NP-MRD: Showing NP-Card for Allocystathionine (NP0000516)

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Record Information

Version

2.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2021-08-09 22:33:03 UTC

NP-MRD ID

NP0000516

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Allocystathionine

Description

Allocystathionine belongs to the class of organic compounds known as cysteines and cysteine derivatives. Cysteine and cysteine derivatives are compounds containing cysteine or a derivative thereof resulting from the reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Allocystathionine is a stereo-isomer of cystathionine. Both cystathionine and allocystathionine are modified amino acids generated by enzymic means from homocysteine and serine. Allocystathionine is a product of enzyme cystathionine synthetase (EC 2.5.1.48) Which converts homocysteine into allocystathionine in the sulfur metabolism pathway. It is also the substrate of enzyme cystathionine beta-lyase (EC 4.4.1.8) In the same pathway (KEGG). Cystathionine and allocystathionine can be used by the enzymes cystathionine gamma-lyase (CTH), cysteine dioxygenase (CDO), and sulfinoalanine decarboxylase to produce hypotaurine and then taurine.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

Allocystathionine.mol
  Mrv1652305271900022D          

 14 13  0  0  0  0            999 V2000
   -2.1434    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.0000    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  6  0  0  0
  1  3  1  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
  1  7  2  0  0  0  0
  1  8  1  0  0  0  0
  9 10  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 10 11  1  0  0  0  0
 10 14  1  0  0  0  0
  6  9  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000516

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C7H14N2O4S/c8-4(6(10)11)1-2-14-3-5(9)7(12)13/h4-5H,1-3,8-9H2,(H,10,11)(H,12,13)/t4-,5?/m0/s1

> <INCHI_KEY>
ILRYLPWNYFXEMH-ROLXFIACSA-N

> <FORMULA>
C7H14N2O4S

> <MOLECULAR_WEIGHT>
222.262

> <EXACT_MASS>
222.067427636

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
22.238630557468987

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-4-[(2-amino-2-carboxyethyl)sulfanyl]butanoic acid

> <ALOGPS_LOGP>
-4.01

> <JCHEM_LOGP>
-5.818502121951177

> <ALOGPS_LOGS>
-1.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
2.514696511113594

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.793798721038319

> <JCHEM_PKA_STRONGEST_BASIC>
9.659588767699923

> <JCHEM_POLAR_SURFACE_AREA>
126.64000000000001

> <JCHEM_REFRACTIVITY>
51.568900000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.73e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-amino-4-[(2-amino-2-carboxyethyl)sulfanyl]butanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Allocystathionine.mol                             
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0      -4.001   0.000   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      -2.667  -2.310   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      -2.667  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -0.770   0.000  0.00  0.00           C+0
HETATM    6  S   UNK     0       1.334   0.000   0.000  0.00  0.00           S+0
HETATM    7  O   UNK     0      -4.001   1.540   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -5.335  -0.770   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.667  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001   1.540   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.667   2.310   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       5.335   2.310   0.000  0.00  0.00           O+0
HETATM   14  N   UNK     0       5.335  -0.770   0.000  0.00  0.00           N+0
CONECT    1    3    7    8                                                  
CONECT    2    3                                                            
CONECT    3    2    1    4                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    9                                                       
CONECT    7    1                                                            
CONECT    8    1                                                            
CONECT    9   10    6                                                       
CONECT   10    9   11   14                                                  
CONECT   11   12   13   10                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   10                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   26    0
END

