NP-MRD: Showing NP-Card for n-[7,11-bis({[(2,3-dihydroxyphenyl)(hydroxy)methylidene]amino})-2,6,10-trioxo-1,5,9-trioxacyclododecan-3-yl]-2,3-dihydroxybenzenecarboximidic acid (NP0287417)

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Record Information

Version

2.0

Created at

2022-09-09 16:28:49 UTC

Updated at

2022-09-09 16:28:50 UTC

NP-MRD ID

NP0287417

Secondary Accession Numbers

None

Natural Product Identification

Common Name

n-[7,11-bis({[(2,3-dihydroxyphenyl)(hydroxy)methylidene]amino})-2,6,10-trioxo-1,5,9-trioxacyclododecan-3-yl]-2,3-dihydroxybenzenecarboximidic acid

Description

n-[7,11-bis({[(2,3-dihydroxyphenyl)(hydroxy)methylidene]amino})-2,6,10-trioxo-1,5,9-trioxacyclododecan-3-yl]-2,3-dihydroxybenzenecarboximidic acid is found in Salmonella enterica and Streptomyces wadayamensis.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251512492D          

 48 51  0  0  0  0            999 V2000
   -2.1434    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5737    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2881    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2881   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0026   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5737   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5737   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -4.1250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  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  2  0  0  0  0
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 17 18  1  0  0  0  0
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 20 25  1  0  0  0  0
 25 26  1  0  0  0  0
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 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
 28 34  1  0  0  0  0
 34 35  1  0  0  0  0
 15 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 37 39  1  0  0  0  0
 39 40  2  0  0  0  0
 40 41  1  0  0  0  0
 41 42  2  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 43 45  2  0  0  0  0
 39 45  1  0  0  0  0
 45 46  1  0  0  0  0
  6 47  2  0  0  0  0
  2 47  1  0  0  0  0
 47 48  1  0  0  0  0
M  END

     RDKit          3D

 75 78  0  0  0  0  0  0  0  0999 V2000
   -1.3901    4.6317   -2.1582 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8403    4.7439   -0.9580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6662    3.5855   -0.1543 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0293    2.3838   -0.6723 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3979    2.2180   -0.1503 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2802    1.9808   -1.2335 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6011    0.7814   -1.7837 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2688    0.3731   -2.9221 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4452   -0.1646   -0.9548 C   0  0  2  0  0  0  0  0  0  0  0  0
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    4.5529   -0.8029   -2.0608 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.5277   -3.6363   -4.2584 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8594   -3.4137   -4.5303 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.7036   -1.3915   -3.1630 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.5598   -0.9744   -0.0482 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2782   -0.9789   -0.6592 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7948   -1.5285    0.0037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6662   -2.2150   -0.6371 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0160   -1.3769    1.4585 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0100   -2.4125    1.8347 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6857   -3.4840    2.6172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4303   -3.5091    2.9925 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4713   -4.5783    3.0972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8269   -5.5593    3.9103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4799   -6.6394    4.4212 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.4788   -5.9296    3.3993 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.2428    8.2319   -0.8110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3927    9.3356   -1.6249 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.8628    2.6266   -1.7726 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6873    3.2175    0.2758 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4978    1.4948    0.6547 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1725    0.4072   -0.3605 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6881   -1.8354   -2.2547 H   0  0  0  0  0  0  0  0  0  0  0  0
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 17 16  2  0
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 10  9  1  0
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 20 59  1  0
M  END


  Mrv1533004251512492D          

 48 51  0  0  0  0            999 V2000
   -2.1434    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.2868   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.4302   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.7158   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5737    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2881    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2881   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0026   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5737   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5737   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -4.1250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  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  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 10 23  1  0  0  0  0
 23 24  2  0  0  0  0
 20 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
 28 34  1  0  0  0  0
 34 35  1  0  0  0  0
 15 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 37 39  1  0  0  0  0
 39 40  2  0  0  0  0
 40 41  1  0  0  0  0
 41 42  2  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 43 45  2  0  0  0  0
 39 45  1  0  0  0  0
 45 46  1  0  0  0  0
  6 47  2  0  0  0  0
  2 47  1  0  0  0  0
 47 48  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0287417

