NP-MRD: Showing NP-Card for (s)-{[(2s,3s,4s)-2-amino-1,3,4-trihydroxy-5-(c-hydroxycarbonimidoyloxy)pentylidene]amino}[(2r,3s,4r,5r)-5-(4-formyl-2-hydroxyimidazol-1-yl)-3,4-dihydroxyoxolan-2-yl]acetic acid (NP0268474)

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Record Information

Version

2.0

Created at

2022-09-08 13:36:09 UTC

Updated at

2022-09-08 13:36:09 UTC

NP-MRD ID

NP0268474

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(s)-{[(2s,3s,4s)-2-amino-1,3,4-trihydroxy-5-(c-hydroxycarbonimidoyloxy)pentylidene]amino}[(2r,3s,4r,5r)-5-(4-formyl-2-hydroxyimidazol-1-yl)-3,4-dihydroxyoxolan-2-yl]acetic acid

Description

Polyoxin N belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. (s)-{[(2s,3s,4s)-2-amino-1,3,4-trihydroxy-5-(c-hydroxycarbonimidoyloxy)pentylidene]amino}[(2r,3s,4r,5r)-5-(4-formyl-2-hydroxyimidazol-1-yl)-3,4-dihydroxyoxolan-2-yl]acetic acid is found in Streptomyces piomogenus. (s)-{[(2s,3s,4s)-2-amino-1,3,4-trihydroxy-5-(c-hydroxycarbonimidoyloxy)pentylidene]amino}[(2r,3s,4r,5r)-5-(4-formyl-2-hydroxyimidazol-1-yl)-3,4-dihydroxyoxolan-2-yl]acetic acid was first documented in 2011 (PMID: 21292022). Based on a literature review a small amount of articles have been published on Polyoxin N (PMID: 23043373) (PMID: 22465029).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082215362D          

 33 34  0  0  1  0            999 V2000
    0.7990   -7.9653    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5135   -7.5528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5135   -6.7278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2279   -7.9653    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9424   -7.5528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6569   -7.9653    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6569   -8.7903    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3713   -7.5528    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3713   -6.7278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0858   -7.9653    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0858   -8.7903    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8003   -7.5528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8003   -6.7278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5148   -7.9653    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2292   -7.5528    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.2292   -6.7278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9437   -6.3153    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5148   -6.3153    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9437   -7.9653    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.6974   -7.6297    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2494   -8.2428    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.0699   -8.1566    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4824   -7.4421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2894   -7.6137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9025   -7.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7309   -6.2547    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3756   -8.4341    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6219   -8.7697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4504   -9.5767    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8369   -8.9573    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.1725   -9.7110    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0299   -8.7858    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.4168   -9.3378    0.0000 O   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  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  1  4  0  0  0
 12 14  2  0  0  0  0
 15 14  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 19 15  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 24 27  1  0  0  0  0
 27 28  2  0  0  0  0
 22 28  1  0  0  0  0
 28 29  1  0  0  0  0
 21 30  1  0  0  0  0
 30 31  1  6  0  0  0
 30 32  1  0  0  0  0
 19 32  1  0  0  0  0
 32 33  1  6  0  0  0
M  END

