Record Information |
---|
Version | 5.0 |
---|
Status | Expected but not Quantified |
---|
Creation Date | 2012-09-11 19:55:00 UTC |
---|
Update Date | 2022-03-07 02:54:18 UTC |
---|
HMDB ID | HMDB0034981 |
---|
Secondary Accession Numbers | |
---|
Metabolite Identification |
---|
Common Name | Sambunigrin |
---|
Description | Sambunigrin, also known as (2S)-sambunigrin or L-prunasin, belongs to the class of organic compounds known as cyanogenic glycosides. These are glycosides in which the aglycone moiety contains a cyanide group. Sambunigrin is found, on average, in the highest concentration within black elderberries (Sambucus nigra). Sambunigrin has also been detected, but not quantified in, fruits and passion fruits (Passiflora edulis). This could make sambunigrin a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Sambunigrin. |
---|
Structure | OC[C@H]1O[C@@H](O[C@H](C#N)C2=CC=CC=C2)[C@H](O)[C@@H](O)[C@@H]1O InChI=1S/C14H17NO6/c15-6-9(8-4-2-1-3-5-8)20-14-13(19)12(18)11(17)10(7-16)21-14/h1-5,9-14,16-19H,7H2/t9-,10-,11-,12+,13-,14-/m1/s1 |
---|
Synonyms | Value | Source |
---|
(2S)-Sambunigrin | ChEBI | (S)-(beta-D-Glucopyranosyloxy)(phenyl)acetonitrile | ChEBI | (S)-Mandelonitrile beta-D-glucoside | ChEBI | (S)-O-beta-D-Glucopyranosylmandelonitrile | ChEBI | (S)-Sambunigrin | ChEBI | L-Prunasin | ChEBI | (S)-(b-D-Glucopyranosyloxy)(phenyl)acetonitrile | Generator | (S)-(Β-D-glucopyranosyloxy)(phenyl)acetonitrile | Generator | (S)-Mandelonitrile b-D-glucoside | Generator | (S)-Mandelonitrile β-D-glucoside | Generator | (S)-O-b-D-Glucopyranosylmandelonitrile | Generator | (S)-O-Β-D-glucopyranosylmandelonitrile | Generator | (2S)-(beta-D-Glucopyranosyloxy)(phenyl)acetonitrile | HMDB | (S)-Prunasin | HMDB | Sambunigrin | MeSH |
|
---|
Chemical Formula | C14H17NO6 |
---|
Average Molecular Weight | 295.2879 |
---|
Monoisotopic Molecular Weight | 295.105587281 |
---|
IUPAC Name | (2S)-2-phenyl-2-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}acetonitrile |
---|
Traditional Name | (S)-prunasin |
---|
CAS Registry Number | 99-19-4 |
---|
SMILES | OC[C@H]1O[C@@H](O[C@H](C#N)C2=CC=CC=C2)[C@H](O)[C@@H](O)[C@@H]1O |
---|
InChI Identifier | InChI=1S/C14H17NO6/c15-6-9(8-4-2-1-3-5-8)20-14-13(19)12(18)11(17)10(7-16)21-14/h1-5,9-14,16-19H,7H2/t9-,10-,11-,12+,13-,14-/m1/s1 |
---|
InChI Key | ZKSZEJFBGODIJW-YOVYLDAJSA-N |
---|
Chemical Taxonomy |
---|
Description | Belongs to the class of organic compounds known as cyanogenic glycosides. These are glycosides in which the aglycone moiety contains a cyanide group. |
---|
Kingdom | Organic compounds |
---|
Super Class | Organic oxygen compounds |
---|
Class | Organooxygen compounds |
---|
Sub Class | Carbohydrates and carbohydrate conjugates |
---|
Direct Parent | Cyanogenic glycosides |
---|
Alternative Parents | |
---|
Substituents | - Cyanogenic glycoside
- Hexose monosaccharide
- O-glycosyl compound
- Monocyclic benzene moiety
- Monosaccharide
- Oxane
- Benzenoid
- Secondary alcohol
- Polyol
- Nitrile
- Carbonitrile
- Acetal
- Organoheterocyclic compound
- Oxacycle
- Primary alcohol
- Organonitrogen compound
- Hydrocarbon derivative
- Alcohol
- Organopnictogen compound
- Organic nitrogen compound
- Aromatic heteromonocyclic compound
|
---|
Molecular Framework | Aromatic heteromonocyclic compounds |
---|
External Descriptors | |
---|
Ontology |
---|
Physiological effect | Not Available |
---|
Disposition | |
---|
Process | Not Available |
---|
Role | |
---|
Physical Properties |
---|
State | Solid |
---|
Experimental Molecular Properties | Property | Value | Reference |
---|
Melting Point | 151 - 152 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 268800 mg/L @ 25 °C (est) | The Good Scents Company Information System | LogP | Not Available | Not Available |
|
---|
Experimental Chromatographic Properties | Not Available |
---|