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=CC(C(=O)NC2COC(=O)C(COC(=O)C(COC2=O)NC(=O)C2=CC=CC(O)=C2O)NC(=O)C2=CC=CC(O)=C2O)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C30H27N3O15/c34-19-7-1-4-13(22(19)37)25(40)31-16-10-46-29(44)18(33-27(42)15-6-3-9-21(36)24(15)39)12-48-30(45)17(11-47-28(16)43)32-26(41)14-5-2-8-20(35)23(14)38/h1-9,16-18,34-39H,10-12H2,(H,31,40)(H,32,41)(H,33,42)

> <INCHI_KEY>
SERBHKJMVBATSJ-UHFFFAOYSA-N

> <FORMULA>
C30H27N3O15

> <MOLECULAR_WEIGHT>
669.552

> <EXACT_MASS>
669.144217181

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
64.39858528030251

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-[7,11-bis(2,3-dihydroxybenzamido)-2,6,10-trioxo-1,5,9-trioxacyclododecan-3-yl]-2,3-dihydroxybenzamide

> <ALOGPS_LOGP>
1.62

> <JCHEM_LOGP>
2.2642207240000003

> <ALOGPS_LOGS>
-3.82

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.299561351870874

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.822545158892101

> <JCHEM_PKA_STRONGEST_BASIC>
-6.328992171650428

> <JCHEM_POLAR_SURFACE_AREA>
287.58

> <JCHEM_REFRACTIVITY>
157.87469999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.00e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
enterobactin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  O   UNK     0      -4.001   0.770   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667  -1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.001  -3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -6.668  -3.850   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -6.668  -5.390   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0      -8.002  -3.080   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      -9.336  -3.850   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -8.002  -6.160   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -9.336  -8.470   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0     -10.669  -6.160   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0     -12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0     -13.337  -6.160   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0     -13.337  -4.620   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0     -14.670  -3.850   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0     -12.003  -3.850   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0     -12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0     -10.669  -1.540   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -8.002  -1.540   0.000  0.00  0.00           O+0
HETATM   25  N   UNK     0     -13.337  -3.080   0.000  0.00  0.00           N+0
HETATM   26  C   UNK     0     -13.337  -1.540   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0     -12.003  -0.770   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0     -14.670  -0.770   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0     -14.670   0.770   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0     -16.004   1.540   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0     -17.338   0.770   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0     -17.338  -0.770   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0     -18.672  -1.540   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0     -16.004  -1.540   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0     -16.004  -3.080   0.000  0.00  0.00           O+0
HETATM   36  N   UNK     0     -10.669  -7.700   0.000  0.00  0.00           N+0
HETATM   37  C   UNK     0     -12.003  -8.470   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0     -13.337  -7.700   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0     -12.003 -10.010   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0     -13.337 -10.780   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0     -13.337 -12.320   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0     -12.003 -13.090   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0     -10.669 -12.320   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      -9.336 -13.090   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0     -10.669 -10.780   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0      -9.336 -10.010   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0      -5.335  -1.540   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0      -6.668  -0.770   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   47                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   47                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   23                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   36                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   25                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   10   24                                                  
CONECT   24   23                                                            
CONECT   25   20   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   34                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   28   35                                                  
CONECT   35   34                                                            
CONECT   36   15   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   40   45                                                  
CONECT   40   39   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42   44   45                                                  
CONECT   44   43                                                            
CONECT   45   43   39   46                                                  
CONECT   46   45                                                            
CONECT   47    6    2   48                                                  
CONECT   48   47                                                            
MASTER        0    0    0    0    0    0    0    0   48    0  102    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₂₇N₃O₁₅

Average Mass

669.5520 Da

Monoisotopic Mass

669.14422 Da

IUPAC Name

N-[7,11-bis(2,3-dihydroxybenzamido)-2,6,10-trioxo-1,5,9-trioxacyclododecan-3-yl]-2,3-dihydroxybenzamide

Traditional Name

enterobactin

CAS Registry Number

Not Available

SMILES

OC1=CC=CC(C(=O)NC2COC(=O)C(COC(=O)C(COC2=O)NC(=O)C2=CC=CC(O)=C2O)NC(=O)C2=CC=CC(O)=C2O)=C1O

InChI Identifier

InChI=1S/C30H27N3O15/c34-19-7-1-4-13(22(19)37)25(40)31-16-10-46-29(44)18(33-27(42)15-6-3-9-21(36)24(15)39)12-48-30(45)17(11-47-28(16)43)32-26(41)14-5-2-8-20(35)23(14)38/h1-9,16-18,34-39H,10-12H2,(H,31,40)(H,32,41)(H,33,42)

