MiMeDB: Showing metabocard for S-(hercyn-2-yl)-L-cysteine S-oxide (MMDBc0056298)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-17 20:22:08 UTC

Update Date

2022-08-12 20:09:40 UTC

Metabolite ID

MMDBc0056298

Metabolite Identification

Common Name

S-(hercyn-2-yl)-L-cysteine S-oxide

Description

hercynylcysteine sulfoxide belongs to the class of organic compounds known as histidine and derivatives. Histidine 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. hercynylcysteine sulfoxide is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on hercynylcysteine sulfoxide.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306172222222D          

 24 24  0  0  1  0            999 V2000
    6.9652    6.5725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8760    6.1544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3834    5.4832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4736    4.9789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5506    3.5107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8159    3.2332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1381    4.2252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1015    2.8207    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2941    5.0651    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3870    3.2332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7791    4.3977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2449    3.2332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1015    1.9957    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9986    2.8977    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3311    4.0537    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6297    5.8188    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    0.6725    2.8207    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3870    4.0582    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5995    4.4839    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4435    3.6440    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    3.5304    1.9957    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5304    2.8207    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.1015    3.6457    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9586    4.3115    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  4  1  0  0  0  0
  7  5  2  0  0  0  0
  8  6  1  0  0  0  0
  9  4  1  6  0  0  0
 10  8  1  0  0  0  0
 11  9  1  0  0  0  0
  8 13  1  1  0  0  0
 14  5  1  0  0  0  0
 14 12  2  0  0  0  0
 15  7  1  0  0  0  0
 15 12  1  0  0  0  0
 16  1  1  0  0  0  0
 16  2  1  0  0  0  0
 16  3  1  0  0  0  0
 16  9  1  0  0  0  0
 17 10  2  0  0  0  0
 18 10  1  0  0  0  0
 19 11  2  0  0  0  0
 20 11  1  0  0  0  0
 22  6  1  0  0  0  0
 22 12  1  0  0  0  0
 22 21  2  0  0  0  0
  8 23  1  1  0  0  0
  9 24  1  1  0  0  0
M  CHG  2  16   1  20  -1
M  END
> <DATABASE_ID>
MMDBc0056298

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@](N)(CS(=O)C1=NC=C(C[C@@]([H])(C([O-])=O)[N+](C)(C)C)N1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C12H20N4O5S/c1-16(2,3)9(11(19)20)4-7-5-14-12(15-7)22(21)6-8(13)10(17)18/h5,8-9H,4,6,13H2,1-3H3,(H2-,14,15,17,18,19,20)/t8-,9-,22?/m0/s1

> <INCHI_KEY>
CSTNDZVKJNPMIG-PTZMPWRZSA-N

> <FORMULA>
C12H20N4O5S

> <MOLECULAR_WEIGHT>
332.38

> <EXACT_MASS>
332.115440934

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
32.51274904369936

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-3-{2-[(2R)-2-amino-2-carboxyethanesulfinyl]-1H-imidazol-5-yl}-2-(trimethylazaniumyl)propanoate

