Np mrd loader

Record Information
Version2.0
Created at2024-09-09 23:19:35 UTC
Updated at2024-09-09 23:19:35 UTC
NP-MRD IDNP0334359
Secondary Accession NumbersNone
Natural Product Identification
Common Namegibberellin A12-aldehyde
DescriptionGibberellin a12-aldehyde is a member of the class of compounds known as c20-gibberellins. C20-gibberellins are gibberellins with carboxy groups in positions 7 and 18 and some also in 20, while others have an aldehyde group in the latter position. Gibberellin a12-aldehyde is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Gibberellin a12-aldehyde can be found in a number of food items such as custard apple, yellow bell pepper, giant butterbur, and java plum, which makes gibberellin a12-aldehyde a potential biomarker for the consumption of these food products.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC20H27O3
Average Mass315.4340 Da
Monoisotopic Mass315.19657 Da
IUPAC Name(1S,2S,3S,4S,8R,9S,12R)-2-formyl-4,8-dimethyl-13-methylidenetetracyclo[10.2.1.0^{1,9}.0^{3,8}]pentadecane-4-carboxylate
Traditional Name(1S,2S,3S,4S,8R,9S,12R)-2-formyl-4,8-dimethyl-13-methylidenetetracyclo[10.2.1.0^{1,9}.0^{3,8}]pentadecane-4-carboxylate
CAS Registry NumberNot Available
SMILES
[H][C@@]12C[C@]3(CC1=C)[C@@]([H])(CC2)[C@@]1(C)CCC[C@](C)(C([O-])=O)[C@@]1([H])[C@]3([H])C=O
InChI Identifier
InChI=1S/C20H28O3/c1-12-9-20-10-13(12)5-6-15(20)18(2)7-4-8-19(3,17(22)23)16(18)14(20)11-21/h11,13-16H,1,4-10H2,2-3H3,(H,22,23)/p-1/t13-,14+,15+,16+,18-,19+,20+/m1/s1
InChI KeyZCTUNYRXJKLWPY-KWTCDADXSA-M
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as c20-gibberellins. These are gibberellins with carboxy groups in positions 7 and 18 and some also in 20, while others have an aldehyde group in the latter position.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassDiterpenoids
Direct ParentC20-gibberellins
Alternative Parents
Substituents
  • Gibberellane diterpenoid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aldehyde
  • Organic anion
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.43ChemAxon
pKa (Strongest Acidic)4.62ChemAxon
pKa (Strongest Basic)-7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area57.2 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity98.91 m³·mol⁻¹ChemAxon
Polarizability12.15 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. MacMillan J, Ward DA, Phillips AL, Sanchez-Beltran MJ, Gaskin P, Lange T, Hedden P: Gibberellin biosynthesis from gibberellin A12-aldehyde in endosperm and embryos of Marah macrocarpus. Plant Physiol. 1997 Apr;113(4):1369-77. doi: 10.1104/pp.113.4.1369. [PubMed:9112781 ]
  2. Kobayashi M, Spray CR, Phinney BO, Gaskin P, MacMillan J: Gibberellin Metabolism in Maize (The Stepwise Conversion of Gibberellin A12-Aldehyde to Gibberellin A20. Plant Physiol. 1996 Feb;110(2):413-418. doi: 10.1104/pp.110.2.413. [PubMed:12226193 ]
  3. Lange T, Hedden P, Graebe JE: Gibberellin biosynthesis in cell-free extracts from developing Cucurbita maxima embryos and the identification of new endogenous gibberellins. Planta. 1993 Mar;189(3):350-8. doi: 10.1007/BF00194431. [PubMed:24178491 ]
  4. Lange T, Hedden P, Graebe JE: Biosynthesis of 12alpha-and 13-hydroxylated gibberellins in a cell-free system from Cucurbita maxima endosperm and the identification of new endogenous gibberellins. Planta. 1993 Mar;189(3):340-9. doi: 10.1007/BF00194430. [PubMed:24178490 ]
  5. Grosselindemann E, Lewis MJ, Hedden P, Graebe JE: Gibberellin biosynthesis from gibberellin A12-aldehyde in a cell-free system from germinating barley (Hordeum vulgare L., cv. Himalaya) embryos. Planta. 1992 Sep;188(2):252-7. doi: 10.1007/BF00216821. [PubMed:24178262 ]
  6. Takahashi M, Kamiya Y, Takahashi N, Graebe JE: Metabolism of gibberellins in a cell-free system from immature seeds of Phaseolus vulgaris L. Planta. 1986 Jun;168(2):190-9. doi: 10.1007/BF00402963. [PubMed:24232021 ]
  7. Birnberg PR, Maki SL, Brenner ML, Davis GC, Carnes MG: An improved enzymatic synthesis of labeled gibberellin A12-aldehyde and gibberellin A12. Anal Biochem. 1986 Feb 15;153(1):1-8. doi: 10.1016/0003-2697(86)90052-7. [PubMed:3754395 ]
  8. Turnbull CG, Crozier A, Schwenen L, Graebe JE: Conversion of [(14)C]gibberellin A 12-aldehyde to C 19- and C 20-gibberellins in a cell-free system from immature seed of Phaseolus coccineus L. Planta. 1985 Jul;165(1):108-13. doi: 10.1007/BF00392218. [PubMed:24240964 ]