InChI Key

SERBHKJMVBATSJ-UHFFFAOYSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Salmonella enterica	LOTUS Database	35616633
Streptomyces wadayamensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclic depsipeptides. These are natural or synthetic compounds having sequences of amino and hydroxy carboxylic acid residues (usually α-amino and α-hydroxy acids) connected in a ring. The residues are commonly but not necessarily regularly alternating.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Peptidomimetics

Sub Class

Depsipeptides

Direct Parent

Cyclic depsipeptides

Alternative Parents

Substituents

Cyclic depsipeptide
Alpha-amino acid ester
N-acyl-alpha amino acid or derivatives
Macrolide
Macrolactam
Alpha-amino acid or derivatives
Salicylic acid or derivatives
Salicylamide
Benzamide
Benzoic acid or derivatives
Tricarboxylic acid or derivatives
Benzoyl
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Vinylogous acid
Carboxamide group
Carboxylic acid ester
Secondary carboxylic acid amide
Lactone
Organoheterocyclic compound
Carboxylic acid derivative
Oxacycle
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

a catecholate siderophore (ENTEROBACTIN )

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	1.62	ALOGPS
logP	2.26	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	7.82	ChemAxon
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	287.58 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	157.87 m³·mol⁻¹	ChemAxon
Polarizability	64.4 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Enterobactin

METLIN ID

Not Available

PubChem Compound

692

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for n-[7,11-bis({[(2,3-dihydroxyphenyl)(hydroxy)methylidene]amino})-2,6,10-trioxo-1,5,9-trioxacyclododecan-3-yl]-2,3-dihydroxybenzenecarboximidic acid (NP0287417)

MOL for NP0287417 (n-[7,11-bis({[(2,3-dihydroxyphenyl)(hydroxy)methylidene]amino})-2,6,10-trioxo-1,5,9-trioxacyclododecan-3-yl]-2,3-dihydroxybenzenecarboximidic acid)

3D MOL for NP0287417 (n-[7,11-bis({[(2,3-dihydroxyphenyl)(hydroxy)methylidene]amino})-2,6,10-trioxo-1,5,9-trioxacyclododecan-3-yl]-2,3-dihydroxybenzenecarboximidic acid)

3D SDF for NP0287417 (n-[7,11-bis({[(2,3-dihydroxyphenyl)(hydroxy)methylidene]amino})-2,6,10-trioxo-1,5,9-trioxacyclododecan-3-yl]-2,3-dihydroxybenzenecarboximidic acid)

3D-SDF for NP0287417 (n-[7,11-bis({[(2,3-dihydroxyphenyl)(hydroxy)methylidene]amino})-2,6,10-trioxo-1,5,9-trioxacyclododecan-3-yl]-2,3-dihydroxybenzenecarboximidic acid)

PDB for NP0287417 (n-[7,11-bis({[(2,3-dihydroxyphenyl)(hydroxy)methylidene]amino})-2,6,10-trioxo-1,5,9-trioxacyclododecan-3-yl]-2,3-dihydroxybenzenecarboximidic acid)

3D PDB for NP0287417 (n-[7,11-bis({[(2,3-dihydroxyphenyl)(hydroxy)methylidene]amino})-2,6,10-trioxo-1,5,9-trioxacyclododecan-3-yl]-2,3-dihydroxybenzenecarboximidic acid)

SMILES for NP0287417 (n-[7,11-bis({[(2,3-dihydroxyphenyl)(hydroxy)methylidene]amino})-2,6,10-trioxo-1,5,9-trioxacyclododecan-3-yl]-2,3-dihydroxybenzenecarboximidic acid)

INCHI for NP0287417 (n-[7,11-bis({[(2,3-dihydroxyphenyl)(hydroxy)methylidene]amino})-2,6,10-trioxo-1,5,9-trioxacyclododecan-3-yl]-2,3-dihydroxybenzenecarboximidic acid)

Structure for NP0287417 (n-[7,11-bis({[(2,3-dihydroxyphenyl)(hydroxy)methylidene]amino})-2,6,10-trioxo-1,5,9-trioxacyclododecan-3-yl]-2,3-dihydroxybenzenecarboximidic acid)

3D Structure for NP0287417 (n-[7,11-bis({[(2,3-dihydroxyphenyl)(hydroxy)methylidene]amino})-2,6,10-trioxo-1,5,9-trioxacyclododecan-3-yl]-2,3-dihydroxybenzenecarboximidic acid)