Gibberellin

Basic Info

Common NameGibberellin(F05888)
2D Structure
FRCD IDF05888
CAS Number77-06-5
PubChem CID6466
FormulaC19H22O6
IUPAC Name

None

InChI Key

IXORZMNAPKEEDV-OBDJNFEBSA-N

InChI

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

Canonical SMILES

CC12C(C=CC3(C1C(C45C3CCC(C4)(C(=C)C5)O)C(=O)O)OC2=O)O

Isomeric SMILES

C[C@@]12[C@H](C=C[C@@]3([C@@H]1[C@@H]([C@]45[C@H]3CC[C@](C4)(C(=C)C5)O)C(=O)O)OC2=O)O

Synonyms
        
            Gibberellic acid GA3
        
            GIBBERELLIC ACID
        
            77-06-5
        
            Gibberellin A3
        
            Gibberellin
        
            Gibreskol
        
            Brellin
        
            Cekugib
        
            Grocel
        
            Gibberellin X
Classifies
                

                  
                    Pesticide
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassLipids and lipid-like molecules
ClassPrenol lipids
SubclassDiterpenoids
Intermediate Tree NodesGibberellins - C19-gibberellins
Direct ParentC19-gibberellin 6-carboxylic acids
Alternative Parents
Molecular FrameworkAliphatic heteropolycyclic compounds
Substituents20-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
DescriptionThis compound 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.

Properties

Property NameProperty Value
Molecular Weight346.379
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count6
Rotatable Bond Count1
Complexity772
Monoisotopic Mass346.142
Exact Mass346.142
XLogP0.2
Formal Charge0
Heavy Atom Count25
Defined Atom Stereocenter Count8
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.7665
Human Intestinal AbsorptionHIA+0.9356
Caco-2 PermeabilityCaco2+0.5079
P-glycoprotein SubstrateSubstrate0.7635
P-glycoprotein InhibitorNon-inhibitor0.7954
Non-inhibitor0.9753
Renal Organic Cation TransporterNon-inhibitor0.7797
Distribution
Subcellular localizationMitochondria0.7926
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7925
CYP450 2D6 SubstrateNon-substrate0.8824
CYP450 3A4 SubstrateSubstrate0.6167
CYP450 1A2 InhibitorNon-inhibitor0.9045
CYP450 2C9 InhibitorNon-inhibitor0.9071
CYP450 2D6 InhibitorNon-inhibitor0.9417
CYP450 2C19 InhibitorNon-inhibitor0.9026
CYP450 3A4 InhibitorNon-inhibitor0.8404
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.9518
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9133
Non-inhibitor0.8341
AMES ToxicityNon AMES toxic0.9133
CarcinogensNon-carcinogens0.9650
Fish ToxicityHigh FHMT0.9962
Tetrahymena Pyriformis ToxicityHigh TPT0.6322
Honey Bee ToxicityHigh HBT0.8114
BiodegradationNot ready biodegradable0.9822
Acute Oral ToxicityIV0.6316
Carcinogenicity (Three-class)Non-required0.4590
Model Value Unit
Absorption
Aqueous solubility-1.9024LogS
Caco-2 Permeability0.8106LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity1.7712LD50, mol/kg
Fish Toxicity0.3376pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.4084pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
PineappleJapan0.2ppm
Egg PlantJapan0.2ppm
Lettuce(Including Cos Lettuce And Leaf Lettuce)Japan0.2ppm
Other HerbsJapan0.2ppm
Other SpicesJapan0.2ppm
Other NutsJapan0.2ppm
WalnutJapan0.2ppm
AlmondJapan0.2ppm
PecanJapan0.2ppm
ChestnutJapan0.2ppm
Ginkgo NutJapan0.2ppm
Other Oil SeedsJapan0.2ppm
RapeseedsJapan0.2ppm
Cotton SeedsJapan0.2ppm
Safflower SeedsJapan0.2ppm
Sesame SeedsJapan0.2ppm
Sunflower SeedsJapan0.2ppm
Other FruitsJapan0.2ppm
DateJapan0.2ppm
Passion FruitJapan0.2ppm

References

TitleJournalDatePubmed ID
Synergistic effect of the combined bio-fungicides ε-poly-l-lysine andchitooligosaccharide in controlling grey mould (Botrytis cinerea) in tomatoes.Int J Food Microbiol2018 Jul 229656220
Exogenous short-term silicon application regulates macro-nutrients, endogenousphytohormones, and protein expression in Oryza sativa L.BMC Plant Biol2018 Jan 429301510
Analysis of the global regulator Lae1 uncovers a connection between Lae1 and the histone acetyltransferase HAT1 in Fusarium fujikuroi.Appl Microbiol Biotechnol2018 Jan29080998
Carbon nanomaterials alter plant physiology and soil bacterial community composition in a rice-soil-bacterial ecosystem.Environ Pollut2018 Jan28947315
Bioherbicides: Current knowledge on weed control mechanism.Ecotoxicol Environ Saf2018 Aug 3029677595
Impacts of exogenous pollutant bisphenol A on characteristics of soybeans.Ecotoxicol Environ Saf2018 Aug 1529655848
Reduced abscisic acid content is responsible for enhanced sucrose accumulation bypotassium nutrition in vegetable soybean seeds.J Plant Res2017 May28247062
The parthenocarpic hydra mutant reveals a new function for a SPOROCYTELESS-likegene in the control of fruit set in tomato.New Phytol2017 May28134991
Abscisic acid regulates seed germination of Vellozia species in response totemperature.Plant Biol (Stuttg)2017 Mar27718313
iTRAQ-based proteomics of sunflower cultivars differing in resistance to parasitic weed Orobanche cumana.Proteomics2017 Jul28618117
Seed tolerance to deterioration in arabidopsis is affected by virus infection.Plant Physiol Biochem2017 Jul28477474
Role of phytohormones in aluminium rhizotoxicity.Plant Cell Environ2016 Oct27352002
The role of gibberellins in improving the resistance of tebuconazole-coated maizeseeds to chilling stress by microencapsulation.Sci Rep2016 Nov 727819337
CLCuMuB βC1 Subverts Ubiquitination by Interacting with NbSKP1s to EnhanceGeminivirus Infection in Nicotiana benthamiana.PLoS Pathog2016 Jun 1727315204
Interplay between pathway-specific and global regulation of the fumonisin gene cluster in the rice pathogen Fusarium fujikuroi.Appl Microbiol Biotechnol2016 Jul26966024
[Effects of fluridone, gibberellin acid and germination temperature ondormancy-breaking for Epimedium wushanense].Zhongguo Zhong Yao Za Zhi2016 Jul28905597
Heterologous expression of chloroplast-localized geranylgeranyl pyrophosphatesynthase confers fast plant growth, early flowering and increased seed yield.Plant Biotechnol J2016 Jan25644367
Gibberellins producing Bacillus methylotrophicus KE2 supports plant growth andenhances nutritional metabolites and food values of lettuce.Plant Physiol Biochem2016 Dec27721133
Reactive oxygen species induced by cold stratification promote germination ofHedysarum scoparium seeds.Plant Physiol Biochem2016 Dec27816822
Silicon: a duo synergy for regulating crop growth and hormonal signaling underabiotic stress conditions.Crit Rev Biotechnol2016 Dec26381374