NP-MRD: Showing NP-Card for Staphyloferrin A (NP0011870)

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Record Information

Version

2.0

Created at

2021-01-05 21:25:39 UTC

Updated at

2021-07-15 17:10:11 UTC

NP-MRD ID

NP0011870

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Staphyloferrin A

Provided By

NPAtlas

Description

Staphyloferrin A 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. Staphyloferrin A is found in Staphylococcus and Staphylococcus hyicus. Staphyloferrin A was first documented in 1990 (PMID: 2379505). Based on a literature review a small amount of articles have been published on staphyloferrin A (PMID: 2139423) (PMID: 23575952) (PMID: 24500249) (PMID: 25050909).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242116593D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306242116593D          

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    6.5529    1.4740   -1.3335 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1681   -0.1886   -0.9779 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2428    1.5862    1.3867 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0296   -1.2237   -1.5867 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3650    0.4364   -1.9438 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5989   -1.3562   -2.6033 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5926   -2.3832   -2.2073 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0716   -2.6241   -0.5301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0570   -1.2733   -0.7562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2477   -0.0645   -1.7494 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0485    0.7890    0.1195 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4029   -0.5386    1.2268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0497    1.5405   -0.3710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2386   -0.5479    1.4796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2538   -1.5871   -0.0948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8860   -0.4900    1.1616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2832   -1.3640   -2.3925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5280   -2.0631   -1.0453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5435   -0.6786   -1.6084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8993   -0.7623    2.4399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4174    2.2408    0.2603 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3636    2.1195    1.9382 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2800   -2.0988    0.7347 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 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  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 19 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 14 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
  5 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
  3 34  1  0  0  0  0
  4 35  1  0  0  0  0
  4 36  1  0  0  0  0
  6 37  1  0  0  0  0
  7 38  1  0  0  0  0
  7 39  1  0  0  0  0
 10 40  1  0  0  0  0
 11 41  1  0  0  0  0
 11 42  1  0  0  0  0
 12 43  1  0  0  0  0
 12 44  1  0  0  0  0
 13 45  1  0  0  0  0
 13 46  1  0  0  0  0
 14 47  1  6  0  0  0
 15 48  1  0  0  0  0
 18 49  1  0  0  0  0
 18 50  1  0  0  0  0
 20 51  1  0  0  0  0
 21 52  1  0  0  0  0
 21 53  1  0  0  0  0
 24 54  1  0  0  0  0
 27 55  1  0  0  0  0
 30 56  1  0  0  0  0
 33 57  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0011870

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C17H24N2O14/c20-9(4-16(32,14(28)29)6-11(22)23)18-3-1-2-8(13(26)27)19-10(21)5-17(33,15(30)31)7-12(24)25/h8,32-33H,1-7H2,(H,18,20)(H,19,21)(H,22,23)(H,24,25)(H,26,27)(H,28,29)(H,30,31)/t8-,16+,17-/m1/s1

> <INCHI_KEY>
VJSIXUQLTJCRCS-PJPOUAMNSA-N

> <FORMULA>
C17H24N2O14

> <MOLECULAR_WEIGHT>
480.379

> <EXACT_MASS>
480.122753461

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
42.9125461214507

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-({[(4R)-4-carboxy-4-[(3R)-3,4-dicarboxy-3-hydroxybutanamido]butyl]carbamoyl}methyl)-2-hydroxybutanedioic acid

> <ALOGPS_LOGP>
-2.00

> <JCHEM_LOGP>
-3.7161709373333336

> <ALOGPS_LOGS>
-1.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-5

> <JCHEM_PKA>
3.4201718373323877

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.911673864595848

> <JCHEM_PKA_STRONGEST_BASIC>
-4.169325327993115

> <JCHEM_POLAR_SURFACE_AREA>
285.15999999999997

> <JCHEM_REFRACTIVITY>
98.05649999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
16

