Sinigrin
precursor
Showing entry for Sinigrin
Identification
- PhytoHub ID
- PHUB000820
- Name
- Sinigrin
- Systematic Name
- 2-Propenyl-glucosinolate
- Synonyms
- [(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (1E)-N-sulfooxybut-3-enimidothioate
- 2-Propenyl glucosinolate
- Allylglucosinolate
- Prop-2-enylglucosinolate
- CAS Number
- Not Available
- Average Mass
- 359.36
- Monoisotopic Mass
- 359.034473479
- Chemical Formula
- C10H17NO9S2
- IUPAC Name
- {[(E)-(1-{[(2S,4S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}but-3-en-1-ylidene)amino]oxy}sulfonic acid
- InChI Key
- PHZOWSSBXJXFOR-IUSWXCLFSA-M
- InChI Identifier
InChI=1S/C10H17NO9S2/c1-2-3-6(11-20-22(16,17)18)21-10-9(15)8(14)7(13)5(4-12)19-10/h2,5,7-10,12-15H,1,3-4H2,(H,16,17,18)/p-1/b11-6+/t5?,7-,8+,9?,10+/m1/s1
- SMILES
OCC1O[C@@H](S\C(CC=C)=N\OS(O)(=O)=O)C(O)[C@@H](O)[C@@H]1O
- Structure
Structure for Sinigrin
Calculated Properties
- Solubility (ALOGPS)
- Not Available
- LogS (ALOGPS)
- Not Available
- LogP (ALOGPS)
- Not Available
- Hydrogen Acceptors
- 9
- Hydrogen Donors
- 5
- Rotatable Bond Count
- 7
- Polar Surface Area
- 166.10999999999999
- Refractivity
- 74.6971
- Polarizability
- 31.949357310703313
- Formal Charge
- 0
- Physiological Charge
- -1
- pKa (strongest basic)
- -0.49160518860207597
- pKa (strongest acidic)
- -3.618347617962352
- Number of Rings
- 1
- Rule of Five
- Yes
- Bioavailability
- No
- Ghose Filter
- No
- Veber's Rule
- No
- MDDR-like Rule
- No
External Links
No external links
Taxonomy as Food Phytochemical
- Family
- N-containing compounds
- Class
- Glucosinolates
- Sub-class
- Not Available
Spectra from Phytohub
| Spectrum Type | Instrument Type | Ion Mode | Collision Energy Level | View | Peaks | |
|---|---|---|---|---|---|---|
| LC-MS/MS | ESI- LC-Q-TOF/MS | Negative | low | View Spectrum | (74.9927,0.746);(79.9592,0.124);(95.9534,0.69);(96.9612,0.999);(358.0267,0.825) |
Food Sources
| Name | Group | |||
|---|---|---|---|---|
| Broccoli | Vegetables, Cabbages | Publications | Show | |
| Brussel sprouts | Vegetables, Cabbages | Publications | Show | |
| Cabbage, red | Vegetables, Cabbages | Publications | Show | |
| Cabbage, White | Vegetables, Cabbages | Publications | Show | |
| Capers | Herbs and Spices | Publications | Show | |
| Cauliflower | Vegetables, Cabbages | Publications | Show | |
| Common cabbage | Vegetables, Cabbages | Publications | Show | |
| Horseradish | Herbs and Spices | Publications | Show | |
| Kale | Vegetables, Cabbages | Publications | Show | |
| Mustard | Condiments and seasonings | Publications | Show | |
| Savoy cabbage | Vegetables, Cabbages | Publications | Show | |
| Wasabi | Herbs and Spices | Publications | Show |
Role as Biomarker of intake
No roles as Biomarker of intake found
Metabolism
| Food Phytochemical | Metabolite | Species | Biofluids | Origin | TMax | CMax | Urinary Excretion | Formula | Monoisotopic mass | ||||
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Sinigrin | Allyl isothiocyanate | human | urine | Not Available | Not Available | Not Available | Not Available | C4H5NS | 99.014270339 | Publications | |||
| Sinigrin | 1-cyano-2,3-epithiopropane | human | urine | Not Available | Not Available | Not Available | Not Available | C4H5NS | 99.014270339 | Publications | |||
| Sinigrin | Allyl isothiocyanate-N-acetyl-L-cysteine | human | plasma, urine | Not Available | Not Available | Not Available | Not Available | Detailed Intervention Studies | |||||
| Sinigrin | 3-butenenitrile | human | urine | Not Available | Not Available | Not Available | Not Available | C4H5N | 67.042199165 | Publications | |||
| Broccoli and mustard glucosinolates | Sinigrin | Not Available | Not Available | Not Available | Not Available | Not Available | Not Available | C10H17NO9S2 | 359.034473479 | Detailed Intervention Studies |
Inter-Individual Variations in Metabolism
| Food Phytochemical | Metabolite | Effect | Value |
|---|