NP-MRD: Showing NP-Card for (+)-(S)-2-(3-hydroxy-4-methoxy-2-oxoindolin-3-yl)acetonitrile (NP0036801)

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Record Information

Version

1.0

Created at

2021-06-20 19:52:45 UTC

Updated at

2021-06-30 00:08:39 UTC

NP-MRD ID

NP0036801

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-(S)-2-(3-hydroxy-4-methoxy-2-oxoindolin-3-yl)acetonitrile

Provided By

JEOL Database JEOL Logo

Description

CHEMBL2063288 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. (+)-(S)-2-(3-hydroxy-4-methoxy-2-oxoindolin-3-yl)acetonitrile is found in Isatis indigotica. It was first documented in 2012 (Chen, M., et al.). Based on a literature review very few articles have been published on CHEMBL2063288.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202121523D          

 26 27  0  0  0  0            999 V2000
    0.8379    1.5086   -4.1852 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5944    0.7538   -3.0045 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6777    0.1956   -2.3936 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9871    0.1821   -2.8899 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0279   -0.4530   -2.1817 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7814   -1.0925   -0.9675 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4872   -1.0687   -0.4969 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4452   -0.4339   -1.1807 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1685   -0.5980   -0.3948 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2593    0.6808    0.0887 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9829   -1.2922   -1.1191 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6157   -2.6173   -1.6302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3250   -3.6682   -2.0271 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6550   -1.4435    0.8203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0354   -1.8071    1.7598 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0167   -1.6557    0.6688 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1153    1.9361   -4.5107 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2077    0.8670   -4.9916 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5264    2.3379   -3.9913 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2394    0.6515   -3.8363 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0346   -0.4496   -2.5945 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5790   -1.5899   -0.4278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8211    0.5133    0.8681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8367   -1.3927   -0.4365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3469   -0.6667   -1.9427 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5728   -2.1733    1.3333 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0  0  0  0
  8  3  2  0  0  0  0
  3  2  1  0  0  0  0
  3  4  1  0  0  0  0
  9 10  1  1  0  0  0
  8  7  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
  5  6  1  0  0  0  0
 12 13  3  0  0  0  0
  6  7  2  0  0  0  0
 16 14  1  0  0  0  0
 14  9  1  0  0  0  0
  4  5  2  0  0  0  0
 14 15  2  0  0  0  0
  7 16  1  0  0  0  0
  2  1  1  0  0  0  0
  4 20  1  0  0  0  0
  5 21  1  0  0  0  0
  6 22  1  0  0  0  0
 16 26  1  0  0  0  0
 10 23  1  0  0  0  0
 11 24  1  0  0  0  0
 11 25  1  0  0  0  0
  1 17  1  0  0  0  0
  1 18  1  0  0  0  0
  1 19  1  0  0  0  0
M  END


  Mrv1652306202121523D          

 26 27  0  0  0  0            999 V2000
    0.8379    1.5086   -4.1852 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5944    0.7538   -3.0045 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6777    0.1956   -2.3936 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9871    0.1821   -2.8899 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0279   -0.4530   -2.1817 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7814   -1.0925   -0.9675 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4872   -1.0687   -0.4969 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4452   -0.4339   -1.1807 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1685   -0.5980   -0.3948 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2593    0.6808    0.0887 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9829   -1.2922   -1.1191 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6157   -2.6173   -1.6302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3250   -3.6682   -2.0271 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6550   -1.4435    0.8203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0354   -1.8071    1.7598 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0167   -1.6557    0.6688 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1153    1.9361   -4.5107 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2077    0.8670   -4.9916 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5264    2.3379   -3.9913 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2394    0.6515   -3.8363 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0346   -0.4496   -2.5945 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5790   -1.5899   -0.4278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8211    0.5133    0.8681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8367   -1.3927   -0.4365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3469   -0.6667   -1.9427 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5728   -2.1733    1.3333 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0  0  0  0
  8  3  2  0  0  0  0
  3  2  1  0  0  0  0
  3  4  1  0  0  0  0
  9 10  1  1  0  0  0
  8  7  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
  5  6  1  0  0  0  0
 12 13  3  0  0  0  0
  6  7  2  0  0  0  0
 16 14  1  0  0  0  0
 14  9  1  0  0  0  0
  4  5  2  0  0  0  0
 14 15  2  0  0  0  0
  7 16  1  0  0  0  0
  2  1  1  0  0  0  0
  4 20  1  0  0  0  0
  5 21  1  0  0  0  0
  6 22  1  0  0  0  0
 16 26  1  0  0  0  0
 10 23  1  0  0  0  0
 11 24  1  0  0  0  0
 11 25  1  0  0  0  0
  1 17  1  0  0  0  0
  1 18  1  0  0  0  0
  1 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0036801

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]1(C(=O)N([H])C2=C([H])C([H])=C([H])C(OC([H])([H])[H])=C12)C([H])([H])C#N

> <INCHI_IDENTIFIER>
InChI=1S/C11H10N2O3/c1-16-8-4-2-3-7-9(8)11(15,5-6-12)10(14)13-7/h2-4,15H,5H2,1H3,(H,13,14)/t11-/m0/s1

> <INCHI_KEY>
OYAAGDGYYVYWQP-NSHDSACASA-N

> <FORMULA>
C11H10N2O3

> <MOLECULAR_WEIGHT>
218.212

> <EXACT_MASS>
218.06914219

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
21.132435574198503

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(3S)-3-hydroxy-4-methoxy-2-oxo-2,3-dihydro-1H-indol-3-yl]acetonitrile

> <ALOGPS_LOGP>
0.63

> <JCHEM_LOGP>
0.0481233033333331

> <ALOGPS_LOGS>
-1.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.255293036248077

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.030855845940952

> <JCHEM_PKA_STRONGEST_BASIC>
-4.4980960251647355

> <JCHEM_POLAR_SURFACE_AREA>
82.35

> <JCHEM_REFRACTIVITY>
57.114300000000014

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.74e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(3S)-3-hydroxy-4-methoxy-2-oxo-1H-indol-3-yl]acetonitrile

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0       0.838   1.509  -4.185  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.594   0.754  -3.005  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.678   0.196  -2.394  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.987   0.182  -2.890  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.028  -0.453  -2.182  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.781  -1.093  -0.968  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.487  -1.069  -0.497  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.445  -0.434  -1.181  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.169  -0.598  -0.395  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.259   0.681   0.089  0.00  0.00           O+0
HETATM   11  C   UNK     0      -0.983  -1.292  -1.119  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.616  -2.617  -1.630  0.00  0.00           C+0
HETATM   13  N   UNK     0      -0.325  -3.668  -2.027  0.00  0.00           N+0
HETATM   14  C   UNK     0       0.655  -1.444   0.820  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.035  -1.807   1.760  0.00  0.00           O+0
HETATM   16  N   UNK     0       2.017  -1.656   0.669  0.00  0.00           N+0
HETATM   17  H   UNK     0      -0.115   1.936  -4.511  0.00  0.00           H+0
HETATM   18  H   UNK     0       1.208   0.867  -4.992  0.00  0.00           H+0
HETATM   19  H   UNK     0       1.526   2.338  -3.991  0.00  0.00           H+0
HETATM   20  H   UNK     0       3.239   0.652  -3.836  0.00  0.00           H+0
HETATM   21  H   UNK     0       5.035  -0.450  -2.595  0.00  0.00           H+0
HETATM   22  H   UNK     0       4.579  -1.590  -0.428  0.00  0.00           H+0
HETATM   23  H   UNK     0      -0.821   0.513   0.868  0.00  0.00           H+0
HETATM   24  H   UNK     0      -1.837  -1.393  -0.437  0.00  0.00           H+0
HETATM   25  H   UNK     0      -1.347  -0.667  -1.943  0.00  0.00           H+0
HETATM   26  H   UNK     0       2.573  -2.173   1.333  0.00  0.00           H+0
CONECT    1    2   17   18   19                                             
CONECT    2    3    1                                                       
CONECT    3    8    2    4                                                  
CONECT    4    3    5   20                                                  
CONECT    5    6    4   21                                                  
CONECT    6    5    7   22                                                  
CONECT    7    8    6   16                                                  
CONECT    8    9    3    7                                                  
CONECT    9    8   10   11   14                                             
CONECT   10    9   23                                                       
CONECT   11    9   12   24   25                                             
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   16    9   15                                                  
CONECT   15   14                                                            
CONECT   16   14    7   26                                                  
CONECT   17    1                                                            
CONECT   18    1                                                            
CONECT   19    1                                                            
CONECT   20    4                                                            
CONECT   21    5                                                            
CONECT   22    6                                                            
CONECT   23   10                                                            
CONECT   24   11                                                            
CONECT   25   11                                                            
CONECT   26   16                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   54    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₁H₁₀N₂O₃

Average Mass

218.2120 Da

Monoisotopic Mass

218.06914 Da

IUPAC Name

2-[(3S)-3-hydroxy-4-methoxy-2-oxo-2,3-dihydro-1H-indol-3-yl]acetonitrile

Traditional Name

2-[(3S)-3-hydroxy-4-methoxy-2-oxo-1H-indol-3-yl]acetonitrile

CAS Registry Number

Not Available

SMILES

[H]O[C@@]1(C(=O)N([H])C2=C([H])C([H])=C([H])C(OC([H])([H])[H])=C12)C([H])([H])C#N

InChI Identifier

InChI=1S/C11H10N2O3/c1-16-8-4-2-3-7-9(8)11(15,5-6-12)10(14)13-7/h2-4,15H,5H2,1H3,(H,13,14)/t11-/m0/s1

InChI Key

OYAAGDGYYVYWQP-NSHDSACASA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Isatis tinctoria	JEOL database	Chen, M., et al, J. Nat. Prod. 75, 1167 (2012)

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
Anisole
Phenol ether
Alkyl aryl ether
Benzenoid
Tertiary alcohol
Carboxamide group
Lactam
Secondary carboxylic acid amide
Carboxylic acid derivative
Ether
Carbonitrile
Nitrile
Azacycle
Hydrocarbon derivative
Organic oxide
Organic nitrogen compound
Alcohol
Cyanide
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Carbonyl group
Aromatic heteropolycyclic compound

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	0.63	ALOGPS
logP	0.048	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	11.03	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	82.35 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	57.11 m³·mol⁻¹	ChemAxon
Polarizability	21.13 Å³	ChemAxon
Number of Rings	2	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

28519215

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

60156060

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Chen, M., et al. (2012). Chen, M., et al, J. Nat. Prod. 75, 1167 (2012). J. Nat. Prod..

Showing NP-Card for (+)-(S)-2-(3-hydroxy-4-methoxy-2-oxoindolin-3-yl)acetonitrile (NP0036801)

MOL for NP0036801 ((+)-(S)-2-(3-hydroxy-4-methoxy-2-oxoindolin-3-yl)acetonitrile)

3D MOL for NP0036801 ((+)-(S)-2-(3-hydroxy-4-methoxy-2-oxoindolin-3-yl)acetonitrile)

3D SDF for NP0036801 ((+)-(S)-2-(3-hydroxy-4-methoxy-2-oxoindolin-3-yl)acetonitrile)

3D-SDF for NP0036801 ((+)-(S)-2-(3-hydroxy-4-methoxy-2-oxoindolin-3-yl)acetonitrile)

PDB for NP0036801 ((+)-(S)-2-(3-hydroxy-4-methoxy-2-oxoindolin-3-yl)acetonitrile)

3D PDB for NP0036801 ((+)-(S)-2-(3-hydroxy-4-methoxy-2-oxoindolin-3-yl)acetonitrile)

SMILES for NP0036801 ((+)-(S)-2-(3-hydroxy-4-methoxy-2-oxoindolin-3-yl)acetonitrile)

INCHI for NP0036801 ((+)-(S)-2-(3-hydroxy-4-methoxy-2-oxoindolin-3-yl)acetonitrile)

Structure for NP0036801 ((+)-(S)-2-(3-hydroxy-4-methoxy-2-oxoindolin-3-yl)acetonitrile)

3D Structure for NP0036801 ((+)-(S)-2-(3-hydroxy-4-methoxy-2-oxoindolin-3-yl)acetonitrile)