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.08e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-({[(4R)-4-carboxy-4-[(3R)-3,4-dicarboxy-3-hydroxybutanamido]butyl]carbamoyl}methyl)-2-hydroxybutanedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 57 56  0  0  0  0  0  0  0  0999 V2000
    7.8303    0.5451    1.4828 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5687    1.2564    0.4796 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1478    2.5164    0.4033 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6669    0.7201   -0.5523 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3470    0.2284    0.0099 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6464    1.2584    0.6471 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5463   -0.3027   -1.1510 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2016   -0.8002   -0.6566 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0074   -0.7092    0.5626 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2709   -1.3218   -1.5734 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9738   -1.7963   -1.3042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0358   -0.8011   -0.9056 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2549   -0.0044    0.2902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9882    0.9111    0.5114 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1831    0.1542    0.7010 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3337    0.2944   -0.1186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3525    1.1260   -1.0828 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5503   -0.5211    0.1198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6304   -0.1535   -0.8801 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0770   -0.4163   -2.1657 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8493   -1.0124   -0.7979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5509   -1.0059    0.4784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5979   -1.7303    0.5639 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1768   -0.2871    1.5831 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9207    1.3010   -0.8634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6988    2.0595   -1.8475 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4630    1.9172    0.2589 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6375    1.7773    1.6581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3572    1.8115    2.6885 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5027    2.5787    1.6250 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5748   -0.8602    0.9816 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1535   -0.7665    2.1694 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2729   -2.0135    0.5677 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1253    3.1046    1.2507 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5529    1.4740   -1.3335 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1681   -0.1886   -0.9779 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2428    1.5862    1.3867 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0296   -1.2237   -1.5867 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3650    0.4364   -1.9438 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5989   -1.3562   -2.6033 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5926   -2.3832   -2.2073 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0716   -2.6241   -0.5301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0570   -1.2733   -0.7562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2477   -0.0645   -1.7494 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0485    0.7890    0.1195 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4029   -0.5386    1.2268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0497    1.5405   -0.3710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2386   -0.5479    1.4796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2538   -1.5871   -0.0948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8860   -0.4900    1.1616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2832   -1.3640   -2.3925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5280   -2.0631   -1.0453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5435   -0.6786   -1.6084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8993   -0.7623    2.4399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4174    2.2408    0.2603 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3636    2.1195    1.9382 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2800   -2.0988    0.7347 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  1
  5  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  6
 19 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 19 25  1  0
 25 26  2  0
 25 27  1  0
 14 28  1  0
 28 29  2  0
 28 30  1  0
  5 31  1  0
 31 32  2  0
 31 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
  6 37  1  0
  7 38  1  0
  7 39  1  0
 10 40  1  0
 11 41  1  0
 11 42  1  0
 12 43  1  0
 12 44  1  0
 13 45  1  0
 13 46  1  0
 14 47  1  6
 15 48  1  0
 18 49  1  0
 18 50  1  0
 20 51  1  0
 21 52  1  0
 21 53  1  0
 24 54  1  0
 27 55  1  0
 30 56  1  0
 33 57  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  O   UNK     0       7.830   0.545   1.483  0.00  0.00           O+0
HETATM    2  C   UNK     0       7.569   1.256   0.480  0.00  0.00           C+0
HETATM    3  O   UNK     0       8.148   2.516   0.403  0.00  0.00           O+0
HETATM    4  C   UNK     0       6.667   0.720  -0.552  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.347   0.228   0.010  0.00  0.00           C+0
HETATM    6  O   UNK     0       4.646   1.258   0.647  0.00  0.00           O+0
HETATM    7  C   UNK     0       4.546  -0.303  -1.151  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.202  -0.800  -0.657  0.00  0.00           C+0
HETATM    9  O   UNK     0       3.007  -0.709   0.563  0.00  0.00           O+0
HETATM   10  N   UNK     0       2.271  -1.322  -1.573  0.00  0.00           N+0
HETATM   11  C   UNK     0       0.974  -1.796  -1.304  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.036  -0.801  -0.906  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.255  -0.004   0.290  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.988   0.911   0.511  0.00  0.00           C+0
HETATM   15  N   UNK     0      -2.183   0.154   0.701  0.00  0.00           N+0
HETATM   16  C   UNK     0      -3.334   0.294  -0.119  0.00  0.00           C+0
HETATM   17  O   UNK     0      -3.353   1.126  -1.083  0.00  0.00           O+0
HETATM   18  C   UNK     0      -4.550  -0.521   0.120  0.00  0.00           C+0
