MiMeDB: Showing metabocard for pyochelin II (MMDBc0032894)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 22:56:45 UTC

Update Date

2022-08-31 21:45:17 UTC

Metabolite ID

MMDBc0032894

Metabolite Identification

Common Name

pyochelin II

Description

A pyochelin that has S-stereochemistry at the thioaminal centre; the diastereoisomer with R-stereochemistry at this centre is pyochelin I. Pseudomonas aeruginosa produces a mixture of pyochelin I (major) and pyochelin I (minor) via co

Structure

MOL SDF PDB SMILES InChI


  Mrv1652311182123562D          

 23 25  0  0  1  0            999 V2000
   -0.0206   -0.8630    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3819   -1.7224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -2.5070    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -2.5070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0470   -1.7224    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1830   -3.1745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1526   -3.9282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3323   -4.5956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1528   -4.5094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4884   -3.7557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0034   -3.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3390   -2.3346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4496   -0.7870    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0470    0.0724    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    0.8570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    0.8570    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3819    0.0724    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1665   -0.1825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6119    1.5245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2763    2.2782    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4324    1.4382    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  2  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  0  0  0  0
  2 14  1  1  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 14 19  1  6  0  0  0
 19 20  1  0  0  0  0
 18 21  1  1  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0032894

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@]1(CSC(=N1)C1=CC=CC=C1O)[C@]1([H])SC[C@H](N1C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H16N2O3S2/c1-16-10(14(18)19)7-21-13(16)9-6-20-12(15-9)8-4-2-3-5-11(8)17/h2-5,9-10,13,17H,6-7H2,1H3,(H,18,19)/t9-,10+,13+/m1/s1

> <INCHI_KEY>
NYBZAGXTZXPYND-NRUUGDAUSA-N

> <FORMULA>
C14H16N2O3S2

> <MOLECULAR_WEIGHT>
324.41

> <EXACT_MASS>
324.060234731

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
33.273714370874785

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,4R)-2-[(4R)-2-(2-hydroxyphenyl)-4,5-dihydro-1,3-thiazol-4-yl]-3-methyl-1,3-thiazolidine-4-carboxylic acid

> <ALOGPS_LOGP>
1.49

> <JCHEM_LOGP>
1.7453949831981788

> <ALOGPS_LOGS>
-3.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.618344340683885

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.6837717697689554

> <JCHEM_PKA_STRONGEST_BASIC>
4.711909639129939

> <JCHEM_POLAR_SURFACE_AREA>
73.13

> <JCHEM_REFRACTIVITY>
85.20259999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.07e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,4R)-2-[(4R)-2-(2-hydroxyphenyl)-4,5-dihydro-1,3-thiazol-4-yl]-3-methyl-1,3-thiazolidine-4-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 18-NOV-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-NOV-21         0                                  
HETATM    1  H   UNK     0      -0.038  -1.611   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.580  -3.215   0.000  0.00  0.00           C+0
HETATM    4  S   UNK     0       2.104  -4.680   0.000  0.00  0.00           S+0
HETATM    5  C   UNK     0       0.564  -4.680   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       0.088  -3.215   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      -0.342  -5.926   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.285  -7.333   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.620  -8.578   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.152  -8.417   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.778  -7.011   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.873  -5.765   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -2.499  -4.358   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   15  H   UNK     0       2.706  -1.469   0.000  0.00  0.00           H+0
HETATM   16  S   UNK     0       0.088   0.135   0.000  0.00  0.00           S+0
HETATM   17  C   UNK     0       0.564   1.600   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.104   1.600   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       2.580   0.135   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       4.044  -0.341   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.009   2.846   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.382   4.253   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       4.540   2.685   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    6   14                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5    2                                                       
CONECT    7    5    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    7   13                                                  
CONECT   13   12                                                            
CONECT   14    2   15   16   19                                             
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   21                                                  
CONECT   19   18   14   20                                                  
CONECT   20   19                                                            
CONECT   21   18   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

Synonyms

Not Available

Molecular Formula

C₁₄H₁₆N₂O₃S₂

Average Mass

324.41

Monoisotopic Mass

324.060234731

IUPAC Name

(2S,4R)-2-[(4R)-2-(2-hydroxyphenyl)-4,5-dihydro-1,3-thiazol-4-yl]-3-methyl-1,3-thiazolidine-4-carboxylic acid

Traditional Name

(2S,4R)-2-[(4R)-2-(2-hydroxyphenyl)-4,5-dihydro-1,3-thiazol-4-yl]-3-methyl-1,3-thiazolidine-4-carboxylic acid

CAS Registry Number

Not Available

SMILES

[H][C@@]1(CSC(=N1)C1=CC=CC=C1O)[C@]1([H])SC[C@H](N1C)C(O)=O

InChI Identifier

InChI=1S/C14H16N2O3S2/c1-16-10(14(18)19)7-21-13(16)9-6-20-12(15-9)8-4-2-3-5-11(8)17/h2-5,9-10,13,17H,6-7H2,1H3,(H,18,19)/t9-,10+,13+/m1/s1

InChI Key

NYBZAGXTZXPYND-NRUUGDAUSA-N

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
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Imidothiolactone
Thiazolidine
Meta-thiazoline
Carboxylic acid
Monocarboxylic acid or derivatives
Thioether
Hemithioaminal
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Dialkylthioether
Azacycle
Organoheterocyclic compound
Organic oxide
Carbonyl group
Hydrocarbon derivative
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Organopnictogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

pyochelin (CHEBI:67185 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.31 g/L	ALOGPS
logP	1.49	ALOGPS
logP	1.75	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	2.68	ChemAxon
pKa (Strongest Basic)	4.71	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	73.13 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	85.2 m³·mol⁻¹	ChemAxon
Polarizability	33.27 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available	2022-08-09	View Spectrum
MS	Mass Spectrum (Electron Ionization)	Not Available	2022-08-06	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum

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

Not Available

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	Proteobacteria	1	Human ; Human sputum; Human subgingival plaque; Human feces	Unknown

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

16738333

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

135499974

PDB ID

Not Available

ChEBI ID

67185

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Huang W, Brewer LK, Jones JW, Nguyen AT, Marcu A, Wishart DS, Oglesby-Sherrouse AG, Kane MA, Wilks A: PAMDB: a comprehensive Pseudomonas aeruginosa metabolome database. Nucleic Acids Res. 2018 Jan 4;46(D1):D575-D580. doi: 10.1093/nar/gkx1061. [PubMed:29106626 ]

Showing metabocard for pyochelin II (MMDBc0032894)

MOL for #<Metabolite:0x00007fecf44304e8>

3D MOL for #<Metabolite:0x00007fecf44304e8>

3D SDF for #<Metabolite:0x00007fecf44304e8>

3D-SDF for #<Metabolite:0x00007fecf44304e8>

PDB for #<Metabolite:0x00007fecf44304e8>

3D PDB for #<Metabolite:0x00007fecf44304e8>

SMILES for #<Metabolite:0x00007fecf44304e8>

INCHI for #<Metabolite:0x00007fecf44304e8>

Structure for #<Metabolite:0x00007fecf44304e8>

3D Structure for #<Metabolite:0x00007fecf44304e8>