> <JCHEM_LOGP>
-8.165577680643995

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
1.5753516402825034

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.8744830266750698

> <JCHEM_PKA_STRONGEST_BASIC>
8.417810720539302

> <JCHEM_POLAR_SURFACE_AREA>
149.2

> <JCHEM_REFRACTIVITY>
102.5762

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-3-{2-[(2R)-2-amino-2-carboxyethanesulfinyl]-3H-imidazol-4-yl}-2-(trimethylammonio)propanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-JUN-22         0                                  
HETATM    1  C   UNK     0      13.002  12.269   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.969  11.488   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.782  10.235   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.217   9.294   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.361   6.553   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.256   6.035   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.591   7.887   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.923   5.265   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.749   9.455   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.589   6.035   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.654   8.209   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.924   6.035   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       3.923   3.725   0.000  0.00  0.00           N+0
HETATM   14  N   UNK     0       9.331   5.409   0.000  0.00  0.00           N+0
HETATM   15  N   UNK     0       8.085   7.567   0.000  0.00  0.00           N+0
HETATM   16  N   UNK     0      12.375  10.862   0.000  0.00  0.00           N+1
HETATM   17  O   UNK     0       1.255   5.265   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       2.589   7.575   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      14.186   8.370   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      12.028   6.802   0.000  0.00  0.00           O-1
HETATM   21  O   UNK     0       6.590   3.725   0.000  0.00  0.00           O+0
HETATM   22  S   UNK     0       6.590   5.265   0.000  0.00  0.00           S+0
HETATM   23  H   UNK     0       3.923   6.805   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0      11.123   8.048   0.000  0.00  0.00           H+0
CONECT    1   16                                                            
CONECT    2   16                                                            
CONECT    3   16                                                            
CONECT    4    7    9                                                       
CONECT    5    7   14                                                       
CONECT    6    8   22                                                       
CONECT    7    4    5   15                                                  
CONECT    8    6   10   13   23                                             
CONECT    9    4   11   16   24                                             
CONECT   10    8   17   18                                                  
CONECT   11    9   19   20                                                  
CONECT   12   14   15   22                                                  
CONECT   13    8                                                            
CONECT   14    5   12                                                       
CONECT   15    7   12                                                       
CONECT   16    1    2    3    9                                             
CONECT   17   10                                                            
CONECT   18   10                                                            
CONECT   19   11                                                            
CONECT   20   11                                                            
CONECT   21   22                                                            
CONECT   22    6   12   21                                                  
CONECT   23    8                                                            
CONECT   24    9                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   48    0
END

Synonyms

Value	Source
Hercynylcysteine sulphoxide	Generator

Molecular Formula

C₁₂H₂₀N₄O₅S

Average Mass

332.38

Monoisotopic Mass

332.115440934

IUPAC Name

(2S)-3-{2-[(2R)-2-amino-2-carboxyethanesulfinyl]-1H-imidazol-5-yl}-2-(trimethylazaniumyl)propanoate

Traditional Name

(2S)-3-{2-[(2R)-2-amino-2-carboxyethanesulfinyl]-3H-imidazol-4-yl}-2-(trimethylammonio)propanoate

CAS Registry Number

Not Available

SMILES

[H][C@](N)(CS(=O)C1=NC=C(C[C@@]([H])(C([O-])=O)[N+](C)(C)C)N1)C(O)=O

InChI Identifier

InChI=1S/C12H20N4O5S/c1-16(2,3)9(11(19)20)4-7-5-14-12(15-7)22(21)6-8(13)10(17)18/h5,8-9H,4,6,13H2,1-3H3,(H2-,14,15,17,18,19,20)/t8-,9-,22?/m0/s1

InChI Key

CSTNDZVKJNPMIG-PTZMPWRZSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as histidine and derivatives. Histidine 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

Histidine and derivatives

Alternative Parents

Substituents

Histidine or derivatives
L-alpha-amino acid
Alpha-amino acid
Imidazolyl carboxylic acid derivative
Aralkylamine
Dicarboxylic acid or derivatives
Tetraalkylammonium salt
Heteroaromatic compound
Quaternary ammonium salt
Imidazole
Azole
Amino acid
Sulfoxide
Carboxylic acid salt
Azacycle
Organoheterocyclic compound
Sulfinyl compound
Carboxylic acid
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organic salt
Organic zwitterion
Primary amine
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Carbonyl group
Amine
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

ammonium betaine (CHEBI:79057 )
sulfoxide (CHEBI:79057 )
L-histidine derivative (CHEBI:79057 )
L-cysteine derivative (CHEBI:79057 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
logP	-8.2	ChemAxon
pKa (Strongest Acidic)	0.87	ChemAxon
pKa (Strongest Basic)	8.42	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	149.2 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	102.58 m³·mol⁻¹	ChemAxon
Polarizability	32.51 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Not Available

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Actinobacteria	3	Human
Eukaryota/Fungi	Ascomycota	2

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

34448532

KEGG Compound ID

Not Available

BioCyc ID

CPD-15277

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

86289740

PDB ID

Not Available

ChEBI ID

79057

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for S-(hercyn-2-yl)-L-cysteine S-oxide (MMDBc0056298)

MOL for #<Metabolite:0x00005634c0f5e880>

3D MOL for #<Metabolite:0x00005634c0f5e880>

3D SDF for #<Metabolite:0x00005634c0f5e880>

3D-SDF for #<Metabolite:0x00005634c0f5e880>

PDB for #<Metabolite:0x00005634c0f5e880>

3D PDB for #<Metabolite:0x00005634c0f5e880>

SMILES for #<Metabolite:0x00005634c0f5e880>

INCHI for #<Metabolite:0x00005634c0f5e880>

Structure for #<Metabolite:0x00005634c0f5e880>

3D Structure for #<Metabolite:0x00005634c0f5e880>