HETATM   19  C   UNK     0      -5.630  -0.154  -0.880  0.00  0.00           C+0
HETATM   20  O   UNK     0      -5.077  -0.416  -2.166  0.00  0.00           O+0
HETATM   21  C   UNK     0      -6.849  -1.012  -0.798  0.00  0.00           C+0
HETATM   22  C   UNK     0      -7.551  -1.006   0.478  0.00  0.00           C+0
HETATM   23  O   UNK     0      -8.598  -1.730   0.564  0.00  0.00           O+0
HETATM   24  O   UNK     0      -7.177  -0.287   1.583  0.00  0.00           O+0
HETATM   25  C   UNK     0      -5.921   1.301  -0.863  0.00  0.00           C+0
HETATM   26  O   UNK     0      -5.699   2.059  -1.847  0.00  0.00           O+0
HETATM   27  O   UNK     0      -6.463   1.917   0.259  0.00  0.00           O+0
HETATM   28  C   UNK     0      -0.638   1.777   1.658  0.00  0.00           C+0
HETATM   29  O   UNK     0      -1.357   1.812   2.688  0.00  0.00           O+0
HETATM   30  O   UNK     0       0.503   2.579   1.625  0.00  0.00           O+0
HETATM   31  C   UNK     0       5.575  -0.860   0.982  0.00  0.00           C+0
HETATM   32  O   UNK     0       5.154  -0.767   2.169  0.00  0.00           O+0
HETATM   33  O   UNK     0       6.273  -2.014   0.568  0.00  0.00           O+0
HETATM   34  H   UNK     0       8.125   3.105   1.251  0.00  0.00           H+0
HETATM   35  H   UNK     0       6.553   1.474  -1.333  0.00  0.00           H+0
HETATM   36  H   UNK     0       7.168  -0.189  -0.978  0.00  0.00           H+0
HETATM   37  H   UNK     0       5.243   1.586   1.387  0.00  0.00           H+0
HETATM   38  H   UNK     0       5.030  -1.224  -1.587  0.00  0.00           H+0
HETATM   39  H   UNK     0       4.365   0.436  -1.944  0.00  0.00           H+0
HETATM   40  H   UNK     0       2.599  -1.356  -2.603  0.00  0.00           H+0
HETATM   41  H   UNK     0       0.593  -2.383  -2.207  0.00  0.00           H+0
HETATM   42  H   UNK     0       1.072  -2.624  -0.530  0.00  0.00           H+0
HETATM   43  H   UNK     0      -1.057  -1.273  -0.756  0.00  0.00           H+0
HETATM   44  H   UNK     0      -0.248  -0.065  -1.749  0.00  0.00           H+0
HETATM   45  H   UNK     0       1.048   0.789   0.120  0.00  0.00           H+0
HETATM   46  H   UNK     0       0.403  -0.539   1.227  0.00  0.00           H+0
HETATM   47  H   UNK     0      -1.050   1.541  -0.371  0.00  0.00           H+0
HETATM   48  H   UNK     0      -2.239  -0.548   1.480  0.00  0.00           H+0
HETATM   49  H   UNK     0      -4.254  -1.587  -0.095  0.00  0.00           H+0
HETATM   50  H   UNK     0      -4.886  -0.490   1.162  0.00  0.00           H+0
HETATM   51  H   UNK     0      -5.283  -1.364  -2.393  0.00  0.00           H+0
HETATM   52  H   UNK     0      -6.528  -2.063  -1.045  0.00  0.00           H+0
HETATM   53  H   UNK     0      -7.543  -0.679  -1.608  0.00  0.00           H+0
HETATM   54  H   UNK     0      -6.899  -0.762   2.440  0.00  0.00           H+0
HETATM   55  H   UNK     0      -7.417   2.241   0.260  0.00  0.00           H+0
HETATM   56  H   UNK     0       1.364   2.119   1.938  0.00  0.00           H+0
HETATM   57  H   UNK     0       7.280  -2.099   0.735  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2   34                                                       
CONECT    4    2    5   35   36                                             
CONECT    5    4    6    7   31                                             
CONECT    6    5   37                                                       
CONECT    7    5    8   38   39                                             
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   40                                                  
CONECT   11   10   12   41   42                                             
CONECT   12   11   13   43   44                                             
CONECT   13   12   14   45   46                                             
CONECT   14   13   15   28   47                                             
CONECT   15   14   16   48                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   49   50                                             
CONECT   19   18   20   21   25                                             
CONECT   20   19   51                                                       
CONECT   21   19   22   52   53                                             
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   54                                                       
CONECT   25   19   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   55                                                       
CONECT   28   14   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   56                                                       
CONECT   31    5   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   57                                                       
CONECT   34    3                                                            
CONECT   35    4                                                            
CONECT   36    4                                                            
CONECT   37    6                                                            
CONECT   38    7                                                            
CONECT   39    7                                                            
CONECT   40   10                                                            
CONECT   41   11                                                            
CONECT   42   11                                                            
CONECT   43   12                                                            
CONECT   44   12                                                            
CONECT   45   13                                                            
CONECT   46   13                                                            
CONECT   47   14                                                            
CONECT   48   15                                                            
CONECT   49   18                                                            
CONECT   50   18                                                            
CONECT   51   20                                                            
CONECT   52   21                                                            
CONECT   53   21                                                            
CONECT   54   24                                                            
CONECT   55   27                                                            
CONECT   56   30                                                            
CONECT   57   33                                                            
MASTER        0    0    0    0    0    0    0    0   57    0  112    0
END

