(1R,2R,5S,8S,9S,10R,11S,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

• ChemBase ID: 5448
• Molecular Formular: C19H22O6
• Molecular Mass: 346.37438
• Monoisotopic Mass: 346.14163842
• SMILES: OC(=O)[C@H]1[C@H]2[C@@]3([C@H]4[C@]51CC(=C)[C@](C5)(O)CC4)OC(=O)[C@@]2([C@H](C=C3)O)C
• Canonical SMILES: OC(=O)[C@H]1[C@H]2[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-OBDJNFEBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2R,5S,8S,9S,10R,11S,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
• IUPAC Traditional name: gibberellin; gibberellinsaeure
• Synonyms: GIBBERELLIN A3; GA₃; Gibberellin A3; GIBBERELLIC ACID

Database IDs

• CAS Number: 77-06-5
• EC Number: 201-001-0
• PubChem SID: 160968876; 99444285
• PubChem CID: 6466

CALCULATED PROPERTIES

JChem

• 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

ALOGPS 2.1

• Log P: 0.66
• LOG S: -2.25
• Solubility (Water): 1.95e+00 g/l

PROPERTIES

Physical Property

• Melting Point: 227°C

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• RTECS: LY8990000
• European Hazard Symbols: Harmful (Xn)
• Risk Statements: R:27-36/37/38
• Safety Statements: S:25-26-36/37/39

Product Information

• Purity: >90%; 90%

DETAILS

MP Biomedicals - 02151180

Crystalline 90%
Gibberellin A3 +10% inactive substance Useful for structure-activity studies.

MP Biomedicals - 05213098

MP Biomedicals Rare Chemical collection

DrugBank - DB07814

Drug information: experimental

REFERENCES

• Serebryakov, E.P., et al., Phytochemistry, 23: 1847, (1984).
• See: Cell Biology Section