COMPND    HMDB0000455
HETATM    1  N1  UNL     1      -3.966  -0.725   1.275  1.00  0.00           N  
HETATM    2  C1  UNL     1      -3.145  -0.644   0.085  1.00  0.00           C  
HETATM    3  C2  UNL     1      -1.668  -0.846   0.393  1.00  0.00           C  
HETATM    4  S1  UNL     1      -0.788  -0.718  -1.193  1.00  0.00           S  
HETATM    5  C3  UNL     1       0.998  -0.939  -0.973  1.00  0.00           C  
HETATM    6  C4  UNL     1       1.505   0.217  -0.175  1.00  0.00           C  
HETATM    7  C5  UNL     1       2.992   0.166   0.088  1.00  0.00           C  
HETATM    8  N2  UNL     1       3.381  -1.007   0.817  1.00  0.00           N  
HETATM    9  C6  UNL     1       3.357   1.377   0.892  1.00  0.00           C  
HETATM   10  O1  UNL     1       3.915   1.247   2.019  1.00  0.00           O  
HETATM   11  O2  UNL     1       3.088   2.632   0.408  1.00  0.00           O  
HETATM   12  C7  UNL     1      -3.276   0.694  -0.570  1.00  0.00           C  
HETATM   13  O3  UNL     1      -4.014   1.578  -0.099  1.00  0.00           O  
HETATM   14  O4  UNL     1      -2.555   0.924  -1.716  1.00  0.00           O  
HETATM   15  H1  UNL     1      -4.100   0.226   1.685  1.00  0.00           H  
HETATM   16  H2  UNL     1      -4.867  -1.218   1.106  1.00  0.00           H  
HETATM   17  H3  UNL     1      -3.516  -1.396  -0.641  1.00  0.00           H  
HETATM   18  H4  UNL     1      -1.558  -1.869   0.819  1.00  0.00           H  
HETATM   19  H5  UNL     1      -1.352  -0.085   1.109  1.00  0.00           H  
HETATM   20  H6  UNL     1       1.443  -0.959  -1.990  1.00  0.00           H  
HETATM   21  H7  UNL     1       1.232  -1.877  -0.427  1.00  0.00           H  
HETATM   22  H8  UNL     1       0.980   0.274   0.790  1.00  0.00           H  
HETATM   23  H9  UNL     1       1.305   1.189  -0.708  1.00  0.00           H  
HETATM   24  H10 UNL     1       3.574   0.263  -0.854  1.00  0.00           H  
HETATM   25  H11 UNL     1       2.606  -1.627   1.080  1.00  0.00           H  
HETATM   26  H12 UNL     1       4.181  -1.490   0.376  1.00  0.00           H  
HETATM   27  H13 UNL     1       2.129   2.914   0.157  1.00  0.00           H  
HETATM   28  H14 UNL     1      -1.879   1.697  -1.803  1.00  0.00           H  
CONECT    1    2   15   16
CONECT    2    3   12   17
CONECT    3    4   18   19
CONECT    4    5
CONECT    5    6   20   21
CONECT    6    7   22   23
CONECT    7    8    9   24
CONECT    8   25   26
CONECT    9   10   10   11
CONECT   11   27
CONECT   12   13   13   14
CONECT   14   28
END

View in JSmol

Synonyms

Value	Source
a-Amino-g-(2-amino-2-carboxyethylmercapto)-butyric acid	HMDB
alpha-Amino-gamma-(2-amino-2-carboxyethylmercapto)-butyric acid	HMDB
DL-Allocystathionine	HMDB
DL-S-(2-Amino-2-carboxyethyl)-homocysteine	HMDB
(2S)-2-Amino-4-[(2-amino-2-carboxyethyl)sulfanyl]butanoate	HMDB
(2S)-2-Amino-4-[(2-amino-2-carboxyethyl)sulphanyl]butanoate	HMDB
(2S)-2-Amino-4-[(2-amino-2-carboxyethyl)sulphanyl]butanoic acid	HMDB

Chemical Formula

C₇H₁₄N₂O₄S

Average Mass

222.2620 Da

Monoisotopic Mass

222.06743 Da

IUPAC Name

(2S)-2-amino-4-[(2-amino-2-carboxyethyl)sulfanyl]butanoic acid

Traditional Name

(2S)-2-amino-4-[(2-amino-2-carboxyethyl)sulfanyl]butanoic acid

CAS Registry Number

535-34-2

SMILES

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

InChI Identifier

InChI=1S/C7H14N2O4S/c8-4(6(10)11)1-2-14-3-5(9)7(12)13/h4-5H,1-3,8-9H2,(H,10,11)(H,12,13)/t4-,5?/m0/s1

InChI Key

ILRYLPWNYFXEMH-ROLXFIACSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	281 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	17.3 g/L	ALOGPS
logP	-4	ALOGPS
logP	-5.8	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	1.79	ChemAxon
pKa (Strongest Basic)	9.66	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	126.64 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	51.57 m³·mol⁻¹	ChemAxon
Polarizability	22.24 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

HMDB0000455

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022055

KNApSAcK ID

Not Available

Chemspider ID

8280480

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10104953

PDB ID

Not Available

ChEBI ID

165853

Good Scents ID

Not Available

References

General References

Cialdella-Kam L, Nieman DC, Sha W, Meaney MP, Knab AM, Shanely RA: Dose-response to 3 months of quercetin-containing supplements on metabolite and quercetin conjugate profile in adults. Br J Nutr. 2013 Jun;109(11):1923-33. doi: 10.1017/S0007114512003972. Epub 2012 Nov 14. [PubMed:23151341 ]

Showing NP-Card for Allocystathionine (NP0000516)

MOL for NP0000516 (Allocystathionine)

3D MOL for NP0000516 (Allocystathionine)

3D SDF for NP0000516 (Allocystathionine)

3D-SDF for NP0000516 (Allocystathionine)

PDB for NP0000516 (Allocystathionine)

3D PDB for NP0000516 (Allocystathionine)

SMILES for NP0000516 (Allocystathionine)

INCHI for NP0000516 (Allocystathionine)

Structure for NP0000516 (Allocystathionine)

3D Structure for NP0000516 (Allocystathionine)