RDKit          3D

57 56  0  0  0  0  0  0  0  0999 V2000
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   -0.6375    1.7773    1.6581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3572    1.8115    2.6885 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5027    2.5787    1.6250 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5748   -0.8602    0.9816 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1535   -0.7665    2.1694 O   0  0  0  0  0  0  0  0  0  0  0  0
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    7.1681   -0.1886   -0.9779 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2428    1.5862    1.3867 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0296   -1.2237   -1.5867 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3650    0.4364   -1.9438 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5989   -1.3562   -2.6033 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5926   -2.3832   -2.2073 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0716   -2.6241   -0.5301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0570   -1.2733   -0.7562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2477   -0.0645   -1.7494 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0485    0.7890    0.1195 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4029   -0.5386    1.2268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0497    1.5405   -0.3710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2386   -0.5479    1.4796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2538   -1.5871   -0.0948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8860   -0.4900    1.1616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2832   -1.3640   -2.3925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5280   -2.0631   -1.0453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5435   -0.6786   -1.6084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8993   -0.7623    2.4399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4174    2.2408    0.2603 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3636    2.1195    1.9382 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2800   -2.0988    0.7347 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  1
  5  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
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 14 28  1  0
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  5 31  1  0
 31 32  2  0
 31 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
  6 37  1  0
  7 38  1  0
  7 39  1  0
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 27 55  1  0
 30 56  1  0
 33 57  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
N(2),N(5)-Di-(1-oxo-3-hydroxy-3,4-dicarboxybutyl)-D-ornithine	ChEBI
N(2),N(5)-Di-(1-oxo-3-hydroxy-3,4-dicarboxylbutyl)ornithine	MeSH

Chemical Formula

C₁₇H₂₄N₂O₁₄

Average Mass

480.3790 Da

Monoisotopic Mass

480.12275 Da

IUPAC Name

(2S)-2-({[(4R)-4-carboxy-4-[(3R)-3,4-dicarboxy-3-hydroxybutanamido]butyl]carbamoyl}methyl)-2-hydroxybutanedioic acid

