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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 00:17:58 UTC
Update Date2022-03-07 02:56:00 UTC
HMDB IDHMDB0038952
Secondary Accession Numbers
  • HMDB38952
Metabolite Identification
Common NameNiazicin
DescriptionNiazicin 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. Based on a literature review very few articles have been published on Niazicin.
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 acidHMDB
(2S,3R,4S,5R,6S)-4,5-Dihydroxy-6-[4-({[methoxy(sulphanyl)methylidene]amino}methyl)phenoxy]-2-methyloxan-3-yl acetateHMDB
(2S,3R,4S,5R,6S)-4,5-Dihydroxy-6-[4-({[methoxy(sulphanyl)methylidene]amino}methyl)phenoxy]-2-methyloxan-3-yl acetic acidHMDB
(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
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
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility1262 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+187.17730932474
DeepCCS[M-H]-184.78130932474
DeepCCS[M-2H]-217.66530932474
DeepCCS[M+Na]+193.16930932474
AllCCS[M+H]+188.232859911
AllCCS[M+H-H2O]+185.932859911
AllCCS[M+NH4]+190.332859911
AllCCS[M+Na]+190.932859911
AllCCS[M-H]-188.232859911
AllCCS[M+Na-2H]-188.832859911
AllCCS[M+HCOO]-189.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
NiazicinCOC(=S)NCC1=CC=C(O[C@@H]2O[C@@H](C)[C@H](OC(C)=O)[C@@H](O)[C@H]2O)C=C14933.4Standard polar33892256
NiazicinCOC(=S)NCC1=CC=C(O[C@@H]2O[C@@H](C)[C@H](OC(C)=O)[C@@H](O)[C@H]2O)C=C12828.0Standard non polar33892256
NiazicinCOC(=S)NCC1=CC=C(O[C@@H]2O[C@@H](C)[C@H](OC(C)=O)[C@@H](O)[C@H]2O)C=C13153.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Niazicin,1TMS,isomer #1COC(=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=C12851.9Semi standard non polar33892256
Niazicin,1TMS,isomer #2COC(=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=C12842.4Semi standard non polar33892256
Niazicin,1TMS,isomer #3COC(=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)C2788.0Semi standard non polar33892256
Niazicin,2TMS,isomer #1COC(=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=C12866.9Semi standard non polar33892256
Niazicin,2TMS,isomer #2COC(=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)C2798.1Semi standard non polar33892256
Niazicin,2TMS,isomer #3COC(=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)C2793.3Semi standard non polar33892256
Niazicin,3TMS,isomer #1COC(=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)C2827.7Semi standard non polar33892256
Niazicin,3TMS,isomer #1COC(=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)C2665.2Standard non polar33892256
Niazicin,1TBDMS,isomer #1COC(=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=C13038.7Semi standard non polar33892256
Niazicin,1TBDMS,isomer #2COC(=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=C13039.7Semi standard non polar33892256
Niazicin,1TBDMS,isomer #3COC(=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)C3049.9Semi standard non polar33892256
Niazicin,2TBDMS,isomer #1COC(=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=C13218.8Semi standard non polar33892256
Niazicin,2TBDMS,isomer #2COC(=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)C3251.9Semi standard non polar33892256
Niazicin,2TBDMS,isomer #3COC(=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)C3251.4Semi standard non polar33892256
Niazicin,3TBDMS,isomer #1COC(=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)C3417.6Semi standard non polar33892256
Niazicin,3TBDMS,isomer #1COC(=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)C3181.2Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Niazicin 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 - Niazicin 10V, Positive-QTOFsplash10-0002-1906000000-ad661c0326abb8c6b1c32019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Niazicin 20V, Positive-QTOFsplash10-0aba-1900000000-6d7c52a48cee8ea9f7232019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Niazicin 40V, Positive-QTOFsplash10-0a4i-1900000000-f5ee9b1bedf16f1011bb2019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Niazicin 10V, Negative-QTOFsplash10-0lzd-3419000000-f81946fcfffeaf3444272019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Niazicin 20V, Negative-QTOFsplash10-0901-4925000000-d881ac2f827a97a89adb2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Niazicin 40V, Negative-QTOFsplash10-0a5d-9700000000-9f357daeb3cb144bddfe2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Niazicin 10V, Positive-QTOFsplash10-000b-0905000000-77f65a387b0cb4ee1a282021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Niazicin 20V, Positive-QTOFsplash10-0a4i-0910000000-a9ec8f060764c26631742021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Niazicin 40V, Positive-QTOFsplash10-0a4i-1901000000-b9ad0701aea3d41c940e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Niazicin 10V, Negative-QTOFsplash10-001i-1019000000-cc5756e6829d62c9af002021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Niazicin 20V, Negative-QTOFsplash10-0a4i-9623000000-5d793a03624b99db314b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Niazicin 40V, Negative-QTOFsplash10-00di-3900000000-531c030518a4f2c8e96d2021-09-24Wishart 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 IDFDB018432
KNApSAcK IDC00057118
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
MarkerDB IDNot Available
Good Scents IDrw1873031
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.. .