(3S,5S)-3,4-dihydroxy-5-[(1R,2R)-1,2,3-trihydroxypropyl]oxolan-2-one

• ChemBase ID: 169649
• Molecular Formular: C7H12O7
• Molecular Mass: 208.16598
• Monoisotopic Mass: 208.05830272
• SMILES: C1(O)[C@@H](OC(=O)[C@H]1O)[C@@H]([C@@H](CO)O)O
• Canonical SMILES: OC[C@H]([C@H]([C@@H]1OC(=O)[C@H](C1O)O)O)O
• InChI: InChI=1S/C7H12O7/c8-1-2(9)3(10)6-4(11)5(12)7(13)14-6/h2-6,8-12H,1H2/t2-,3-,4?,5+,6+/m1/s1
• InChIKey: VIVCRCODGMFTFY-VGHHYEQRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,5S)-3,4-dihydroxy-5-[(1R,2R)-1,2,3-trihydroxypropyl]oxolan-2-one
• IUPAC Traditional name: (3S,5S)-3,4-dihydroxy-5-[(1R,2R)-1,2,3-trihydroxypropyl]oxolan-2-one
• Synonyms: (2ξ)-D-Glucoheptonic Acid γ-Lactone; Glucoheptonic Acid γ-Lactone; D-Glucoheptonolactone; D-Glucoheptono-1,4-lactone

Database IDs

• CAS Number: 60046-25-5
• PubChem SID: 162263781
• PubChem CID: 71317081

CALCULATED PROPERTIES

• Acid pKa: 11.607878
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): -3.3756084
• LogD (pH = 7.4): -3.375635
• Log P: -3.3756082
• Molar Refractivity: 40.7413 cm^3
• Polarizability: 17.148533 Å^3
• Polar Surface Area: 127.45 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - G416500

It is used in the synthesis of Howiinol A and its analogs. Howiinol A was one of the active antitumor constituents from the root and stem bark of Goniothamus howii (Annonaceae), and it was synthesized in 9 steps from α-D-glucoheptonic γ-lactone. Twenty-si

REFERENCES

• Dhanvantari, S., et al.: J. Biol. Chem., 275, 29887 (2000)
• Kjellin, U., et al.: Langmuir, 17, 1941 (2000)