MiMeDB: Showing metabocard for N-[(R)-4-phosphopantothenoyl]-L-cysteine (MMDBc0056115)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-17 20:17:05 UTC

Update Date

2022-08-12 20:09:35 UTC

Metabolite ID

MMDBc0056115

Metabolite Identification

Common Name

N-[(R)-4-phosphopantothenoyl]-L-cysteine

Description

N-[(R)-4-phosphonatopantothenoyl]-L-cysteinate(3-) belongs to the class of organic compounds known as hybrid peptides. Hybrid peptides are compounds containing at least two different types of amino acids (alpha, beta, gamma, delta) linked to each other through a peptide bond. N-[(R)-4-phosphonatopantothenoyl]-L-cysteinate(3-) 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 very few articles have been published on N-[(R)-4-phosphonatopantothenoyl]-L-cysteinate(3-).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306172222172D          

 27 26  0  0  1  0            999 V2000
   -1.1566    3.9336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9816    2.5046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2836    0.3316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5691    0.7441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7125   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2836    3.6316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9980   -1.7309    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2836   -0.4934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8546    2.8066    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8546    1.9816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2836   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5691    3.2191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5691    1.5691    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9980   -0.9059    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5691   -0.9059    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -0.1401    3.2191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1401    1.5691    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -1.5691   -1.7309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2836   -2.9684    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -3.7125    5.2816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5855    5.5836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4105    4.1546    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2836    4.4566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9980    4.8691    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4270   -1.7309    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9980   -2.5559    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5691    2.3941    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  7  5  1  0  0  0  0
  8  3  1  0  0  0  0
 10  9  1  0  0  0  0
 11  7  1  0  0  0  0
 12  1  1  0  0  0  0
 12  2  1  0  0  0  0
 12  6  1  0  0  0  0
 12  9  1  0  0  0  0
 13  4  1  4  0  0  0
 13 10  2  0  0  0  0
  7 14  1  1  0  0  0
 14  8  2  0  0  0  0
  8 15  1  4  0  0  0
  9 16  1  6  0  0  0
 17 10  1  0  0  0  0
 18 11  2  0  0  0  0
 19 11  1  0  0  0  0
 23  6  1  0  0  0  0
 24 20  1  0  0  0  0
 24 21  1  0  0  0  0
 24 22  2  0  0  0  0
 24 23  1  0  0  0  0
 25  5  1  0  0  0  0
  7 26  1  1  0  0  0
  9 27  1  6  0  0  0
M  CHG  3  15  -1  17  -1  19  -1
M  END


  Mrv1652306172222172D          

 27 26  0  0  1  0            999 V2000
   -1.1566    3.9336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9816    2.5046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2836    0.3316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5691    0.7441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7125   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2836    3.6316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9980   -1.7309    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2836   -0.4934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8546    2.8066    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8546    1.9816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2836   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5691    3.2191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5691    1.5691    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9980   -0.9059    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5691   -0.9059    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -0.1401    3.2191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1401    1.5691    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -1.5691   -1.7309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2836   -2.9684    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -3.7125    5.2816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5855    5.5836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4105    4.1546    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2836    4.4566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9980    4.8691    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4270   -1.7309    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9980   -2.5559    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5691    2.3941    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  7  5  1  0  0  0  0
  8  3  1  0  0  0  0
 10  9  1  0  0  0  0
 11  7  1  0  0  0  0
 12  1  1  0  0  0  0
 12  2  1  0  0  0  0
 12  6  1  0  0  0  0
 12  9  1  0  0  0  0
 13  4  1  4  0  0  0
 13 10  2  0  0  0  0
  7 14  1  1  0  0  0
 14  8  2  0  0  0  0
  8 15  1  4  0  0  0
  9 16  1  6  0  0  0
 17 10  1  0  0  0  0
 18 11  2  0  0  0  0
 19 11  1  0  0  0  0
 23  6  1  0  0  0  0
 24 20  1  0  0  0  0
 24 21  1  0  0  0  0
 24 22  2  0  0  0  0
 24 23  1  0  0  0  0
 25  5  1  0  0  0  0
  7 26  1  1  0  0  0
  9 27  1  6  0  0  0
M  CHG  3  15  -1  17  -1  19  -1
M  END
> <DATABASE_ID>
MMDBc0056115

