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Showing metabocard for 1H-Indole-2,3-dione (HMDB0061933)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2014-10-09 19:58:34 UTC
Update Date2023-02-21 17:30:36 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?1677000636
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0061933 (1H-Indole-2,3-dione)

  Mrv0541 02231215572D          

 11 12  0  0  0  0            999 V2000
   -0.1712   -0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
  2 10  1  0  0  0  0
 10 11  2  0  0  0  0
M  END
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3D MOL for HMDB0061933 (1H-Indole-2,3-dione)

HMDB0240740
     RDKit          3D
Isatin
 16 17  0  0  0  0  0  0  0  0999 V2000
    3.6810    0.5857   -0.4175 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4306    0.3857   -0.2757 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4400    1.3985   -0.1806 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1944    0.7368   -0.0325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0860    1.2414    0.1023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1557    0.3790    0.2339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0226   -0.9951    0.2394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7420   -1.4896    0.1044 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3433   -0.6317   -0.0288 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7710   -0.8985   -0.1835 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3412   -2.0356   -0.2300 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6450    2.4283   -0.2186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1944    2.3145    0.0985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1595    0.7861    0.3393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8906   -1.6403    0.3453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5959   -2.5653    0.1041 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10  2  1  0
  9  4  1  0
  3 12  1  0
  5 13  1  0
  6 14  1  0
  7 15  1  0
  8 16  1  0
M  END
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3D SDF for HMDB0061933 (1H-Indole-2,3-dione)

  Mrv0541 02231215572D          

 11 12  0  0  0  0            999 V2000
   -0.1712   -0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
  2 10  1  0  0  0  0
 10 11  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0061933

> <DATABASE_NAME>
hmdb

> <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_KEY>
JXDYKVIHCLTXOP-UHFFFAOYSA-N

> <FORMULA>
C8H5NO2

> <MOLECULAR_WEIGHT>
147.1308

> <EXACT_MASS>
147.032028409

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
13.801558706834744

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,3-dihydro-1H-indole-2,3-dione

> <ALOGPS_LOGP>
0.89

> <JCHEM_LOGP>
1.601543561333333

> <ALOGPS_LOGS>
-1.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.925314965375605

> <JCHEM_PKA_STRONGEST_BASIC>
-5.622783761200125

> <JCHEM_POLAR_SURFACE_AREA>
46.17

> <JCHEM_REFRACTIVITY>
40.475

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.77e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
isatin

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0061933 (1H-Indole-2,3-dione)

HMDB0240740
     RDKit          3D
Isatin
 16 17  0  0  0  0  0  0  0  0999 V2000
    3.6810    0.5857   -0.4175 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4306    0.3857   -0.2757 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4400    1.3985   -0.1806 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1944    0.7368   -0.0325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0860    1.2414    0.1023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1557    0.3790    0.2339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0226   -0.9951    0.2394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7420   -1.4896    0.1044 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3433   -0.6317   -0.0288 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7710   -0.8985   -0.1835 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3412   -2.0356   -0.2300 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6450    2.4283   -0.2186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1944    2.3145    0.0985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1595    0.7861    0.3393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8906   -1.6403    0.3453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5959   -2.5653    0.1041 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10  2  1  0
  9  4  1  0
  3 12  1  0
  5 13  1  0
  6 14  1  0
  7 15  1  0
  8 16  1  0
M  END
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PDB for HMDB0061933 (1H-Indole-2,3-dione)

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      -0.320  -1.303   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       2.126  -0.057   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.650  -4.013   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   10                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    4   10                                                  
CONECT   10    9    2   11                                                  
CONECT   11   10                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   24    0
END
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3D PDB for HMDB0061933 (1H-Indole-2,3-dione)

COMPND    HMDB0240740
HETATM    1  O1  UNL     1       3.681   0.586  -0.418  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.431   0.386  -0.276  1.00  0.00           C  
HETATM    3  N1  UNL     1       1.440   1.398  -0.181  1.00  0.00           N  
HETATM    4  C2  UNL     1       0.194   0.737  -0.032  1.00  0.00           C  
HETATM    5  C3  UNL     1      -1.086   1.241   0.102  1.00  0.00           C  
HETATM    6  C4  UNL     1      -2.156   0.379   0.234  1.00  0.00           C  
HETATM    7  C5  UNL     1      -2.023  -0.995   0.239  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.742  -1.490   0.104  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.343  -0.632  -0.029  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.771  -0.898  -0.183  1.00  0.00           C  
HETATM   11  O2  UNL     1       2.341  -2.036  -0.230  1.00  0.00           O  
HETATM   12  H1  UNL     1       1.645   2.428  -0.219  1.00  0.00           H  
HETATM   13  H2  UNL     1      -1.194   2.315   0.098  1.00  0.00           H  
HETATM   14  H3  UNL     1      -3.159   0.786   0.339  1.00  0.00           H  
HETATM   15  H4  UNL     1      -2.891  -1.640   0.345  1.00  0.00           H  
HETATM   16  H5  UNL     1      -0.596  -2.565   0.104  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   10
CONECT    3    4   12
CONECT    4    5    5    9
CONECT    5    6   13
CONECT    6    7    7   14
CONECT    7    8   15
CONECT    8    9    9   16
CONECT    9   10
CONECT   10   11   11
END
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SMILES for HMDB0061933 (1H-Indole-2,3-dione)

O=C1NC2=CC=CC=C2C1=O
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INCHI for HMDB0061933 (1H-Indole-2,3-dione)

InChI=1S/C8H5NO2/c10-7-5-3-1-2-4-6(5)9-8(7)11/h1-4H,(H,9,10,11)
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View in JSmolView NMR AssignmentsView Stereo Labels
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
Biological locationSource
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
Predicted Chromatographic Properties
Spectra
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]