NP-MRD: Showing NP-Card for Oxindole (NP0023637)

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Record Information

Version

1.0

Created at

2021-01-06 08:42:13 UTC

Updated at

2021-07-15 17:42:17 UTC

NP-MRD ID

NP0023637

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Oxindole

Provided By

NPAtlas

Description

1,3-Dihydro-(2H)-indol-2-one, also known as 2-oxindole or 2-indolinone, 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. 1,3-Dihydro-(2H)-indol-2-one is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Oxindole is found in Penicillium sp. It was first documented in 1992 (PMID: 1341576). Based on a literature review a significant number of articles have been published on 1,3-Dihydro-(2H)-indol-2-one (PMID: 9528122) (PMID: 24433962) (PMID: 24500796) (PMID: 34089254) (PMID: 34028260) (PMID: 33775093).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242120433D          

 17 18  0  0  0  0            999 V2000
   -3.6127   -0.7199    0.2079 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3421   -0.4907    0.1473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7108    0.7383   -0.3542 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2619    0.5081   -0.2156 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8093    1.3584   -0.5445 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0932    0.9175   -0.3216 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3033   -0.3390    0.2156 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2438   -1.1551    0.5304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0700   -0.7351    0.3154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3189   -1.3782    0.5516 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8975    0.8436   -1.4561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0531    1.6479    0.1908 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6265    2.3470   -0.9676 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9000    1.5824   -0.5796 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3308   -0.6357    0.3703 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4011   -2.1410    0.9516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4411   -2.3484    0.9583 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  2  1  0  0  0  0
  9  4  1  0  0  0  0
  3 11  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
 10 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0023637

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C8H7NO/c10-8-5-6-3-1-2-4-7(6)9-8/h1-4H,5H2,(H,9,10)

> <INCHI_KEY>
JYGFTBXVXVMTGB-UHFFFAOYSA-N

> <FORMULA>
C8H7NO

> <MOLECULAR_WEIGHT>
133.1473

> <EXACT_MASS>
133.052763851

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
13.874099190750835

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,3-dihydro-1H-indol-2-one

> <ALOGPS_LOGP>
0.98

> <JCHEM_LOGP>
1.0720501869999999

> <ALOGPS_LOGS>
-1.70

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.284746640939577

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.136061880454271

> <JCHEM_PKA_STRONGEST_BASIC>
-5.488596497373129

> <JCHEM_POLAR_SURFACE_AREA>
29.1

> <JCHEM_REFRACTIVITY>
39.584900000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.68e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
oxindole

> <JCHEM_VEBER_RULE>
1

$$$$

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      -3.613  -0.720   0.208  0.00  0.00           O+0
HETATM    2  C   UNK     0      -2.342  -0.491   0.147  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.711   0.738  -0.354  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.262   0.508  -0.216  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.809   1.358  -0.545  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.093   0.918  -0.322  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.303  -0.339   0.216  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.244  -1.155   0.530  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.070  -0.735   0.315  0.00  0.00           C+0
HETATM   10  N   UNK     0      -1.319  -1.378   0.552  0.00  0.00           N+0
HETATM   11  H   UNK     0      -1.898   0.844  -1.456  0.00  0.00           H+0
HETATM   12  H   UNK     0      -2.053   1.648   0.191  0.00  0.00           H+0
HETATM   13  H   UNK     0       0.627   2.347  -0.968  0.00  0.00           H+0
HETATM   14  H   UNK     0       2.900   1.582  -0.580  0.00  0.00           H+0
HETATM   15  H   UNK     0       3.331  -0.636   0.370  0.00  0.00           H+0
HETATM   16  H   UNK     0       1.401  -2.141   0.952  0.00  0.00           H+0
HETATM   17  H   UNK     0      -1.441  -2.348   0.958  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3   10                                                  
CONECT    3    2    4   11   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    2   17                                                  
CONECT   11    3                                                            
CONECT   12    3                                                            
CONECT   13    5                                                            
CONECT   14    6                                                            
CONECT   15    7                                                            
CONECT   16    8                                                            
CONECT   17   10                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

View in JSmol View NMR Assignments

Synonyms

Value	Source
1,3-Dihydroindol-2-one	ChEBI
2-Indolinone	ChEBI
2-Oxindole	ChEBI
Oxindole	ChEBI
1,3-Dihydro-2H-indol-2-one	HMDB
2,3-Dihydro-1H-indol-2-one	HMDB
2-Indolone	HMDB
2-oxo-2,3-Dihydroindole	HMDB
2-Oxoindole	HMDB
2-Oxoindoline	HMDB
indol-2(3H)-One	HMDB
Indoline-2-one	HMDB
Oxindol	HMDB
2-Hydroxyindole	MeSH
2-Oxindole perchlorate	MeSH
Diclofenac impurity e	MeSH
indol-2-Ol	MeSH
1H-indol-2-Ol	MeSH

