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(3R,4S,5R)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid
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ChemBase ID:
119443
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Molecular Formular:
C7H10O5
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Molecular Mass:
174.1513
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Monoisotopic Mass:
174.05282342
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SMILES and InChIs
SMILES:
C1(=C[C@H]([C@H]([C@@H](C1)O)O)O)C(=O)O
Canonical SMILES:
O[C@@H]1CC(=C[C@H]([C@H]1O)O)C(=O)O
InChI:
InChI=1S/C7H10O5/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1,4-6,8-10H,2H2,(H,11,12)/t4-,5-,6-/m1/s1
InChIKey:
JXOHGGNKMLTUBP-HSUXUTPPSA-N
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Cite this record
CBID:119443 http://www.chembase.cn/molecule-119443.html
NAMES AND DATABASE IDS
NAMES AND DATABASE IDS
Names Database IDs
IUPAC name
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(3R,4S,5R)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid
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IUPAC Traditional name
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Synonyms
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Shikimic acid
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(3R,4S,5R)-3,4,5-trihydroxycyclohex-1-enecarboxylic acid
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(3R,4S,5R)-(-)-3,4,5-Trihydroxy-1-cyclohexenecarboxylic acid
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Shikimic acid
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L-Shikimic acid
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NSC 59257
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(3R,4S,5R)-3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic Acid
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3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic acid
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(-)-Shikimic acid
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(-)-莽草酸
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CAS Number
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EC Number
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MDL Number
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Beilstein Number
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Merck Index
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PubChem SID
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PubChem CID
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CHEBI ID
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CHEMBL
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Chemspider ID
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KEGG ID
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Wikipedia Title
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DATA SOURCES
DATA SOURCES
All Sources Commercial Sources Non-commercial Sources
CALCULATED PROPERTIES
CALCULATED PROPERTIES
JChem
Acid pKa
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4.103319
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H Acceptors
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5
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H Donor
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4
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LogD (pH = 5.5)
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-3.0506496
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LogD (pH = 7.4)
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-4.7369246
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Log P
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-1.6400741
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Molar Refractivity
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38.9603 cm3
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Polarizability
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15.229941 Å3
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Polar Surface Area
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97.99 Å2
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Rotatable Bonds
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1
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Lipinski's Rule of Five
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true
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DETAILS
DETAILS
Wikipedia
Sigma Aldrich
TRC
Sigma Aldrich -
S5375
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Biochem/physiol Actions Biosynthetic precursor of aromatic amino acids, as well as many alkaloids and other aromatic metabolites. 包装 10 mg in autosmp vl |
Sigma Aldrich -
85091
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Other Notes Intermediate in the biosynthesis of aromatic amino acids 1; Preparation of derivatives 2,3 |
Toronto Research Chemicals -
S357100
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Naturally occurring (-)-form is a major biosynthetic precursor of phenylalanine, tyrosine, and tryptophan and hence of the majority of plant alkaloids. It is also involved in the biosynthesis of lignin, flavonpids and other important aromatic compounds. |
REFERENCES
REFERENCES
From Suppliers
Google Scholar
PubMed
Google Books
- • Evans, I.A., et al.: Nature, 250, 348 (1974)
- • Harborne, J.B., et al.: Biosynthesis, 6, 40 (1974)
- • Key intermediate in the biosynthesis of aromatic amino acids.
- • Monograph: E. Haslam, Shikimic Acid, Wiley, Chichester (1993). Reviews: Chem. Rev., 65, 435 (1965); Tetrahedron, 34, 3353 (1978); Biosynthesis, 6, 40 (1980); Natural Prod. Rep., 10, 233 (1993); Synthesis, 179 (1993).
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PATENTS
PATENTS
PubChem Patent
Google Patent