NP-MRD: Showing NP-Card for n-[(2s,3s,4s,5r,6r)-6-{[(2s,3s,4r,5s)-1,4-diamino-2,5,6-trihydroxyhexan-3-yl]oxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]ethanimidic acid (NP0328529)

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Record Information

Version

2.0

Created at

2022-09-12 12:05:07 UTC

Updated at

2022-09-12 12:05:07 UTC

NP-MRD ID

NP0328529

Secondary Accession Numbers

None

Natural Product Identification

Common Name

n-[(2s,3s,4s,5r,6r)-6-{[(2s,3s,4r,5s)-1,4-diamino-2,5,6-trihydroxyhexan-3-yl]oxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]ethanimidic acid

Description

Sorbistin B belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity. n-[(2s,3s,4s,5r,6r)-6-{[(2s,3s,4r,5s)-1,4-diamino-2,5,6-trihydroxyhexan-3-yl]oxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]ethanimidic acid is found in Pseudomonas fluorescens. n-[(2s,3s,4s,5r,6r)-6-{[(2s,3s,4r,5s)-1,4-diamino-2,5,6-trihydroxyhexan-3-yl]oxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]ethanimidic acid was first documented in 1976 (PMID: 993102). Based on a literature review a small amount of articles have been published on Sorbistin B (PMID: 418887) (PMID: 1010799) (PMID: 993100).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122214052D          

 26 26  0  0  1  0            999 V2000
   -5.2520   -0.0809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4270   -0.0809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0145   -0.7954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0145    0.6336    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1895    0.6336    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7770    1.3480    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1895    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7770    2.7770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9520    1.3480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5395    0.6336    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145    0.6336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3020    1.3480    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3020    2.7770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5395    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9520    2.7770    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.3480    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9355    0.6336    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9355    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5230    2.7770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1730    2.7770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9520   -0.0809    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5395   -0.7954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7770   -0.0809    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1895   -0.7954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  4  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 12 11  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 10 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
  5 25  1  0  0  0  0
 25 26  1  1  0  0  0
M  END

     RDKit          3D

 55 55  0  0  0  0  0  0  0  0999 V2000
   -4.8645    1.3951   -0.9967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1752    0.2828   -0.0776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4950    0.0235    0.2601 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2695   -0.4571    0.4236 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8450   -0.3179    0.1713 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2026   -1.6376    0.4717 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6586   -2.5961   -0.6415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0581   -2.6218   -0.6329 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8207   -1.6424    0.4269 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2825   -0.3622    0.6634 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0428   -0.3579    0.9723 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9004    0.1449   -0.0028 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8877   -0.9038   -0.3324 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6658   -1.2554    0.7533 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1347   -2.1871   -0.7123 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1416   -3.2019   -1.0814 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5053    1.4110    0.5565 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3450    2.2991    0.7691 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4248    2.1594   -0.3365 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9270    2.4789   -1.5843 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8587    1.7178   -0.3078 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1560    1.4339    1.0405 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0833    0.3249    1.7101 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4415   -0.5515    2.7472 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3550    0.8248    1.0011 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9052    1.8869    0.1838 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7618    1.7122   -1.5863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5441    2.3140   -0.4493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0846    1.1563   -1.7442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9327   -0.8339   -0.0254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6826   -0.0630   -0.9030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5543   -2.0988    1.4049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3253   -3.6271   -0.4036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2759   -2.2874   -1.6170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3292   -2.9791    0.2597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4028    0.1489   -0.3206 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2444    0.4014   -0.8835 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5066   -0.6947   -1.2283 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5753   -1.4941    0.4180 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4355   -1.9983   -1.5373 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6414   -2.6127    0.1807 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6663   -3.3977   -0.2031 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7958   -2.7424   -1.7695 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9773    1.1957    1.5096 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6371    3.1886    1.2130 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0239    2.5569   -0.2102 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4916    3.2048    0.1608 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3918    2.0405   -2.3336 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1520    0.9491   -1.0066 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5554    2.5901   -0.5361 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1251    1.4644    1.2175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6329    1.1772    2.1822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3600   -0.3675    3.0676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0654    1.2118    1.7269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8012    1.5946   -0.7497 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  6  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 12 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 10 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 25  5  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  3 30  1  0
  5 31  1  6
  6 32  1  1
  7 33  1  0
  7 34  1  0
  8 35  1  0
 10 36  1  6
 12 37  1  6
 13 38  1  6
 14 39  1  0
 15 40  1  0
 15 41  1  0
 16 42  1  0
 16 43  1  0
 17 44  1  1
 18 45  1  0
 18 46  1  0
 19 47  1  1
 20 48  1  0
 21 49  1  0
 21 50  1  0
 22 51  1  0
 23 52  1  1
 24 53  1  0
 25 54  1  1
 26 55  1  0
M  END


