NP-MRD: Showing NP-Card for Pyochelin (NP0021951)

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Record Information

Version

1.0

Created at

2021-01-06 07:11:34 UTC

Updated at

2021-07-15 17:37:44 UTC

NP-MRD ID

NP0021951

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Pyochelin

Provided By

NPAtlas

Description

Pyochelin is found in Burkholderia cepacia and Pseudomonas aeruginosa. It was first documented in 1981 (PMID: 6794030). Based on a literature review very few articles have been published on pyochelin I (PMID: 12040125) (PMID: 15259361).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242105203D          

 37 39  0  0  0  0            999 V2000
    1.4732   -1.7652    0.6743 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9877   -0.5112    0.2030 N   0  0  1  0  0  0  0  0  0  0  0  0
    3.3615   -0.3842    0.4276 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8369    0.9134    0.9177 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0536    1.1235    1.1011 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9496    1.9289    1.1872 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1517   -0.8033   -0.8211 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0576   -0.0036   -2.0704 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.5329   -0.1727   -1.0753 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6292    1.0277   -1.1904 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2049    1.2653   -2.6260 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3494    0.2660   -2.5708 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5757    0.4375   -0.8119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7987    0.1751   -0.1154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8991   -0.2460   -0.8587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1330   -0.5356   -0.3404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2850   -0.3969    1.0153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2295    0.0140    1.7793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9673    0.3098    1.2454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9634    0.7128    2.0630 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4765    0.8195   -0.3561 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3520   -2.4412   -0.2032 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4862   -1.6429    1.1720 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1602   -2.2121    1.4283 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6400   -1.2117    1.1698 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8790    2.3912    2.0740 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1715   -1.8851   -0.9461 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1259   -0.3110   -0.7736 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0094   -1.0769   -1.5076 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2217    1.9533   -0.9146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0102    2.3063   -2.8538 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8507    0.7490   -3.3564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8090   -0.3663   -1.9440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9518   -0.8601   -0.9754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2613   -0.6245    1.4365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3687    0.1177    2.8476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0567    0.9395    1.7848 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  3  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 13 21  2  0  0  0  0
  9  2  1  0  0  0  0
 21 10  1  0  0  0  0
 19 14  1  0  0  0  0
  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
  3 25  1  1  0  0  0
  6 26  1  0  0  0  0
  7 27  1  0  0  0  0
  7 28  1  0  0  0  0
  9 29  1  6  0  0  0
 10 30  1  1  0  0  0
 11 31  1  0  0  0  0
 11 32  1  0  0  0  0
 15 33  1  0  0  0  0
 16 34  1  0  0  0  0
 17 35  1  0  0  0  0
 18 36  1  0  0  0  0
 20 37  1  0  0  0  0
M  END

     RDKit          3D

 37 39  0  0  0  0  0  0  0  0999 V2000
    1.4732   -1.7652    0.6743 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9877   -0.5112    0.2030 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3615   -0.3842    0.4276 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8369    0.9134    0.9177 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0536    1.1235    1.1011 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9496    1.9289    1.1872 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1517   -0.8033   -0.8211 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0576   -0.0036   -2.0704 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.5329   -0.1727   -1.0753 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6292    1.0277   -1.1904 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2049    1.2653   -2.6260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3494    0.2660   -2.5708 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5757    0.4375   -0.8119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7987    0.1751   -0.1154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8991   -0.2460   -0.8587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1330   -0.5356   -0.3404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2850   -0.3969    1.0153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2295    0.0140    1.7793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9673    0.3098    1.2454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9634    0.7128    2.0630 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4765    0.8195   -0.3561 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3520   -2.4412   -0.2032 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4862   -1.6429    1.1720 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1602   -2.2121    1.4283 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6400   -1.2117    1.1698 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8790    2.3912    2.0740 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1715   -1.8851   -0.9461 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1259   -0.3110   -0.7736 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0094   -1.0769   -1.5076 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2217    1.9533   -0.9146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0102    2.3063   -2.8538 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8507    0.7490   -3.3564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8090   -0.3663   -1.9440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9518   -0.8601   -0.9754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2613   -0.6245    1.4365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3687    0.1177    2.8476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0567    0.9395    1.7848 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
  4  5  2  0
  4  6  1  0
  3  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 13 21  2  0
  9  2  1  0
 21 10  1  0
 19 14  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  1
  6 26  1  0
  7 27  1  0
  7 28  1  0
  9 29  1  6
 10 30  1  1
 11 31  1  0
 11 32  1  0
 15 33  1  0
 16 34  1  0
 17 35  1  0
 18 36  1  0
 20 37  1  0
M  END


