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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-08-12 23:44:01 UTC
Update Date2020-07-21 18:31:35 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
GibberelateHMDB
Gibberelic acidHMDB
GibberelinHMDB
GibberellinsHMDB
GibberillateHMDB
Gibberillic acidHMDB
GA(3) gibberellinHMDB
GA3 gibberellinHMDB
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

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point234 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility5 mg/mLNot Available
LogP0.24HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility1.95 g/LALOGPS
logP0.66ALOGPS
logP0.35ChemAxon
logS-2.2ALOGPS
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
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-06r7-1962110000-9177c556fa6efad1c774Spectrum
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-06r6-1962210000-a42d3ddb71fce133830eSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-067l-0963100000-6f900069528062a9617dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0pdr-5229000000-ca2cc506a5a34ba66af0Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00b9-7531690000-6f8b76893b13c7428e22Spectrum
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Negativesplash10-006x-0691000000-17b74d24c35961a24e49Spectrum
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-004r-0089000000-8d300c6db336d16982a7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0005-0039000000-50b6ebc557b9ada50d23Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0076-1592000000-08bd6776369f44c15040Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-006x-1971000000-4e30b067ec25f0d63da2Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-000i-0093000000-d1f3b7e68a1b78bbf2f4Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-000i-0092000000-196f2c32602b9c5f73baSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0002-0019000000-39a25c8c230a57aedc68Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0002-0019000000-206c614d4a7293c7afcdSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-000i-0091000000-e7b5a66ef5dbd698c22aSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-000i-0091000000-c7e1532d564d2bd5045cSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-004r-0069000000-46593ed0c0579cd9c345Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-004r-0069000000-bf21fc973b2bd1baa853Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01t9-0029000000-dbd2761f6bef9faffa5aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03gi-0249000000-7985bca540521d6fe6b3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001r-1392000000-f0c7ffeb48b0ad103a30Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0019000000-87518c245603d07ff79cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0faj-0049000000-773fc25a8c0de9d6410dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-3291000000-5f5b232ca9fa294273f0Spectrum
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 ID7995349
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
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 ]