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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 09:52:19 UTC
Update Date2021-10-01 21:41:44 UTC
HMDB IDHMDB0252148
Secondary Accession NumbersNone
Metabolite Identification
Common NameExotoxin
Description2-[(5-{[5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy]-3,5-dihydroxy-4-(phosphonooxy)hexanedioic acid belongs to the class of organic compounds known as purine nucleosides. Purine nucleosides are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety. Based on a literature review very few articles have been published on 2-[(5-{[5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy]-3,5-dihydroxy-4-(phosphonooxy)hexanedioic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). Exotoxin is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Exotoxin 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
2-[(5-{[5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy]-3,5-dihydroxy-4-(phosphonooxy)hexanedioateGenerator
Thuringiensin, sodium saltMeSH
beta-Exotoxin, bacillus thuringiensisMeSH
ExotoxinsMeSH
Chemical FormulaC22H32N5O19P
Average Molecular Weight701.488
Monoisotopic Molecular Weight701.142910828
IUPAC Name2-[(5-{[5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy]-3,5-dihydroxy-4-(phosphonooxy)hexanedioic acid
Traditional Nameexotoxin
CAS Registry NumberNot Available
SMILES
NC1=C2N=CN(C3OC(COC4C(CO)OC(OC(C(O)C(OP(O)(O)=O)C(O)C(O)=O)C(O)=O)C(O)C4O)C(O)C3O)C2=NC=N1
InChI Identifier
InChI=1S/C22H32N5O19P/c23-17-7-18(25-3-24-17)27(4-26-7)19-10(31)8(29)6(43-19)2-42-14-5(1-28)44-22(11(32)9(14)30)45-16(21(37)38)12(33)15(13(34)20(35)36)46-47(39,40)41/h3-6,8-16,19,22,28-34H,1-2H2,(H,35,36)(H,37,38)(H2,23,24,25)(H2,39,40,41)
InChI KeyOTLLEIBWKHEHGU-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as purine nucleosides. Purine nucleosides are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleosides
Sub ClassNot Available
Direct ParentPurine nucleosides
Alternative Parents
Substituents
  • Purine nucleoside
  • Fatty acyl glycoside of mono- or disaccharide
  • Fatty acyl glycoside
  • Glucuronic acid or derivatives
  • O-glycosyl compound
  • N-glycosyl compound
  • Glycosyl compound
  • Disaccharide
  • 6-aminopurine
  • Imidazopyrimidine
  • Medium-chain hydroxy acid
  • Purine
  • Medium-chain fatty acid
  • Hydroxy fatty acid
  • Aminopyrimidine
  • Beta-hydroxy acid
  • Monoalkyl phosphate
  • Alpha-hydroxy acid
  • Dicarboxylic acid or derivatives
  • Hydroxy acid
  • Fatty acyl
  • Fatty acid
  • N-substituted imidazole
  • Imidolactam
  • Organic phosphoric acid derivative
  • Oxane
  • Phosphoric acid ester
  • Alkyl phosphate
  • Pyrimidine
  • Tetrahydrofuran
  • Imidazole
  • Azole
  • Heteroaromatic compound
  • Amino acid or derivatives
  • Secondary alcohol
  • Amino acid
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Carboxylic acid
  • Dialkyl ether
  • Acetal
  • Ether
  • Azacycle
  • Oxacycle
  • Amine
  • Organic oxygen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Carbonyl group
  • Primary amine
  • Organic oxide
  • Primary alcohol
  • Alcohol
  • Hydrocarbon derivative
  • Organopnictogen compound
  • 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
logP-1.9ALOGPS
logP-8.7ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)0.95ChemAxon
pKa (Strongest Basic)4.97ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count22ChemAxon
Hydrogen Donor Count12ChemAxon
Polar Surface Area389.51 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity141.11 m³·mol⁻¹ChemAxon
Polarizability61.43 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+234.0230932474
DeepCCS[M-H]-232.12530932474
DeepCCS[M-2H]-265.79230932474
DeepCCS[M+Na]+240.99330932474
AllCCS[M+H]+235.732859911
AllCCS[M+H-H2O]+235.332859911
AllCCS[M+NH4]+236.132859911
AllCCS[M+Na]+236.232859911
AllCCS[M-H]-233.832859911
AllCCS[M+Na-2H]-235.632859911
AllCCS[M+HCOO]-237.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
ExotoxinNC1=C2N=CN(C3OC(COC4C(CO)OC(OC(C(O)C(OP(O)(O)=O)C(O)C(O)=O)C(O)=O)C(O)C4O)C(O)C3O)C2=NC=N15036.9Standard polar33892256
ExotoxinNC1=C2N=CN(C3OC(COC4C(CO)OC(OC(C(O)C(OP(O)(O)=O)C(O)C(O)=O)C(O)=O)C(O)C4O)C(O)C3O)C2=NC=N14146.5Standard non polar33892256
ExotoxinNC1=C2N=CN(C3OC(COC4C(CO)OC(OC(C(O)C(OP(O)(O)=O)C(O)C(O)=O)C(O)=O)C(O)C4O)C(O)C3O)C2=NC=N15893.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Exotoxin GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Exotoxin GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Exotoxin GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Exotoxin GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Exotoxin GC-MS (TMS_1_5) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Exotoxin GC-MS (TMS_1_6) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Exotoxin GC-MS (TMS_1_7) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Exotoxin GC-MS (TMS_1_8) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Exotoxin GC-MS (TMS_1_9) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Exotoxin GC-MS (TMS_1_10) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Exotoxin GC-MS (TMS_1_11) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Exotoxin GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Exotoxin GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Exotoxin GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Exotoxin GC-MS (TMS_2_4) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Exotoxin GC-MS (TMS_2_5) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Exotoxin GC-MS (TMS_2_6) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Exotoxin GC-MS (TMS_2_7) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Exotoxin GC-MS (TMS_2_8) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Exotoxin GC-MS (TMS_2_9) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Exotoxin GC-MS (TMS_2_10) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Exotoxin GC-MS (TMS_2_11) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Exotoxin GC-MS (TMS_2_12) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Exotoxin GC-MS (TMS_2_13) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Exotoxin GC-MS (TMS_2_14) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Exotoxin 10V, Positive-QTOFsplash10-0019-0950105300-127e5ec9f161a04684f62021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Exotoxin 20V, Positive-QTOFsplash10-000i-0900000000-f23faa529854fc353aa22021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Exotoxin 40V, Positive-QTOFsplash10-000i-2910000000-5bdefa857bfdef743a9b2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Exotoxin 10V, Negative-QTOFsplash10-0udi-0030201900-a3fc2947c697ee56d3232021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Exotoxin 20V, Negative-QTOFsplash10-003r-3970202000-68bcd014d4910c886be22021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Exotoxin 40V, Negative-QTOFsplash10-003r-4910000000-fbb3608803f5370ed9382021-10-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-10-13Wishart 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 ID269364
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
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 ]

Enzymes

General function:
Involved in calcium ion binding
Specific function:
Endocytic receptor involved in endocytosis and in phagocytosis of apoptotic cells. Required for early embryonic development. Involved in cellular lipid homeostasis. Involved in the plasma clearance of chylomicron remnants and activated LRPAP1 (alpha 2-macroglobulin), as well as the local metabolism of complexes between plasminogen activators and their endogenous inhibitors. May modulate cellular events, such as APP metabolism, kinase-dependent intracellular signaling, neuronal calcium signaling as well as neurotransmission
Gene Name:
LRP1
Uniprot ID:
Q07954
Molecular weight:
504570.7
General function:
Not Available
Specific function:
Component of Salmonella pathogenicity island 2 (SPI-2) type III secretion system, required for secretion of some type III-secreted effectors including the SpvB exotoxin.
Gene Name:
SSAV
Uniprot ID:
D0ZWU0
Molecular weight:
75320.9
General function:
Not Available
Specific function:
Component of Salmonella pathogenicity island 2 (SPI-2) type III secretion system, required for secretion of some type III-secreted effectors including the SpvB exotoxin.
Gene Name:
SSAV
Uniprot ID:
B5FII7
Molecular weight:
75320.9
General function:
Not Available
Specific function:
Component of Salmonella pathogenicity island 2 (SPI-2) type III secretion system, required for secretion of some type III-secreted effectors including the SpvB exotoxin.
Gene Name:
SSAJ
Uniprot ID:
D0ZWT5
Molecular weight:
28521.27
General function:
Not Available
Specific function:
Essential for the first step in the synthesis of diphthamide, a post-translational modification of histidine which occurs in elongation factor 2 (EEF2) and which can be ADP-ribosylated by diphtheria toxin and by Pseudomonas exotoxin A (Eta).Down-regulation increases extracellular release of proteoglycans, indicating a possible role in the secretion process. Stimulates binding of GNEFR to SEC5.
Gene Name:
DPH3
Uniprot ID:
Q96FX2
Molecular weight:
9240.135
General function:
Not Available
Specific function:
Has been proposed to act as a receptor for neuronostatin, a peptide derived from the somatostatin/SST precursor (PubMed:22933024). Involved in blood sugar regulation through the induction of glucagon in response to low glucose (By similarity).(Microbial infection) Required for intoxication by Pseudomonas aeruginosa exotoxin A and Campylobacter jejuni CDT. May contribute to the retrograde transport of bacterial toxins, including cholera toxin, from the trans-Golgi network to the endoplasmic reticulum.
Gene Name:
GPR107
Uniprot ID:
Q5VW38
Molecular weight:
66989.725
General function:
Not Available
Specific function:
Catalyzes the demethylation of diphthine methyl ester to form diphthine, an intermediate diphthamide biosynthesis, a post-translational modification of histidine which occurs in translation elongation factor 2 (EEF2) which can be ADP-ribosylated by diphtheria toxin and by Pseudomonas exotoxin A (Eta).
Gene Name:
DPH7
Uniprot ID:
Q9BTV6
Molecular weight:
50574.915
General function:
Not Available
Specific function:
Stimulates the ATPase activity of several Hsp70-type chaperones. This ability is enhanced by iron-binding. The iron-bound form is redox-active and can function as electron carrier. Plays a role in the diphthamide biosynthesis, a post-translational modification of histidine which occurs in translation elongation factor 2 (EEF2) which can be ADP-ribosylated by diphtheria toxin and by Pseudomonas exotoxin A (Eta).
Gene Name:
DNAJC24
Uniprot ID:
Q6P3W2
Molecular weight:
17139.16