  Mrv1652306242105203D          

 37 39  0  0  0  0            999 V2000
    1.4732   -1.7652    0.6743 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9877   -0.5112    0.2030 N   0  0  1  0  0  0  0  0  0  0  0  0
    3.3615   -0.3842    0.4276 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8369    0.9134    0.9177 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0536    1.1235    1.1011 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9496    1.9289    1.1872 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1517   -0.8033   -0.8211 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0576   -0.0036   -2.0704 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.5329   -0.1727   -1.0753 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6292    1.0277   -1.1904 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2049    1.2653   -2.6260 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3494    0.2660   -2.5708 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5757    0.4375   -0.8119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7987    0.1751   -0.1154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8991   -0.2460   -0.8587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1330   -0.5356   -0.3404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2850   -0.3969    1.0153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2295    0.0140    1.7793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9673    0.3098    1.2454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9634    0.7128    2.0630 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4765    0.8195   -0.3561 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3520   -2.4412   -0.2032 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4862   -1.6429    1.1720 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1602   -2.2121    1.4283 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6400   -1.2117    1.1698 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8790    2.3912    2.0740 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1715   -1.8851   -0.9461 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1259   -0.3110   -0.7736 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0094   -1.0769   -1.5076 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2217    1.9533   -0.9146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0102    2.3063   -2.8538 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8507    0.7490   -3.3564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8090   -0.3663   -1.9440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9518   -0.8601   -0.9754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2613   -0.6245    1.4365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3687    0.1177    2.8476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0567    0.9395    1.7848 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  3  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 13 21  2  0  0  0  0
  9  2  1  0  0  0  0
 21 10  1  0  0  0  0
 19 14  1  0  0  0  0
  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
  3 25  1  1  0  0  0
  6 26  1  0  0  0  0
  7 27  1  0  0  0  0
  7 28  1  0  0  0  0
  9 29  1  6  0  0  0
 10 30  1  1  0  0  0
 11 31  1  0  0  0  0
 11 32  1  0  0  0  0
 15 33  1  0  0  0  0
 16 34  1  0  0  0  0
 17 35  1  0  0  0  0
 18 36  1  0  0  0  0
 20 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0021951

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)[C@@]1([H])N(C([H])([H])[H])[C@]([H])(SC1([H])[H])[C@]1([H])N=C(SC1([H])[H])C1=C([H])C([H])=C([H])C([H])=C1O[H]

> <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-GBIKHYSHSA-N

> <FORMULA>
C14H16N2O3S2

> <MOLECULAR_WEIGHT>
324.418

> <EXACT_MASS>
324.060233768

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
32.75089418166173

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,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>
1.7453949831981777

> <ALOGPS_LOGS>
-3.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.618344340683889

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.6837717697689567

> <JCHEM_PKA_STRONGEST_BASIC>
4.711909639129938

> <JCHEM_POLAR_SURFACE_AREA>
73.13000000000001

> <JCHEM_REFRACTIVITY>
85.20260000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.07e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,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

