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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2013-07-22 15:28:56 UTC
Update Date2019-07-23 07:15:47 UTC
HMDB IDHMDB0061113
Secondary Accession Numbers
  • HMDB61113
Metabolite Identification
Common NameSulforaphane-N-acetylcysteine
DescriptionSulforaphane-N-acetylcysteine (SFN-NAC) is a metabolite of sulforophane which is a metabolite of glucoraphanin which is found in cauliflower and broccoli sprouts (PMID: 16166336 ; PMID: 21372038 ). It is excreted in urine. Glucoraphanin is a glucosinolate compound that is converted in the gut to sulforaphane, an isothiocyanate, by the action of myrosinase enzymes from the plants (PMID: 21372038 ). Sulforaphane blocks the initiation stage in carcinogenesis by inhibiting enzymes that convert procarcinogens to carcinogens and by inducing phase 2 enzymes that detoxify carcinogens and facilitate their excretion from the body.
Structure
Data?1563866147
SynonymsNot Available
Chemical FormulaC11H20N2O4S3
Average Molecular Weight340.482
Monoisotopic Molecular Weight340.058519208
IUPAC Name2-acetamido-3-{[(4-methanesulfinylbutyl)carbamothioyl]sulfanyl}propanoic acid
Traditional Name2-acetamido-3-{[(4-methanesulfinylbutyl)carbamothioyl]sulfanyl}propanoic acid
CAS Registry NumberNot Available
SMILES
CC(=O)NC(CSC(=S)NCCCCS(C)=O)C(O)=O
InChI Identifier
InChI=1S/C11H20N2O4S3/c1-8(14)13-9(10(15)16)7-19-11(18)12-5-3-4-6-20(2)17/h9H,3-7H2,1-2H3,(H,12,18)(H,13,14)(H,15,16)
InChI KeyIIHBKTCHILXGOT-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as n-acyl-alpha amino acids. These are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentN-acyl-alpha amino acids
Alternative Parents
Substituents
  • N-acyl-alpha-amino acid
  • Cysteine or derivatives
  • Fatty acid
  • Dithiocarbamic acid ester
  • Acetamide
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Sulfoxide
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Sulfinyl compound
  • Sulfenyl compound
  • Organopnictogen compound
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organic oxide
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.21 g/LALOGPS
logP0.12ALOGPS
logP-0.94ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)3.97ChemAxon
pKa (Strongest Basic)-1.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area95.5 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity86.94 m³·mol⁻¹ChemAxon
Polarizability34.93 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01ox-8291000000-e81490bff2198a3458d1JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0304-9315000000-a2b75d67573b4313927fJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0911000000-87511a4d8e77d795d6adJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-046s-3942000000-27777b70fe40a8242de0JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05ur-9800000000-266ac3cc0b847069cc07JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-9333000000-99ab70797f5c4536214bJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-9000000000-bf15cd425f563ac53884JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-9100000000-cc8a4cfc228bfad3c5f4JSpectraViewer | MoNA
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not Quantified Adult (>18 years old)Both
Normal
details
UrineDetected but not Quantified Adult (>18 years old)Both
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound45040443
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Conaway CC, Wang CX, Pittman B, Yang YM, Schwartz JE, Tian D, McIntee EJ, Hecht SS, Chung FL: Phenethyl isothiocyanate and sulforaphane and their N-acetylcysteine conjugates inhibit malignant progression of lung adenomas induced by tobacco carcinogens in A/J mice. Cancer Res. 2005 Sep 15;65(18):8548-57. [PubMed:16166336 ]
  2. Egner PA, Chen JG, Wang JB, Wu Y, Sun Y, Lu JH, Zhu J, Zhang YH, Chen YS, Friesen MD, Jacobson LP, Munoz A, Ng D, Qian GS, Zhu YR, Chen TY, Botting NP, Zhang Q, Fahey JW, Talalay P, Groopman JD, Kensler TW: Bioavailability of Sulforaphane from two broccoli sprout beverages: results of a short-term, cross-over clinical trial in Qidong, China. Cancer Prev Res (Phila). 2011 Mar;4(3):384-95. doi: 10.1158/1940-6207.CAPR-10-0296. [PubMed:21372038 ]