NP-MRD: Showing NP-Card for n-[(2r,3s,6r,7s,10r,11s)-7,11-bis[(2-{[(2,3-dihydroxyphenyl)(hydroxy)methylidene]amino}-1-hydroxyethylidene)amino]-2,6,10-trimethyl-4,8,12-trioxo-1,5,9-trioxacyclododecan-3-yl]-2-{[(2,3-dihydroxyphenyl)(hydroxy)methylidene]amino}ethanimidic acid (NP0168504)

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Record Information

Version

2.0

Created at

2022-09-03 04:19:29 UTC

Updated at

2022-09-03 04:19:30 UTC

NP-MRD ID

NP0168504

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Description

n-[(2r,3s,6r,7s,10r,11s)-7,11-bis[(2-{[(2,3-dihydroxyphenyl)(hydroxy)methylidene]amino}-1-hydroxyethylidene)amino]-2,6,10-trimethyl-4,8,12-trioxo-1,5,9-trioxacyclododecan-3-yl]-2-{[(2,3-dihydroxyphenyl)(hydroxy)methylidene]amino}ethanimidic acid is found in Apis cerana, Bacillus velezensis and Corynebacterium glutamicum. n-[(2r,3s,6r,7s,10r,11s)-7,11-bis[(2-{[(2,3-dihydroxyphenyl)(hydroxy)methylidene]amino}-1-hydroxyethylidene)amino]-2,6,10-trimethyl-4,8,12-trioxo-1,5,9-trioxacyclododecan-3-yl]-2-{[(2,3-dihydroxyphenyl)(hydroxy)methylidene]amino}ethanimidic acid was first documented in 2001 (PMID: 11112781).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533005191511422D          

 63 66  0  0  0  0            999 V2000
   -1.0898    1.1242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2901    1.2392    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4436    0.8622    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4839    0.0382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2795   -0.2829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2095   -0.4087    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1431   -1.2805    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5102   -1.8072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1704   -1.3125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6096   -2.6357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4389   -2.9112    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4767   -3.7424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7817   -4.1869    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2092   -4.1220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9042   -3.6775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6366   -4.0571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6741   -4.8812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9791   -5.3258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0166   -6.1499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2467   -4.9462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5517   -5.3907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9432   -0.0316    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3898    0.7101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6367   -0.4785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3705   -0.1014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0648   -0.5970    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4108    0.7225    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2493    0.9902    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5866    1.7597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7828    1.9455    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1776    2.3931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0505    3.2355    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8044    3.6609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5148    3.2414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8126    4.4859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5311    4.8913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5393    5.7162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8289    6.1358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1104    5.7304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4000    6.1499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1022    4.9054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3837    4.5000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7174    1.1694    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8233    0.6896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7577    1.9934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0642    2.4403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1421    3.3101    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3304    2.0633    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3143    2.6573    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1445    2.5347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9180    1.7415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9864    2.7456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6743    2.2411    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3961    2.6573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3965    3.4823    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1103    2.2444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8250    2.6565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5393    2.2436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5388    1.4186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8241    1.0065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8237    0.1815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1099    1.4194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3952    1.0073    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  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  1  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  2  0  0  0  0
 12 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  1  0  0  0  0
 18 20  2  0  0  0  0
 14 20  1  0  0  0  0
 20 21  1  0  0  0  0
  6 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  1  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 39 41  2  0  0  0  0
 35 41  1  0  0  0  0
 41 42  1  0  0  0  0
 27 43  1  0  0  0  0
 43 44  1  6  0  0  0
 43 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  2  0  0  0  0
 46 48  1  0  0  0  0
  2 48  1  0  0  0  0
 48 49  1  1  0  0  0
 49 50  1  0  0  0  0
 50 51  2  0  0  0  0
 50 52  1  0  0  0  0
 52 53  1  0  0  0  0
 53 54  1  0  0  0  0
 54 55  2  0  0  0  0
 54 56  1  0  0  0  0
 56 57  2  0  0  0  0
 57 58  1  0  0  0  0
 58 59  2  0  0  0  0
 59 60  1  0  0  0  0
 60 61  1  0  0  0  0
 60 62  2  0  0  0  0
 56 62  1  0  0  0  0
 62 63  1  0  0  0  0
M  END

