NP-MRD: Showing NP-Card for glutathioselenol (NP0272965)

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Record Information

Version

2.0

Created at

2022-09-08 19:49:21 UTC

Updated at

2022-09-08 19:49:22 UTC

NP-MRD ID

NP0272965

Secondary Accession Numbers

None

Natural Product Identification

Common Name

glutathioselenol

Description

glutathioselenol is found in Apis cerana.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 38 37  0  0  0  0  0  0  0  0999 V2000
    5.0716   -0.3475    2.6332 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1608   -1.2188    1.8833 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0083   -0.3522    1.4406 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9654   -1.0742    0.6555 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9082   -0.0902    0.2956 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9792    1.1329    0.6393 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2445   -0.4596   -0.4542 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2830    0.4593   -0.8203 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4075    0.5861   -2.3331 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1602    1.1852   -3.0060 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.6098    3.2713   -2.3510 Se  0  0  0  0  0  2  0  0  0  0  0  0
   -2.5587   -0.0002   -0.2211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5566   -1.0478    0.4696 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7799    0.7069   -0.4041 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9800    0.1918    0.2135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1452    1.0608   -0.0897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9783    2.0737   -0.7933 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3839    0.7248    0.4153 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9437   -1.7229    0.7183 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4337   -2.5049   -0.1242 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2733   -1.3661    0.4886 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9884    0.6137    2.2347 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7367   -0.2814    3.6309 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8553   -2.0622    2.5134 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4297    0.4425    0.7777 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5114    0.1258    2.3077 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5200   -1.9234    1.2515 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3321   -1.5023   -0.2980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3275   -1.4534   -0.7468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0545    1.4864   -0.4422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6670   -0.3923   -2.7795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1996    1.3089   -2.5935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0819    3.6364   -1.0300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7526    1.5691   -0.9792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2059   -0.8507   -0.1135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7684    0.1596    1.3220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5134   -0.0188    1.0673 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0006   -2.0663    0.4885 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  8 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 18  1  0
 16 17  2  0
  2 19  1  0
 19 21  1  0
 19 20  2  0
  1 22  1  0
  1 23  1  0
  2 24  1  1
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  7 29  1  0
  8 30  1  1
  9 31  1  0
  9 32  1  0
 11 33  1  0
 14 34  1  0
 15 35  1  0
 15 36  1  0
 18 37  1  0
 21 38  1  0
M  END


  Mrv1652303042016532D          

 21 20  0  0  0  0            999 V2000
 9999.299210000.0195    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.5847 9999.6070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.870310000.0195    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1558 9999.6070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.441310000.0195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.7269 9999.6070    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.441310000.8450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5847 9998.7821    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.0136 9999.6070    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10000.728710000.0195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.4448 9999.6070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.158810000.0195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.8729 9999.6070    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10003.586910000.0195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.3030 9999.6070    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.586910000.8450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.8729 9998.7821    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10000.728710000.8450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.299210000.8450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.584710001.2578    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
 9997.868210000.8430    0.0000 Se  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  9  1  0  0  0  0
  1 19  1  6  0  0  0
  2  3  1  0  0  0  0
  2  8  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 18  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 17  1  1  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0272965

> <DATABASE_NAME>
NP-MRD

> <SMILES>
N[C@@H](CCC(=O)N[C@@H](CS[SeH])C(=O)NCC(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H17N3O6SSe/c11-5(10(18)19)1-2-7(14)13-6(4-20-21)9(17)12-3-8(15)16/h5-6,21H,1-4,11H2,(H,12,17)(H,13,14)(H,15,16)(H,18,19)/t5-,6-/m0/s1

> <INCHI_KEY>
UUYVRXVWXDDDGX-WDSKDSINSA-N

> <FORMULA>
C10H17N3O6SSe

> <MOLECULAR_WEIGHT>
386.29

> <EXACT_MASS>
387.000328

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
31.656279684531814

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)carbamoyl]-2-(selanylsulfanyl)ethyl]carbamoyl}butanoic acid

