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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2022-03-07 02:51:58 UTC
HMDB IDHMDB0015380
Secondary Accession Numbers
  • HMDB15380
Metabolite Identification
Common NameOlsalazine
DescriptionOlsalazine, also known as dipentum or olsalazine sodium, belongs to the class of organic compounds known as azobenzenes. These are organonitrogen aromatic compounds that contain a central azo group, where each nitrogen atom is conjugated to a benzene ring. It is sold under the name Dipentum. Olsalazine is a drug which is used for the treatment of inflammatory bowel disease and ulcerative colitis. Olsalazine gained Food and Drug Administration (FDA) approval in 1990. Olsalazine is an extremely weak basic (essentially neutral) compound (based on its pKa). Like balsalazide, olsalazine is believed to deliver mesalazine, or 5-aminosalicylic acid (5-ASA), past the small intestine, directly to the large intestine, which is the active site of disease in ulcerative colitis. The chemical name is 3,3' -azobis (6-hydroxybenzoate)salicylic acid. The drug is supplied by UCB Pharma. Olsalazine is an anti-inflammatory drug used in the treatment of inflammatory bowel disease such as ulcerative colitis. It is sold as the disodium salt. The Australian biotech company Giaconda has developed a combination therapy for treating constipation-predominant irritable bowel syndrome that uses olsalazine and the anti-gout drug colchicine.
Structure
Data?1582753290
Synonyms
ValueSource
DipentumHMDB
Olsalazine sodiumHMDB
Chemical FormulaC14H10N2O6
Average Molecular Weight302.239
Monoisotopic Molecular Weight302.053886062
IUPAC Name5-[(E)-2-(3-carboxy-4-hydroxyphenyl)diazen-1-yl]-2-hydroxybenzoic acid
Traditional Nameolsalazine
CAS Registry Number15722-48-2
SMILES
OC(=O)C1=CC(=CC=C1O)\N=N\C1=CC=C(O)C(=C1)C(O)=O
InChI Identifier
InChI=1S/C14H10N2O6/c17-11-3-1-7(5-9(11)13(19)20)15-16-8-2-4-12(18)10(6-8)14(21)22/h1-6,17-18H,(H,19,20)(H,21,22)/b16-15+
InChI KeyQQBDLJCYGRGAKP-FOCLMDBBSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as azobenzenes. These are organonitrogen aromatic compounds that contain a central azo group, where each nitrogen atom is conjugated to a benzene ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzobenzenes
Sub ClassNot Available
Direct ParentAzobenzenes
Alternative Parents
Substituents
  • Azobenzene
  • Hydroxybenzoic acid
  • Salicylic acid or derivatives
  • Salicylic acid
  • Benzoic acid or derivatives
  • Benzoic acid
  • Benzoyl
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Dicarboxylic acid or derivatives
  • Benzenoid
  • Vinylogous acid
  • Azo compound
  • Organic 1,3-dipolar compound
  • Carboxylic acid
  • Carboxylic acid derivative
  • Propargyl-type 1,3-dipolar organic compound
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point240 °C (decomposition)Not Available
Boiling PointNot AvailableNot Available
Water Solubility0.078 g/LNot Available
LogP2.3Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.078 g/LALOGPS
logP2.77ALOGPS
logP4.39ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)2.93ChemAxon
pKa (Strongest Basic)-0.019ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area139.78 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity78.85 m³·mol⁻¹ChemAxon
Polarizability28.61 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]+164.72330932474
DeepCCS[M-H]-162.36530932474
DeepCCS[M-2H]-195.37930932474
DeepCCS[M+Na]+170.81630932474
AllCCS[M+H]+166.632859911
AllCCS[M+H-H2O]+163.232859911
AllCCS[M+NH4]+169.732859911
AllCCS[M+Na]+170.632859911
AllCCS[M-H]-165.532859911
AllCCS[M+Na-2H]-164.832859911
AllCCS[M+HCOO]-164.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