     RDKit          3D

105108  0  0  0  0  0  0  0  0999 V2000
    2.0366    0.6930    3.5220 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1239    1.0244    2.0669 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1345   -0.1498    1.3325 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8634   -0.6950    0.3594 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9788   -1.3584    0.5130 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4695   -0.6062   -1.0597 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2645   -1.5893   -1.8140 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5009   -1.5332   -3.1976 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0186   -0.6020   -3.8742 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3043   -2.5665   -3.8806 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8823   -3.5018   -2.9137 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8330   -3.0598   -1.9686 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1326   -1.8087   -2.0798 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4709   -3.8173   -0.9398 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3780   -3.1400   -0.0936 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0219   -3.7572    0.9417 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8114   -5.0853    1.2072 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9182   -5.7425    0.3640 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7328   -7.1024    0.6757 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2659   -5.1339   -0.6783 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4164   -5.8616   -1.4393 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0127   -1.0268   -1.2979 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4735   -1.8763   -0.1707 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1786    0.0184   -1.5561 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9354    0.4178   -2.0992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2926    0.4289   -3.3584 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0756    0.9715   -1.2888 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0252   -0.1330   -1.0036 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1822   -0.2550   -1.4386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4153    0.9686   -2.2662 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5314   -0.8787   -1.6851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5201   -2.0616   -0.8211 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6758   -2.8670   -0.8019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6902   -2.5971   -1.5116 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7057   -4.0512    0.0713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6455   -4.3760    0.8590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7239   -5.5293    1.6652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8569   -6.2872    1.6341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9054   -5.9508    0.8472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0657   -6.7208    0.8103 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8895   -4.8069    0.0164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8972   -4.4493   -0.7571 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5650    1.7383   -0.1685 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4682    2.9197    0.2180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2322    1.0646    1.0223 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.1760    7.5135    1.4573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2750    8.1730    1.0018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5619    8.2570   -0.3467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7112    7.6589   -1.1995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9337    7.7042   -2.5679 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5598    6.9633   -0.7612 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2212    6.3990   -1.7211 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3685   -0.2023    3.6896 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5687    1.4805    4.1548 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0097    0.4451    3.9886 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.5204    0.3830   -1.5120 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.1120   -2.1352   -4.4624 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6353   -3.1601   -4.5392 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5797   -4.4891   -2.9535 H   0  0  0  0  0  0  0  0  0  0  0  0
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    8.7185   -3.1994    1.5700 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.5169   -0.8336   -0.3126 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.7057   -2.3092   -0.2443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7369   -3.7916    0.9040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8762   -5.7837    2.2853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9439   -7.2015    2.2614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8173   -6.4380    0.2295 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1533005191511422D          

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M  END
> <DATABASE_ID>
NP0168504

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1OC(=O)[C@@H](NC(=O)CNC(=O)C2=CC=CC(O)=C2O)[C@@H](C)OC(=O)[C@@H](NC(=O)CNC(=O)C2=CC=CC(O)=C2O)[C@@H](C)OC(=O)[C@H]1NC(=O)CNC(=O)C1=CC=CC(O)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C39H42N6O18/c1-16-28(43-25(49)13-40-34(55)19-7-4-10-22(46)31(19)52)37(58)62-18(3)30(45-27(51)15-42-36(57)21-9-6-12-24(48)33(21)54)39(60)63-17(2)29(38(59)61-16)44-26(50)14-41-35(56)20-8-5-11-23(47)32(20)53/h4-12,16-18,28-30,46-48,52-54H,13-15H2,1-3H3,(H,40,55)(H,41,56)(H,42,57)(H,43,49)(H,44,50)(H,45,51)/t16-,17-,18-,28+,29+,30+/m1/s1

