  • Dicarboxylic acid or derivatives
  • Gamma butyrolactone
  • Cyclic alcohol
  • Tetrahydrofuran
  • Tertiary alcohol
  • Carboxylic acid ester
  • Secondary alcohol
  • Lactone
  • Carboxylic acid derivative
  • Carboxylic acid
  • Oxacycle
  • Organoheterocyclic compound
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Alcohol
  • Organooxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point234 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility5 mg/mLNot Available
LogP0.24HANSCH,C ET AL. (1995)
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.95 g/LALOGPS
logP10(0.66) g/LALOGPS
logP10(0.35) g/LChemAxon
logS10(-2.2) g/LALOGPS
pKa (Strongest Acidic)4.16ChemAxon
pKa (Strongest Basic)-0.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area104.06 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity86.42 m³·mol⁻¹ChemAxon
Polarizability36.35 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+178.62231661259
DarkChem[M-H]-173.42231661259

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Gibberellin A3,1TMS,#1C=C1C[C@]23C[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@]12C=C[C@H](O)[C@@](C)(C(=O)O1)[C@H]2[C@@H]3C(=O)O2724.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
Gibberellin A3,1TMS,#2C=C1C[C@]23C[C@@]1(O)CC[C@H]2[C@@]12C=C[C@H](O)[C@@](C)(C(=O)O1)[C@H]2[C@@H]3C(=O)O[Si](C)(C)C2666.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
Gibberellin A3,1TMS,#3C=C1C[C@]23C[C@@]1(O)CC[C@H]2[C@@]12C=C[C@H](O[Si](C)(C)C)[C@@](C)(C(=O)O1)[C@H]2[C@@H]3C(=O)O2732.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
Gibberellin A3,2TMS,#1C=C1C[C@]23C[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@]12C=C[C@H](O[Si](C)(C)C)[C@@](C)(C(=O)O1)[C@H]2[C@@H]3C(=O)O2768.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
Gibberellin A3,2TMS,#2C=C1C[C@]23C[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@]12C=C[C@H](O)[C@@](C)(C(=O)O1)[C@H]2[C@@H]3C(=O)O[Si](C)(C)C2730.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
Gibberellin A3,2TMS,#3C=C1C[C@]23C[C@@]1(O)CC[C@H]2[C@@]12C=C[C@H](O[Si](C)(C)C)[C@@](C)(C(=O)O1)[C@H]2[C@@H]3C(=O)O[Si](C)(C)C2720.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
Gibberellin A3,3TMS,#1C=C1C[C@]23C[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@]12C=C[C@H](O[Si](C)(C)C)[C@@](C)(C(=O)O1)[C@H]2[C@@H]3C(=O)O[Si](C)(C)C2760.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
Gibberellin A3,1TBDMS,#1C=C1C[C@]23C[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@]12C=C[C@H](O)[C@@](C)(C(=O)O1)[C@H]2[C@@H]3C(=O)O2933.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
Gibberellin A3,1TBDMS,#2C=C1C[C@]23C[C@@]1(O)CC[C@H]2[C@@]12C=C[C@H](O)[C@@](C)(C(=O)O1)[C@H]2[C@@H]3C(=O)O[Si](C)(C)C(C)(C)C2897.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
Gibberellin A3,1TBDMS,#3C=C1C[C@]23C[C@@]1(O)CC[C@H]2[C@@]12C=C[C@H](O[Si](C)(C)C(C)(C)C)[C@@](C)(C(=O)O1)[C@H]2[C@@H]3C(=O)O2932.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
Gibberellin A3,2TBDMS,#1C=C1C[C@]23C[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@]12C=C[C@H](O[Si](C)(C)C(C)(C)C)[C@@](C)(C(=O)O1)[C@H]2[C@@H]3C(=O)O3181.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
Gibberellin A3,2TBDMS,#2C=C1C[C@]23C[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@]12C=C[C@H](O)[C@@](C)(C(=O)O1)[C@H]2[C@@H]3C(=O)O[Si](C)(C)C(C)(C)C3159.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
Gibberellin A3,2TBDMS,#3C=C1C[C@]23C[C@@]1(O)CC[C@H]2[C@@]12C=C[C@H](O[Si](C)(C)C(C)(C)C)[C@@](C)(C(=O)O1)[C@H]2[C@@H]3C(=O)O[Si](C)(C)C(C)(C)C3156.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
Gibberellin A3,3TBDMS,#1C=C1C[C@]23C[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@]12C=C[C@H](O[Si](C)(C)C(C)(C)C)[C@@](C)(C(=O)O1)[C@H]2[C@@H]3C(=O)O[Si](C)(C)C(C)(C)C3403.