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@](O)(C([O-])=NCCC([O-])=N[C@@]([H])(CS)C([O-])=O)C(C)(C)COP(O)(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C12H23N2O9PS/c1-12(2,6-23-24(20,21)22)9(16)10(17)13-4-3-8(15)14-7(5-25)11(18)19/h7,9,16,25H,3-6H2,1-2H3,(H,13,17)(H,14,15)(H,18,19)(H2,20,21,22)/p-3/t7-,9-/m0/s1

> <INCHI_KEY>
XQYALQVLCNHCFT-CBAPKCEASA-K

> <FORMULA>
C12H20N2O9PS

> <MOLECULAR_WEIGHT>
399.33

> <EXACT_MASS>
399.064359144

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
36.18917698931742

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
-3

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-2-[(3-{[(2R)-2-hydroxy-3,3-dimethyl-1-oxido-4-(phosphonooxy)butylidene]amino}-1-oxidopropylidene)amino]-3-sulfanylpropanoate

> <JCHEM_LOGP>
-1.9785502582844015

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
2.3464415609693954

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.5993812662903424

> <JCHEM_PKA_STRONGEST_BASIC>
4.951977819267322

> <JCHEM_POLAR_SURFACE_AREA>
197.95999999999998

> <JCHEM_REFRACTIVITY>
120.3888

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-2-[(3-{[(2R)-2-hydroxy-3,3-dimethyl-1-oxido-4-(phosphonooxy)butylidene]amino}-1-oxidopropylidene)amino]-3-sulfanylpropanoate

> <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      -2.159   7.343   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.699   4.675   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.263   0.619   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.929   1.389   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.930  -4.001   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.263   6.779   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.596  -3.231   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.263  -0.921   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.595   5.239   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.595   3.699   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.263  -4.001   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.929   6.009   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      -2.929   2.929   0.000  0.00  0.00           N+0
HETATM   14  N   UNK     0      -5.596  -1.691   0.000  0.00  0.00           N+0
HETATM   15  O   UNK     0      -2.929  -1.691   0.000  0.00  0.00           O-1
HETATM   16  O   UNK     0      -0.262   6.009   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -0.262   2.929   0.000  0.00  0.00           O-1
HETATM   18  O   UNK     0      -2.929  -3.231   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -4.263  -5.541   0.000  0.00  0.00           O-1
HETATM   20  O   UNK     0      -6.930   9.859   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -4.826  10.423   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -6.366   7.755   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -4.263   8.319   0.000  0.00  0.00           O+0
HETATM   24  P   UNK     0      -5.596   9.089   0.000  0.00  0.00           P+0
HETATM   25  S   UNK     0      -8.264  -3.231   0.000  0.00  0.00           S+0
HETATM   26  H   UNK     0      -5.596  -4.771   0.000  0.00  0.00           H+0
HETATM   27  H   UNK     0      -2.929   4.469   0.000  0.00  0.00           H+0
CONECT    1   12                                                            
CONECT    2   12                                                            
CONECT    3    4    8                                                       
CONECT    4    3   13                                                       
CONECT    5    7   25                                                       
CONECT    6   12   23                                                       
CONECT    7    5   11   14   26                                             
CONECT    8    3   14   15                                                  
CONECT    9   10   12   16   27                                             
CONECT   10    9   13   17                                                  
CONECT   11    7   18   19                                                  
CONECT   12    1    2    6    9                                             
CONECT   13    4   10                                                       
CONECT   14    7    8                                                       
CONECT   15    8                                                            
CONECT   16    9                                                            
CONECT   17   10                                                            
CONECT   18   11                                                            
CONECT   19   11                                                            
CONECT   20   24                                                            
CONECT   21   24                                                            
CONECT   22   24                                                            
CONECT   23    6   24                                                       
CONECT   24   20   21   22   23                                             
CONECT   25    5                                                            
CONECT   26    7                                                            
CONECT   27    9                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   52    0
END