OlsalazineOC(=O)C1=CC(=CC=C1O)\N=N\C1=CC=C(O)C(=C1)C(O)=O4221.6Standard polar33892256
OlsalazineOC(=O)C1=CC(=CC=C1O)\N=N\C1=CC=C(O)C(=C1)C(O)=O2893.7Standard non polar33892256
OlsalazineOC(=O)C1=CC(=CC=C1O)\N=N\C1=CC=C(O)C(=C1)C(O)=O2911.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Olsalazine,1TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC(/N=N/C2=CC=C(O)C(C(=O)O)=C2)=CC=C1O3202.1Semi standard non polar33892256
Olsalazine,1TMS,isomer #2C[Si](C)(C)OC1=CC=C(/N=N/C2=CC=C(O)C(C(=O)O)=C2)C=C1C(=O)O3186.3Semi standard non polar33892256
Olsalazine,2TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC(/N=N/C2=CC=C(O[Si](C)(C)C)C(C(=O)O)=C2)=CC=C1O3078.7Semi standard non polar33892256
Olsalazine,2TMS,isomer #2C[Si](C)(C)OC(=O)C1=CC(/N=N/C2=CC=C(O)C(C(=O)O[Si](C)(C)C)=C2)=CC=C1O3053.3Semi standard non polar33892256
Olsalazine,2TMS,isomer #3C[Si](C)(C)OC(=O)C1=CC(/N=N/C2=CC=C(O)C(C(=O)O)=C2)=CC=C1O[Si](C)(C)C3080.9Semi standard non polar33892256
Olsalazine,2TMS,isomer #4C[Si](C)(C)OC1=CC=C(/N=N/C2=CC=C(O[Si](C)(C)C)C(C(=O)O)=C2)C=C1C(=O)O3081.7Semi standard non polar33892256
Olsalazine,3TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC(/N=N/C2=CC=C(O[Si](C)(C)C)C(C(=O)O[Si](C)(C)C)=C2)=CC=C1O3016.8Semi standard non polar33892256
Olsalazine,3TMS,isomer #2C[Si](C)(C)OC(=O)C1=CC(/N=N/C2=CC=C(O[Si](C)(C)C)C(C(=O)O)=C2)=CC=C1O[Si](C)(C)C3041.2Semi standard non polar33892256
Olsalazine,4TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC(/N=N/C2=CC=C(O[Si](C)(C)C)C(C(=O)O[Si](C)(C)C)=C2)=CC=C1O[Si](C)(C)C3061.9Semi standard non polar33892256
Olsalazine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC(/N=N/C2=CC=C(O)C(C(=O)O)=C2)=CC=C1O3476.5Semi standard non polar33892256
Olsalazine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C(/N=N/C2=CC=C(O)C(C(=O)O)=C2)C=C1C(=O)O3502.5Semi standard non polar33892256
Olsalazine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC(/N=N/C2=CC=C(O[Si](C)(C)C(C)(C)C)C(C(=O)O)=C2)=CC=C1O3608.3Semi standard non polar33892256
Olsalazine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C1=CC(/N=N/C2=CC=C(O)C(C(=O)O[Si](C)(C)C(C)(C)C)=C2)=CC=C1O3546.2Semi standard non polar33892256
Olsalazine,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)C1=CC(/N=N/C2=CC=C(O)C(C(=O)O)=C2)=CC=C1O[Si](C)(C)C(C)(C)C3602.1Semi standard non polar33892256
Olsalazine,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC1=CC=C(/N=N/C2=CC=C(O[Si](C)(C)C(C)(C)C)C(C(=O)O)=C2)C=C1C(=O)O3638.2Semi standard non polar33892256
Olsalazine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC(/N=N/C2=CC=C(O[Si](C)(C)C(C)(C)C)C(C(=O)O[Si](C)(C)C(C)(C)C)=C2)=CC=C1O3690.6Semi standard non polar33892256
Olsalazine,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C1=CC(/N=N/C2=CC=C(O[Si](C)(C)C(C)(C)C)C(C(=O)O)=C2)=CC=C1O[Si](C)(C)C(C)(C)C3790.9Semi standard non polar33892256
Olsalazine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC(/N=N/C2=CC=C(O[Si](C)(C)C(C)(C)C)C(C(=O)O[Si](C)(C)C(C)(C)C)=C2)=CC=C1O[Si](C)(C)C(C)(C)C3864.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Olsalazine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-1941000000-280432522076c6c2ecde2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Olsalazine GC-MS (4 TMS) - 70eV, Positivesplash10-007k-3091060000-9240a61a4df477ec469a2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Olsalazine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Olsalazine 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 - Olsalazine 10V, Positive-QTOFsplash10-0udi-0169000000-eec3ced209a0cbb0db942016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Olsalazine 20V, Positive-QTOFsplash10-0pbi-0192000000-1871f32f63f2569241512016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Olsalazine 