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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2014-10-09 19:58:34 UTC
Update Date2021-10-13 11:55:12 UTC
HMDB IDHMDB0061933
Secondary Accession Numbers
  • HMDB61933
Metabolite Identification
Common Name1H-Indole-2,3-dione
Description1H-Indole-2,3-dione, also known as isatin or 2,3 dioxoindoline, belongs to the class of organic compounds known as indolines. Indolines are compounds containing an indole moiety, which consists of pyrrolidine ring fused to benzene to form 2,3-dihydroindole. 1H-Indole-2,3-dione is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on 1H-Indole-2,3-dione.
Structure
Data?1563866248
Synonyms
ValueSource
Indole-2,3-dioneChEBI
IsatinHMDB
2,3 DioxoindolineHMDB
2,3-DioxoindolineHMDB
1H-Indole-2,3-dioneKEGG
Chemical FormulaC8H5NO2
Average Molecular Weight147.1308
Monoisotopic Molecular Weight147.032028409
IUPAC Name2,3-dihydro-1H-indole-2,3-dione
Traditional Nameisatin
CAS Registry Number91-56-5
SMILES
O=C1NC2=CC=CC=C2C1=O
InChI Identifier
InChI=1S/C8H5NO2/c10-7-5-3-1-2-4-6(5)9-8(7)11/h1-4H,(H,9,10,11)
InChI KeyJXDYKVIHCLTXOP-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as indolines. Indolines are compounds containing an indole moiety, which consists of pyrrolidine ring fused to benzene to form 2,3-dihydroindole.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassIndolines
Direct ParentIndolines
Alternative Parents
Substituents
  • Dihydroindole
  • Aryl ketone
  • Benzenoid
  • Vinylogous amide
  • Carboxamide group
  • Ketone
  • Lactam
  • Secondary carboxylic acid amide
  • Carboxylic acid derivative
  • Azacycle
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting Point203.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Boiling Point360.30 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility15270 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP0.830The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility2.77 g/LALOGPS
logP0.89ALOGPS
logP1.6ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)8.93ChemAxon
pKa (Strongest Basic)-5.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.17 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity40.48 m³·mol⁻¹ChemAxon
Polarizability13.8 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+132.00531661259
DarkChem[M-H]-127.31531661259
DeepCCS[M+H]+125.29630932474
DeepCCS[M-H]-121.96630932474
DeepCCS[M-2H]-159.09730932474
DeepCCS[M+Na]+134.18130932474
AllCCS[M+H]+129.432859911
AllCCS[M+H-H2O]+124.632859911
AllCCS[M+NH4]+133.832859911
AllCCS[M+Na]+135.132859911
AllCCS[M-H]-126.332859911
AllCCS[M+Na-2H]-127.132859911
AllCCS[M+HCOO]-128.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
1H-Indole-2,3-dioneO=C1NC2=CC=CC=C2C1=O2791.4Standard polar33892256
1H-Indole-2,3-dioneO=C1NC2=CC=CC=C2C1=O1657.1Standard non polar33892256
1H-Indole-2,3-dioneO=C1NC2=CC=CC=C2C1=O1664.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
1H-Indole-2,3-dione,1TMS,isomer #1C[Si](C)(C)N1C(=O)C(=O)C2=CC=CC=C211602.2Semi standard non polar33892256
1H-Indole-2,3-dione,1TMS,isomer #1C[Si](C)(C)N1C(=O)C(=O)C2=CC=CC=C211627.6Standard non polar33892256
1H-Indole-2,3-dione,1TMS,isomer #1C[Si](C)(C)N1C(=O)C(=O)C2=CC=CC=C212141.1Standard polar33892256
1H-Indole-2,3-dione,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C(=O)C(=O)C2=CC=CC=C211867.2Semi standard non polar33892256
1H-Indole-2,3-dione,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C(=O)C(=O)C2=CC=CC=C211853.1Standard non polar33892256
1H-Indole-2,3-dione,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C(=O)C(=O)C2=CC=CC=C212263.3Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 1H-Indole-2,3-dione GC-MS (Non-derivatized) - 70eV, Positivesplash10-014j-3900000000-cfbe2c69370cb821719e2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1H-Indole-2,3-dione GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1H-Indole-2,3-dione GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 1H-Indole-2,3-dione LC-ESI-QQ , negative-QTOFsplash10-0002-0900000000-b7740f917ea3a513cccf2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1H-Indole-2,3-dione LC-ESI-QQ , negative-QTOFsplash10-014i-0900000000-7cc1e59d64b0f9fe75c72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1H-Indole-2,3-dione LC-ESI-QQ , negative-QTOFsplash10-0006-9200000000-7222eca5f15462cb52d62017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1H-Indole-2,3-dione LC-ESI-QQ , negative-QTOFsplash10-0006-9000000000-9d8ae3e3d93ebbae650e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1H-Indole-2,3-dione LC-ESI-QQ , negative-QTOFsplash10-0006-9000000000-5f853d2ccc4bbe2b3a892017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1H-Indole-2,3-dione LC-ESI-QTOF , positive-QTOFsplash10-0002-0900000000-4d14e90a2ccd915ec0282017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1H-Indole-2,3-dione LC-ESI-QTOF , positive-QTOFsplash10-0002-1900000000-efd2670c6d91416ca1232017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1H-Indole-2,3-dione LC-ESI-QTOF , positive-QTOFsplash10-001l-3900000000-a768411b3bdce1e8bbf72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1H-Indole-2,3-dione LC-ESI-QTOF , positive-QTOFsplash10-0f89-3900000000-00d17037a416b9858a302017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1H-Indole-2,3-dione LC-ESI-QTOF , positive-QTOFsplash10-0fc0-7900000000-b2e65fbe547a142b1b3e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1H-Indole-2,3-dione LC-ESI-QQ , positive-QTOFsplash10-001j-0900000000-6129e4681971547874232017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1H-Indole-2,3-dione LC-ESI-QQ , positive-QTOFsplash10-01ot-6900000000-e172235ae1d7d5980b782017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1H-Indole-2,3-dione LC-ESI-QQ , positive-QTOFsplash10-0g5d-9600000000-3abf3b0049a56410c6362017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1H-Indole-2,3-dione LC-ESI-QQ , positive-QTOFsplash10-014l-9100000000-0fb3353ec5204cb4b15c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1H-Indole-2,3-dione LC-ESI-QQ , positive-QTOFsplash10-0ik9-9000000000-82722063406d135a28ca2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1H-Indole-2,3-dione 50V, Positive-QTOFsplash10-0fc0-7900000000-b2e65fbe547a142b1b3e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1H-Indole-2,3-dione 20V, Positive-QTOFsplash10-0002-1900000000-efd2670c6d91416ca1232021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1H-Indole-2,3-dione 10V, Positive-QTOFsplash10-0002-0900000000-4d14e90a2ccd915ec0282021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1H-Indole-2,3-dione 30V, Positive-QTOFsplash10-001l-3900000000-a768411b3bdce1e8bbf72021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1H-Indole-2,3-dione 10V, Positive-QTOFsplash10-0002-0900000000-e31d27d5029a58203e082016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1H-Indole-2,3-dione 20V, Positive-QTOFsplash10-0002-0900000000-a71d92faa742d62f15dc2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1H-Indole-2,3-dione 40V, Positive-QTOFsplash10-00kg-9200000000-4c49ea126a926312a0442016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1H-Indole-2,3-dione 10V, Negative-QTOFsplash10-0002-0900000000-664b6d8a1a57af39e0322016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1H-Indole-2,3-dione 20V, Negative-QTOFsplash10-0002-1900000000-4fdb6fbe94e7299a7a8a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1H-Indole-2,3-dione 40V, Negative-QTOFsplash10-0006-9300000000-e0ec72a316f86a8a46152016-08-03Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
    • Zerihun T. Dame, ...
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB02095
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDC00026981
Chemspider ID6787
KEGG Compound IDC11129
BioCyc IDISATIN
BiGG IDNot Available
Wikipedia LinkIsatin
METLIN IDNot Available
PubChem Compound7054
PDB IDNot Available
ChEBI ID27539
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1252271
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Karali N, Gursoy A, Kandemirli F, Shvets N, Kaynak FB, Ozbey S, Kovalishyn V, Dimoglo A: Synthesis and structure-antituberculosis activity relationship of 1H-indole-2,3-dione derivatives. Bioorg Med Chem. 2007 Sep 1;15(17):5888-904. Epub 2007 Jun 2. [PubMed:17561405 ]
  2. Guzel O, Karali N, Salman A: Synthesis and antituberculosis activity of 5-methyl/trifluoromethoxy-1H-indole-2,3-dione 3-thiosemicarbazone derivatives. Bioorg Med Chem. 2008 Oct 1;16(19):8976-87. doi: 10.1016/j.bmc.2008.08.050. Epub 2008 Aug 27. [PubMed:18804379 ]
  3. Kassab SE, Hegazy GH, Eid NM, Amin KM, El-Gendy AA: Synthesis of 1H-indole-2,3-dione-3-thiosemicarbazone ribonucleosides as antibacterial agents. Nucleosides Nucleotides Nucleic Acids. 2010 Jan;29(1):72-80. doi: 10.1080/15257770903459267. [PubMed:20391194 ]
  4. Shahlaei M, Fassihi A, Nezami A: QSAR study of some 5-methyl/trifluoromethoxy- 1H-indole-2,3-dione-3-thiosemicarbazone derivatives as anti-tubercular agents. Res Pharm Sci. 2009 Jul;4(2):123-31. [PubMed:21589807 ]
  5. Maamri K, Zouihri H, Essassi el M, Ng SW: 5-Bromo-1-(prop-2-en-1-yl)-2,3-dihydro-1H-indole-2,3-dione. Acta Crystallogr Sect E Struct Rep Online. 2012 Jan;68(Pt 1):o240. doi: 10.1107/S160053681105447X. Epub 2011 Dec 23. [PubMed:22259522 ]
  6. Premanathan M, Radhakrishnan S, Kulangiappar K, Singaravelu G, Thirumalaiarasu V, Sivakumar T, Kathiresan K: Antioxidant & anticancer activities of isatin (1H-indole-2,3-dione), isolated from the flowers of Couroupita guianensis Aubl. Indian J Med Res. 2012 Nov;136(5):822-6. [PubMed:23287130 ]
  7. George Y. Lesher, Donald F. Page, Monte D. Gruett, '1H-Indole-2,3-dione derivatives.' U.S. Patent US4322533, issued March 30, 1982. [Link]