(1S,2R,5S)-1,5-dimethyl-3-methylidene-4-oxo-6-oxabicyclo[3.1.0]hexane-2-carboxylic acid

• ChemBase ID: 128376
• Molecular Formular: C9H10O4
• Molecular Mass: 182.1733
• Monoisotopic Mass: 182.0579088
• SMILES: O=C1C(=C)[C@@H](C(=O)O)[C@@]2(O[C@]12C)C
• Canonical SMILES: OC(=O)[C@@H]1C(=C)C(=O)[C@@]2([C@@]1(C)O2)C
• InChI: InChI=1S/C9H10O4/c1-4-5(7(11)12)8(2)9(3,13-8)6(4)10/h5H,1H2,2-3H3,(H,11,12)/t5-,8-,9+/m0/s1
• InChIKey: HBECYYFDLZZMPL-WLGLDCGKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,5S)-1,5-dimethyl-3-methylidene-4-oxo-6-oxabicyclo[3.1.0]hexane-2-carboxylic acid
• IUPAC Traditional name: methylenomycin A
• Synonyms: Methylenomycin A

Database IDs

• CAS Number: 52775-76-5
• PubChem SID: 162222684
• PubChem CID: 10899285
• Chemspider ID: 9074545
• Wikipedia Title: Methylenomycin_A

CALCULATED PROPERTIES

• Acid pKa: 3.9529886
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -0.7520038
• LogD (pH = 7.4): -2.3827467
• Log P: 0.80266184
• Molar Refractivity: 42.8053 cm^3
• Polarizability: 16.991568 Å^3
• Polar Surface Area: 66.9 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 341.2 °C
• Flash Point: 141.2 °C