(1R,2R,5S,8S,9S,10R,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: 119594
• Molecular Formular: C19H22O6
• Molecular Mass: 346.37438
• Monoisotopic Mass: 346.14163842
• SMILES: [C@@]123[C@@H]([C@@](C(=O)O1)([C@H](C=C3)O)C)[C@@H]([C@]13[C@H]2CC[C@](C1)(C(=C)C3)O)C(=O)O
• 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-SNTJWBGVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2R,5S,8S,9S,10R,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,10R,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; gibberellin A3
• Synonyms: Berelex; Gibrescol; Gibberellin A3; Gibrofit; Activol; GA3; Gibberellic acid; (1S,2S,4aR,4bR,7S,9aS,10S,10aR)-2,7-dihydroxy-1-methyl-8-methylene-13-oxo-1,2,4b,5,6,7,8,9,10,10a-decahydro-4a,1-(epoxymethano)-7,9a-methanobenzo[a]azulene-10-carboxylic acid

Database IDs

• CAS Number: 77-06-5
• PubChem SID: 162107687
• PubChem CID: 9819600

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

PROPERTIES

Pharmacology Properties

• Mechanism of Action: Plant growth factor.; Stimulates the cells of germinating seeds to produce mRNA molecules that code for hydrolytic enzymes

Product Information

• Biological Source: Produced by Gibberella fujikuroi and present in higher plants
• Application(s): Plant growth regulator; Used as an experimental research mutagen; Used in malting of barley

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