(2S,3S)-2,3-dihydroxybutanedioic acid; [(1S,4R)-4-aminocyclopent-2-en-1-yl]methanol

• ChemBase ID: 159966
• Molecular Formular: C10H17NO7
• Molecular Mass: 263.24448
• Monoisotopic Mass: 263.10050189
• SMILES: C1=C[C@H](C[C@H]1N)CO.[C@@H]([C@H](O)C(=O)O)(O)C(=O)O
• Canonical SMILES: OC(=O)[C@H]([C@@H](C(=O)O)O)O.OC[C@@H]1C=C[C@@H](C1)N
• InChI: InChI=1S/C6H11NO.C4H6O6/c7-6-2-1-5(3-6)4-8;5-1(3(7)8)2(6)4(9)10/h1-2,5-6,8H,3-4,7H2;1-2,5-6H,(H,7,8)(H,9,10)/t5-,6+;1-,2-/m10/s1
• InChIKey: LTSTZOJHLZNDFG-ZGMNSGLWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S)-2,3-dihydroxybutanedioic acid; [(1S,4R)-4-aminocyclopent-2-en-1-yl]methanol
• IUPAC Traditional name: D-tartaric acid; [(1S,4R)-4-aminocyclopent-2-en-1-yl]methanol
• Synonyms: (1S,4R)-cis-4-Amino-2-cyclopentene-1-methanol (2S,3S)-2,3-Dihydroxybutanedioate; (1S,4R)-cis-4-Amino-2-cyclopentene-1-methanol D-Tartrate; (1S-cis)-4-Amino-2-cyclopentene-1-methanol D-Tartrate

Database IDs

• CAS Number: 229177-52-0
• PubChem SID: 162254101
• PubChem CID: 10355372

CALCULATED PROPERTIES

• Acid pKa: 2.719041
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -5.323427
• LogD (pH = 7.4): -7.890869
• Log P: -1.8287998
• Molar Refractivity: 26.2134 cm^3
• Polarizability: 10.871467 Å^3
• Polar Surface Area: 115.06 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A603640

(1S,4R)-cis-4-Amino-2-cyclopentene-1-methanol is an Abacavir intermediate; antiviral therapeutic nucleoside analog.

REFERENCES

• Clapper, D., et al.: J. Biol. Chem., 262, 9561 (1987)
• Zhang, F., et al.: Bioorg. Med. Chem., 7, 653 (1987)
• Shuto, S., et al.: J. Med. Chem., 46, 4741 (1987)
• Shuto, S., et al.: Curr. Med. Chem., 11, 827 (1987)