NP-MRD: Showing NP-Card for (2s,3r,4r)-4,8-diamino-2,3,5,7,9-pentahydroxy-n-[1-(c-hydroxycarbonimidoyl)-2-(c-hydroxycarbonimidoylamino)ethyl]nonanimidic acid (NP0142572)

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Record Information

Version

1.0

Created at

2022-09-01 21:08:54 UTC

Updated at

2022-09-01 21:08:55 UTC

NP-MRD ID

NP0142572

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3r,4r)-4,8-diamino-2,3,5,7,9-pentahydroxy-n-[1-(c-hydroxycarbonimidoyl)-2-(c-hydroxycarbonimidoylamino)ethyl]nonanimidic acid

Description

Zwittermicin A belongs to the class of organic compounds known as hybrid peptides. Hybrid peptides are compounds containing at least two different types of amino acids (alpha, beta, gamma, delta) linked to each other through a peptide bond. It was first documented in 2009 (PMID: 19898544). Based on a literature review a significant number of articles have been published on Zwittermicin A (PMID: 35157135) (PMID: 34400725) (PMID: 31622586) (PMID: 30533731) (PMID: 28149292) (PMID: 26274952).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309012223082D          

 27 26  0  0  1  0            999 V2000
   -2.0033    2.1434    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2888    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2888    3.3809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5743    2.1434    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1401    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8546    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5691    2.5559    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2836    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2836    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9980    2.5559    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9980    3.3809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    2.1434    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7125    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270    2.5559    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4270    3.3809    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1414    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1414    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5704    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5704    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2849    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2849    3.3809    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8546    1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5691    0.9059    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1401    0.9059    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
  7  6  1  4  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  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  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
  6 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
M  END

     RDKit          3D

 55 54  0  0  0  0  0  0  0  0999 V2000
    6.3892    0.8731    2.5565 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2469    0.7241    1.5501 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8750    1.6268    0.7048 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6457    2.9128    1.1791 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7283    1.2442   -0.6490 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2025    0.0237   -1.1585 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7116   -0.1058   -0.9686 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2700   -1.3916   -1.5282 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0566   -1.6734   -1.8115 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8631   -2.9662   -2.3390 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9288   -0.7510   -1.6177 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3351   -0.3816   -2.8314 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1348   -1.3396   -0.6980 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7230   -2.4523   -1.2354 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0758   -0.2467   -0.2780 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3153    0.8883    0.2783 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0242   -0.6486    0.8324 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8534   -1.6898    0.4788 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7066    0.5483    1.4333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7109    1.2391    0.6021 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1202    2.3915    1.3218 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8820    0.4250    0.1837 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.6977    1.3198   -0.6735 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7837    0.0280    1.3123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2375   -0.8178    2.2405 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3611   -0.0949    0.4447 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2172    1.0957    1.1201 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1845   -1.2197    1.0668 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2883   -2.1275    0.5759 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4076    3.1329    2.1166 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0479    1.9529   -1.3833 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7337   -0.8763   -0.7210 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4057   -0.0534   -2.2699 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2050    0.6749   -1.5827 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8044   -3.7445   -1.7175 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2888    0.1761   -1.1382 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1574    0.5929   -2.8824 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4084   -1.6719    0.2348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6667   -2.5378   -2.2104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6657    0.1523   -1.1165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0494    1.5472   -0.4811 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5536    0.5439    0.7208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4130   -1.0737    1.7064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7934   -1.9588   -0.4618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8857    1.2334    1.7681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2053    0.2601    2.4012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1632    1.6715   -0.2843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5567    2.1671    2.1605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6105   -0.4783   -0.3703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1989    0.7520   -1.3839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0832    2.0292   -1.1401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7024   -0.4667    0.9109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1618    0.9530    1.8324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8004   -1.5662    2.5082 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9048    1.9470    0.6912 H   0  0  0  0  0  0  0  0  0  0  0  0
 23 22  1  0
 22 24  1  0
 24 25  1  0
 22 20  1  0
 20 21  1  0
 20 19  1  0
 19 17  1  0
 17 18  1  0
 17 15  1  0
 15 16  1  0
 15 13  1  0
 13 14  1  0
 13 11  1  0
 11 12  1  0
 11  9  1  0
  9 10  1  0
  9  8  2  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  3  1  0
  3  4  1  0
  3  2  2  0
  7 26  1  0
 26 27  1  0
 26 28  2  0
 23 50  1  0
 23 51  1  0
 22 49  1  6
 24 52  1  0
 24 53  1  0
 25 54  1  0
 20 47  1  6
 21 48  1  0
 19 45  1  0
 19 46  1  0
 17 43  1  1
 18 44  1  0
 15 40  1  6
 16 41  1  0
 16 42  1  0
 13 38  1  1
 14 39  1  0
 11 36  1  1
 12 37  1  0
 10 35  1  0
  7 34  1  6
  6 32  1  0
  6 33  1  0
  5 31  1  0
  4 30  1  0
  2  1  1  0
 27 55  1  0
 28 29  1  0
M  END