Traditional Name

(2S)-2-({[(4R)-4-carboxy-4-[(3R)-3,4-dicarboxy-3-hydroxybutanamido]butyl]carbamoyl}methyl)-2-hydroxybutanedioic acid

CAS Registry Number

Not Available

SMILES

OC(=O)CC(O)(CC(=O)NCCC[C@@H](NC(=O)CC(O)(CC(O)=O)C(O)=O)C(O)=O)C(O)=O

InChI Identifier

InChI=1S/C17H24N2O14/c20-9(4-16(32,14(28)29)6-11(22)23)18-3-1-2-8(13(26)27)19-10(21)5-17(33,15(30)31)7-12(24)25/h8,32-33H,1-7H2,(H,18,20)(H,19,21)(H,22,23)(H,24,25)(H,26,27)(H,28,29)(H,30,31)/t8-,16?,17?/m1/s1

InChI Key

VJSIXUQLTJCRCS-PJPOUAMNSA-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
Staphylococcus	NPAtlas	2379505
Staphylococcus hyicus	LOTUS Database	35616633

Chemical Taxonomy

Classification

Not classified

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	-2	ALOGPS
logP	-3.7	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	2.91	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	-5	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	285.16 Å²	ChemAxon
Rotatable Bond Count	16	ChemAxon
Refractivity	98.06 m³·mol⁻¹	ChemAxon
Polarizability	42.91 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA024679

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

34449072

KEGG Compound ID

Not Available

BioCyc ID

CPD-12589

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

46926095

PDB ID

Not Available

ChEBI ID

84711

Good Scents ID

Not Available

References

General References

Konetschny-Rapp S, Jung G, Meiwes J, Zahner H: Staphyloferrin A: a structurally new siderophore from staphylococci. Eur J Biochem. 1990 Jul 20;191(1):65-74. doi: 10.1111/j.1432-1033.1990.tb19094.x. [PubMed:2379505 ]
Meiwes J, Fiedler HP, Haag H, Zahner H, Konetschny-Rapp S, Jung G: Isolation and characterization of staphyloferrin A, a compound with siderophore activity from Staphylococcus hyicus DSM 20459. FEMS Microbiol Lett. 1990 Jan 15;55(1-2):201-5. doi: 10.1111/j.1574-6968.1990.tb13863.x. [PubMed:2139423 ]
Milner SJ, Seve A, Snelling AM, Thomas GH, Kerr KG, Routledge A, Duhme-Klair AK: Staphyloferrin A as siderophore-component in fluoroquinolone-based Trojan horse antibiotics. Org Biomol Chem. 2013 Jun 7;11(21):3461-8. doi: 10.1039/c3ob40162f. Epub 2013 Apr 11. [PubMed:23575952 ]
Pandey RK, Jarvis GG, Low PS: Chemical synthesis of staphyloferrin A and its application for Staphylococcus aureus detection. Org Biomol Chem. 2014 Mar 21;12(11):1707-10. doi: 10.1039/c3ob41230j. [PubMed:24500249 ]
Cooper JD, Hannauer M, Marolda CL, Briere LA, Heinrichs DE: Identification of a positively charged platform in Staphylococcus aureus HtsA that is essential for ferric staphyloferrin A transport. Biochemistry. 2014 Aug 12;53(31):5060-9. doi: 10.1021/bi500729h. Epub 2014 Jul 28. [PubMed:25050909 ]

Showing NP-Card for Staphyloferrin A (NP0011870)

MOL for NP0011870 (Staphyloferrin A)

3D MOL for NP0011870 (Staphyloferrin A)

3D SDF for NP0011870 (Staphyloferrin A)

3D-SDF for NP0011870 (Staphyloferrin A)

PDB for NP0011870 (Staphyloferrin A)

3D PDB for NP0011870 (Staphyloferrin A)

SMILES for NP0011870 (Staphyloferrin A)

INCHI for NP0011870 (Staphyloferrin A)

Structure for NP0011870 (Staphyloferrin A)

3D Structure for NP0011870 (Staphyloferrin A)