NP-MRD: Showing NP-Card for (2s)-2-{[(2r)-2-amino-2-carboxyethyl]sulfanyl}butanedioic acid (NP0160190)

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Record Information

Version

2.0

Created at

2022-09-02 18:05:06 UTC

Updated at

2022-09-02 18:05:06 UTC

NP-MRD ID

NP0160190

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-2-{[(2r)-2-amino-2-carboxyethyl]sulfanyl}butanedioic acid

Description

SCHEMBL20362609 belongs to the class of organic compounds known as l-cysteine-s-conjugates. L-cysteine-S-conjugates are compounds containing L-cysteine where the thio-group is conjugated. (2s)-2-{[(2r)-2-amino-2-carboxyethyl]sulfanyl}butanedioic acid is found in Amanita pantherina. SCHEMBL20362609 is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05041401552D          

 17 16  0  0  1  0            999 V2000
    1.9224    1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2211    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355    1.0164    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2079    1.4289    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6368    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2079    2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355    0.1914    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3513    1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6368    2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3645    1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4934    2.6664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9224    2.6664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4934    1.0164    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355    1.8414    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9224    1.8414    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  4  1  1  0  0  0  0
  5  1  1  0  0  0  0
  6  3  1  0  0  0  0
  7  4  1  0  0  0  0
  3  8  1  1  0  0  0
  9  5  2  0  0  0  0
 10  5  1  0  0  0  0
 11  6  2  0  0  0  0
 12  6  1  0  0  0  0
 13  7  2  0  0  0  0
 14  7  1  0  0  0  0
 15  2  1  0  0  0  0
  4 15  1  1  0  0  0
  3 16  1  1  0  0  0
  4 17  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0160190

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@](N)(CS[C@@]([H])(CC(O)=O)C(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C7H11NO6S/c8-3(6(11)12)2-15-4(7(13)14)1-5(9)10/h3-4H,1-2,8H2,(H,9,10)(H,11,12)(H,13,14)/t3-,4-/m0/s1

> <INCHI_KEY>
XPKKFTKCRVIDAG-IMJSIDKUSA-N

> <FORMULA>
C7H11NO6S

> <MOLECULAR_WEIGHT>
237.23

> <EXACT_MASS>
237.030707779

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
21.383654961824313

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-{[(2R)-2-amino-2-carboxyethyl]sulfanyl}butanedioic acid

> <ALOGPS_LOGP>
-3.06

> <JCHEM_LOGP>
-3.396525091529572

> <ALOGPS_LOGS>
-1.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.7469468649438293

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.649191277949932

> <JCHEM_PKA_STRONGEST_BASIC>
9.14023551771947

> <JCHEM_POLAR_SURFACE_AREA>
137.92000000000002

> <JCHEM_REFRACTIVITY>
49.636100000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.04e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-{[(2R)-2-amino-2-carboxyethyl]sulfanyl}butanedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-MAY-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-MAY-14         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM    9  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   15  S   UNK     0       0.000   0.000   0.000  0.00  0.00           S+0
HETATM   16  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   17  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1    4    5                                                       
CONECT    2    3   15                                                       
CONECT    3    2    6    8   16                                             
CONECT    4    1    7   15   17                                             
CONECT    5    1    9   10                                                  
CONECT    6    3   11   12                                                  
CONECT    7    4   13   14                                                  
CONECT    8    3                                                            
CONECT    9    5                                                            
CONECT   10    5                                                            
CONECT   11    6                                                            
CONECT   12    6                                                            
CONECT   13    7                                                            
CONECT   14    7                                                            
CONECT   15    2    4                                                       
CONECT   16    3                                                            
CONECT   17    4                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   32    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₇H₁₁NO₆S

Average Mass

237.2300 Da

Monoisotopic Mass

237.03071 Da

IUPAC Name

(2S)-2-{[(2R)-2-amino-2-carboxyethyl]sulfanyl}butanedioic acid

Traditional Name

(2S)-2-{[(2R)-2-amino-2-carboxyethyl]sulfanyl}butanedioic acid

CAS Registry Number

Not Available

SMILES

[H][C@](N)(CS[C@@]([H])(CC(O)=O)C(O)=O)C(O)=O

InChI Identifier

InChI=1S/C7H11NO6S/c8-3(6(11)12)2-15-4(7(13)14)1-5(9)10/h3-4H,1-2,8H2,(H,9,10)(H,11,12)(H,13,14)/t3-,4-/m0/s1

InChI Key

XPKKFTKCRVIDAG-IMJSIDKUSA-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
Amanita pantherina	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as l-cysteine-s-conjugates. L-cysteine-S-conjugates are compounds containing L-cysteine where the thio-group is conjugated.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

L-cysteine-S-conjugates

Alternative Parents

Substituents

L-cysteine-s-conjugate
Alpha-amino acid
L-alpha-amino acid
Tricarboxylic acid or derivatives
Thia fatty acid
Fatty acyl
Amino acid
Carboxylic acid
Thioether
Sulfenyl compound
Dialkylthioether
Organic nitrogen compound
Organic oxygen compound
Primary amine
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Organic oxide
Amine
Carbonyl group
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic 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	-3.1	ALOGPS
logP	-3.4	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	1.65	ChemAxon
pKa (Strongest Basic)	9.14	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	137.92 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	49.64 m³·mol⁻¹	ChemAxon
Polarizability	21.38 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10263540

PDB ID

CML

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s)-2-{[(2r)-2-amino-2-carboxyethyl]sulfanyl}butanedioic acid (NP0160190)

MOL for NP0160190 ((2s)-2-{[(2r)-2-amino-2-carboxyethyl]sulfanyl}butanedioic acid)

3D MOL for NP0160190 ((2s)-2-{[(2r)-2-amino-2-carboxyethyl]sulfanyl}butanedioic acid)

3D SDF for NP0160190 ((2s)-2-{[(2r)-2-amino-2-carboxyethyl]sulfanyl}butanedioic acid)

3D-SDF for NP0160190 ((2s)-2-{[(2r)-2-amino-2-carboxyethyl]sulfanyl}butanedioic acid)

PDB for NP0160190 ((2s)-2-{[(2r)-2-amino-2-carboxyethyl]sulfanyl}butanedioic acid)

3D PDB for NP0160190 ((2s)-2-{[(2r)-2-amino-2-carboxyethyl]sulfanyl}butanedioic acid)

SMILES for NP0160190 ((2s)-2-{[(2r)-2-amino-2-carboxyethyl]sulfanyl}butanedioic acid)

INCHI for NP0160190 ((2s)-2-{[(2r)-2-amino-2-carboxyethyl]sulfanyl}butanedioic acid)

Structure for NP0160190 ((2s)-2-{[(2r)-2-amino-2-carboxyethyl]sulfanyl}butanedioic acid)

3D Structure for NP0160190 ((2s)-2-{[(2r)-2-amino-2-carboxyethyl]sulfanyl}butanedioic acid)