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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-08-12 23:44:01 UTC
Update Date2019-07-23 05:45:50 UTC
HMDB IDHMDB0003559
Secondary Accession Numbers
  • HMDB03559
Metabolite Identification
Common NameGibberellin A3
DescriptionGibberellic acid, also called 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. Gibberelic acid is a simple gibberellin promoting growth and elongation of cells. Affects decomposition of plants. 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?1563860749
Synonyms
ValueSource
(+)-Gibberellic acidChEBI
GA3ChEBI
Gibberellic acidChEBI
Gibberellic acid ga3ChEBI
GibberellinChEBI
Gibberellin 3ChEBI
GibberellinsaeureChEBI
(+)-GibberellateGenerator
GibberellateGenerator
Gibberellate ga3Generator
2b-Hydroxygibberellin 1HMDB
BerelexHMDB
BrellinHMDB
Gib-solHMDB
Gib-tabsHMDB
Gibb-tabsHMDB
GibberelateHMDB
Gibberelic acidHMDB
GibberelinHMDB
Gibberellin 1HMDB
Gibberellin XHMDB
GibberellinsHMDB
GibberillateHMDB
Gibberillic acidHMDB
Gibberellic acid, monopotassium saltHMDB
GA(3) gibberellinHMDB
GA3 gibberellinHMDB
Gibberellic acid, monosodium saltHMDB
Gibberellic acid, (1alpha,2beta,4aalpha,4bbeta,6alpha,10beta)-isomerHMDB
Gibberellic acid, monoammonium saltHMDB
Gibberellic acid, potassium saltHMDB
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[9.3.2.1⁵,⁸.0¹,¹⁰.0²,⁸]heptadec-13-ene-9-carboxylic acid
Traditional Namegibberellic 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
Polarizability48.43 ųChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-06r7-1962110000-9177c556fa6efad1c774JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-06r6-1962210000-a42d3ddb71fce133830eJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-067l-0963100000-6f900069528062a9617dJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0pdr-5229000000-ca2cc506a5a34ba66af0JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00b9-7531690000-6f8b76893b13c7428e22JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Negativesplash10-006x-0691000000-17b74d24c35961a24e49JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-004r-0089000000-8d300c6db336d16982a7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0005-0039000000-50b6ebc557b9ada50d23JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0076-1592000000-08bd6776369f44c15040JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-006x-1971000000-4e30b067ec25f0d63da2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-000i-0093000000-d1f3b7e68a1b78bbf2f4JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-000i-0092000000-196f2c32602b9c5f73baJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0002-0019000000-39a25c8c230a57aedc68JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0002-0019000000-206c614d4a7293c7afcdJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-000i-0091000000-e7b5a66ef5dbd698c22aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-000i-0091000000-c7e1532d564d2bd5045cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-004r-0069000000-46593ed0c0579cd9c345JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-004r-0069000000-bf21fc973b2bd1baa853JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01t9-0029000000-dbd2761f6bef9faffa5aJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03gi-0249000000-7985bca540521d6fe6b3JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001r-1392000000-f0c7ffeb48b0ad103a30JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0019000000-87518c245603d07ff79cJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0faj-0049000000-773fc25a8c0de9d6410dJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-3291000000-5f5b232ca9fa294273f0JSpectraViewer | MoNA
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
FoodDB IDFDB013644
KNApSAcK IDC00000003
Chemspider ID7995349
KEGG Compound IDC01699
BioCyc IDGIBBERELLIN
BiGG IDNot Available
Wikipedia LinkGibberellic_acid
METLIN ID6954
PubChem Compound9819600
PDB IDNot Available
ChEBI ID28833
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 ]