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Gibberellin A3 GC-MS (3 TMS)splash10-06r7-1962110000-9177c556fa6efad1c7742014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Gibberellin A3 GC-MS (3 TMS)splash10-06r6-1962210000-a42d3ddb71fce133830e2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Gibberellin A3 GC-MS (Non-derivatized)splash10-067l-0963100000-6f900069528062a9617d2014-06-16HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Gibberellin A3 GC-MS (Non-derivatized) - 70eV, Positivesplash10-0pdr-5229000000-ca2cc506a5a34ba66af02017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Gibberellin A3 GC-MS (3 TMS) - 70eV, Positivesplash10-00b9-7531690000-6f8b76893b13c7428e222017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Gibberellin A3 GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Gibberellin A3 GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Gibberellin A3 DI-ESI-qTof , Negative-QTOFsplash10-006x-0691000000-17b74d24c35961a24e492017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gibberellin A3 DI-ESI-qTof , Positive-QTOFsplash10-004r-0089000000-8d300c6db336d16982a72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gibberellin A3 LC-ESI-QQ , negative-QTOFsplash10-0005-0039000000-50b6ebc557b9ada50d232017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gibberellin A3 LC-ESI-QQ , negative-QTOFsplash10-0076-1592000000-08bd6776369f44c150402017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gibberellin A3 LC-ESI-QQ , negative-QTOFsplash10-006x-1971000000-4e30b067ec25f0d63da22017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gibberellin A3 Linear Ion Trap , negative-QTOFsplash10-000i-0093000000-d1f3b7e68a1b78bbf2f42017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gibberellin A3 Linear Ion Trap , negative-QTOFsplash10-000i-0092000000-196f2c32602b9c5f73ba2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gibberellin A3 Linear Ion Trap , negative-QTOFsplash10-0002-0019000000-39a25c8c230a57aedc682017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gibberellin A3 Linear Ion Trap , negative-QTOFsplash10-0002-0019000000-206c614d4a7293c7afcd2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gibberellin A3 Linear Ion Trap , negative-QTOFsplash10-000i-0091000000-e7b5a66ef5dbd698c22a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gibberellin A3 Linear Ion Trap , negative-QTOFsplash10-000i-0091000000-c7e1532d564d2bd5045c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gibberellin A3 Linear Ion Trap , positive-QTOFsplash10-004r-0069000000-46593ed0c0579cd9c3452017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gibberellin A3 Linear Ion Trap , positive-QTOFsplash10-004r-0069000000-bf21fc973b2bd1baa8532017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gibberellin A3 20V, Negative-QTOFsplash10-006x-2692000000-149d66a60d549fb2825b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gibberellin A3 40V, Negative-QTOFsplash10-0006-2930000000-e3e6971d87376cd059742021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gibberellin A3 10V, Negative-QTOFsplash10-0002-0169000000-223cda14569af5407aa42021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gibberellin A3 35V, Negative-QTOFsplash10-000f-0690000000-aa9335a970ea9ab52ed22021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gibberellin A3 15V, Negative-QTOFsplash10-0002-0149000000-1b52adcaf5e960cc13b32021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gibberellin A3 30V, Negative-QTOFsplash10-006x-3791000000-b006d7e314cd964921a82021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gibberellin A3 10V, Positive-QTOFsplash10-01t9-0029000000-dbd2761f6bef9faffa5a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gibberellin A3 20V, Positive-QTOFsplash10-03gi-0249000000-7985bca540521d6fe6b32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gibberellin A3 40V, Positive-QTOFsplash10-001r-1392000000-f0c7ffeb48b0ad103a302016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gibberellin A3 10V, Negative-QTOFsplash10-0002-0019000000-87518c245603d07ff79c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gibberellin A3 20V, Negative-QTOFsplash10-0faj-0049000000-773fc25a8c0de9d6410d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gibberellin A3 40V, Negative-QTOFsplash10-0a4i-3291000000-5f5b232ca9fa294273f02016-08-03Wishart 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 IDDB07814
Phenol Explorer Compound IDNot Available
FooDB IDFDB005727
KNApSAcK IDC00000003
Chemspider ID6223
KEGG Compound IDC01699
BioCyc IDGIBBERELLIN
BiGG IDNot Available
Wikipedia LinkGibberellic_acid
METLIN ID6954
PubChem Compound6466
PDB IDNot Available
ChEBI ID28833
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1133321
References
Synthesis ReferenceLischewski, Manfred; Adam, Guenter. Gibberellin compounds. Ger. (East) (1979), 10 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Yamaki T, Takeda K: [A simple bioassay method of urinary indoleacetic acid, a cancer growth factor]. J UOEH. 1986 Mar 20;8 Suppl:297-302. [PubMed:3460143 ]