NP-MRD: Showing NP-Card for 2-amino-3-[(2-carboxy-2-methylethyl)sulfanyl]propanoic acid (NP0224334)

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Record Information

Version

2.0

Created at

2022-09-06 02:39:58 UTC

Updated at

2022-09-06 02:39:58 UTC

NP-MRD ID

NP0224334

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-amino-3-[(2-carboxy-2-methylethyl)sulfanyl]propanoic acid

Description

(2R,2'S)-Isobuteine belongs to the class of organic compounds known as cysteine and derivatives. Cysteine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom (2R,2'S)-Isobuteine is a very strong basic compound (based on its pKa). Outside of the human body, (2R,2'S)-Isobuteine has been detected, but not quantified in, onion-family vegetables. 2-amino-3-[(2-carboxy-2-methylethyl)sulfanyl]propanoic acid is found in Asparagus officinalis. This could make (2R,2's)-isobuteine a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061305132D          

 13 12  0  0  0  0            999 V2000
   -0.9355   -0.1914    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
    1.2079   -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  0  0  0  0  0  0  0  0  0  0
    1.9224   -1.0164    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
    2.6368   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9224   -0.1914    0.0000 N   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
    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
    0.4934   -1.0164    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  8  5  1  0  0  0  0
  9  6  2  0  0  0  0
 10  6  1  0  0  0  0
 11  7  2  0  0  0  0
 12  7  1  0  0  0  0
 13  2  1  0  0  0  0
 13  3  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0224334

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(CSCC(N)C(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C7H13NO4S/c1-4(6(9)10)2-13-3-5(8)7(11)12/h4-5H,2-3,8H2,1H3,(H,9,10)(H,11,12)

> <INCHI_KEY>
QSPWUNSFUXUUDG-UHFFFAOYSA-N

> <FORMULA>
C7H13NO4S

> <MOLECULAR_WEIGHT>
207.247

> <EXACT_MASS>
207.056528599

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
20.59806022747814

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-3-[(2-carboxy-2-methylethyl)sulfanyl]propanoic acid

> <ALOGPS_LOGP>
-2.49

> <JCHEM_LOGP>
-2.307267739540217

> <ALOGPS_LOGS>
-1.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
4.3781447094705745

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.078315521558558

> <JCHEM_PKA_STRONGEST_BASIC>
9.14232944076914

> <JCHEM_POLAR_SURFACE_AREA>
100.62000000000002

> <JCHEM_REFRACTIVITY>
48.2823

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.25e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-amino-3-[(2-carboxy-2-methylethyl)sulfanyl]propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -1.746  -0.357   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.413  -2.667   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.255  -2.667   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.746  -1.897   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.588  -1.897   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.080  -2.667   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.922  -2.667   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       3.588  -0.357   0.000  0.00  0.00           N+0
HETATM    9  O   UNK     0      -4.414  -1.897   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -3.080  -4.207   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       6.256  -1.897   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       4.922  -4.207   0.000  0.00  0.00           O+0
HETATM   13  S   UNK     0       0.921  -1.897   0.000  0.00  0.00           S+0
CONECT    1    4                                                            
CONECT    2    4   13                                                       
CONECT    3    5   13                                                       
CONECT    4    1    2    6                                                  
CONECT    5    3    7    8                                                  
CONECT    6    4    9   10                                                  
CONECT    7    5   11   12                                                  
CONECT    8    5                                                            
CONECT    9    6                                                            
CONECT   10    6                                                            
CONECT   11    7                                                            
CONECT   12    7                                                            
CONECT   13    2    3                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END

View in JSmol

Synonyms

Value	Source
S-(2-Carboxypropyl)cysteine	HMDB
S-(2-Carboxypropyl)cysteine, (D)-isomer	HMDB
2-Amino-3-[(2-carboxy-2-methylethyl)sulfanyl]propanoate	Generator
2-Amino-3-[(2-carboxy-2-methylethyl)sulphanyl]propanoate	Generator
2-Amino-3-[(2-carboxy-2-methylethyl)sulphanyl]propanoic acid	Generator

Chemical Formula

C₇H₁₃NO₄S

Average Mass

207.2470 Da

Monoisotopic Mass

207.05653 Da

IUPAC Name

2-amino-3-[(2-carboxy-2-methylethyl)sulfanyl]propanoic acid

Traditional Name

2-amino-3-[(2-carboxy-2-methylethyl)sulfanyl]propanoic acid

CAS Registry Number

Not Available

SMILES

CC(CSCC(N)C(O)=O)C(O)=O

InChI Identifier

InChI=1S/C7H13NO4S/c1-4(6(9)10)2-13-3-5(8)7(11)12/h4-5H,2-3,8H2,1H3,(H,9,10)(H,11,12)

InChI Key

QSPWUNSFUXUUDG-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
Asparagus officinalis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cysteine and derivatives. Cysteine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Cysteine and derivatives

Alternative Parents

Substituents

Cysteine or derivatives
Alpha-amino acid
Dicarboxylic acid or derivatives
Amino acid
Carboxylic acid
Thioether
Sulfenyl compound
Dialkylthioether
Amine
Organic nitrogen compound
Primary amine
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Organic oxygen compound
Organic oxide
Carbonyl group
Hydrocarbon derivative
Organopnictogen compound
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	-2.5	ALOGPS
logP	-2.3	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	2.08	ChemAxon
pKa (Strongest Basic)	9.14	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	100.62 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	48.28 m³·mol⁻¹	ChemAxon
Polarizability	20.6 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

HMDB0030411

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB002273

KNApSAcK ID

Not Available

Chemspider ID

13664198

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14889929

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-amino-3-[(2-carboxy-2-methylethyl)sulfanyl]propanoic acid (NP0224334)

MOL for NP0224334 (2-amino-3-[(2-carboxy-2-methylethyl)sulfanyl]propanoic acid)

3D MOL for NP0224334 (2-amino-3-[(2-carboxy-2-methylethyl)sulfanyl]propanoic acid)

3D SDF for NP0224334 (2-amino-3-[(2-carboxy-2-methylethyl)sulfanyl]propanoic acid)

3D-SDF for NP0224334 (2-amino-3-[(2-carboxy-2-methylethyl)sulfanyl]propanoic acid)

PDB for NP0224334 (2-amino-3-[(2-carboxy-2-methylethyl)sulfanyl]propanoic acid)

3D PDB for NP0224334 (2-amino-3-[(2-carboxy-2-methylethyl)sulfanyl]propanoic acid)

SMILES for NP0224334 (2-amino-3-[(2-carboxy-2-methylethyl)sulfanyl]propanoic acid)

INCHI for NP0224334 (2-amino-3-[(2-carboxy-2-methylethyl)sulfanyl]propanoic acid)

Structure for NP0224334 (2-amino-3-[(2-carboxy-2-methylethyl)sulfanyl]propanoic acid)

3D Structure for NP0224334 (2-amino-3-[(2-carboxy-2-methylethyl)sulfanyl]propanoic acid)