> <ALOGPS_LOGP>
-3.18

> <JCHEM_LOGP>
-5.720542937699446

> <ALOGPS_LOGS>
-1.68

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.1340412404021727

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.301196187067966

> <JCHEM_PKA_STRONGEST_BASIC>
9.074082580127

> <JCHEM_POLAR_SURFACE_AREA>
158.82000000000002

> <JCHEM_REFRACTIVITY>
82.24210000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.05e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-amino-4-{[(1R)-1-(carboxymethylcarbamoyl)-2-(selanylsulfanyl)ethyl]carbamoyl}butanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-MAR-20         0                                  
HETATM    1  C   UNK     0    8665.3598666.703   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8664.0258665.933   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0    8662.6918666.703   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0    8661.3578665.933   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8660.0248666.703   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0    8658.6908665.933   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0    8660.0248668.244   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0    8664.0258664.393   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0    8666.6928665.933   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0    8668.0278666.703   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8669.3648665.933   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8670.6968666.703   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8672.0298665.933   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8673.3628666.703   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0    8674.6998665.933   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0    8673.3628668.244   0.000  0.00  0.00           O+0
HETATM   17  N   UNK     0    8672.0298664.393   0.000  0.00  0.00           N+0
HETATM   18  O   UNK     0    8668.0278668.244   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0    8665.3598668.244   0.000  0.00  0.00           C+0
HETATM   20  S   UNK     0    8664.0258669.015   0.000  0.00  0.00           S+0
HETATM   21 Se   UNK     0    8662.6878668.240   0.000  0.00  0.00          Se+0
CONECT    1    2    9   19                                                  
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    2                                                            
CONECT    9    1   10                                                       
CONECT   10    9   11   18                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   17                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   13                                                            
CONECT   18   10                                                            
CONECT   19    1   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   40    0
END

View in JSmol

Synonyms

Value	Source
GSSeH	ChEBI
Glutathione selenopersulfide	HMDB
L-gamma-Glutamyl-3-(selenosulfeno)-L-alanylglycine	HMDB
L-γ-Glutamyl-3-(selenosulfeno)-L-alanylglycine	HMDB
Se-Glutathione	HMDB

Chemical Formula

C₁₀H₁₇N₃O₆SSe

Average Mass

386.2900 Da

Monoisotopic Mass

387.00033 Da

IUPAC Name

(2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)carbamoyl]-2-(selanylsulfanyl)ethyl]carbamoyl}butanoic acid

Traditional Name

(2S)-2-amino-4-{[(1R)-1-(carboxymethylcarbamoyl)-2-(selanylsulfanyl)ethyl]carbamoyl}butanoic acid

CAS Registry Number

Not Available

SMILES

N[C@@H](CCC(=O)N[C@@H](CS[SeH])C(=O)NCC(O)=O)C(O)=O

InChI Identifier

InChI=1S/C10H17N3O6SSe/c11-5(10(18)19)1-2-7(14)13-6(4-20-21)9(17)12-3-8(15)16/h5-6,21H,1-4,11H2,(H,12,17)(H,13,14)(H,15,16)(H,18,19)/t5-,6-/m0/s1

InChI Key

UUYVRXVWXDDDGX-WDSKDSINSA-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
Apis cerana	LOTUS Database	35616633

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Oligopeptides

Alternative Parents

Substituents

Alpha-oligopeptide
Gamma-glutamyl alpha peptide
Glutamine or derivatives
N-acyl-alpha amino acid or derivatives
N-acyl-alpha-amino acid
Alpha-amino acid amide
Cysteine or derivatives
Alpha-amino acid
N-substituted-alpha-amino acid
Alpha-amino acid or derivatives
L-alpha-amino acid
N-acyl-amine
Fatty acyl
Fatty acid
Dicarboxylic acid or derivatives
Fatty amide
Secondary carboxylic acid amide
Carboxamide group
Amino acid
Amino acid or derivatives
Thioselenide
Carboxylic acid
Sulfenyl compound
Organosulfur compound
Primary amine
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Carbonyl group
Amine
Organic oxide
Organopnictogen compound
Primary aliphatic amine
Organooxygen compound
Organonitrogen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

glutathione derivative (CHEBI:64729 )
thioselenide (CHEBI:64729 )

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	-3.2	ALOGPS
logP	-5.7	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	1.3	ChemAxon
pKa (Strongest Basic)	9.07	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	158.82 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	82.24 m³·mol⁻¹	ChemAxon
Polarizability	31.66 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

28532780

KEGG Compound ID

C18871

BioCyc ID

CPD-13909

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

64729

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for glutathioselenol (NP0272965)

MOL for NP0272965 (glutathioselenol)

3D MOL for NP0272965 (glutathioselenol)

3D SDF for NP0272965 (glutathioselenol)

3D-SDF for NP0272965 (glutathioselenol)

PDB for NP0272965 (glutathioselenol)

3D PDB for NP0272965 (glutathioselenol)

SMILES for NP0272965 (glutathioselenol)

INCHI for NP0272965 (glutathioselenol)

Structure for NP0272965 (glutathioselenol)

3D Structure for NP0272965 (glutathioselenol)