  Mrv1652309012223082D          

 27 26  0  0  1  0            999 V2000
   -2.0033    2.1434    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2888    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2888    3.3809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5743    2.1434    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1401    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8546    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5691    2.5559    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2836    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2836    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9980    2.5559    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9980    3.3809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    2.1434    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7125    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270    2.5559    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4270    3.3809    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1414    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1414    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5704    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5704    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2849    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2849    3.3809    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8546    1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5691    0.9059    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1401    0.9059    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
  7  6  1  4  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  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  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
  6 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0142572

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC(CO)C(O)CC(O)[C@@H](N)[C@@H](O)[C@H](O)C(O)=NC(CNC(O)=N)C(O)=N

> <INCHI_IDENTIFIER>
InChI=1S/C13H28N6O8/c14-4(3-20)6(21)1-7(22)8(15)9(23)10(24)12(26)19-5(11(16)25)2-18-13(17)27/h4-10,20-24H,1-3,14-15H2,(H2,16,25)(H,19,26)(H3,17,18,27)/t4?,5?,6?,7?,8-,9-,10+/m1/s1

> <INCHI_KEY>
FYIPKJHNWFVEIR-WMNLMFOASA-N

> <FORMULA>
C13H28N6O8

> <MOLECULAR_WEIGHT>
396.401

> <EXACT_MASS>
396.196861886

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
37.85590414219608

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
13

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4R)-4,8-diamino-2,3,5,7,9-pentahydroxy-N-[1-(C-hydroxycarbonimidoyl)-2-[(C-hydroxycarbonimidoyl)amino]ethyl]nonanimidic acid

> <ALOGPS_LOGP>
-2.53

> <JCHEM_LOGP>
-12.106191498697491

> <ALOGPS_LOGS>
-2.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA>
-1.0374778580617203

> <JCHEM_PKA_STRONGEST_ACIDIC>
-3.2494140906152023

> <JCHEM_PKA_STRONGEST_BASIC>
15.012034143292759

> <JCHEM_POLAR_SURFACE_AREA>
285.96999999999997

> <JCHEM_REFRACTIVITY>
111.2126

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.11e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4R)-4,8-diamino-2,3,5,7,9-pentahydroxy-N-[1-(C-hydroxycarbonimidoyl)-2-(C-hydroxycarbonimidoylamino)ethyl]nonanimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 01-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   01-SEP-22         0                                  
HETATM    1  N   UNK     0      -3.739   4.001   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      -2.406   4.771   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -2.406   6.311   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0      -1.072   4.001   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       0.262   4.771   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.595   4.001   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       2.929   4.771   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       4.263   4.001   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.263   2.461   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       5.596   4.771   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.596   6.311   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       6.930   4.001   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       6.930   2.461   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       8.264   4.771   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       8.264   6.311   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       9.597   4.001   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       9.597   2.461   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      10.931   4.771   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.265   4.001   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      12.265   2.461   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      13.598   4.771   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0      13.598   6.311   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0      14.932   4.001   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      16.266   4.771   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.595   2.461   0.000  0.00  0.00           C+0
HETATM   26  N   UNK     0       2.929   1.691   0.000  0.00  0.00           N+0
HETATM   27  O   UNK     0       0.262   1.691   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   25                                                  
CONECT    7    6    8                                                       
CONECT    8    7    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   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23                                                            
CONECT   25    6   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   52    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₃H₂₈N₆O₈