  Mrv1652309122214052D          

 26 26  0  0  1  0            999 V2000
   -5.2520   -0.0809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4270   -0.0809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0145   -0.7954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0145    0.6336    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1895    0.6336    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7770    1.3480    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1895    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7770    2.7770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9520    1.3480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5395    0.6336    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145    0.6336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3020    1.3480    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3020    2.7770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5395    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9520    2.7770    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.3480    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9355    0.6336    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9355    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5230    2.7770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1730    2.7770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9520   -0.0809    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5395   -0.7954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7770   -0.0809    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1895   -0.7954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  4  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 12 11  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 10 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
  5 25  1  0  0  0  0
 25 26  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0328529

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(O)=N[C@@H]1[C@@H](CO)O[C@H](O[C@H]([C@@H](O)CN)[C@H](N)[C@H](O)CO)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C14H29N3O9/c1-5(20)17-10-8(4-19)25-14(12(24)11(10)23)26-13(6(21)2-15)9(16)7(22)3-18/h6-14,18-19,21-24H,2-4,15-16H2,1H3,(H,17,20)/t6-,7+,8+,9+,10+,11-,12+,13+,14+/m0/s1

> <INCHI_KEY>
UWAJGPKPIKRBHZ-BOPCDOEQSA-N

> <FORMULA>
C14H29N3O9

> <MOLECULAR_WEIGHT>
383.398

> <EXACT_MASS>
383.190379526

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
37.6692754683574

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-[(3S,6R)-6-{[(2S,3S,4R,5S)-1,4-diamino-2,5,6-trihydroxyhexan-3-yl]oxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]ethanimidic acid

> <JCHEM_LOGP>
-7.623783631624189

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA>
12.34679931885244

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.587489868701849

> <JCHEM_PKA_STRONGEST_BASIC>
9.54795176946477

> <JCHEM_POLAR_SURFACE_AREA>
224.46999999999997

> <JCHEM_REFRACTIVITY>
85.75489999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
N-[(3S,6R)-6-{[(2S,3S,4R,5S)-1,4-diamino-2,5,6-trihydroxyhexan-3-yl]oxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]ethanimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0      -9.804  -0.151   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -8.264  -0.151   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -7.494  -1.485   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0      -7.494   1.183   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      -5.954   1.183   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.184   2.516   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.954   3.850   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -5.184   5.184   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -3.644   2.516   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -2.874   1.183   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.334   1.183   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -0.564   2.516   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -0.564   5.184   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -2.874   3.850   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0      -3.644   5.184   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       0.976   2.516   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       1.746   1.183   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0       1.746   3.850   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       0.976   5.184   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       3.286   3.850   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       4.056   5.184   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -3.644  -0.151   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -2.874  -1.485   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -5.184  -0.151   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -5.954  -1.485   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   25                                                  
CONECT    6    5    7    9                                                  
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    6   10                                                       
CONECT   10    9   11   23                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15                                                            
CONECT   17   12   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21                                                            
CONECT   23   10   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23    5   26                                                  
CONECT   26   25                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   52    0
END

View in JSmol

Synonyms

Value	Source
Sorbistins	MeSH
Sorbistins, sorbistin a2	MeSH
Sorbistins, sorbistin b	MeSH
Sorbistins, sorbistin C	MeSH
Sorbistins, sorbistin D	MeSH

Chemical Formula

C₁₄H₂₉N₃O₉

Average Mass

383.3980 Da

Monoisotopic Mass

383.19038 Da

IUPAC Name

N-[(3S,6R)-6-{[(2S,3S,4R,5S)-1,4-diamino-2,5,6-trihydroxyhexan-3-yl]oxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]ethanimidic acid

Traditional Name

N-[(3S,6R)-6-{[(2S,3S,4R,5S)-1,4-diamino-2,5,6-trihydroxyhexan-3-yl]oxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]ethanimidic acid

CAS Registry Number

Not Available

SMILES

CC(O)=N[C@@H]1[C@@H](CO)O[C@H](O[C@H]([C@@H](O)CN)[C@H](N)[C@H](O)CO)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C14H29N3O9/c1-5(20)17-10-8(4-19)25-14(12(24)11(10)23)26-13(6(21)2-15)9(16)7(22)3-18/h6-14,18-19,21-24H,2-4,15-16H2,1H3,(H,17,20)/t6-,7+,8+,9+,10+,11-,12+,13+,14+/m0/s1

InChI Key

UWAJGPKPIKRBHZ-BOPCDOEQSA-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
Pseudomonas fluorescens	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Hexoses

