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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:46:44 UTC
Update Date2022-03-07 02:53:11 UTC
HMDB IDHMDB0031945
Secondary Accession Numbers
  • HMDB31945
Metabolite Identification
Common NameNiaziminin
DescriptionNiaziminin 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 niaziminin (niaziminin A and niaziminin B, respectively) differ in the orientation of the NH group with respect to sulfur. Niaziminin is the 4'-O-acetyl derivative of niazimicin.
Structure
Data?1564597549
Synonyms
ValueSource
Niaziminin aHMDB
Niaziminin bHMDB
NiaziminineHMDB
Niaziminine aHMDB
Niaziminine bHMDB
O-Ethyl-4-[(4'-O-acetyl-alpha-L-rhamnosyloxy)benzyl]thiocarbamateHMDB
O-Ethyl-4-[(4’-O-acetyl-α-L-rhamnosyloxy)benzyl]thiocarbamateHMDB
O-Ethyl 4-[(4'-O-acetyl-alpha-L-rhamnosyloxy)benzyl]thiocarbamateHMDB
O-Ethyl 4-[(4’-O-acetyl-α-L-rhamnosyloxy)benzyl]thiocarbamateHMDB
(e)-O-Ethyl 4-[(4'-O-acetyl-alpha-L-rhamnosyloxy)benzyl]thiocarbamateHMDB
(e)-O-Ethyl 4-[(4’-O-acetyl-α-L-rhamnosyloxy)benzyl]thiocarbamateHMDB
(e)-O-Ethyl-4-[(4'-O-acetyl-alpha-L-rhamnosyloxy)benzyl]thiocarbamateHMDB
(e)-O-Ethyl-4-[(4’-O-acetyl-α-L-rhamnosyloxy)benzyl]thiocarbamateHMDB
(Z)-O-Ethyl 4-[(4'-O-acetyl-alpha-L-rhamnosyloxy)benzyl]thiocarbamateHMDB
(Z)-O-Ethyl 4-[(4’-O-acetyl-α-L-rhamnosyloxy)benzyl]thiocarbamateHMDB
(Z)-O-Ethyl-4-[(4'-O-acetyl-alpha-L-rhamnosyloxy)benzyl]thiocarbamateHMDB
(Z)-O-Ethyl-4-[(4’-O-acetyl-α-L-rhamnosyloxy)benzyl]thiocarbamateHMDB
NiazimininHMDB
Chemical FormulaC18H25NO7S
Average Molecular Weight399.46
Monoisotopic Molecular Weight399.135173323
IUPAC Name(2S,3R,4S,5R,6S)-6-(4-{[(ethoxymethanethioyl)amino]methyl}phenoxy)-4,5-dihydroxy-2-methyloxan-3-yl acetate
Traditional Name(2S,3R,4S,5R,6S)-6-(4-{[(ethoxymethanethioyl)amino]methyl}phenoxy)-4,5-dihydroxy-2-methyloxan-3-yl acetate
CAS Registry Number147821-56-5
SMILES
CCOC(=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/C18H25NO7S/c1-4-23-18(27)19-9-12-5-7-13(8-6-12)26-17-15(22)14(21)16(10(2)24-17)25-11(3)20/h5-8,10,14-17,21-22H,4,9H2,1-3H3,(H,19,27)/t10-,14-,15+,16-,17-/m0/s1
InChI KeyNZQNGCULBWTLGQ-DXJAZKPLSA-N
Chemical Taxonomy
Description 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
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point168 - 170 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.14 g/LALOGPS
logP1.66ALOGPS
logP1.7ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)8.69ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area106.48 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity100.07 m³·mol⁻¹ChemAxon
Polarizability41.42 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+189.94430932474
DeepCCS[M-H]-187.54830932474
DeepCCS[M-2H]-220.43230932474
DeepCCS[M+Na]+195.85630932474
AllCCS[M+H]+193.732859911
AllCCS[M+H-H2O]+191.432859911
AllCCS[M+NH4]+195.932859911
AllCCS[M+Na]+196.532859911
AllCCS[M-H]-191.232859911
AllCCS[M+Na-2H]-191.932859911
AllCCS[M+HCOO]-192.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
NiazimininCCOC(=S)NCC1=CC=C(O[C@@H]2O[C@@H](C)[C@H](OC(C)=O)[C@@H](O)[C@H]2O)C=C14989.0Standard polar33892256
NiazimininCCOC(=S)NCC1=CC=C(O[C@@H]2O[C@@H](C)[C@H](OC(C)=O)[C@@H](O)[C@H]2O)C=C12858.8Standard non polar33892256
NiazimininCCOC(=S)NCC1=CC=C(O[C@@H]2O[C@@H](C)[C@H](OC(C)=O)[C@@H](O)[C@H]2O)C=C13231.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Niaziminin,1TMS,isomer #1CCOC(=S)NCC1=CC=C(O[C@@H]2O[C@@H](C)[C@H](OC(C)=O)[C@@H](O[Si](C)(C)C)[C@H]2O)C=C12885.2Semi standard non polar33892256
Niaziminin,1TMS,isomer #2CCOC(=S)NCC1=CC=C(O[C@@H]2O[C@@H](C)[C@H](OC(C)=O)[C@@H](O)[C@H]2O[Si](C)(C)C)C=C12874.0Semi standard non polar33892256