> <INCHI_KEY>
RCQTVEFBFUNTGM-BDVHUIKKSA-N

> <FORMULA>
C39H42N6O18

> <MOLECULAR_WEIGHT>
882.789

> <EXACT_MASS>
882.255558536

> <JCHEM_ACCEPTOR_COUNT>
15

> <JCHEM_ATOM_COUNT>
105

> <JCHEM_AVERAGE_POLARIZABILITY>
85.33643455827867

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
12

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-[(2R,3S,6R,7S,10R,11S)-7,11-bis({2-[(2,3-dihydroxyphenyl)formamido]acetamido})-2,6,10-trimethyl-4,8,12-trioxo-1,5,9-trioxacyclododecan-3-yl]-2-[(2,3-dihydroxyphenyl)formamido]acetamide

> <ALOGPS_LOGP>
1.86

> <JCHEM_LOGP>
0.19809607899999981

> <ALOGPS_LOGS>
-4.12

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.303234079393881

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.826383682203321

> <JCHEM_PKA_STRONGEST_BASIC>
-6.328959602365413

> <JCHEM_POLAR_SURFACE_AREA>
374.87999999999994

> <JCHEM_REFRACTIVITY>
209.54160000000007

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.73e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-[(2R,3S,6R,7S,10R,11S)-7,11-bis({2-[(2,3-dihydroxyphenyl)formamido]acetamido})-2,6,10-trimethyl-4,8,12-trioxo-1,5,9-trioxacyclododecan-3-yl]-2-[(2,3-dihydroxyphenyl)formamido]acetamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-MAY-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-MAY-15         0                                  
HETATM    1  C   UNK     0      -2.034   2.099   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.542   2.313   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.828   1.609   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       0.903   0.071   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.388  -0.528   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -0.391  -0.763   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      -0.267  -2.390   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       0.952  -3.373   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.185  -2.450   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.138  -4.920   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       2.686  -5.434   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       2.757  -6.986   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.459  -7.816   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.124  -7.694   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.421  -6.865   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.788  -7.573   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.858  -9.112   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.561  -9.941   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       5.631 -11.480   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.194  -9.233   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.897 -10.063   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -1.761  -0.059   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.594   1.326   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -3.055  -0.893   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -4.425  -0.189   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -5.721  -1.114   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -4.500   1.349   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0      -6.065   1.848   0.000  0.00  0.00           N+0
HETATM   29  C   UNK     0      -6.695   3.285   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -5.195   3.632   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -7.798   4.467   0.000  0.00  0.00           C+0
HETATM   32  N   UNK     0      -7.561   6.040   0.000  0.00  0.00           N+0
HETATM   33  C   UNK     0      -8.968   6.834   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0     -10.294   6.051   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -8.984   8.374   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0     -10.325   9.130   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0     -10.340  10.670   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -9.014  11.453   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -7.673  10.697   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      -6.347  11.480   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      -7.657   9.157   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      -6.316   8.400   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      -3.206   2.183   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      -1.537   1.287   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0      -3.281   3.721   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0      -1.987   4.555   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0      -2.132   6.179   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0      -0.617   3.851   0.000  0.00  0.00           C+0
HETATM   49  N   UNK     0       0.587   4.960   0.000  0.00  0.00           N+0
HETATM   50  C   UNK     0       2.136   4.731   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0       1.714   3.251   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0       3.708   5.125   0.000  0.00  0.00           C+0
HETATM   53  N   UNK     0       4.992   4.183   0.000  0.00  0.00           N+0
HETATM   54  C   UNK     0       6.339   4.960   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0       6.340   6.500   0.000  0.00  0.00           O+0
HETATM   56  C   UNK     0       7.673   4.190   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0       9.007   4.959   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      10.340   4.188   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0      10.339   2.648   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0       9.005   1.879   0.000  0.00  0.00           C+0
HETATM   61  O   UNK     0       9.004   0.339   0.000  0.00  0.00           O+0
HETATM   62  C   UNK     0       7.672   2.650   0.000  0.00  0.00           C+0
HETATM   63  O   UNK     0       6.338   1.880   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   48                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   22                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   20                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   14   21                                                  
CONECT   21   20                                                            
CONECT   22    6   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   43                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36   41                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   35   42                                                  
CONECT   42   41                                                            
CONECT   43   27   44   45                                                  
CONECT   44   43                                                            
CONECT   45   43   46                                                       
CONECT   46   45   47   48                                                  
CONECT   47   46                                                            
CONECT   48   46    2   49                                                  
CONECT   49   48   50                                                       
CONECT   50   49   51   52                                                  
CONECT   51   50                                                            
CONECT   52   50   53                                                       
CONECT   53   52   54                                                       
CONECT   54   53   55   56                                                  
CONECT   55   54                                                            
CONECT   56   54   57   62                                                  
CONECT   57   56   58                                                       
CONECT   58   57   59                                                       
CONECT   59   58   60                                                       
CONECT   60   59   61   62                                                  
CONECT   61   60                                                            
CONECT   62   60   56   63                                                  
CONECT   63   62                                                            
MASTER        0    0    0    0    0    0    0    0   63    0  132    0
END

