You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-12 00:17:58 UTC
Update Date2019-08-01 16:36:33 UTC
HMDB IDHMDB0038952
Secondary Accession Numbers
  • HMDB38952
Metabolite Identification
Common NameNiazicin
DescriptionNiazicin is a glucosinolate and a naturally occurring thiocarbamate. It has been isolated from the leaves of Moringa oleifera (horseradish tree). It is found in fats and oils, herbs and spices, and green vegetables. The trans and cis rotamers of niazicin (niazicin A and niazicin B, respectively) differ in the orientation of the NH group with respect to sulfur.
Structure
Data?1564677393
Synonyms
ValueSource
(2S,3R,4S,5R,6S)-4,5-Dihydroxy-6-[4-({[methoxy(sulfanyl)methylidene]amino}methyl)phenoxy]-2-methyloxan-3-yl acetic acidGenerator
(2S,3R,4S,5R,6S)-4,5-Dihydroxy-6-[4-({[methoxy(sulphanyl)methylidene]amino}methyl)phenoxy]-2-methyloxan-3-yl acetateGenerator
(2S,3R,4S,5R,6S)-4,5-Dihydroxy-6-[4-({[methoxy(sulphanyl)methylidene]amino}methyl)phenoxy]-2-methyloxan-3-yl acetic acidGenerator
(E)-O-Methyl 4-[(4'-O-acetyl-alpha-L-rhamnosyloxy)benzyl]thiocarbamateHMDB
(E)-O-Methyl 4-[(4’-O-acetyl-α-L-rhamnosyloxy)benzyl]thiocarbamateHMDB
(E)-O-Methyl-4-[(4'-O-acetyl-alpha-L-rhamnosyloxy)benzyl]thiocarbamateHMDB
(E)-O-Methyl-4-[(4’-O-acetyl-α-L-rhamnosyloxy)benzyl]thiocarbamateHMDB
(Z)-O-Methyl 4-[(4'-O-acetyl-alpha-L-rhamnosyloxy)benzyl]thiocarbamateHMDB
(Z)-O-Methyl 4-[(4’-O-acetyl-α-L-rhamnosyloxy)benzyl]thiocarbamateHMDB
(Z)-O-Methyl-4-[(4'-O-acetyl-alpha-L-rhamnosyloxy)benzyl]thiocarbamateHMDB
(Z)-O-Methyl-4-[(4’-O-acetyl-α-L-rhamnosyloxy)benzyl]thiocarbamateHMDB
Niazicin AHMDB
Niazicin BHMDB
O-Methyl 4-[(4'-O-acetyl-alpha-L-rhamnosyloxy)benzyl]thiocarbamateHMDB
O-Methyl 4-[(4’-O-acetyl-α-L-rhamnosyloxy)benzyl]thiocarbamateHMDB
O-Methyl-4-[(4'-O-acetyl-alpha-L-rhamnosyloxy)benzyl]thiocarbamateHMDB
O-Methyl-4-[(4’-O-acetyl-α-L-rhamnosyloxy)benzyl]thiocarbamateHMDB
Chemical FormulaC17H23NO7S
Average Molecular Weight385.43
Monoisotopic Molecular Weight385.119523259
IUPAC Name(2S,3R,4S,5R,6S)-4,5-dihydroxy-6-(4-{[(methoxymethanethioyl)amino]methyl}phenoxy)-2-methyloxan-3-yl acetate
Traditional Name(2S,3R,4S,5R,6S)-4,5-dihydroxy-6-(4-{[(methoxymethanethioyl)amino]methyl}phenoxy)-2-methyloxan-3-yl acetate
CAS Registry Number159768-74-8
SMILES
COC(=S)NCC1=CC=C(O[C@@H]2O[C@@H](C)[C@H](OC(C)=O)[C@@H](O)[C@H]2O)C=C1
InChI Identifier
InChI=1S/C17H23NO7S/c1-9-15(24-10(2)19)13(20)14(21)16(23-9)25-12-6-4-11(5-7-12)8-18-17(26)22-3/h4-7,9,13-16,20-21H,8H2,1-3H3,(H,18,26)/t9-,13-,14+,15-,16-/m0/s1
InChI KeyHMXLIRAHSHWREJ-QOYUQHOESA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentPhenolic glycosides
Alternative Parents
Substituents
  • Phenolic glycoside
  • Hexose monosaccharide
  • O-glycosyl compound
  • Phenoxy compound
  • Phenol ether
  • Monocyclic benzene moiety
  • Monosaccharide
  • Oxane
  • Benzenoid
  • Thiocarbamic acid ester
  • 1,2-diol
  • Carboxylic acid ester
  • Secondary alcohol
  • Thiocarbamic acid derivative
  • Monocarboxylic acid or derivatives
  • Acetal
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Organosulfur compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Role

Biological role:

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 Solubility0.13 g/LALOGPS
logP1.15ALOGPS
logP1.34ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)8.76ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area106.48 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity95.32 m³·mol⁻¹ChemAxon
Polarizability39.32 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-1906000000-ad661c0326abb8c6b1c3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0aba-1900000000-6d7c52a48cee8ea9f723Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-1900000000-f5ee9b1bedf16f1011bbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0lzd-3419000000-f81946fcfffeaf344427Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0901-4925000000-d881ac2f827a97a89adbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a5d-9700000000-9f357daeb3cb144bddfeSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB018432
KNApSAcK IDNot Available
Chemspider ID8244197
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10068657
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .