NP-MRD: Showing NP-Card for (R)-Glucoisatisin (NP0068900)

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Record Information

Version

2.0

Created at

2022-04-28 14:10:31 UTC

Updated at

2022-04-28 14:10:32 UTC

NP-MRD ID

NP0068900

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(R)-Glucoisatisin

Description

(R)-Glucoisatisin is found in Isatis tinctoria L .

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282216102D          

 37 39  0  0  1  0            999 V2000
    0.6001    5.7397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2132    5.1876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0416    4.3807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2570    4.1257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3561    4.6777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1845    5.4847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0705    4.2652    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8990    3.4583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4510    2.8452    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0785    3.3720    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3340    2.6576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1590    2.6576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5715    3.3720    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5715    1.9431    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3965    1.9431    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8090    1.2286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6340    1.2286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0465    0.5142    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6340   -0.2003    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8090   -0.2003    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.8090    0.6247    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8090   -1.0253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9840   -0.2003    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0465    1.9431    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.8715    1.9431    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    6.5215    3.3720    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  2  0  0  0  0
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  3  4  2  0  0  0  0
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  1  6  1  0  0  0  0
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M  END

     RDKit          3D

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   -4.4282   -2.2123    0.8019 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7025   -3.6638    1.1349 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652304282216102D          

 37 39  0  0  1  0            999 V2000
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    3.6340   -0.2003    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8090   -0.2003    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
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    7.3465    1.9431    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  2  0  0  0  0
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 29 30  1  0  0  0  0
 25 30  1  0  0  0  0
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 28 33  1  6  0  0  0
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M  END
> <DATABASE_ID>
NP0068900

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H](S\C(C[C@H](OC(=O)C[C@H]2C(=O)NC3=CC=CC=C23)C=C)=N\OS(O)(=O)=O)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C21H26N2O12S2/c1-2-10(33-16(25)8-12-11-5-3-4-6-13(11)22-20(12)29)7-15(23-35-37(30,31)32)36-21-19(28)18(27)17(26)14(9-24)34-21/h2-6,10,12,14,17-19,21,24,26-28H,1,7-9H2,(H,22,29)(H,30,31,32)/b23-15+/t10-,12-,14-,17-,18+,19-,21+/m1/s1

> <INCHI_KEY>
NTDBYDWMVLRHLG-LPISQVGCSA-N

> <FORMULA>
C21H26N2O12S2

> <MOLECULAR_WEIGHT>
562.56

> <EXACT_MASS>
562.092716633

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
51.80217336192413

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[(E)-[(3S)-3-({2-[(3R)-2-oxo-2,3-dihydro-1H-indol-3-yl]acetyl}oxy)-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}pent-4-en-1-ylidene]amino]oxy}sulfonic acid

> <ALOGPS_LOGP>
-0.93

> <JCHEM_LOGP>
-2.456292422264339

> <ALOGPS_LOGS>
-2.45

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.691324192714537

> <JCHEM_PKA_STRONGEST_ACIDIC>
-3.6115743764955264

> <JCHEM_PKA_STRONGEST_BASIC>
-0.4795617884142024

> <JCHEM_POLAR_SURFACE_AREA>
221.50999999999993

> <JCHEM_REFRACTIVITY>
127.59319999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.99e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(E)-[(3S)-3-({2-[(3R)-2-oxo-1,3-dihydroindol-3-yl]acetyl}oxy)-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}pent-4-en-1-ylidene]amino]oxysulfonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       1.120  10.714   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.265   9.684   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.944   8.177   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.480   7.701   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.665   8.732   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.344  10.238   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      -1.998   7.962   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      -1.678   6.455   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -2.709   5.311   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -0.147   6.294   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.623   4.961   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.163   4.961   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.933   6.294   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       2.933   3.627   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.473   3.627   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.243   2.293   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.783   2.293   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       7.553   0.960   0.000  0.00  0.00           N+0
HETATM   19  O   UNK     0       6.783  -0.374   0.000  0.00  0.00           O+0
HETATM   20  S   UNK     0       5.243  -0.374   0.000  0.00  0.00           S+0
HETATM   21  O   UNK     0       5.243   1.166   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       5.243  -1.914   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       3.703  -0.374   0.000  0.00  0.00           O+0
HETATM   24  S   UNK     0       7.553   3.627   0.000  0.00  0.00           S+0
HETATM   25  C   UNK     0       9.093   3.627   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.863   4.961   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      11.403   4.961   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      12.173   3.627   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      11.403   2.293   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       9.863   2.293   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      12.173   0.960   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      13.713   0.960   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      13.713   3.627   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      12.173   6.294   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       9.093   6.294   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       5.243   4.961   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       6.783   4.961   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8    4   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   36                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   24                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22   23                                             
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   20                                                            
CONECT   24   17   25                                                       
CONECT   25   24   26   30                                                  
CONECT   26   25   27   35                                                  
CONECT   27   26   28   34                                                  
CONECT   28   27   29   33                                                  
CONECT   29   28   30   31                                                  
CONECT   30   29   25                                                       
CONECT   31   29   32                                                       
CONECT   32   31                                                            
CONECT   33   28                                                            
CONECT   34   27                                                            
CONECT   35   26                                                            
CONECT   36   15   37                                                       
CONECT   37   36                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₆N₂O₁₂S₂

Average Mass

562.5600 Da

Monoisotopic Mass

562.09272 Da

IUPAC Name

{[(E)-[(3S)-3-({2-[(3R)-2-oxo-2,3-dihydro-1H-indol-3-yl]acetyl}oxy)-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}pent-4-en-1-ylidene]amino]oxy}sulfonic acid

Traditional Name

[(E)-[(3S)-3-({2-[(3R)-2-oxo-1,3-dihydroindol-3-yl]acetyl}oxy)-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}pent-4-en-1-ylidene]amino]oxysulfonic acid

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@@H](S\C(C[C@H](OC(=O)C[C@H]2C(=O)NC3=CC=CC=C23)C=C)=N\OS(O)(=O)=O)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C21H26N2O12S2/c1-2-10(33-16(25)8-12-11-5-3-4-6-13(11)22-20(12)29)7-15(23-35-37(30,31)32)36-21-19(28)18(27)17(26)14(9-24)34-21/h2-6,10,12,14,17-19,21,24,26-28H,1,7-9H2,(H,22,29)(H,30,31,32)/b23-15+/t10-,12-,14-,17-,18+,19-,21+/m1/s1

InChI Key

NTDBYDWMVLRHLG-LPISQVGCSA-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
Isatis tinctoria L	Plant	KNApSAcK

Chemical Taxonomy

Classification

Not classified

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	-0.93	ALOGPS
logP	-2.5	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	-3.6	ChemAxon
pKa (Strongest Basic)	-0.48	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	221.51 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	127.59 m³·mol⁻¹	ChemAxon
Polarizability	51.8 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

Not Available

References

General References

Not Available

Showing NP-Card for (R)-Glucoisatisin (NP0068900)

MOL for NP0068900 ((R)-Glucoisatisin)

3D MOL for NP0068900 ((R)-Glucoisatisin)

3D SDF for NP0068900 ((R)-Glucoisatisin)

3D-SDF for NP0068900 ((R)-Glucoisatisin)

PDB for NP0068900 ((R)-Glucoisatisin)

3D PDB for NP0068900 ((R)-Glucoisatisin)

SMILES for NP0068900 ((R)-Glucoisatisin)

INCHI for NP0068900 ((R)-Glucoisatisin)

Structure for NP0068900 ((R)-Glucoisatisin)

3D Structure for NP0068900 ((R)-Glucoisatisin)