ChemFOnt: Showing chemical card for Gibberellin A3 (CFc000001923)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:46:40 UTC

Chemfont ID

CFc000001923

Molecule Identification

Common Name

Gibberellin A3

Definition

Gibberellic 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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Gibberellin	MeSH

Chemical Formula

C₁₉H₂₂O₆

Average Molecular Weight

346.3744

Monoisotopic Molecular Weight

346.141638436

IUPAC Name

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

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 Number

77-06-5

SMILES

CC12C3C(C(O)=O)C45CC(=C)C(O)(C4)CCC5C3(OC1=O)C=CC2O

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)

InChI Key

IXORZMNAPKEEDV-UHFFFAOYSA-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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

C19-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 Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0003559)
Membrane (HMDB: HMDB0003559)

Source

Exogenous

Exogenous (HMDB: HMDB0003559)

Food

Fruit

Pome

Apple (FooDB: FOOD00105)
Pear (FooDB: FOOD00152)

Tropical fruit

Mango (FooDB: FOOD00106)
Papaya (FooDB: FOOD00041)

Citrus

Sweet orange (FooDB: FOOD00057)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)

Berry

Strawberry (FooDB: FOOD00083)
Common grape (FooDB: FOOD00204)

Drupe

Cereal and cereal product

Cereal

Barley (FooDB: FOOD00088)
Corn (FooDB: FOOD00205)
Oat (FooDB: FOOD00022)
Rye (FooDB: FOOD00169)
Common wheat (FooDB: FOOD00187)

Vegetable

Leaf vegetable

Other vegetable

Okra (FooDB: FOOD00420)

Root vegetable

Swede (FooDB: FOOD00028)

Tuber

Sweet potato (FooDB: FOOD00092)

Gourd

Herb and spice

Oilseed crop

Safflower (FooDB: FOOD00042)

Herb

Turnip (FooDB: FOOD00036)
Soft-necked garlic (FooDB: FOOD00850)

Pulse

Pea

Common pea (FooDB: FOOD00141)
Cowpea (FooDB: FOOD00202)

Bean

Lima bean (FooDB: FOOD00133)
Scarlet bean (FooDB: FOOD00132)

Other pulse

White lupine (FooDB: FOOD00403)

Tea

Endogenous

Endogenous (HMDB: HMDB0003559)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	1.95 g/L	ALOGPS
logP	0.66	ALOGPS
logP	0.35	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	4.16	ChemAxon
pKa (Strongest Basic)	-0.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	104.06 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	86.42 m³·mol⁻¹	ChemAxon
Polarizability	34.86 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0252716

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB013644

KNApSAcK ID

C00000003

Chemspider ID

455898

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Gibberellin

METLIN ID

Not Available

PubChem Compound

522636

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Lischewski, Manfred; Adam, Guenter. Gibberellin compounds. Ger. (East) (1979), 10 pp.

Showing chemical card for Gibberellin A3 (CFc000001923)

MOL for CFc000001923 (Gibberellin A3)

3D MOL for CFc000001923 (Gibberellin A3)

3D SDF for CFc000001923 (Gibberellin A3)

3D-SDF for CFc000001923 (Gibberellin A3)

PDB for CFc000001923 (Gibberellin A3)

3D PDB for CFc000001923 (Gibberellin A3)

SMILES for CFc000001923 (Gibberellin A3)

INCHI for CFc000001923 (Gibberellin A3)

Structure for CFc000001923 (Gibberellin A3)

3D Structure for CFc000001923 (Gibberellin A3)