Synonyms

Value	Source
N-[(R)-4-Phosphopantothenoyl]-L-cysteine	ChEBI
N-[(R)-4-Phosphonatopantothenoyl]-L-cysteinic acid(3-)	Generator

Molecular Formula

C₁₂H₂₀N₂O₉PS

Average Mass

399.33

Monoisotopic Mass

399.064359144

IUPAC Name

(2R)-2-[(3-{[(2R)-2-hydroxy-3,3-dimethyl-1-oxido-4-(phosphonooxy)butylidene]amino}-1-oxidopropylidene)amino]-3-sulfanylpropanoate

Traditional Name

(2R)-2-[(3-{[(2R)-2-hydroxy-3,3-dimethyl-1-oxido-4-(phosphonooxy)butylidene]amino}-1-oxidopropylidene)amino]-3-sulfanylpropanoate

CAS Registry Number

Not Available

SMILES

[H][C@](O)(C([O-])=NCCC([O-])=N[C@@]([H])(CS)C([O-])=O)C(C)(C)COP(O)(O)=O

InChI Identifier

InChI=1S/C12H23N2O9PS/c1-12(2,6-23-24(20,21)22)9(16)10(17)13-4-3-8(15)14-7(5-25)11(18)19/h7,9,16,25H,3-6H2,1-2H3,(H,13,17)(H,14,15)(H,18,19)(H2,20,21,22)/p-3/t7-,9-/m0/s1

InChI Key

XQYALQVLCNHCFT-CBAPKCEASA-K

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hybrid peptides. Hybrid peptides are compounds containing at least two different types of amino acids (alpha, beta, gamma, delta) linked to each other through a peptide bond.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Peptidomimetics

Sub Class

Hybrid peptides

Direct Parent

Hybrid peptides

Alternative Parents

Substituents

Hybrid peptide
N-acyl-alpha amino acid or derivatives
N-acyl-alpha-amino acid
N-acyl-l-alpha-amino acid
Cysteine or derivatives
Beta amino acid or derivatives
Alpha-amino acid or derivatives
Organic phosphoric acid derivative
Fatty amide
N-acyl-amine
Fatty acyl
Monosaccharide
Alkyl phosphate
Phosphoric acid ester
Carboxamide group
Secondary alcohol
Secondary carboxylic acid amide
Alkylthiol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Alcohol
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organic anion
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

organophosphonate oxoanion (CHEBI:59458 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
logP	-2	ChemAxon
pKa (Strongest Acidic)	1.6	ChemAxon
pKa (Strongest Basic)	4.95	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	197.96 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	120.39 m³·mol⁻¹	ChemAxon
Polarizability	36.19 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

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
Bacteria	Proteobacteria	8	Human ; Human feces
Bacteria	Firmicutes	2	Human feces; Human
Bacteria	Spirochaetes	1	Human
Archaea/Archaea	Euryarchaeota	2
Bacteria	Actinobacteria	4	Cattle ; Human
Bacteria	nah	1
Eukaryota/Fungi	Ascomycota	1

Exposure Sources

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

26333197

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25245609

PDB ID

Not Available

ChEBI ID

59458

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 N-[(R)-4-phosphopantothenoyl]-L-cysteine (MMDBc0056115)

MOL for #<Metabolite:0x00007fdb58945828>

3D MOL for #<Metabolite:0x00007fdb58945828>

3D SDF for #<Metabolite:0x00007fdb58945828>

3D-SDF for #<Metabolite:0x00007fdb58945828>

PDB for #<Metabolite:0x00007fdb58945828>

3D PDB for #<Metabolite:0x00007fdb58945828>

SMILES for #<Metabolite:0x00007fdb58945828>

INCHI for #<Metabolite:0x00007fdb58945828>

Structure for #<Metabolite:0x00007fdb58945828>

3D Structure for #<Metabolite:0x00007fdb58945828>