Alternative Parents

Substituents

Hexose monosaccharide
Oxane
1,3-aminoalcohol
Acetamide
1,2-aminoalcohol
Amino acid or derivatives
Carboxamide group
Secondary alcohol
Secondary carboxylic acid amide
Oxacycle
Organoheterocyclic compound
Polyol
Acetal
Carboxylic acid derivative
Primary amine
Primary aliphatic amine
Organopnictogen compound
Organonitrogen compound
Organic oxide
Carbonyl group
Organic nitrogen compound
Amine
Alcohol
Primary alcohol
Hydrocarbon derivative
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic 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
logP	-7.6	ChemAxon
pKa (Strongest Acidic)	5.59	ChemAxon
pKa (Strongest Basic)	9.55	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	224.47 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	85.75 m³·mol⁻¹	ChemAxon
Polarizability	37.67 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00018111

Chemspider ID

151632

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

173742

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Konishi M, Kamata S, Tsuno T, Numata K, Tsukiura H: Sorbistin, a new aminoglycoside antibiotic complex of bacterial origin. III. Structure determination. J Antibiot (Tokyo). 1976 Nov;29(11):1152-62. doi: 10.7164/antibiotics.29.1152. [PubMed:993102 ]
Nara K, Sumino Y, Katamoto K, Akiyma S, Asai M: The chemistry of aminoglycoside antibiotics from Pseudomonas flurescence. I. Isolation, characterization and partial structure of P-2563(P) (sorbistin A1) and P-2563(A) (sorbistin B). Chem Pharm Bull (Tokyo). 1978 Apr;26(4):1075-82. doi: 10.1248/cpb.26.1075. [PubMed:418887 ]
Naito T, Nakagawa S, Narita Y, Kawaguchi H: Chemical modification of sorbistin. I. N-acyl analogs of sorbistin. J Antibiot (Tokyo). 1976 Dec;29(12):1286-96. doi: 10.7164/antibiotics.29.1286. [PubMed:1010799 ]
Tsukiura H, Hanada M, Saito K, Fujisawa K, Miyaki T: Sorbistin, a new aminoglycoside antibiotic complex of bacterial origin. I. Production, isolation and properties. J Antibiot (Tokyo). 1976 Nov;29(11):1137-46. doi: 10.7164/antibiotics.29.1137. [PubMed:993100 ]
LOTUS database [Link]

Showing NP-Card for n-[(2s,3s,4s,5r,6r)-6-{[(2s,3s,4r,5s)-1,4-diamino-2,5,6-trihydroxyhexan-3-yl]oxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]ethanimidic acid (NP0328529)

MOL for NP0328529 (n-[(2s,3s,4s,5r,6r)-6-{[(2s,3s,4r,5s)-1,4-diamino-2,5,6-trihydroxyhexan-3-yl]oxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]ethanimidic acid)

3D MOL for NP0328529 (n-[(2s,3s,4s,5r,6r)-6-{[(2s,3s,4r,5s)-1,4-diamino-2,5,6-trihydroxyhexan-3-yl]oxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]ethanimidic acid)

3D SDF for NP0328529 (n-[(2s,3s,4s,5r,6r)-6-{[(2s,3s,4r,5s)-1,4-diamino-2,5,6-trihydroxyhexan-3-yl]oxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]ethanimidic acid)

3D-SDF for NP0328529 (n-[(2s,3s,4s,5r,6r)-6-{[(2s,3s,4r,5s)-1,4-diamino-2,5,6-trihydroxyhexan-3-yl]oxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]ethanimidic acid)

PDB for NP0328529 (n-[(2s,3s,4s,5r,6r)-6-{[(2s,3s,4r,5s)-1,4-diamino-2,5,6-trihydroxyhexan-3-yl]oxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]ethanimidic acid)

3D PDB for NP0328529 (n-[(2s,3s,4s,5r,6r)-6-{[(2s,3s,4r,5s)-1,4-diamino-2,5,6-trihydroxyhexan-3-yl]oxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]ethanimidic acid)

SMILES for NP0328529 (n-[(2s,3s,4s,5r,6r)-6-{[(2s,3s,4r,5s)-1,4-diamino-2,5,6-trihydroxyhexan-3-yl]oxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]ethanimidic acid)

INCHI for NP0328529 (n-[(2s,3s,4s,5r,6r)-6-{[(2s,3s,4r,5s)-1,4-diamino-2,5,6-trihydroxyhexan-3-yl]oxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]ethanimidic acid)

Structure for NP0328529 (n-[(2s,3s,4s,5r,6r)-6-{[(2s,3s,4r,5s)-1,4-diamino-2,5,6-trihydroxyhexan-3-yl]oxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]ethanimidic acid)

3D Structure for NP0328529 (n-[(2s,3s,4s,5r,6r)-6-{[(2s,3s,4r,5s)-1,4-diamino-2,5,6-trihydroxyhexan-3-yl]oxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]ethanimidic acid)