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Record Information
Version1.0
Created at2020-11-23 19:38:12 UTC
Updated at2021-08-19 23:59:15 UTC
NP-MRD IDNP0002697
Secondary Accession NumbersNone
Natural Product Identification
Common NameGibberellic acid
DescriptionGibberellin A3, also known as GA3 or gibberellic acid, 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. Thus, gibberellin A3 is considered to be an isoprenoid. Gibberellin A3 exists in all living organisms, ranging from bacteria to humans. Gibberellin A3 has been detected, but not quantified in, several different foods, such as chickens (Gallus gallus), barleys (Hordeum vulgare), sunflowers (Helianthus annuus), common peas (Pisum sativum), and common wheats (Triticum aestivum). This could make gibberellin A3 a potential biomarker for the consumption of these foods. Gibberellin A3 is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. It was first documented in 1986 (PMID: 3460143). Based on a literature review a significant number of articles have been published on Gibberellin A3 (PMID: 17984079) (PMID: 18948165) (PMID: 19815399) (PMID: 21216576).
Structure
Thumb
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 a3HMDB
GAHMDB
Gibberellin ga3HMDB
Gibberellin A3MeSH
Chemical FormulaC19H22O6
Average Mass346.3744 Da
Monoisotopic Mass346.14164 Da
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 NumberNot Available
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
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 500 MHz, D2O, experimental)Wishart Lab2021-06-20View Spectrum
Species
Species of Origin
Species NameSourceReference
Abelmoschus esculentusKNApSAcK Database
Althaea roseaKNApSAcK Database
Arabidopsis thalianaKNApSAcK Database
Avena sativaKNApSAcK Database
Brassica campestrisKNApSAcK Database
Brassica napusKNApSAcK Database
Bruguiera gymnorrhizaKNApSAcK Database
Calystegia soldanellaKNApSAcK Database
Camellia sinensisKNApSAcK Database
Carica papayaKNApSAcK Database
Carthamus tinctoriusKNApSAcK Database
Cassia fistulaKNApSAcK Database
Citrus sinensisKNApSAcK Database
Cucumis meloKNApSAcK Database
Cucumis sativusKNApSAcK Database
Dalbergia dolichopetalaKNApSAcK Database
Fragaria spp.KNApSAcK Database
Fragaria x ananassaKNApSAcK Database
Gossypium hirsutumKNApSAcK Database
Hordeum vulgareKNApSAcK Database
Ipomoea batatasKNApSAcK Database
Ipomoea reptansKNApSAcK Database
Ipomoea tricolorKNApSAcK Database
Lactuca sativaKNApSAcK Database
Lolium temulentumKNApSAcK Database
Lupinus albusKNApSAcK Database
Malus domesticaKNApSAcK Database
Mangifera indicaKNApSAcK Database
Marah macrocarpusKNApSAcK Database
Pennisetum glaucumKNApSAcK Database
Pharbitis purpureaKNApSAcK Database
Phaseolus coccineusKNApSAcK Database
Phaseolus lunatusKNApSAcK Database
Phaseolus multiflorusKNApSAcK Database
Picea abiesKNApSAcK Database
Pinus attenuataKNApSAcK Database
Pinus sylvestrisKNApSAcK Database
Pisum sativumKNApSAcK Database
Prunus aviumKNApSAcK Database
Prunus cerasusKNApSAcK Database
Prunus persicaKNApSAcK Database
Pseudotsuga menziesiiKNApSAcK Database
Pyrus communisKNApSAcK Database
Quamoclit pennataKNApSAcK Database
Rhizophora mucronataKNApSAcK Database
Saccharum spp.KNApSAcK Database
Secale cerealeKNApSAcK Database
Sechium eduleKNApSAcK Database
Senna toraKNApSAcK Database
Sonneratia apetalaKNApSAcK Database
Triticum aestivumKNApSAcK Database
Vigna unguiculataKNApSAcK Database
Vitis viniferaKNApSAcK Database
Zea maysKNApSAcK Database
Species Where Detected
Species NameSourceReference
Bacillus licheniformisKNApSAcK Database
Bacillus pumilusKNApSAcK Database
Fusarium fujikuroiKNApSAcK Database
Gibberella fujikuroiKNApSAcK Database
Gluconacetobacter diazotrophicusKNApSAcK Database
Herbaspirillum seropedicaeKNApSAcK Database
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 ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting Point234.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Boiling PointNot AvailableNot Available
Water Solubility5000 mg/L @ 25 °C (exp)The Good Scents Company Information System
LogP0.240The Good Scents Company Information System
Predicted Properties
PropertyValueSource
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
External Links
HMDB IDHMDB0003559
DrugBank IDDB07814
Phenol Explorer Compound IDNot Available
FoodDB 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
Good Scents IDrw1133321
References
General References
  1. Ulrich EL, Akutsu H, Doreleijers JF, Harano Y, Ioannidis YE, Lin J, Livny M, Mading S, Maziuk D, Miller Z, Nakatani E, Schulte CF, Tolmie DE, Kent Wenger R, Yao H, Markley JL: BioMagResBank. Nucleic Acids Res. 2008 Jan;36(Database issue):D402-8. doi: 10.1093/nar/gkm957. Epub 2007 Nov 4. [PubMed:17984079 ]
  2. 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 ]
  3. Erin N, Afacan B, Ersoy Y, Ercan F, Balci MK: Gibberellic acid, a plant growth regulator, increases mast cell recruitment and alters Substance P levels. Toxicology. 2008 Dec 5;254(1-2):75-81. doi: 10.1016/j.tox.2008.09.020. Epub 2008 Oct 2. [PubMed:18948165 ]
  4. Troudi A, Mahjoubi Samet A, Zeghal N: Hepatotoxicity induced by gibberellic acid in adult rats and their progeny. Exp Toxicol Pathol. 2010 Nov;62(6):637-42. doi: 10.1016/j.etp.2009.08.010. Epub 2009 Oct 7. [PubMed:19815399 ]
  5. Troudi A, Bouaziz H, Soudani N, Ben Amara I, Boudawara T, Touzani H, Lyoussi B, Zeghal N: Neurotoxicity and oxidative stress induced by gibberellic acid in rats during late pregnancy and early postnatal periods: biochemical and histological changes. Exp Toxicol Pathol. 2012 Sep;64(6):583-90. doi: 10.1016/j.etp.2010.11.017. Epub 2011 Jan 8. [PubMed:21216576 ]