Glucoraphanin
precursor
Showing entry for Glucoraphanin
Identification
- PhytoHub ID
- PHUB000814
- Name
- Glucoraphanin
- Systematic Name
- 4-Methylsulfinylbutyl-glucosinolate
- Synonyms
- 1-isothiocyanato-4-(methylsulfinyl)butane
- 3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (1E)-5-methylsulfinyl-N-sulfooxypentanimidothioate
- 4-(Methylsulfinyl)butylglucosinolate
- 4-Methylsulfinylbutyl glucosinolate
- CAS Number
- Not Available
- Average Mass
- 436.49
- Monoisotopic Mass
- 436.041133014
- Chemical Formula
- C12H22NO10S3
- IUPAC Name
- (3S,4S,6S)-2-(hydroxymethyl)-6-{[(1E)-5-methanesulfinyl-1-[(sulfonatooxy)imino]pentyl]sulfanyl}oxane-3,4,5-triol
- InChI Key
- GMMLNKINDDUDCF-HTTMVCNMSA-M
- InChI Identifier
InChI=1S/C12H23NO10S3/c1-25(18)5-3-2-4-8(13-23-26(19,20)21)24-12-11(17)10(16)9(15)7(6-14)22-12/h7,9-12,14-17H,2-6H2,1H3,(H,19,20,21)/p-1/b13-8+/t7?,9-,10+,11?,12+,25?/m1/s1
- SMILES
CS(=O)CCCC\C(S[C@@H]1OC(CO)[C@@H](O)[C@H](O)C1O)=N/OS([O-])(=O)=O
- Structure
Structure for Glucoraphanin
Calculated Properties
- Solubility (ALOGPS)
- 2.47e+01 g/l
- LogS (ALOGPS)
- -1.26
- LogP (ALOGPS)
- -0.98
- Hydrogen Acceptors
- 10
- Hydrogen Donors
- 4
- Rotatable Bond Count
- 10
- Polar Surface Area
- 186.00999999999996
- Refractivity
- 92.4973
- Polarizability
- 40.76342761559253
- Formal Charge
- -1
- Physiological Charge
- -1
- pKa (strongest basic)
- -0.44263264665621455
- pKa (strongest acidic)
- -3.7136513569538323
- Number of Rings
- 1
- Rule of Five
- Yes
- Bioavailability
- Yes
- 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 | Positive | low | View Spectrum | (234.0055,0.254);(260.0299,0.217);(396.0591,0.999);(476.0121,0.191) | |
| LC-MS/MS | ESI- LC-Q-TOF/MS | Negative | low | View Spectrum | (74.9931,0.335);(79.959,0.106);(95.9534,0.788);(96.9612,0.818);(178.0188,0.271);(372.046,0.255);(436.0406,0.999) |
Food Sources
| Name | Group | |||
|---|---|---|---|---|
| Broccoli | Vegetables, Cabbages | Publications | Show | |
| Broccoli sprouts | Vegetables, Cabbages | Show | ||
| Brussel sprouts | Vegetables, Cabbages | Publications | Show | |
| Cabbage, red | Vegetables, Cabbages | Publications | Show | |
| Cauliflower | Vegetables, Cabbages | Publications | Show | |
| Rocket salad | Vegetables, Leaf vegetables | Publications | Show | |
| Swede (Rutabaga) | Vegetables, Root vegetables | 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 | ||||
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Glucoraphanin | Glucoraphanin | human | plasma, urine | Not Available | Not Available | Not Available | Not Available | C12H22NO10S3 | 436.041133014 | Detailed Intervention Studies | |||
| Glucoraphanin | Sulforaphane | human | urine | host metabolism | Not Available | Not Available | Not Available | C6H11NOS2 | 177.028206326 | Detailed Intervention Studies | |||
| Glucoraphanin | Sulforaphane-N-acetyl-L-cysteine | human | plasma, urine | host metabolism | Not Available | Not Available | Not Available | C11H20N2O4S3 | 340.058520654 | Detailed Intervention Studies | |||
| Glucoraphanin | 2-thiothiazolidine-4-carboxylic acid | human | plasma, urine | Not Available | Not Available | Not Available | Not Available | C4H5NO2S2 | 162.976170753 | Detailed Intervention Studies | |||
| Glucoraphanin | Sulforaphane-cysteine | human | plasma, urine | Not Available | Not Available | Not Available | Not Available | C9H18N2O3S3 | 298.04795597 | Detailed Intervention Studies | |||
| Glucoraphanin | Sulforaphane-cysteine-glycine | human | plasma, urine | Not Available | Not Available | Not Available | Not Available | C11H21N3O4S3 | 355.06941969 | Detailed Intervention Studies | |||
| Glucoraphanin | Sulforaphane-glutathione | human | plasma, urine | Not Available | Not Available | Not Available | Not Available | C16H28N4O7S3 | 484.11201278 | Detailed Intervention Studies | |||
| Glucoraphanin | Erucin-glutathione | human | plasma, urine | Not Available | Not Available | Not Available | Not Available | Detailed Intervention Studies | Publications | ||||
| Glucoraphanin | Erucin-cysteine | human | plasma, urine | Not Available | Not Available | Not Available | Not Available | Publications | |||||
| Glucoraphanin | Erucin-cysteine-glycine | human | plasma, urine | Not Available | Not Available | Not Available | Not Available | Publications | |||||
| Glucoraphanin | Erucin-N-acetyl-cysteine | human | plasma, urine | Not Available | Not Available | Not Available | Not Available | Publications | |||||
| Glucoraphanin | Erucin | human | plasma, urine | Not Available | Not Available | Not Available | Not Available | C6H11NS2 | 161.033291706 | Publications | |||
| Broccoli glucosinolates | Glucoraphanin | Not Available | Not Available | Not Available | Not Available | Not Available | Not Available | C12H22NO10S3 | 436.041133014 | Detailed Intervention Studies | |||
| Broccoli and mustard glucosinolates | Glucoraphanin | Not Available | Not Available | Not Available | Not Available | Not Available | Not Available | C12H22NO10S3 | 436.041133014 | Detailed Intervention Studies |
Inter-Individual Variations in Metabolism
| Food Phytochemical | Metabolite | Effect | Value | |||
|---|---|---|---|---|---|---|
| Glucoraphanin | Sulforaphane | Bmi | Effect, continuous | Publications | ||
| Glucoraphanin | Sulforaphane-N-acetyl-L-cysteine | Bmi | Effect, continuous | Publications | ||
| Glucoraphanin | Sulforaphane-cysteine | Bmi | Effect, continuous | Publications | ||
| Glucoraphanin | Sulforaphane-cysteine-glycine | Bmi | Effect, continuous | Publications | ||
| Glucoraphanin | Sulforaphane-glutathione | Bmi | Effect, continuous | Publications |