NP-MRD: Showing NP-Card for Cystathionine sulfoxide (NP0086968)

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Record Information

Version

2.0

Created at

2022-05-11 16:36:00 UTC

Updated at

2022-05-11 16:36:00 UTC

NP-MRD ID

NP0086968

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cystathionine sulfoxide

Description

Cystathionine sulfoxide belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. Cystathionine sulfoxide was first documented in 1996 (PMID: 8843190). Cystathionine sulfoxide is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 29 28  0  0  0  0  0  0  0  0999 V2000
   -4.2319    1.1741    0.9777 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2118    0.6520    0.0412 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8818    0.6615    0.7300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7831    0.1640   -0.1340 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8136    0.2220    0.7364 S   0  0  0  0  0  4  0  0  0  0  0  0
    1.1876    1.6495    1.0731 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0579   -0.4058   -0.4173 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3960   -0.3625    0.2975 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7325    0.9909    0.6945 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4779   -0.9744   -0.5070 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5459   -0.3296   -0.7777 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2946   -2.2730   -0.9586 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5723   -0.7301   -0.3301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9728   -1.3543   -1.2120 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6172   -1.3648    0.3236 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9531    1.6441    0.3864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7528    1.9297    1.5183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1703    1.3366   -0.8178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9067    0.0422    1.6776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6105    1.6840    1.0990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9127   -0.8562   -0.4926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6641    0.8590   -1.0070 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8200   -1.4601   -0.6269 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0600    0.1487   -1.3633 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2724   -1.0225    1.2042 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3027    1.6331    0.0084 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4007    1.1805    1.6753 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4081   -2.5109   -1.3586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5287   -2.3276    0.6805 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
  5  4  1  6
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 12  1  0
 10 11  2  0
  2 13  1  0
 13 15  1  0
 13 14  2  0
  1 16  1  0
  1 17  1  0
  2 18  1  6
  3 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  7 23  1  0
  7 24  1  0
  8 25  1  1
  9 26  1  0
  9 27  1  0
 12 28  1  0
 15 29  1  0
M  END


  Mrv0541 02231219312D          

 15 14  0  0  1  0            999 V2000
   28.2117  -14.0127    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   31.0696  -14.0127    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.6393  -13.6002    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.2117  -14.8377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.3551  -12.7752    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.3538  -14.8377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.6406  -14.8377    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.0682  -12.7752    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.6406  -14.0127    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   26.0682  -13.6002    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   28.9262  -13.6002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4971  -13.6002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7828  -14.0127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3551  -13.6002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3538  -14.0127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  2  0  0  0  0
  1 11  1  0  0  0  0
  1 12  1  0  0  0  0
  2 14  1  0  0  0  0
  3 15  1  0  0  0  0
  5 14  2  0  0  0  0
  6 15  2  0  0  0  0
  9  7  1  1  0  0  0
 10  8  1  1  0  0  0
  9 11  1  0  0  0  0
  9 14  1  0  0  0  0
 10 13  1  0  0  0  0
 10 15  1  0  0  0  0
 12 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0086968

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C7H14N2O5S/c8-4(6(10)11)1-2-15(14)3-5(9)7(12)13/h4-5H,1-3,8-9H2,(H,10,11)(H,12,13)/t4-,5-,15?/m0/s1

> <INCHI_KEY>
JNUGGJHCMRWUDV-FMMPLYQGSA-N

> <FORMULA>
C7H14N2O5S

> <MOLECULAR_WEIGHT>
238.261

> <EXACT_MASS>
238.062342258

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
22.812631619771928

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-4-[(2R)-2-amino-2-carboxyethanesulfinyl]butanoic acid

> <ALOGPS_LOGP>
-4.16

> <JCHEM_LOGP>
-7.781679131338605

> <ALOGPS_LOGS>
-0.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
2.0380252164398796