$$$$

     RDKit          3D

 37 39  0  0  0  0  0  0  0  0999 V2000
    1.4732   -1.7652    0.6743 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9877   -0.5112    0.2030 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3615   -0.3842    0.4276 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8369    0.9134    0.9177 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0536    1.1235    1.1011 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9496    1.9289    1.1872 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1517   -0.8033   -0.8211 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0576   -0.0036   -2.0704 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.5329   -0.1727   -1.0753 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6292    1.0277   -1.1904 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2049    1.2653   -2.6260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3494    0.2660   -2.5708 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5757    0.4375   -0.8119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7987    0.1751   -0.1154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8991   -0.2460   -0.8587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1330   -0.5356   -0.3404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2850   -0.3969    1.0153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2295    0.0140    1.7793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9673    0.3098    1.2454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9634    0.7128    2.0630 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4765    0.8195   -0.3561 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3520   -2.4412   -0.2032 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4862   -1.6429    1.1720 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1602   -2.2121    1.4283 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6400   -1.2117    1.1698 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8790    2.3912    2.0740 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1715   -1.8851   -0.9461 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1259   -0.3110   -0.7736 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0094   -1.0769   -1.5076 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2217    1.9533   -0.9146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0102    2.3063   -2.8538 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8507    0.7490   -3.3564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8090   -0.3663   -1.9440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9518   -0.8601   -0.9754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2613   -0.6245    1.4365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3687    0.1177    2.8476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0567    0.9395    1.7848 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
  4  5  2  0
  4  6  1  0
  3  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 13 21  2  0
  9  2  1  0
 21 10  1  0
 19 14  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  1
  6 26  1  0
  7 27  1  0
  7 28  1  0
  9 29  1  6
 10 30  1  1
 11 31  1  0
 11 32  1  0
 15 33  1  0
 16 34  1  0
 17 35  1  0
 18 36  1  0
 20 37  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       1.473  -1.765   0.674  0.00  0.00           C+0
HETATM    2  N   UNK     0       1.988  -0.511   0.203  0.00  0.00           N+0
HETATM    3  C   UNK     0       3.361  -0.384   0.428  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.837   0.913   0.918  0.00  0.00           C+0
HETATM    5  O   UNK     0       5.054   1.123   1.101  0.00  0.00           O+0
HETATM    6  O   UNK     0       2.950   1.929   1.187  0.00  0.00           O+0
HETATM    7  C   UNK     0       4.152  -0.803  -0.821  0.00  0.00           C+0
HETATM    8  S   UNK     0       3.058  -0.004  -2.070  0.00  0.00           S+0
HETATM    9  C   UNK     0       1.533  -0.173  -1.075  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.629   1.028  -1.190  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.205   1.265  -2.626  0.00  0.00           C+0
HETATM   12  S   UNK     0      -1.349   0.266  -2.571  0.00  0.00           S+0
HETATM   13  C   UNK     0      -1.576   0.438  -0.812  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.799   0.175  -0.115  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.899  -0.246  -0.859  0.00  0.00           C+0
HETATM   16  C   UNK     0      -5.133  -0.536  -0.340  0.00  0.00           C+0
HETATM   17  C   UNK     0      -5.285  -0.397   1.015  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.229   0.014   1.779  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.967   0.310   1.245  0.00  0.00           C+0
HETATM   20  O   UNK     0      -1.963   0.713   2.063  0.00  0.00           O+0
HETATM   21  N   UNK     0      -0.477   0.820  -0.356  0.00  0.00           N+0
HETATM   22  H   UNK     0       1.352  -2.441  -0.203  0.00  0.00           H+0
HETATM   23  H   UNK     0       0.486  -1.643   1.172  0.00  0.00           H+0
HETATM   24  H   UNK     0       2.160  -2.212   1.428  0.00  0.00           H+0
HETATM   25  H   UNK     0       3.640  -1.212   1.170  0.00  0.00           H+0
HETATM   26  H   UNK     0       2.879   2.391   2.074  0.00  0.00           H+0
HETATM   27  H   UNK     0       4.172  -1.885  -0.946  0.00  0.00           H+0
HETATM   28  H   UNK     0       5.126  -0.311  -0.774  0.00  0.00           H+0
HETATM   29  H   UNK     0       1.009  -1.077  -1.508  0.00  0.00           H+0
HETATM   30  H   UNK     0       1.222   1.953  -0.915  0.00  0.00           H+0
HETATM   31  H   UNK     0      -0.010   2.306  -2.854  0.00  0.00           H+0
HETATM   32  H   UNK     0       0.851   0.749  -3.356  0.00  0.00           H+0
HETATM   33  H   UNK     0      -3.809  -0.366  -1.944  0.00  0.00           H+0
HETATM   34  H   UNK     0      -5.952  -0.860  -0.975  0.00  0.00           H+0
HETATM   35  H   UNK     0      -6.261  -0.625   1.437  0.00  0.00           H+0
HETATM   36  H   UNK     0      -4.369   0.118   2.848  0.00  0.00           H+0
HETATM   37  H   UNK     0      -1.057   0.940   1.785  0.00  0.00           H+0
CONECT    1    2   22   23   24                                             
CONECT    2    1    3    9                                                  
CONECT    3    2    4    7   25                                             
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4   26                                                       
CONECT    7    3    8   27   28                                             
CONECT    8    7    9                                                       
CONECT    9    8   10    2   29                                             
CONECT   10    9   11   21   30                                             
CONECT   11   10   12   31   32                                             
CONECT   12   11   13                                                       
CONECT   13   12   14   21                                                  
CONECT   14   13   15   19                                                  
CONECT   15   14   16   33                                                  
CONECT   16   15   17   34                                                  
CONECT   17   16   18   35                                                  
CONECT   18   17   19   36                                                  
CONECT   19   18   20   14                                                  
CONECT   20   19   37                                                       
CONECT   21   13   10                                                       
CONECT   22    1                                                            
CONECT   23    1                                                            
CONECT   24    1                                                            
CONECT   25    3                                                            
CONECT   26    6                                                            
CONECT   27    7                                                            
CONECT   28    7                                                            
CONECT   29    9                                                            
CONECT   30   10                                                            
CONECT   31   11                                                            
CONECT   32   11                                                            
CONECT   33   15                                                            
CONECT   34   16                                                            
CONECT   35   17                                                            
CONECT   36   18                                                            
CONECT   37   20                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   78    0
END

