NP-MRD: Showing NP-Card for 2,3-indolinedione (NP0015871)

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Record Information

Version

2.0

Created at

2021-01-06 01:00:57 UTC

Updated at

2021-08-19 23:59:54 UTC

NP-MRD ID

NP0015871

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,3-indolinedione

Provided By

NPAtlas

Description

1H-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. 2,3-indolinedione is found in Alteromonas sp., Calanthe discolor, Capparis spinosa, Cephalanceropsis gracilis, Couroupita guianensis, Homo sapiens and Isatis indigotica . 2,3-indolinedione was first documented in 1989 (PMID: 2781297). Based on a literature review a significant number of articles have been published on 1H-Indole-2,3-dione (PMID: 17561405) (PMID: 18804379) (PMID: 20391194) (PMID: 21589807) (PMID: 22259522) (PMID: 23287130).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117233D          

 16 17  0  0  0  0            999 V2000
    3.7758   -0.2095   -0.0247 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5204   -0.1289   -0.0167 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6965    1.0264   -0.0276 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3145    0.6889   -0.0125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8614    1.4294   -0.0147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1110    0.8494    0.0030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1457   -0.5303    0.0236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9959   -1.2887    0.0263 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2469   -0.6899    0.0083 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6058   -1.2612    0.0067 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9204   -2.4798    0.0224 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0312    2.0083   -0.0445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8254    2.5085   -0.0308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0195    1.4423    0.0010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1188   -0.9990    0.0377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0338   -2.3658    0.0424 H   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
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10  2  1  0  0  0  0
  9  4  1  0  0  0  0
  3 12  1  0  0  0  0
  5 13  1  0  0  0  0
  6 14  1  0  0  0  0
  7 15  1  0  0  0  0
  8 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0015871

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]N1C(=O)C(=O)C2=C([H])C([H])=C([H])C([H])=C12

> <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_ATOM_COUNT>
16

> <JCHEM_AVERAGE_POLARIZABILITY>
13.80155870683469

> <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

$$$$

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  O   UNK     0       3.776  -0.210  -0.025  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.520  -0.129  -0.017  0.00  0.00           C+0
HETATM    3  N   UNK     0       1.696   1.026  -0.028  0.00  0.00           N+0
HETATM    4  C   UNK     0       0.315   0.689  -0.013  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.861   1.429  -0.015  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.111   0.849   0.003  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.146  -0.530   0.024  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.996  -1.289   0.026  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.247  -0.690   0.008  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.606  -1.261   0.007  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.920  -2.480   0.022  0.00  0.00           O+0
HETATM   12  H   UNK     0       2.031   2.008  -0.045  0.00  0.00           H+0
HETATM   13  H   UNK     0      -0.825   2.509  -0.031  0.00  0.00           H+0
HETATM   14  H   UNK     0      -3.019   1.442   0.001  0.00  0.00           H+0
HETATM   15  H   UNK     0      -3.119  -0.999   0.038  0.00  0.00           H+0
HETATM   16  H   UNK     0      -1.034  -2.366   0.042  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3   10                                                  
CONECT    3    2    4   12                                                  
CONECT    4    3    5    9                                                  
CONECT    5    4    6   13                                                  
CONECT    6    5    7   14                                                  
CONECT    7    6    8   15                                                  
CONECT    8    7    9   16                                                  
CONECT    9    8   10    4                                                  
CONECT   10    9   11    2                                                  
CONECT   11   10                                                            
CONECT   12    3                                                            
CONECT   13    5                                                            
CONECT   14    6                                                            
CONECT   15    7                                                            
CONECT   16    8                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

View in JSmol View NMR Assignments

Synonyms

Value	Source
Indole-2,3-dione	ChEBI
Isatin	HMDB
2,3 Dioxoindoline	HMDB
2,3-Dioxoindoline	HMDB
1H-Indole-2,3-dione	KEGG