View in JSmol

Synonyms

Value	Source
2,3-Dihydroxybenzoate-glycine-threonine trimeric ester	ChEBI
2,3-Dihydroxybenzoic acid-glycine-threonine trimeric ester	Generator

Chemical Formula

C₃₉H₄₂N₆O₁₈

Average Mass

882.7890 Da

Monoisotopic Mass

882.25556 Da

IUPAC Name

N-[(2R,3S,6R,7S,10R,11S)-7,11-bis({2-[(2,3-dihydroxyphenyl)formamido]acetamido})-2,6,10-trimethyl-4,8,12-trioxo-1,5,9-trioxacyclododecan-3-yl]-2-[(2,3-dihydroxyphenyl)formamido]acetamide

Traditional Name

N-[(2R,3S,6R,7S,10R,11S)-7,11-bis({2-[(2,3-dihydroxyphenyl)formamido]acetamido})-2,6,10-trimethyl-4,8,12-trioxo-1,5,9-trioxacyclododecan-3-yl]-2-[(2,3-dihydroxyphenyl)formamido]acetamide

CAS Registry Number

Not Available

SMILES

C[C@H]1OC(=O)[C@@H](NC(=O)CNC(=O)C2=CC=CC(O)=C2O)[C@@H](C)OC(=O)[C@@H](NC(=O)CNC(=O)C2=CC=CC(O)=C2O)[C@@H](C)OC(=O)[C@H]1NC(=O)CNC(=O)C1=CC=CC(O)=C1O

InChI Identifier

InChI=1S/C39H42N6O18/c1-16-28(43-25(49)13-40-34(55)19-7-4-10-22(46)31(19)52)37(58)62-18(3)30(45-27(51)15-42-36(57)21-9-6-12-24(48)33(21)54)39(60)63-17(2)29(38(59)61-16)44-26(50)14-41-35(56)20-8-5-11-23(47)32(20)53/h4-12,16-18,28-30,46-48,52-54H,13-15H2,1-3H3,(H,40,55)(H,41,56)(H,42,57)(H,43,49)(H,44,50)(H,45,51)/t16-,17-,18-,28+,29+,30+/m1/s1

InChI Key

RCQTVEFBFUNTGM-BDVHUIKKSA-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
Apis cerana	LOTUS Database	35616633
Bacillus velezensis	LOTUS Database	35616633
Corynebacterium glutamicum	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
Macrolactam
Macrolide
N-acyl-alpha amino acid or derivatives
Alpha-amino acid or derivatives
Tricarboxylic acid or derivatives
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Carboxylic acid ester
Lactone
Carboximidic acid
Carboximidic acid derivative
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organic oxide
Hydrocarbon derivative
Organopnictogen compound
Carbonyl group
Organic nitrogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

catechols (CHEBI:31432 )
macrocyclic lactone (CHEBI:31432 )
crown compound (CHEBI:31432 )

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	1.86	ALOGPS
logP	0.2	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	7.83	ChemAxon
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	12	ChemAxon
Polar Surface Area	374.88 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	209.54 m³·mol⁻¹	ChemAxon
Polarizability	85.34 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