     RDKit          3D

 56 57  0  0  0  0  0  0  0  0999 V2000
    2.6347    0.9070    2.0012 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6533    1.6852    1.3316 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7383    2.0005    0.7273 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7773    3.0695   -0.1931 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8466    1.2478    1.0253 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9630   -0.1421    0.8913 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8162   -0.6519   -0.5052 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7996   -0.0123   -1.2818 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4581   -0.5035   -1.1189 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724   -1.0636   -2.4232 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4882   -1.4247   -0.3573 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1385   -2.7252   -0.3710 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1723   -1.4575   -1.0110 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1409   -1.7719   -2.3823 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0379   -1.2295   -0.4622 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2129   -0.8936    0.8996 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0246   -2.0890    1.7538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2038   -1.9851    2.9853 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3435   -3.2820    1.1603 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6230   -0.4065    1.1365 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9227    0.7388    0.3936 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2868    0.8650    0.6532 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9003    1.9451   -0.0797 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5640    2.4369   -1.2683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4409    3.4568   -1.5474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4831    4.3019   -2.7289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6371    4.1216   -3.6391 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2994    3.5649   -0.5141 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9682    2.6303    0.3975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6346    2.4328    1.6126 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8112   -0.4849    0.2593 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9805   -0.8169    0.9343 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6578   -1.3943    0.7035 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0905   -2.0752    1.8522 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6086    3.6409   -0.1496 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2070   -0.6608    1.5233 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0050   -0.3858    1.2508 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0968   -1.7505   -0.5365 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2190   -0.6312   -1.9217 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1141    0.5328   -1.1460 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4069   -0.7460   -2.8513 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3993   -1.0170    0.6546 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0467   -3.2280    0.5253 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8864   -3.2842   -1.2045 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0775   -2.7401   -2.6940 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5136   -0.0882    1.1756 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1478   -3.4870    0.1965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7252   -0.1276    2.2053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3821    1.0461    1.7551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7683    2.1274   -1.9189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2176    5.0809   -2.8523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1142    1.5729    1.8351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9206   -0.5080   -0.8352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5252   -1.3688    0.3149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3422   -2.0734   -0.0917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.8991    1.6425 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 11  1  0
 11  9  1  0
  9 10  1  0
  9  7  1  0
  7  8  1  0
  7  6  1  0
  6  5  1  0
  5  3  1  0
  3  4  1  0
  3  2  2  0
 11 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 20  1  0
 20 21  1  0
 21 22  1  0
 22 31  1  0
 31 32  1  0
 31 33  1  0
 33 34  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 25 28  1  0
 28 29  2  0
 29 30  1  0
 16 17  1  0
 17 19  1  0
 17 18  2  0
 33 20  1  0
 29 23  1  0
 12 43  1  0
 12 44  1  0
 11 42  1  1
  9 40  1  6
 10 41  1  0
  7 38  1  1
  8 39  1  0
  6 36  1  0
  6 37  1  0
  4 35  1  0
  2  1  1  0
 14 45  1  0
 16 46  1  1
 20 48  1  1
 22 49  1  1
 31 53  1  6
 32 54  1  0
 33 55  1  6
 34 56  1  0
 24 50  1  0
 26 51  1  0
 30 52  1  0
 19 47  1  0
M  END


  Mrv1652309082215362D          

 33 34  0  0  1  0            999 V2000
    0.7990   -7.9653    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5135   -7.5528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5135   -6.7278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2279   -7.9653    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9424   -7.5528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6569   -7.9653    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6569   -8.7903    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3713   -7.5528    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3713   -6.7278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0858   -7.9653    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0858   -8.7903    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8003   -7.5528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8003   -6.7278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5148   -7.9653    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2292   -7.5528    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.2292   -6.7278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9437   -6.3153    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5148   -6.3153    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9437   -7.9653    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.6974   -7.6297    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2494   -8.2428    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.0699   -8.1566    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4824   -7.4421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2894   -7.6137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9025   -7.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7309   -6.2547    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3756   -8.4341    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6219   -8.7697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4504   -9.5767    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8369   -8.9573    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.1725   -9.7110    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0299   -8.7858    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.4168   -9.3378    0.0000 O   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  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  1  4  0  0  0
 12 14  2  0  0  0  0
 15 14  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 19 15  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 24 27  1  0  0  0  0
 27 28  2  0  0  0  0
 22 28  1  0  0  0  0
 28 29  1  0  0  0  0
 21 30  1  0  0  0  0
 30 31  1  6  0  0  0
 30 32  1  0  0  0  0
 19 32  1  0  0  0  0
 32 33  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0268474

> <DATABASE_NAME>
NP-MRD

> <SMILES>
N[C@@H]([C@H](O)[C@@H](O)COC(O)=N)C(O)=N[C@@H]([C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=C(C=O)N=C1O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H23N5O12/c17-6(8(24)5(23)3-32-15(18)30)12(27)20-7(14(28)29)11-9(25)10(26)13(33-11)21-1-4(2-22)19-16(21)31/h1-2,5-11,13,23-26H,3,17H2,(H2,18,30)(H,19,31)(H,20,27)(H,28,29)/t5-,6-,7-,8+,9-,10+,11+,13+/m0/s1

> <INCHI_KEY>
OSWKWKBETDCHCA-OHRMCWGFSA-N

> <FORMULA>
C16H23N5O12

> <MOLECULAR_WEIGHT>
477.383

> <EXACT_MASS>
477.134321201

> <JCHEM_ACCEPTOR_COUNT>
16

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
42.340318703597724

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-{[(2S,3S,4S)-2-amino-1,3,4-trihydroxy-5-(C-hydroxycarbonimidoyloxy)pentylidene]amino}-2-[(2R,3S,4R,5R)-5-(4-formyl-2-hydroxy-1H-imidazol-1-yl)-3,4-dihydroxyoxolan-2-yl]acetic acid