Niaziminin,1TMS,isomer #3CCOC(=S)N(CC1=CC=C(O[C@@H]2O[C@@H](C)[C@H](OC(C)=O)[C@@H](O)[C@H]2O)C=C1)[Si](C)(C)C2842.5Semi standard non polar33892256
Niaziminin,2TMS,isomer #1CCOC(=S)NCC1=CC=C(O[C@@H]2O[C@@H](C)[C@H](OC(C)=O)[C@@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)C=C12894.3Semi standard non polar33892256
Niaziminin,2TMS,isomer #2CCOC(=S)N(CC1=CC=C(O[C@@H]2O[C@@H](C)[C@H](OC(C)=O)[C@@H](O[Si](C)(C)C)[C@H]2O)C=C1)[Si](C)(C)C2857.9Semi standard non polar33892256
Niaziminin,2TMS,isomer #3CCOC(=S)N(CC1=CC=C(O[C@@H]2O[C@@H](C)[C@H](OC(C)=O)[C@@H](O)[C@H]2O[Si](C)(C)C)C=C1)[Si](C)(C)C2859.4Semi standard non polar33892256
Niaziminin,3TMS,isomer #1CCOC(=S)N(CC1=CC=C(O[C@@H]2O[C@@H](C)[C@H](OC(C)=O)[C@@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)C=C1)[Si](C)(C)C2878.8Semi standard non polar33892256
Niaziminin,3TMS,isomer #1CCOC(=S)N(CC1=CC=C(O[C@@H]2O[C@@H](C)[C@H](OC(C)=O)[C@@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)C=C1)[Si](C)(C)C2771.5Standard non polar33892256
Niaziminin,1TBDMS,isomer #1CCOC(=S)NCC1=CC=C(O[C@@H]2O[C@@H](C)[C@H](OC(C)=O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)C=C13072.7Semi standard non polar33892256
Niaziminin,1TBDMS,isomer #2CCOC(=S)NCC1=CC=C(O[C@@H]2O[C@@H](C)[C@H](OC(C)=O)[C@@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)C=C13068.8Semi standard non polar33892256
Niaziminin,1TBDMS,isomer #3CCOC(=S)N(CC1=CC=C(O[C@@H]2O[C@@H](C)[C@H](OC(C)=O)[C@@H](O)[C@H]2O)C=C1)[Si](C)(C)C(C)(C)C3109.6Semi standard non polar33892256
Niaziminin,2TBDMS,isomer #1CCOC(=S)NCC1=CC=C(O[C@@H]2O[C@@H](C)[C@H](OC(C)=O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O[Si](C)(C)C(C)(C)C)C=C13230.1Semi standard non polar33892256
Niaziminin,2TBDMS,isomer #2CCOC(=S)N(CC1=CC=C(O[C@@H]2O[C@@H](C)[C@H](OC(C)=O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)C=C1)[Si](C)(C)C(C)(C)C3299.3Semi standard non polar33892256
Niaziminin,2TBDMS,isomer #3CCOC(=S)N(CC1=CC=C(O[C@@H]2O[C@@H](C)[C@H](OC(C)=O)[C@@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C3302.9Semi standard non polar33892256
Niaziminin,3TBDMS,isomer #1CCOC(=S)N(CC1=CC=C(O[C@@H]2O[C@@H](C)[C@H](OC(C)=O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C3438.8Semi standard non polar33892256
Niaziminin,3TBDMS,isomer #1CCOC(=S)N(CC1=CC=C(O[C@@H]2O[C@@H](C)[C@H](OC(C)=O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C3270.2Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Niaziminin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Niaziminin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Niaziminin 10V, Positive-QTOFsplash10-0udi-0142900000-fc19eb15bb925049c2bc2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Niaziminin 20V, Positive-QTOFsplash10-0pb9-0931100000-ce1665fef4b236ac2ceb2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Niaziminin 40V, Positive-QTOFsplash10-0ab9-0901000000-59f4434d5267de88a0942021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Niaziminin 10V, Negative-QTOFsplash10-03di-0009000000-d09dd0313ccdc12a7c6f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Niaziminin 20V, Negative-QTOFsplash10-0a4i-9423000000-0a42c91310748246785c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Niaziminin 40V, Negative-QTOFsplash10-00di-3911000000-78294d8ab4aa2d3ac27f2021-09-23Wishart LabView Spectrum
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 IDFDB031410
KNApSAcK IDC00057081
Chemspider ID8199431
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10023860
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents 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.. .