Chemical Formula

C₈H₅NO₂

Average Mass

147.1308 Da

Monoisotopic Mass

147.03203 Da

IUPAC Name

2,3-dihydro-1H-indole-2,3-dione

Traditional Name

isatin

CAS Registry Number

Not Available

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

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Alteromonas sp.	NPAtlas	2781297
Calanthe discolor	LOTUS Database	35616633
Calanthe discolor Lindl	KNApSAcK Database	22123792
Calanthe liukiuensis Schltr	KNApSAcK Database	22123792
Capparis spinosa	LOTUS Database	35616633
Cephalanceropsis gracilis	-	KNApSAcK
Couroupita guianensis	LOTUS Database	35616633
Homo sapiens	LOTUS Database	35616633
Isatis indigotica	KNApSAcK Database	22123792
Isatis tinctoria	Plant	KNApSAcK

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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indolines

Direct Parent

Indolines

Alternative Parents

Not Available

Substituents

Not Available

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	203.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Boiling Point	360.30 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	15270 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	0.830	The Good Scents Company Information System

Predicted Properties

Property	Value	Source
logP	0.89	ALOGPS
logP	1.6	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	8.93	ChemAxon
pKa (Strongest Basic)	-5.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.17 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	40.48 m³·mol⁻¹	ChemAxon
Polarizability	13.8 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA005025

HMDB ID

HMDB0061933

DrugBank ID

DB02095

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Isatin

METLIN ID

Not Available

PubChem Compound

7054

PDB ID

Not Available

ChEBI ID

27539

Good Scents ID

rw1252271

References

General References

Gil-Turnes MS, Hay ME, Fenical W: Symbiotic marine bacteria chemically defend crustacean embryos from a pathogenic fungus. Science. 1989 Oct 6;246(4926):116-8. doi: 10.1126/science.2781297. [PubMed:2781297 ]
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. doi: 10.1016/j.bmc.2007.05.063. Epub 2007 Jun 2. [PubMed:17561405 ]
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 ]
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 ]
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 ]
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 ]
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 ]
Igosheva N, Lorz C, O'Conner E, Glover V, Mehmet H: Isatin, an endogenous monoamine oxidase inhibitor, triggers a dose- and time-dependent switch from apoptosis to necrosis in human neuroblastoma cells. Neurochem Int. 2005 Aug;47(3):216-24. doi: 10.1016/j.neuint.2005.02.011. [PubMed:15876476 ]
Medvedev A, Igosheva N, Crumeyrolle-Arias M, Glover V: Isatin: role in stress and anxiety. Stress. 2005 Sep;8(3):175-83. doi: 10.1080/10253890500342321. [PubMed:16236622 ]
Zou P, Koh HL: Determination of indican, isatin, indirubin and indigotin in Isatis indigotica by liquid chromatography/electrospray ionization tandem mass spectrometry. Rapid Commun Mass Spectrom. 2007;21(7):1239-46. doi: 10.1002/rcm.2954. [PubMed:17330218 ]
Minami M, Hamaue N, Hirafuji M, Saito H, Hiroshige T, Ogata A, Tashiro K, Parvez SH: Isatin, an endogenous MAO inhibitor, and a rat model of Parkinson's disease induced by the Japanese encephalitis virus. J Neural Transm Suppl. 2006;(71):87-95. doi: 10.1007/978-3-211-33328-0_10. [PubMed:17447419 ]
Buneeva O, Gnedenko O, Zgoda V, Kopylov A, Glover V, Ivanov A, Medvedev A, Archakov A: Isatin-binding proteins of rat and mouse brain: proteomic identification and optical biosensor validation. Proteomics. 2010 Jan;10(1):23-37. doi: 10.1002/pmic.200900492. [PubMed:19834914 ]

Showing NP-Card for 2,3-indolinedione (NP0015871)

MOL for NP0015871 (2,3-indolinedione)

3D MOL for NP0015871 (2,3-indolinedione)

3D SDF for NP0015871 (2,3-indolinedione)

3D-SDF for NP0015871 (2,3-indolinedione)

PDB for NP0015871 (2,3-indolinedione)

3D PDB for NP0015871 (2,3-indolinedione)

SMILES for NP0015871 (2,3-indolinedione)

INCHI for NP0015871 (2,3-indolinedione)

Structure for NP0015871 (2,3-indolinedione)

3D Structure for NP0015871 (2,3-indolinedione)