(1R,2R,5S,8S,9S,11S,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: 303834
• Molecular Formular: C19H22O6
• Molecular Mass: 346.37438
• Monoisotopic Mass: 346.14163842
• SMILES: C[C@@]12[C@H](C=C[C@@]3(C1[C@@H]([C@]14[C@H]3CC[C@](C1)(C(=C)C4)O)C(=O)O)OC2=O)O
• 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-XEWSHXLDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2R,5S,8S,9S,11S,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,11S,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: Gibberellic acid; 赤霉酸

Database IDs

• CAS Number: 77-06-5
• EC Number: 201-001-0
• MDL Number: MFCD00079329
• Beilstein Number: 54346
• Merck Index: 144419

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

Physical Property

• Apperance: Powder
• Melting Point: 222°C dec.
• Optical Rotation: +78 (c=2 in methanol)

Safety Information

• RTECS: LY8990000
• European Hazard Symbols: Irritant (Xi)
• Risk Statements: 36
• Safety Statements: 26-60
• TSCA Listed: 是
• GHS Pictograms: GHS07
• GHS Hazard statements: H319
• GHS Precautionary statements: P280-P264-P305+P351+P338-P337+P313

Product Information

• Purity: 98%