> <JCHEM_LOGP>
-7.598908755737079

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
2.288308707005349

> <JCHEM_PKA_STRONGEST_ACIDIC>
-3.212378330093766

> <JCHEM_PKA_STRONGEST_BASIC>
11.540294068368388

> <JCHEM_POLAR_SURFACE_AREA>
294.49

> <JCHEM_REFRACTIVITY>
111.07099999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(S)-{[(2S,3S,4S)-2-amino-1,3,4-trihydroxy-5-(C-hydroxycarbonimidoyloxy)pentylidene]amino}[(2R,3S,4R,5R)-5-(4-formyl-2-hydroxyimidazol-1-yl)-3,4-dihydroxyoxolan-2-yl]acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  N   UNK     0       1.491 -14.869   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       2.825 -14.099   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.825 -12.559   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       4.159 -14.869   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       5.492 -14.099   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.826 -14.869   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.826 -16.409   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       8.160 -14.099   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       8.160 -12.559   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       9.494 -14.869   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       9.494 -16.409   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      10.827 -14.099   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      10.827 -12.559   0.000  0.00  0.00           O+0
HETATM   14  N   UNK     0      12.161 -14.869   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0      13.495 -14.099   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.495 -12.559   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      14.828 -11.789   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      12.161 -11.789   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      14.828 -14.869   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      16.235 -14.242   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      17.266 -15.387   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0      18.797 -15.226   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0      19.567 -13.892   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      21.073 -14.212   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      22.218 -13.182   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      21.898 -11.675   0.000  0.00  0.00           O+0
HETATM   27  N   UNK     0      21.234 -15.744   0.000  0.00  0.00           N+0
HETATM   28  C   UNK     0      19.828 -16.370   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      19.507 -17.876   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      16.496 -16.720   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      17.122 -18.127   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      14.989 -16.400   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      13.845 -17.431   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   19                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   15   20   32                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   30                                                  
CONECT   22   21   23   28                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   27                                                  
CONECT   25   24   26                                                       
CONECT   26   25                                                            
CONECT   27   24   28                                                       
CONECT   28   27   22   29                                                  
CONECT   29   28                                                            
CONECT   30   21   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   19   33                                                  
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₂₃N₅O₁₂

Average Mass

477.3830 Da

Monoisotopic Mass

477.13432 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

N[C@@H]([C@H](O)[C@@H](O)COC(O)=N)C(O)=N[C@@H]([C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=C(C=O)N=C1O)C(O)=O

InChI Identifier

InChI=1S/C16H23N5O12/c17-6(8(24)5(23)3-32-15(18)30)12(27)20-7(14(28)29)11-9(25)10(26)13(33-11)21-1-4(2-22)19-16(21)31/h1-2,5-11,13,23-26H,3,17H2,(H2,18,30)(H,19,31)(H,20,27)(H,28,29)/t5-,6-,7-,8+,9-,10+,11+,13+/m0/s1

InChI Key

OSWKWKBETDCHCA-OHRMCWGFSA-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
Streptomyces piomogenus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Dipeptides

Alternative Parents

Substituents

Alpha-dipeptide
N-acyl-alpha amino acid or derivatives
N-acyl-alpha-amino acid
N-acyl-l-alpha-amino acid
Alpha-amino acid amide
N-glycosyl compound
Glycosyl compound
Alpha-amino acid or derivatives
Imidazolyl carboxylic acid derivative
Imidazole-4-carbonyl group
Aryl-aldehyde
Fatty amide
Fatty acyl
N-substituted imidazole
N-acyl-amine
Imidazole
Vinylogous amide
Carbamic acid ester
Azole
1,3-aminoalcohol
Oxolane
Heteroaromatic compound
Amino acid or derivatives
Amino acid
Carboxamide group
Urea
Secondary carboxylic acid amide
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Organoheterocyclic compound
Azacycle
Oxacycle
Organonitrogen compound
Hydrocarbon derivative
Organic oxygen compound
Aldehyde
Alcohol
Carbonyl group
Organic oxide
Organic nitrogen compound
Primary aliphatic amine
Organopnictogen compound
Amine
Primary amine
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

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

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

78437968

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

102269641

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Li J, Li L, Tian Y, Niu G, Tan H: Hybrid antibiotics with the nikkomycin nucleoside and polyoxin peptidyl moieties. Metab Eng. 2011 May;13(3):336-44. doi: 10.1016/j.ymben.2011.01.002. Epub 2011 Feb 1. [PubMed:21292022 ]
Li J, Li L, Feng C, Chen Y, Tan H: Novel polyoxins generated by heterologously expressing polyoxin biosynthetic gene cluster in the sanN inactivated mutant of Streptomyces ansochromogenes. Microb Cell Fact. 2012 Oct 8;11:135. doi: 10.1186/1475-2859-11-135. [PubMed:23043373 ]
Zhai L, Lin S, Qu D, Hong X, Bai L, Chen W, Deng Z: Engineering of an industrial polyoxin producer for the rational production of hybrid peptidyl nucleoside antibiotics. Metab Eng. 2012 Jul;14(4):388-93. doi: 10.1016/j.ymben.2012.03.006. Epub 2012 Mar 24. [PubMed:22465029 ]
LOTUS database [Link]

