(1R,2R,5S,8S,9S,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

• ChemBase ID: 169626
• Molecular Formular: C19H22O6
• Molecular Mass: 346.37438
• Monoisotopic Mass: 346.14163842
• SMILES: [C@@]12(C(=O)O[C@@]3(C=C[C@@H]1O)C2[C@@H]([C@]12[C@H]3CC[C@](C1)(C(=C)C2)O)C(=O)O)C
• Canonical SMILES: OC(=O)[C@H]1C2[C@]3([C@H]4[C@]51CC(=C)[C@](C5)(O)CC4)C=C[C@@H]([C@]2(C)C(=O)O3)O
• 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
• InChIKey: IXORZMNAPKEEDV-OHSBXDGMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2R,5S,8S,9S,11R,12S)-5,12-dihydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1^5,^8.0^1,^1^0.0^2,^8]heptadec-13-ene-9-carboxylic acid
• IUPAC Traditional name: (1R,2R,5S,8S,9S,11R,12S)-5,12-dihydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1^5,^8.0^1,^1^0.0^2,^8]heptadec-13-ene-9-carboxylic acid
• Synonyms: (1α,2β,4aα,4bβ,10β)-2,4a,7-Trihydroxy-1-methyl-8-methylenegibb-3-ene-1,10-dicarboxylic Acid 1,4a-Lactone,; Gibberellin A3; (+)-Gibberellic Acid; (+)-Gibberellin A3; Activol; Arbostim; Berelex; GA; GA3; GibGro; Gibberellic Acid GA3; Gibberellin GA3; Gibrescol; Gibreskol; Grocel GA3; Maxon; NSC 14190; NSC 19450; Pro-Gibb; Pro-Gibb Plus; Ralex; Release LC; RyzUp; TU 64-3-103-75; Gibberellic Acid, 90%

Database IDs

• CAS Number: 77-06-5
• PubChem SID: 162263758
• PubChem CID: 44575418

CALCULATED PROPERTIES

• Acid pKa: 4.163467
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -1.0024102
• LogD (pH = 7.4): -2.7070677
• Log P: 0.3509133
• Molar Refractivity: 86.4155 cm^3
• Polarizability: 34.211063 Å^3
• Polar Surface Area: 104.06 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - G377450

Gibberellic Acid is a a pentacyclic diterpene acid. Gibberellic Acid is a hormone that is found in plants which promotes the growth and elongation of cells. Gibberellic acid acts as a plant growth regulator on account of its physiological and morphologica

REFERENCES

• Bayle, J. et al.: Chem. Biol., 13, 99 (2006)
• Ihara, S. et al.: J. Cell Sci., 119, 500 (2006)
• Suh, B. et al.: Science, 314, 1454 (2006)
• Rinaudo, K. et al.: Nat. Biotechnol., 25, 795 (2006)