111553

KEGG Compound ID

C12219

BioCyc ID

CPD-9984

BiGG ID

Not Available

Wikipedia Link

Bacillibactin

METLIN ID

Not Available

PubChem Compound

125349

PDB ID

Not Available

ChEBI ID

31432

Good Scents ID

Not Available

References

General References

May JJ, Wendrich TM, Marahiel MA: The dhb operon of Bacillus subtilis encodes the biosynthetic template for the catecholic siderophore 2,3-dihydroxybenzoate-glycine-threonine trimeric ester bacillibactin. J Biol Chem. 2001 Mar 9;276(10):7209-17. doi: 10.1074/jbc.M009140200. Epub 2000 Dec 8. [PubMed:11112781 ]
Dertz EA, Xu J, Stintzi A, Raymond KN: Bacillibactin-mediated iron transport in Bacillus subtilis. J Am Chem Soc. 2006 Jan 11;128(1):22-3. doi: 10.1021/ja055898c. [PubMed:16390102 ]
Miethke M, Westers H, Blom EJ, Kuipers OP, Marahiel MA: Iron starvation triggers the stringent response and induces amino acid biosynthesis for bacillibactin production in Bacillus subtilis. J Bacteriol. 2006 Dec;188(24):8655-7. doi: 10.1128/JB.01049-06. Epub 2006 Sep 29. [PubMed:17012385 ]
Abergel RJ, Zawadzka AM, Hoette TM, Raymond KN: Enzymatic hydrolysis of trilactone siderophores: where chiral recognition occurs in enterobactin and bacillibactin iron transport. J Am Chem Soc. 2009 Sep 9;131(35):12682-92. doi: 10.1021/ja903051q. [PubMed:19673474 ]
Wilson MK, Abergel RJ, Arceneaux JE, Raymond KN, Byers BR: Temporal production of the two Bacillus anthracis siderophores, petrobactin and bacillibactin. Biometals. 2010 Feb;23(1):129-34. doi: 10.1007/s10534-009-9272-x. Epub 2009 Oct 9. [PubMed:19816776 ]
Lee JY, Passalacqua KD, Hanna PC, Sherman DH: Regulation of petrobactin and bacillibactin biosynthesis in Bacillus anthracis under iron and oxygen variation. PLoS One. 2011;6(6):e20777. doi: 10.1371/journal.pone.0020777. Epub 2011 Jun 6. [PubMed:21673962 ]
Hertlein G, Muller S, Garcia-Gonzalez E, Poppinga L, Sussmuth RD, Genersch E: Production of the catechol type siderophore bacillibactin by the honey bee pathogen Paenibacillus larvae. PLoS One. 2014 Sep 19;9(9):e108272. doi: 10.1371/journal.pone.0108272. eCollection 2014. [PubMed:25237888 ]
LOTUS database [Link]

Showing NP-Card for n-[(2r,3s,6r,7s,10r,11s)-7,11-bis[(2-{[(2,3-dihydroxyphenyl)(hydroxy)methylidene]amino}-1-hydroxyethylidene)amino]-2,6,10-trimethyl-4,8,12-trioxo-1,5,9-trioxacyclododecan-3-yl]-2-{[(2,3-dihydroxyphenyl)(hydroxy)methylidene]amino}ethanimidic acid (NP0168504)

MOL for NP0168504 (n-[(2r,3s,6r,7s,10r,11s)-7,11-bis[(2-{[(2,3-dihydroxyphenyl)(hydroxy)methylidene]amino}-1-hydroxyethylidene)amino]-2,6,10-trimethyl-4,8,12-trioxo-1,5,9-trioxacyclododecan-3-yl]-2-{[(2,3-dihydroxyphenyl)(hydroxy)methylidene]amino}ethanimidic acid)

