NP-MRD: Showing NP-Card for 3-(1,3-thiazol-2-yl)indole-2,3-diol (NP0312948)

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Record Information

Version

1.0

Created at

2022-09-11 10:09:54 UTC

Updated at

2022-09-11 10:09:54 UTC

NP-MRD ID

NP0312948

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-(1,3-thiazol-2-yl)indole-2,3-diol

Description

3-Hydroxy-3-(thiazol-2-yl)indolin-2-one 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. 3-Hydroxy-3-(thiazol-2-yl)indolin-2-one 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. 3-(1,3-thiazol-2-yl)indole-2,3-diol is found in Arabidopsis thaliana. It was first documented in 2009 (PMID: 19567706). Based on a literature review very few articles have been published on 3-hydroxy-3-(thiazol-2-yl)indolin-2-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112212092D          

 16 18  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
    1.3018   -2.1741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5314   -1.9238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6263   -2.7433    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1239   -3.0868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6823   -2.4795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2773   -1.7607    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  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  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 12 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0312948

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=NC2=CC=CC=C2C1(O)C1=NC=CS1

> <INCHI_IDENTIFIER>
InChI=1S/C11H8N2O2S/c14-9-11(15,10-12-5-6-16-10)7-3-1-2-4-8(7)13-9/h1-6,15H,(H,13,14)

> <INCHI_KEY>
BURKMBCVRAOKIE-UHFFFAOYSA-N

> <FORMULA>
C11H8N2O2S

> <MOLECULAR_WEIGHT>
232.26

> <EXACT_MASS>
232.03064868

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
22.43245432231012

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(1,3-thiazol-2-yl)-3H-indole-2,3-diol

> <JCHEM_LOGP>
0.9889850514232418

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.509734719715016

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.9511602096184721

> <JCHEM_PKA_STRONGEST_BASIC>
1.8563343761022382

> <JCHEM_POLAR_SURFACE_AREA>
65.71000000000001

> <JCHEM_REFRACTIVITY>
61.14209999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
3-(1,3-thiazol-2-yl)indole-2,3-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         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       2.430  -4.058   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.992  -3.591   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       1.169  -5.121   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0      -0.231  -5.762   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.274  -4.628   0.000  0.00  0.00           C+0
HETATM   16  S   UNK     0      -0.518  -3.287   0.000  0.00  0.00           S+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   12                                             
CONECT   11   10                                                            
CONECT   12   10   13   16                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   12                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   36    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₁H₈N₂O₂S

Average Mass

232.2600 Da

Monoisotopic Mass

232.03065 Da

IUPAC Name

3-(1,3-thiazol-2-yl)-3H-indole-2,3-diol

Traditional Name

3-(1,3-thiazol-2-yl)indole-2,3-diol

CAS Registry Number

Not Available

SMILES

OC1=NC2=CC=CC=C2C1(O)C1=NC=CS1

InChI Identifier

InChI=1S/C11H8N2O2S/c14-9-11(15,10-12-5-6-16-10)7-3-1-2-4-8(7)13-9/h1-6,15H,(H,13,14)

InChI Key

BURKMBCVRAOKIE-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Arabidopsis thaliana	LOTUS Database	35616633

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

Substituents

Dihydroindole
Benzenoid
Azole
Tertiary alcohol
Thiazole
Heteroaromatic compound
Carboxamide group
Lactam
Secondary carboxylic acid amide
Carboxylic acid derivative
Azacycle
Organopnictogen compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Alcohol
Carbonyl group
Organic oxide
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

tertiary alcohol (CHEBI:65024 )
1,3-thiazole (CHEBI:65024 )
oxindole (CHEBI:65024 )

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	0.99	ChemAxon
pKa (Strongest Acidic)	0.95	ChemAxon
pKa (Strongest Basic)	1.86	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	65.71 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	61.14 m³·mol⁻¹	ChemAxon
Polarizability	22.43 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4458170

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5297666

PDB ID

Not Available

ChEBI ID

65024

Good Scents ID

Not Available

References

General References

Bottcher C, Westphal L, Schmotz C, Prade E, Scheel D, Glawischnig E: The multifunctional enzyme CYP71B15 (PHYTOALEXIN DEFICIENT3) converts cysteine-indole-3-acetonitrile to camalexin in the indole-3-acetonitrile metabolic network of Arabidopsis thaliana. Plant Cell. 2009 Jun;21(6):1830-45. doi: 10.1105/tpc.109.066670. Epub 2009 Jun 30. [PubMed:19567706 ]
LOTUS database [Link]

Showing NP-Card for 3-(1,3-thiazol-2-yl)indole-2,3-diol (NP0312948)

MOL for NP0312948 (3-(1,3-thiazol-2-yl)indole-2,3-diol)

3D MOL for NP0312948 (3-(1,3-thiazol-2-yl)indole-2,3-diol)

3D SDF for NP0312948 (3-(1,3-thiazol-2-yl)indole-2,3-diol)

3D-SDF for NP0312948 (3-(1,3-thiazol-2-yl)indole-2,3-diol)

PDB for NP0312948 (3-(1,3-thiazol-2-yl)indole-2,3-diol)

3D PDB for NP0312948 (3-(1,3-thiazol-2-yl)indole-2,3-diol)

SMILES for NP0312948 (3-(1,3-thiazol-2-yl)indole-2,3-diol)

INCHI for NP0312948 (3-(1,3-thiazol-2-yl)indole-2,3-diol)

Structure for NP0312948 (3-(1,3-thiazol-2-yl)indole-2,3-diol)

3D Structure for NP0312948 (3-(1,3-thiazol-2-yl)indole-2,3-diol)