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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 23:05:13 UTC
Update Date2022-11-23 22:29:22 UTC
HMDB IDHMDB0260026
Secondary Accession NumbersNone
Metabolite Identification
Common NameZinostatin
DescriptionZinostatin, also known as neocarzinostatin, belongs to the class of organic compounds known as aminoglycosides. These are molecules or a portion of a molecule composed of amino-modified sugars. Based on a literature review a significant number of articles have been published on Zinostatin. This compound has been identified in human blood as reported by (PMID: 31557052 ). Zinostatin is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Zinostatin is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
Structure
Thumb
Synonyms
ValueSource
11-{[4,5-dihydroxy-6-methyl-3-(methylamino)oxan-2-yl]oxy}-4-(2-oxo-1,3-dioxolan-4-yl)-5-oxatricyclo[8.3.0.0,]tridec-1(13)-en-2,7-diyn-12-yl 2-hydroxy-7-methoxy-5-methylnaphthalene-1-carboxylic acidHMDB
NeocarzinostatinHMDB
Chemical FormulaC35H35NO12
Average Molecular Weight661.66
Monoisotopic Molecular Weight661.215925571
IUPAC Name11-{[4,5-dihydroxy-6-methyl-3-(methylamino)oxan-2-yl]oxy}-4-(2-oxo-1,3-dioxolan-4-yl)-5-oxatricyclo[8.3.0.0^{4,6}]tridec-1(13)-en-2,7-diyn-12-yl 2-hydroxy-7-methoxy-5-methylnaphthalene-1-carboxylate
Traditional Name11-{[4,5-dihydroxy-6-methyl-3-(methylamino)oxan-2-yl]oxy}-4-(2-oxo-1,3-dioxolan-4-yl)-5-oxatricyclo[8.3.0.0^{4,6}]tridec-1(13)-en-2,7-diyn-12-yl 2-hydroxy-7-methoxy-5-methylnaphthalene-1-carboxylate
CAS Registry NumberNot Available
SMILES
CNC1C(O)C(O)C(C)OC1OC1C(OC(=O)C2=C(O)C=CC3=C(C)C=C(OC)C=C23)C=C2C#CC3(OC3C#CCC12)C1COC(=O)O1
InChI Identifier
InChI=1S/C35H35NO12/c1-16-12-19(42-4)14-22-20(16)8-9-23(37)27(22)32(40)45-24-13-18-10-11-35(26-15-43-34(41)46-26)25(48-35)7-5-6-21(18)31(24)47-33-28(36-3)30(39)29(38)17(2)44-33/h8-9,12-14,17,21,24-26,28-31,33,36-39H,6,15H2,1-4H3
InChI KeyBLXZMHNVKCEIJX-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aminoglycosides. These are molecules or a portion of a molecule composed of amino-modified sugars.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentAminoglycosides
Alternative Parents
Substituents
  • Aminoglycoside core
  • 1-naphthalenecarboxylic acid or derivatives
  • Glycosyl compound
  • 2-naphthol
  • O-glycosyl compound
  • Naphthalene
  • Salicylic acid or derivatives
  • Anisole
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monosaccharide
  • Carbonic acid diester
  • Oxane
  • Benzenoid
  • Ynone
  • Meta-dioxolane
  • Vinylogous acid
  • Carbonic acid derivative
  • 1,2-diol
  • Carboxylic acid ester
  • Amino acid or derivatives
  • 1,2-aminoalcohol
  • Secondary alcohol
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Secondary amine
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Dialkyl ether
  • Secondary aliphatic amine
  • Oxirane
  • Ether
  • Organonitrogen compound
  • Carbonyl group
  • Alcohol
  • Hydrocarbon derivative
  • Amine
  • Organopnictogen compound
  • Organic oxide
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic 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 SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP1.89ALOGPS
logP3.91ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)9.52ChemAxon
pKa (Strongest Basic)8.1ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area174.77 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity166.61 m³·mol⁻¹ChemAxon
Polarizability66.09 ųChemAxon
Number of Rings7ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
AllCCS[M+H]+248.1732859911
AllCCS[M+H-H2O]+247.40332859911
AllCCS[M+Na]+249.02832859911
AllCCS[M+NH4]+248.84232859911
AllCCS[M-H]-233.3332859911
AllCCS[M+Na-2H]-235.75932859911
AllCCS[M+HCOO]-238.5532859911
DeepCCS[M-2H]-270.1830932474
DeepCCS[M+Na]+244.36930932474

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.5.99 minutes32390414
Predicted by Siyang on May 30, 202212.0484 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20222.87 minutes32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid2458.1 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid180.0 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid182.5 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid180.4 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid81.8 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid577.0 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid595.7 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)841.8 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid820.3 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid372.7 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1516.7 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid304.9 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid347.2 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate307.1 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA140.5 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water25.6 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
ZINOSTATINCNC1C(O)C(O)C(C)OC1OC1C(OC(=O)C2=C(O)C=CC3=C(C)C=C(OC)C=C23)C=C2C#CC3(OC3C#CCC12)C1COC(=O)O16838.6Standard polar33892256
ZINOSTATINCNC1C(O)C(O)C(C)OC1OC1C(OC(=O)C2=C(O)C=CC3=C(C)C=C(OC)C=C23)C=C2C#CC3(OC3C#CCC12)C1COC(=O)O15012.6Standard non polar33892256
ZINOSTATINCNC1C(O)C(O)C(C)OC1OC1C(OC(=O)C2=C(O)C=CC3=C(C)C=C(OC)C=C23)C=C2C#CC3(OC3C#CCC12)C1COC(=O)O15426.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Zinostatin GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Zinostatin GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Zinostatin GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Zinostatin GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Zinostatin GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Zinostatin GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Zinostatin GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Zinostatin GC-MS (TMS_2_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Zinostatin GC-MS (TMS_2_5) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Zinostatin GC-MS (TMS_2_6) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Zinostatin GC-MS (TMS_3_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Zinostatin GC-MS (TMS_3_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Zinostatin GC-MS (TMS_3_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Zinostatin GC-MS (TMS_3_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Zinostatin GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Zinostatin GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Zinostatin GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Zinostatin GC-MS (TBDMS_1_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Zinostatin GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Zinostatin GC-MS (TBDMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Zinostatin GC-MS (TBDMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Zinostatin GC-MS (TBDMS_2_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Zinostatin GC-MS (TBDMS_2_5) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Zinostatin GC-MS (TBDMS_2_6) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID21232997
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound76632185
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. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]