Record Information |
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Version | 1.0 |
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Created at | 2022-02-14 20:48:30 UTC |
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Updated at | 2022-03-10 22:19:57 UTC |
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NP-MRD ID | NP0044314 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | D-Arabinose 5-phosphate |
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Description | D-Arabinose 5-phosphate, also known as arabinose-5-p or 5-O-phosphono-D-arabinose, belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups. D-Arabinose 5-phosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). D-Arabinose 5-phosphate exists in all living organisms, ranging from bacteria to humans. Outside of the human body, D-Arabinose 5-phosphate has been detected, but not quantified in, several different foods, such as arrowhead, japanese persimmons, common hazelnuts, broad beans, and cloudberries. This could make D-arabinose 5-phosphate a potential biomarker for the consumption of these foods. The 5-phospho derivative of D-arabinose. D-Arabinose 5-phosphate is expected to be in Cannabis as all living plants are known to produce and metabolize it. |
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Structure | O[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)C=O InChI=1S/C5H11O8P/c6-1-3(7)5(9)4(8)2-13-14(10,11)12/h1,3-5,7-9H,2H2,(H2,10,11,12)/t3-,4-,5+/m1/s1 |
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Synonyms | Value | Source |
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5-O-Phosphono-D-arabinose | ChEBI | D-a-5-p | ChEBI | D-Arabinose 5-phosphoric acid | Generator | Arabinose-5-p | HMDB | Arabinose-5P | HMDB | Arabinose 5-phosphate, di-li salt | HMDB | Arabinose 5-phosphate | HMDB | Arabinose 5-phosphate, (beta-D)-isomer | HMDB |
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Chemical Formula | C5H11O8P |
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Average Mass | 230.1098 Da |
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Monoisotopic Mass | 230.01915 Da |
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IUPAC Name | {[(2R,3R,4S)-2,3,4-trihydroxy-5-oxopentyl]oxy}phosphonic acid |
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Traditional Name | arabinose 5-phosphate |
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CAS Registry Number | 13137-52-5 |
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SMILES | O[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)C=O |
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InChI Identifier | InChI=1S/C5H11O8P/c6-1-3(7)5(9)4(8)2-13-14(10,11)12/h1,3-5,7-9H,2H2,(H2,10,11,12)/t3-,4-,5+/m1/s1 |
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InChI Key | PPQRONHOSHZGFQ-WDCZJNDASA-N |
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Experimental Spectra |
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| Not Available | Predicted Spectra |
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| Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 13C NMR Spectrum (1D, 25 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups. |
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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 | Carbohydrates and carbohydrate conjugates |
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Direct Parent | Pentose phosphates |
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Alternative Parents | |
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Substituents | - Pentose phosphate
- Monosaccharide phosphate
- Monoalkyl phosphate
- Beta-hydroxy aldehyde
- Organic phosphoric acid derivative
- Phosphoric acid ester
- Alkyl phosphate
- Alpha-hydroxyaldehyde
- Secondary alcohol
- Polyol
- Hydrocarbon derivative
- Aldehyde
- Organic oxide
- Carbonyl group
- Alcohol
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Physical Properties |
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State | Not Available |
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Experimental Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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General References | - Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
- Meredith TC, Woodard RW: Escherichia coli YrbH is a D-arabinose 5-phosphate isomerase. J Biol Chem. 2003 Aug 29;278(35):32771-7. doi: 10.1074/jbc.M303661200. Epub 2003 Jun 12. [PubMed:12805358 ]
- Allison TM, Hutton RD, Cochrane FC, Yeoman JA, Jameson GB, Parker EJ: Targeting the role of a key conserved motif for substrate selection and catalysis by 3-deoxy-D-manno-octulosonate 8-phosphate synthase. Biochemistry. 2011 May 10;50(18):3686-95. doi: 10.1021/bi200251f. Epub 2011 Apr 18. [PubMed:21438567 ]
- Bleakley PA, Arora KK, Williams JF: Evidence that aldolase and D-arabinose 5-phosphate are components of pentose pathway reactions in liver in vitro. Biochem Int. 1984 Apr;8(4):491-500. [PubMed:6541043 ]
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