Chemical Formula

C₈H₇NO

Average Mass

133.1473 Da

Monoisotopic Mass

133.05276 Da

IUPAC Name

2,3-dihydro-1H-indol-2-one

Traditional Name

oxindole

CAS Registry Number

Not Available

SMILES

O=C1CC2=CC=CC=C2N1

InChI Identifier

InChI=1S/C8H7NO/c10-8-5-6-3-1-2-4-7(6)9-8/h1-4H,5H2,(H,9,10)

InChI Key

JYGFTBXVXVMTGB-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
Penicillium sp.	NPAtlas	9528122

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	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	0.98	ALOGPS
logP	1.07	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	12.14	ChemAxon
pKa (Strongest Basic)	-5.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	29.1 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	39.58 m³·mol⁻¹	ChemAxon
Polarizability	13.87 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA002938

HMDB ID

HMDB0061918

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

284794

KEGG Compound ID

C12312

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

321710

PDB ID

Not Available

ChEBI ID

31697

Good Scents ID

Not Available

References

General References

Witter L, Anke T, Sterner O: A new inhibitor of synovial phospholipase A2 from fermentations of Penicillium sp. 62-92. Z Naturforsch C J Biosci. 1998 Jan-Feb;53(1-2):60-4. doi: 10.1515/znc-1998-1-212. [PubMed:9528122 ]
Haun M, Pereira MF, Hoffmann ME, Joyas A, Campos V, Filardi LD, de Castro SL, Duran N: Bacterial chemistry. VI. Biological activities and cytotoxicity of 1,3-dihydro-2H-indol-2-one derivatives. Biol Res. 1992;25(1):21-5. [PubMed:1341576 ]
Scala A, Cordaro M, Grassi G, Piperno A, Barberi G, Cascio A, Risitano F: Direct synthesis of C3-mono-functionalized oxindoles from N-unprotected 2-oxindole and their antileishmanial activity. Bioorg Med Chem. 2014 Feb 1;22(3):1063-9. doi: 10.1016/j.bmc.2013.12.039. Epub 2013 Dec 25. [PubMed:24433962 ]
Zhang X, Qu Y, Ma Q, Kong C, Zhou H, Cao X, Shen W, Shen E, Zhou J: Production of indirubin from tryptophan by recombinant Escherichia coli containing naphthalene dioxygenase genes from Comamonas sp. MQ. Appl Biochem Biotechnol. 2014 Mar;172(6):3194-206. doi: 10.1007/s12010-014-0743-3. Epub 2014 Feb 6. [PubMed:24500796 ]
Bargavi S, Gouthaman S, Sugunalakshmi M, Lakshmi S: Synthesis, spectroscopic investigation, crystal structure analysis, quantum chemical study, biological activity and molecular docking of three isatin derivatives. Acta Crystallogr C Struct Chem. 2021 Jun 1;77(Pt 6):299-311. doi: 10.1107/S2053229621004940. Epub 2021 May 26. [PubMed:34089254 ]
Yang J, Zhang G, Wang Z, Meng J, Wen H: Metabolic Study of Stable Isotope Labeled Indolinone Derivative in Hepatocyte Cell by UPLC/Q TOF MS. J Am Soc Mass Spectrom. 2021 Jun 2;32(6):1538-1544. doi: 10.1021/jasms.1c00146. Epub 2021 May 24. [PubMed:34028260 ]
Zhang CH, Huang R, Zhang ZW, Lin J, Yan SJ: An Environmentally Benign Cascade Reaction of 1,1-Enediamines (EDAMs) for Site-Selective Synthesis of Highly Functionalized 2,10-Dihydro-1H-imidazo[1',2':1,6]pyrido[2,3-b]indoles and Pyrroles. J Org Chem. 2021 Apr 16;86(8):5744-5756. doi: 10.1021/acs.joc.1c00211. Epub 2021 Mar 27. [PubMed:33775093 ]

Showing NP-Card for Oxindole (NP0023637)

MOL for NP0023637 (Oxindole)

3D MOL for NP0023637 (Oxindole)

3D SDF for NP0023637 (Oxindole)

3D-SDF for NP0023637 (Oxindole)

PDB for NP0023637 (Oxindole)

3D PDB for NP0023637 (Oxindole)

SMILES for NP0023637 (Oxindole)

INCHI for NP0023637 (Oxindole)

Structure for NP0023637 (Oxindole)

3D Structure for NP0023637 (Oxindole)