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.3336077563224649

> <JCHEM_PKA_STRONGEST_BASIC>
9.198622559762587

> <JCHEM_POLAR_SURFACE_AREA>
143.70999999999998

> <JCHEM_REFRACTIVITY>
53.20500000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.06e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cystathionine sulfoxide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0      52.662 -26.157   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0      57.997 -26.157   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      45.993 -25.387   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      52.662 -27.697   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      56.663 -23.847   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      47.327 -27.697   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0      55.329 -27.697   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0      48.661 -23.847   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      55.329 -26.157   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      48.661 -25.387   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      53.995 -25.387   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      51.328 -25.387   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      49.995 -26.157   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      56.663 -25.387   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      47.327 -26.157   0.000  0.00  0.00           C+0
CONECT    1    4   11   12                                                  
CONECT    2   14                                                            
CONECT    3   15                                                            
CONECT    4    1                                                            
CONECT    5   14                                                            
CONECT    6   15                                                            
CONECT    7    9                                                            
CONECT    8   10                                                            
CONECT    9    7   11   14                                                  
CONECT   10    8   13   15                                                  
CONECT   11    1    9                                                       
CONECT   12    1   13                                                       
CONECT   13   10   12                                                       
CONECT   14    2    5    9                                                  
CONECT   15    3    6   10                                                  
MASTER        0    0    0    0    0    0    0    0   15    0   28    0
END

View in JSmol

Synonyms

Value	Source
Cystathionine sulphoxide	Generator
[R-(R,s)]-2-amino-4-[(2-amino-2-carboxyethyl)sulfinyl]-butanoate	HMDB
[R-(R,s)]-2-amino-4-[(2-amino-2-carboxyethyl)sulfinyl]-butanoic acid	HMDB
(2S)-2-Amino-4-[(2R)-2-amino-2-carboxyethanesulfinyl]butanoate	HMDB
(2S)-2-Amino-4-[(2R)-2-amino-2-carboxyethanesulphinyl]butanoate	HMDB
(2S)-2-Amino-4-[(2R)-2-amino-2-carboxyethanesulphinyl]butanoic acid	HMDB
Cystathionine sulfoxide	MeSH

Chemical Formula

C₇H₁₄N₂O₅S

Average Mass

238.2610 Da

Monoisotopic Mass

238.06234 Da

IUPAC Name

(2S)-2-amino-4-[(2R)-2-amino-2-carboxyethanesulfinyl]butanoic acid

Traditional Name

cystathionine sulfoxide

CAS Registry Number

Not Available

SMILES

N[C@@H](CCS(=O)C[C@H](N)C(O)=O)C(O)=O

InChI Identifier

InChI=1S/C7H14N2O5S/c8-4(6(10)11)1-2-15(14)3-5(9)7(12)13/h4-5H,1-3,8-9H2,(H,10,11)(H,12,13)/t4-,5-,15?/m0/s1

InChI Key

JNUGGJHCMRWUDV-FMMPLYQGSA-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
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

L-alpha-amino acids

Alternative Parents

Substituents

L-alpha-amino acid
Thia fatty acid
Dicarboxylic acid or derivatives
Fatty acyl
Fatty acid
Sulfoxide
Amino acid
Carboxylic acid
Sulfinyl compound
Amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Primary amine
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
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	-4.2	ALOGPS
logP	-7.8	ChemAxon
logS	-0.77	ALOGPS
pKa (Strongest Acidic)	1.33	ChemAxon
pKa (Strongest Basic)	9.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	143.71 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	53.2 m³·mol⁻¹	ChemAxon
Polarizability	22.81 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

HMDB0002399

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022995

KNApSAcK ID

Not Available

Chemspider ID

149828

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6666

PubChem Compound

171386

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zhang J, Sugahara K, Sagara Y, Hashimoto K, Masuoka N, Kodama H: Identification of cyclic cystathionine sulfoxide and N-acetylcyclic cystathionine in the urine of a patient with cystathioninuria using liquid chromatography-mass spectrometry with an atmospheric pressure chemical ionization interface system. Metabolism. 1996 Oct;45(10):1312-6. doi: 10.1016/s0026-0495(96)90253-x. [PubMed:8843190 ]

Showing NP-Card for Cystathionine sulfoxide (NP0086968)

MOL for NP0086968 (Cystathionine sulfoxide)

3D MOL for NP0086968 (Cystathionine sulfoxide)

3D SDF for NP0086968 (Cystathionine sulfoxide)

3D-SDF for NP0086968 (Cystathionine sulfoxide)

PDB for NP0086968 (Cystathionine sulfoxide)

3D PDB for NP0086968 (Cystathionine sulfoxide)

SMILES for NP0086968 (Cystathionine sulfoxide)

INCHI for NP0086968 (Cystathionine sulfoxide)

Structure for NP0086968 (Cystathionine sulfoxide)

3D Structure for NP0086968 (Cystathionine sulfoxide)