40V, Positive-QTOFsplash10-0zi0-4940000000-5242870d6e92c57703752016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Olsalazine 10V, Negative-QTOFsplash10-0udi-0269000000-d99f02b963a55874115d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Olsalazine 20V, Negative-QTOFsplash10-0r00-0291000000-d498e8b80c9d6157a43e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Olsalazine 40V, Negative-QTOFsplash10-0a4i-0920000000-9308cf8b2a3270fdbe452016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Olsalazine 10V, Positive-QTOFsplash10-000i-0091000000-0407edb727a6dc86736b2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Olsalazine 20V, Positive-QTOFsplash10-00kr-0290000000-15f46b8ccd52040f0d872021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Olsalazine 40V, Positive-QTOFsplash10-0c33-0690000000-835682abfe82b09946d92021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Olsalazine 10V, Negative-QTOFsplash10-0udi-0019000000-6f1fdd414a31404ce61f2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Olsalazine 20V, Negative-QTOFsplash10-08fr-0091000000-8f61d29ce7524211d1112021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Olsalazine 40V, Negative-QTOFsplash10-03di-0090000000-4e4e69e7208a4f9deb462021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01250 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01250 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01250
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID10642377
KEGG Compound IDC07323
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkOlsalazine
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID101369
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 ReferencesNot Available

Enzymes

General function:
Involved in thiopurine S-methyltransferase activity
Specific function:
Catalyzes the S-methylation of thiopurine drugs such as 6-mercaptopurine.
Gene Name:
TPMT
Uniprot ID:
P51580
Molecular weight:
28180.09
References
  1. Lewis LD, Benin A, Szumlanski CL, Otterness DM, Lennard L, Weinshilboum RM, Nierenberg DW: Olsalazine and 6-mercaptopurine-related bone marrow suppression: a possible drug-drug interaction. Clin Pharmacol Ther. 1997 Oct;62(4):464-75. [PubMed:9357398 ]
  2. Lennard L: TPMT in the treatment of Crohn's disease with azathioprine. Gut. 2002 Aug;51(2):143-6. [PubMed:12117866 ]
  3. Lennard L: Clinical implications of thiopurine methyltransferase--optimization of drug dosage and potential drug interactions. Ther Drug Monit. 1998 Oct;20(5):527-31. [PubMed:9780130 ]
  4. Shipkova M, Niedmann PD, Armstrong VW, Oellerich M, Wieland E: Determination of thiopurine methyltransferase activity in isolated human erythrocytes does not reflect putative in vivo enzyme inhibition by sulfasalazine. Clin Chem. 2004 Feb;50(2):438-41. [PubMed:14752016 ]
General function:
Involved in cytokine activity
Specific function:
Produced by lymphocytes activated by specific antigens or mitogens. IFN-gamma, in addition to having antiviral activity, has important immunoregulatory functions. It is a potent activator of macrophages, it has antiproliferative effects on transformed cells and it can potentiate the antiviral and antitumor effects of the type I interferons
Gene Name:
IFNG
Uniprot ID:
P01579
Molecular weight:
19348.2
References
  1. Egan LJ, Sandborn WJ: Inhibition of nuclear factor kappaB by sulfasalazine: a new target for inflammatory bowel disease therapy? Gastroenterology. 1998 Nov;115(5):1295-6. [PubMed:9797390 ]
  2. Ito R, Shin-Ya M, Kishida T, Urano A, Takada R, Sakagami J, Imanishi J, Kita M, Ueda Y, Iwakura Y, Kataoka K, Okanoue T, Mazda O: Interferon-gamma is causatively involved in experimental inflammatory bowel disease in mice. Clin Exp Immunol. 2006 Nov;146(2):330-8. [PubMed:17034586 ]