3D MOL for NP0168504 (n-[(2r,3s,6r,7s,10r,11s)-7,11-bis[(2-{[(2,3-dihydroxyphenyl)(hydroxy)methylidene]amino}-1-hydroxyethylidene)amino]-2,6,10-trimethyl-4,8,12-trioxo-1,5,9-trioxacyclododecan-3-yl]-2-{[(2,3-dihydroxyphenyl)(hydroxy)methylidene]amino}ethanimidic acid)

3D SDF for NP0168504 (n-[(2r,3s,6r,7s,10r,11s)-7,11-bis[(2-{[(2,3-dihydroxyphenyl)(hydroxy)methylidene]amino}-1-hydroxyethylidene)amino]-2,6,10-trimethyl-4,8,12-trioxo-1,5,9-trioxacyclododecan-3-yl]-2-{[(2,3-dihydroxyphenyl)(hydroxy)methylidene]amino}ethanimidic acid)

3D-SDF for NP0168504 (n-[(2r,3s,6r,7s,10r,11s)-7,11-bis[(2-{[(2,3-dihydroxyphenyl)(hydroxy)methylidene]amino}-1-hydroxyethylidene)amino]-2,6,10-trimethyl-4,8,12-trioxo-1,5,9-trioxacyclododecan-3-yl]-2-{[(2,3-dihydroxyphenyl)(hydroxy)methylidene]amino}ethanimidic acid)

PDB for NP0168504 (n-[(2r,3s,6r,7s,10r,11s)-7,11-bis[(2-{[(2,3-dihydroxyphenyl)(hydroxy)methylidene]amino}-1-hydroxyethylidene)amino]-2,6,10-trimethyl-4,8,12-trioxo-1,5,9-trioxacyclododecan-3-yl]-2-{[(2,3-dihydroxyphenyl)(hydroxy)methylidene]amino}ethanimidic acid)

3D PDB for NP0168504 (n-[(2r,3s,6r,7s,10r,11s)-7,11-bis[(2-{[(2,3-dihydroxyphenyl)(hydroxy)methylidene]amino}-1-hydroxyethylidene)amino]-2,6,10-trimethyl-4,8,12-trioxo-1,5,9-trioxacyclododecan-3-yl]-2-{[(2,3-dihydroxyphenyl)(hydroxy)methylidene]amino}ethanimidic acid)

SMILES for NP0168504 (n-[(2r,3s,6r,7s,10r,11s)-7,11-bis[(2-{[(2,3-dihydroxyphenyl)(hydroxy)methylidene]amino}-1-hydroxyethylidene)amino]-2,6,10-trimethyl-4,8,12-trioxo-1,5,9-trioxacyclododecan-3-yl]-2-{[(2,3-dihydroxyphenyl)(hydroxy)methylidene]amino}ethanimidic acid)

INCHI for NP0168504 (n-[(2r,3s,6r,7s,10r,11s)-7,11-bis[(2-{[(2,3-dihydroxyphenyl)(hydroxy)methylidene]amino}-1-hydroxyethylidene)amino]-2,6,10-trimethyl-4,8,12-trioxo-1,5,9-trioxacyclododecan-3-yl]-2-{[(2,3-dihydroxyphenyl)(hydroxy)methylidene]amino}ethanimidic acid)

Structure for NP0168504 (n-[(2r,3s,6r,7s,10r,11s)-7,11-bis[(2-{[(2,3-dihydroxyphenyl)(hydroxy)methylidene]amino}-1-hydroxyethylidene)amino]-2,6,10-trimethyl-4,8,12-trioxo-1,5,9-trioxacyclododecan-3-yl]-2-{[(2,3-dihydroxyphenyl)(hydroxy)methylidene]amino}ethanimidic acid)

3D Structure for NP0168504 (n-[(2r,3s,6r,7s,10r,11s)-7,11-bis[(2-{[(2,3-dihydroxyphenyl)(hydroxy)methylidene]amino}-1-hydroxyethylidene)amino]-2,6,10-trimethyl-4,8,12-trioxo-1,5,9-trioxacyclododecan-3-yl]-2-{[(2,3-dihydroxyphenyl)(hydroxy)methylidene]amino}ethanimidic acid)