RDKit          3D

37 39  0  0  0  0  0  0  0  0999 V2000
    1.4732   -1.7652    0.6743 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9877   -0.5112    0.2030 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3615   -0.3842    0.4276 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8369    0.9134    0.9177 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0536    1.1235    1.1011 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9496    1.9289    1.1872 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1517   -0.8033   -0.8211 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0576   -0.0036   -2.0704 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.5329   -0.1727   -1.0753 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6292    1.0277   -1.1904 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2049    1.2653   -2.6260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3494    0.2660   -2.5708 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5757    0.4375   -0.8119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7987    0.1751   -0.1154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8991   -0.2460   -0.8587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1330   -0.5356   -0.3404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2850   -0.3969    1.0153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2295    0.0140    1.7793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9673    0.3098    1.2454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9634    0.7128    2.0630 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4765    0.8195   -0.3561 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3520   -2.4412   -0.2032 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4862   -1.6429    1.1720 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1602   -2.2121    1.4283 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6400   -1.2117    1.1698 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8790    2.3912    2.0740 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1715   -1.8851   -0.9461 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1259   -0.3110   -0.7736 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0094   -1.0769   -1.5076 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2217    1.9533   -0.9146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0102    2.3063   -2.8538 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8507    0.7490   -3.3564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8090   -0.3663   -1.9440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9518   -0.8601   -0.9754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2613   -0.6245    1.4365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3687    0.1177    2.8476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0567    0.9395    1.7848 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
  4  5  2  0
  4  6  1  0
  3  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 13 21  2  0
  9  2  1  0
 21 10  1  0
 19 14  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  1
  6 26  1  0
  7 27  1  0
  7 28  1  0
  9 29  1  6
 10 30  1  1
 11 31  1  0
 11 32  1  0
 15 33  1  0
 16 34  1  0
 17 35  1  0
 18 36  1  0
 20 37  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(4'r,2''R,4''r)-2'-(2-hydroxyphenyl)-3''-methyl-2'',3'',4'',4',5'-hexahydro-[2,4']-bisthiazolyl-4''-carboxylic acid	ChEBI
(4'r,2''R,4''r)-2'-(2-hydroxyphenyl)-3''-methyl-2'',3'',4'',4',5'-hexahydro-[2,4']-bisthiazolyl-4''-carboxylate	Generator
Pyochelin	MeSH

Chemical Formula

C₁₄H₁₆N₂O₃S₂

Average Mass

324.4180 Da

Monoisotopic Mass

324.06023 Da

IUPAC Name

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

Traditional Name

(2R,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

CN1[C@H](SC[C@H]1C(O)=O)[C@H]1CSC(=N1)C1=CC=CC=C1O

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-GBIKHYSHSA-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
Burkholderia cepacia	LOTUS Database	35616633
Pseudomonas aeruginosa	NPAtlas	6794030

Species Where Detected

Species Name	Source	Reference
Pseudomonas akbaalia 8(C)X	KNApSAcK Database	22123792

Chemical Taxonomy

Description

This compound 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:67183 )

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	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	32.75 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

External Links

NPAtlas ID

NPA013123

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00015907

Chemspider ID

16738332

KEGG Compound ID

Not Available

BioCyc ID

CPD-9992

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5287441

PDB ID

Not Available

ChEBI ID

67183

Good Scents ID

Not Available

References

General References

Cox CD, Rinehart KL Jr, Moore ML, Cook JC Jr: Pyochelin: novel structure of an iron-chelating growth promoter for Pseudomonas aeruginosa. Proc Natl Acad Sci U S A. 1981 Jul;78(7):4256-60. doi: 10.1073/pnas.78.7.4256. [PubMed:6794030 ]
Crosa JH, Walsh CT: Genetics and assembly line enzymology of siderophore biosynthesis in bacteria. Microbiol Mol Biol Rev. 2002 Jun;66(2):223-49. doi: 10.1128/MMBR.66.2.223-249.2002. [PubMed:12040125 ]
Schlegel K, Taraz K, Budzikiewicz H: The stereoisomers of pyochelin, a siderophore of Pseudomonas aeruginosa. Biometals. 2004 Aug;17(4):409-14. doi: 10.1023/b:biom.0000029437.42633.73. [PubMed:15259361 ]

Showing NP-Card for Pyochelin (NP0021951)

MOL for NP0021951 (Pyochelin)

3D MOL for NP0021951 (Pyochelin)

3D SDF for NP0021951 (Pyochelin)

3D-SDF for NP0021951 (Pyochelin)

PDB for NP0021951 (Pyochelin)

3D PDB for NP0021951 (Pyochelin)

SMILES for NP0021951 (Pyochelin)

INCHI for NP0021951 (Pyochelin)

Structure for NP0021951 (Pyochelin)

3D Structure for NP0021951 (Pyochelin)