Record Information |
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Version |
1.0 |
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Update Date |
1/22/2018 11:54:54 AM |
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Metabolite ID | PAMDB110055 |
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Identification |
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Name: |
shikimate |
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Description: | A cyclohexenecarboxylate that is the conjugate base of shikimic acid. |
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Structure |
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Synonyms: | -
shikimic acid
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(3R,4S,5R)--3,4,5-trihydroxycyclohex-1-ene-1-carboxylate
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Chemical Formula: |
C7H9O5
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Average Molecular Weight: |
173.14 |
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Monoisotopic Molecular
Weight: |
174.0528234315 |
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InChI Key: |
JXOHGGNKMLTUBP-HSUXUTPPSA-M |
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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)/p-1/t4-,5-,6-/m1/s1 |
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CAS
number: |
138-59-0 |
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IUPAC Name: | (3R,4S,5R)--3,4,5-trihydroxycyclohex-1-ene-1-carboxylate |
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Traditional IUPAC Name: |
(-)-shikimate |
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SMILES: | C1(=C(CC(C(O)C(O)1)O)C(=O)[O-]) |
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Chemical Taxonomy |
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Taxonomy Description | This compound belongs to the class of organic compounds known as shikimic acids and derivatves. These are cyclitols containing a cyclohexanecarboxylic acid substituted with three hydroxyl groups at positions 3, 4, and 5. |
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Kingdom |
Organic compounds |
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Super Class | Organic oxygen compounds |
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Class |
Organooxygen compounds |
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Sub Class | Alcohols and polyols |
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Direct Parent |
Shikimic acids and derivatves |
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Alternative Parents |
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Substituents |
- Shikimic acid or derivatives
- Secondary alcohol
- Polyol
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Organic oxide
- Hydrocarbon derivative
- Carbonyl group
- Organic anion
- Aliphatic homomonocyclic compound
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Molecular Framework |
Aliphatic homomonocyclic compounds |
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External Descriptors |
- a small molecule (SHIKIMATE)
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Physical Properties |
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State: |
Solid |
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Charge: | -1 |
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Melting point: |
186 °C |
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Experimental Properties: |
Property | Value | Reference |
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Melting Point | 186 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 150 mg/mL at 21 °C | Not Available | LogP | Not Available | Not Available |
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Predicted Properties |
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Biological Properties |
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Cellular Locations: |
Not Available |
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Reactions: | |
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Pathways: |
Not Available |
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Spectra |
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Spectra: |
Spectrum Type | Description | Splash Key | |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS) | splash10-0udj-0970000000-42465cd3f3e138b0bc12 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) | splash10-0udi-0790000000-1100443abb8605953f58 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS) | splash10-00di-9450000000-e6ca954dc1a9c1cc4285 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-MS (4 TMS) | splash10-0udi-0491000000-49993b9b18e12b9461fc | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS | Not Available |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-004i-0900000000-e6ca4ce5acb44dc23a74 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-004r-9700000000-18afe769b0ef5ba3fbdb | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-000i-9100000000-7d0218e803b828de53b2 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-01b9-1900000000-fd80f5e7f51d927e8e15 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-0a4i-9300000000-cf8a3148fd132540bf97 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative | splash10-0a4i-9000000000-ed28bc20ae43473043c9 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative | splash10-0a4i-9000000000-65249fc24f2de4acf2c7 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative | splash10-0a4i-9000000000-26dfc876ae35c2cdb845 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative | splash10-006x-9600000000-3a5ab91754d9d837d8b4 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | Not Available |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | Not Available |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | Not Available |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | Not Available |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | Not Available |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | Not Available |
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1D NMR | 1H NMR Spectrum | Not Available |
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1D NMR | 1H NMR Spectrum | Not Available |
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1D NMR | 13C NMR Spectrum | Not Available |
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2D NMR | [1H,1H] 2D NMR Spectrum | Not Available |
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2D NMR | [1H,13C] 2D NMR Spectrum | Not Available |
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References |
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References: |
- Liu Y, Xie MX, Jiang M, Wang YD: Spectroscopic investigation of the interaction between human serum albumin and three organic acids. Spectrochim Acta A Mol Biomol Spectrosc. 2005 Jul;61(9):2245-51. [15911418 ]
- Rose GA: Studies on the chemical nature of urinary chemiluminescence. Br J Urol. 1976 Feb;48(1):61-71. [5168 ]
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Synthesis Reference: |
Not Available |
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Material Safety Data Sheet (MSDS) |
Download (PDF) |
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Links |
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External Links: |
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