Predicted Molecular Properties | |
---|
Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
---|
Sambunigrin,1TMS,isomer #1 | C[Si](C)(C)OC[C@H]1O[C@@H](O[C@H](C#N)C2=CC=CC=C2)[C@H](O)[C@@H](O)[C@@H]1O | 2246.2 | Semi standard non polar | 33892256 | Sambunigrin,1TMS,isomer #2 | C[Si](C)(C)O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@H](C#N)C1=CC=CC=C1 | 2253.3 | Semi standard non polar | 33892256 | Sambunigrin,1TMS,isomer #3 | C[Si](C)(C)O[C@H]1[C@H](O)[C@@H](CO)O[C@@H](O[C@H](C#N)C2=CC=CC=C2)[C@@H]1O | 2259.1 | Semi standard non polar | 33892256 | Sambunigrin,1TMS,isomer #4 | C[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](O[C@H](C#N)C2=CC=CC=C2)[C@H](O)[C@H]1O | 2257.8 | Semi standard non polar | 33892256 | Sambunigrin,2TMS,isomer #1 | C[Si](C)(C)OC[C@H]1O[C@@H](O[C@H](C#N)C2=CC=CC=C2)[C@H](O[Si](C)(C)C)[C@@H](O)[C@@H]1O | 2243.9 | Semi standard non polar | 33892256 | Sambunigrin,2TMS,isomer #2 | C[Si](C)(C)OC[C@H]1O[C@@H](O[C@H](C#N)C2=CC=CC=C2)[C@H](O)[C@@H](O[Si](C)(C)C)[C@@H]1O | 2266.4 | Semi standard non polar | 33892256 | Sambunigrin,2TMS,isomer #3 | C[Si](C)(C)OC[C@H]1O[C@@H](O[C@H](C#N)C2=CC=CC=C2)[C@H](O)[C@@H](O)[C@@H]1O[Si](C)(C)C | 2267.1 | Semi standard non polar | 33892256 | Sambunigrin,2TMS,isomer #4 | C[Si](C)(C)O[C@H]1[C@H](O)[C@@H](CO)O[C@@H](O[C@H](C#N)C2=CC=CC=C2)[C@@H]1O[Si](C)(C)C | 2269.4 | Semi standard non polar | 33892256 | Sambunigrin,2TMS,isomer #5 | C[Si](C)(C)O[C@H]1[C@H](O)[C@@H](O[Si](C)(C)C)[C@H](O[C@H](C#N)C2=CC=CC=C2)O[C@@H]1CO | 2269.0 | Semi standard non polar | 33892256 | Sambunigrin,2TMS,isomer #6 | C[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](O[C@H](C#N)C2=CC=CC=C2)[C@H](O)[C@H]1O[Si](C)(C)C | 2259.7 | Semi standard non polar | 33892256 | Sambunigrin,3TMS,isomer #1 | C[Si](C)(C)OC[C@H]1O[C@@H](O[C@H](C#N)C2=CC=CC=C2)[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O | 2280.5 | Semi standard non polar | 33892256 | Sambunigrin,3TMS,isomer #2 | C[Si](C)(C)OC[C@H]1O[C@@H](O[C@H](C#N)C2=CC=CC=C2)[C@H](O[Si](C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C | 2281.8 | Semi standard non polar | 33892256 | Sambunigrin,3TMS,isomer #3 | C[Si](C)(C)OC[C@H]1O[C@@H](O[C@H](C#N)C2=CC=CC=C2)[C@H](O)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C | 2286.7 | Semi standard non polar | 33892256 | Sambunigrin,3TMS,isomer #4 | C[Si](C)(C)O[C@H]1[C@H](O[Si](C)(C)C)[C@@H](CO)O[C@@H](O[C@H](C#N)C2=CC=CC=C2)[C@@H]1O[Si](C)(C)C | 2277.7 | Semi standard non polar | 33892256 | Sambunigrin,4TMS,isomer #1 | C[Si](C)(C)OC[C@H]1O[C@@H](O[C@H](C#N)C2=CC=CC=C2)[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C | 2301.9 | Semi standard non polar | 33892256 | Sambunigrin,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](O[C@H](C#N)C2=CC=CC=C2)[C@H](O)[C@@H](O)[C@@H]1O | 2491.4 | Semi standard non polar | 33892256 | Sambunigrin,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@H](C#N)C1=CC=CC=C1 | 2489.6 | Semi standard non polar | 33892256 | Sambunigrin,1TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)O[C@H]1[C@H](O)[C@@H](CO)O[C@@H](O[C@H](C#N)C2=CC=CC=C2)[C@@H]1O | 2487.5 | Semi standard non polar | 33892256 | Sambunigrin,1TBDMS,isomer #4 | CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](O[C@H](C#N)C2=CC=CC=C2)[C@H](O)[C@H]1O | 2500.5 | Semi standard non polar | 33892256 | Sambunigrin,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](O[C@H](C#N)C2=CC=CC=C2)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O | 2726.6 | Semi standard non polar | 33892256 | Sambunigrin,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](O[C@H](C#N)C2=CC=CC=C2)[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O | 2729.7 | Semi standard non polar | 33892256 | Sambunigrin,2TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](O[C@H](C#N)C2=CC=CC=C2)[C@H](O)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C | 2741.7 | Semi standard non polar | 33892256 | Sambunigrin,2TBDMS,isomer #4 | CC(C)(C)[Si](C)(C)O[C@H]1[C@H](O)[C@@H](CO)O[C@@H](O[C@H](C#N)C2=CC=CC=C2)[C@@H]1O[Si](C)(C)C(C)(C)C | 2722.0 | Semi standard non polar | 33892256 | Sambunigrin,2TBDMS,isomer #5 | CC(C)(C)[Si](C)(C)O[C@H]1[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[C@H](C#N)C2=CC=CC=C2)O[C@@H]1CO | 2723.1 | Semi standard non polar | 33892256 | Sambunigrin,2TBDMS,isomer #6 | CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](O[C@H](C#N)C2=CC=CC=C2)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C | 2715.5 | Semi standard non polar | 33892256 | Sambunigrin,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](O[C@H](C#N)C2=CC=CC=C2)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O | 2924.2 | Semi standard non polar | 33892256 | Sambunigrin,3TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](O[C@H](C#N)C2=CC=CC=C2)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C | 2914.5 | Semi standard non polar | 33892256 | Sambunigrin,3TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](O[C@H](C#N)C2=CC=CC=C2)[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C | 2925.5 | Semi standard non polar | 33892256 | Sambunigrin,3TBDMS,isomer #4 | CC(C)(C)[Si](C)(C)O[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](CO)O[C@@H](O[C@H](C#N)C2=CC=CC=C2)[C@@H]1O[Si](C)(C)C(C)(C)C | 2916.4 | Semi standard non polar | 33892256 | Sambunigrin,4TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](O[C@H](C#N)C2=CC=CC=C2)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C | 3108.6 | Semi standard non polar | 33892256 |
|
---|
| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
---|
Predicted GC-MS | Predicted GC-MS Spectrum - Sambunigrin GC-MS (Non-derivatized) - 70eV, Positive | splash10-02e9-5970000000-af7eea9783215b5077ec | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Sambunigrin GC-MS (4 TMS) - 70eV, Positive | splash10-014i-2411490000-eb6d4c8c77d360144d24 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Sambunigrin GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
---|
Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Sambunigrin 10V, Positive-QTOF | splash10-001j-0950000000-94af28ff3325aa91829f | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Sambunigrin 20V, Positive-QTOF | splash10-00lr-0900000000-c209318aed53a776a604 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Sambunigrin 40V, Positive-QTOF | splash10-067i-3900000000-f46229fde33733da738a | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Sambunigrin 10V, Negative-QTOF | splash10-000x-1890000000-a1a34454361f8a461a19 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Sambunigrin 20V, Negative-QTOF | splash10-001i-2910000000-9efa8331da9f7f35adb0 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Sambunigrin 40V, Negative-QTOF | splash10-003r-9800000000-6551bbcd67cdb9809506 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Sambunigrin 10V, Negative-QTOF | splash10-0006-0950000000-911e901878111f3552da | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Sambunigrin 20V, Negative-QTOF | splash10-0gc0-1910000000-e65f091dbdc8f43dd35c | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Sambunigrin 40V, Negative-QTOF | splash10-00lr-2900000000-ae791f613076bd282606 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Sambunigrin 10V, Positive-QTOF | splash10-014j-0930000000-b073c628b5ae90962ddb | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Sambunigrin 20V, Positive-QTOF | splash10-0159-1930000000-0195cac2f79233b86e61 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Sambunigrin 40V, Positive-QTOF | splash10-014i-6900000000-14cef03a9110265ac2a2 | 2021-09-22 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
---|
Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum |
|
---|