(1R,2R,5R,8R,9S,10R,11S,12S)-12-hydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1^{5,8}.0^{1,10}.0^{2,8}]heptadecane-9-carboxylic acid

• ChemBase ID: 5449
• Molecular Formular: C19H24O5
• Molecular Mass: 332.39086
• Monoisotopic Mass: 332.16237387
• SMILES: C1C[C@H](O)[C@@]2([C@H]3[C@H](C(=O)O)[C@]45[C@H]([C@]13OC2=O)CC[C@@H](C4)C(=C)C5)C
• Canonical SMILES: C=C1C[C@@]23C[C@@H]1CC[C@H]3[C@@]13[C@H]([C@@H]2C(=O)O)[C@@](C)([C@H](CC1)O)C(=O)O3
• InChI: InChI=1S/C19H24O5/c1-9-7-18-8-10(9)3-4-11(18)19-6-5-12(20)17(2,16(23)24-19)14(19)13(18)15(21)22/h10-14,20H,1,3-8H2,2H3,(H,21,22)/t10-,11-,12+,13-,14-,17-,18+,19-/m1/s1
• InChIKey: RSQSQJNRHICNNH-NFMPGMCNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2R,5R,8R,9S,10R,11S,12S)-12-hydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1^{5,8}.0^{1,10}.0^{2,8}]heptadecane-9-carboxylic acid
• IUPAC Traditional name: gibberellin 4
• Synonyms: GIBBERELLIN A4

Database IDs

• PubChem SID: 160968877; 99444286
• PubChem CID: 92109

CALCULATED PROPERTIES

JChem

• Acid pKa: 4.288334
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 0.32484943
• LogD (pH = 7.4): -1.4111365
• Log P: 1.5603198
• Molar Refractivity: 84.0788 cm^3
• Polarizability: 33.795246 Å^3
• Polar Surface Area: 83.83 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.38
• LOG S: -2.44
• Solubility (Water): 1.19e+00 g/l

DETAILS

DrugBank - DB07815

Drug information: experimental