Showing NP-Card for (s)-{[(2s,3s,4s)-2-amino-1,3,4-trihydroxy-5-(c-hydroxycarbonimidoyloxy)pentylidene]amino}[(2r,3s,4r,5r)-5-(4-formyl-2-hydroxyimidazol-1-yl)-3,4-dihydroxyoxolan-2-yl]acetic acid (NP0268474)

MOL for NP0268474 ((s)-{[(2s,3s,4s)-2-amino-1,3,4-trihydroxy-5-(c-hydroxycarbonimidoyloxy)pentylidene]amino}[(2r,3s,4r,5r)-5-(4-formyl-2-hydroxyimidazol-1-yl)-3,4-dihydroxyoxolan-2-yl]acetic acid)

3D MOL for NP0268474 ((s)-{[(2s,3s,4s)-2-amino-1,3,4-trihydroxy-5-(c-hydroxycarbonimidoyloxy)pentylidene]amino}[(2r,3s,4r,5r)-5-(4-formyl-2-hydroxyimidazol-1-yl)-3,4-dihydroxyoxolan-2-yl]acetic acid)

3D SDF for NP0268474 ((s)-{[(2s,3s,4s)-2-amino-1,3,4-trihydroxy-5-(c-hydroxycarbonimidoyloxy)pentylidene]amino}[(2r,3s,4r,5r)-5-(4-formyl-2-hydroxyimidazol-1-yl)-3,4-dihydroxyoxolan-2-yl]acetic acid)

3D-SDF for NP0268474 ((s)-{[(2s,3s,4s)-2-amino-1,3,4-trihydroxy-5-(c-hydroxycarbonimidoyloxy)pentylidene]amino}[(2r,3s,4r,5r)-5-(4-formyl-2-hydroxyimidazol-1-yl)-3,4-dihydroxyoxolan-2-yl]acetic acid)

PDB for NP0268474 ((s)-{[(2s,3s,4s)-2-amino-1,3,4-trihydroxy-5-(c-hydroxycarbonimidoyloxy)pentylidene]amino}[(2r,3s,4r,5r)-5-(4-formyl-2-hydroxyimidazol-1-yl)-3,4-dihydroxyoxolan-2-yl]acetic acid)

3D PDB for NP0268474 ((s)-{[(2s,3s,4s)-2-amino-1,3,4-trihydroxy-5-(c-hydroxycarbonimidoyloxy)pentylidene]amino}[(2r,3s,4r,5r)-5-(4-formyl-2-hydroxyimidazol-1-yl)-3,4-dihydroxyoxolan-2-yl]acetic acid)

SMILES for NP0268474 ((s)-{[(2s,3s,4s)-2-amino-1,3,4-trihydroxy-5-(c-hydroxycarbonimidoyloxy)pentylidene]amino}[(2r,3s,4r,5r)-5-(4-formyl-2-hydroxyimidazol-1-yl)-3,4-dihydroxyoxolan-2-yl]acetic acid)

INCHI for NP0268474 ((s)-{[(2s,3s,4s)-2-amino-1,3,4-trihydroxy-5-(c-hydroxycarbonimidoyloxy)pentylidene]amino}[(2r,3s,4r,5r)-5-(4-formyl-2-hydroxyimidazol-1-yl)-3,4-dihydroxyoxolan-2-yl]acetic acid)

Structure for NP0268474 ((s)-{[(2s,3s,4s)-2-amino-1,3,4-trihydroxy-5-(c-hydroxycarbonimidoyloxy)pentylidene]amino}[(2r,3s,4r,5r)-5-(4-formyl-2-hydroxyimidazol-1-yl)-3,4-dihydroxyoxolan-2-yl]acetic acid)

3D Structure for NP0268474 ((s)-{[(2s,3s,4s)-2-amino-1,3,4-trihydroxy-5-(c-hydroxycarbonimidoyloxy)pentylidene]amino}[(2r,3s,4r,5r)-5-(4-formyl-2-hydroxyimidazol-1-yl)-3,4-dihydroxyoxolan-2-yl]acetic acid)