Average Mass

396.4010 Da

Monoisotopic Mass

396.19686 Da

IUPAC Name

(2S,3R,4R)-4,8-diamino-2,3,5,7,9-pentahydroxy-N-[1-(C-hydroxycarbonimidoyl)-2-[(C-hydroxycarbonimidoyl)amino]ethyl]nonanimidic acid

Traditional Name

(2S,3R,4R)-4,8-diamino-2,3,5,7,9-pentahydroxy-N-[1-(C-hydroxycarbonimidoyl)-2-(C-hydroxycarbonimidoylamino)ethyl]nonanimidic acid

CAS Registry Number

Not Available

SMILES

NC(CO)C(O)CC(O)[C@@H](N)[C@@H](O)[C@H](O)C(O)=NC(CNC(O)=N)C(O)=N

InChI Identifier

InChI=1S/C13H28N6O8/c14-4(3-20)6(21)1-7(22)8(15)9(23)10(24)12(26)19-5(11(16)25)2-18-13(17)27/h4-10,20-24H,1-3,14-15H2,(H2,16,25)(H,19,26)(H3,17,18,27)/t4?,5?,6?,7?,8-,9-,10+/m1/s1

InChI Key

FYIPKJHNWFVEIR-WMNLMFOASA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hybrid peptides. Hybrid peptides are compounds containing at least two different types of amino acids (alpha, beta, gamma, delta) linked to each other through a peptide bond.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Peptidomimetics

Sub Class

Hybrid peptides

Direct Parent

Hybrid peptides

Alternative Parents

Substituents

Hybrid peptide
N-acyl-alpha amino acid or derivatives
Gamma amino acid or derivatives
Alpha-amino acid or derivatives
N-substituted-alpha-amino acid
Fatty acyl
N-acyl-amine
Monosaccharide
Fatty amide
1,3-aminoalcohol
Urea
Secondary carboxylic acid amide
Secondary alcohol
Primary carboxylic acid amide
Carbonic acid derivative
Carboxamide group
Amino acid or derivatives
1,2-aminoalcohol
Polyol
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary amine
Primary alcohol
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Carbonyl group
Amine
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic 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	-2.5	ALOGPS
logP	-12	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	-3.2	ChemAxon
pKa (Strongest Basic)	15.01	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	13	ChemAxon
Polar Surface Area	285.97 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	111.21 m³·mol⁻¹	ChemAxon
Polarizability	37.86 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

19981807

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Zwittermicin A

METLIN ID

Not Available

PubChem Compound

21120914

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Dhole A, Shelat H: Non-Rhizobial Endophytes Associated with Nodules of Vigna radiata L. and Their Combined Activity with Rhizobium sp. Curr Microbiol. 2022 Feb 14;79(4):103. doi: 10.1007/s00284-022-02792-x. [PubMed:35157135 ]
Sun H, Xiang X, Li Q, Lin H, Wang X, Sun J, Luo L, Zheng A: Comparative genome analysis of Bacillus thuringiensis strain HD521 and HS18-1. Sci Rep. 2021 Aug 16;11(1):16590. doi: 10.1038/s41598-021-96133-w. [PubMed:34400725 ]
Prasertanan T, Palmer DRJ: The kanosamine biosynthetic pathway in Bacillus cereus UW85: Functional and kinetic characterization of KabA, KabB, and KabC. Arch Biochem Biophys. 2019 Nov 15;676:108139. doi: 10.1016/j.abb.2019.108139. Epub 2019 Oct 14. [PubMed:31622586 ]
Schreier HJ: Draft Genome Sequence of Marine Bacillus sp. Strain ISO11, a Candidate Finfish and Shellfish Probiotic. Microbiol Resour Announc. 2018 Oct 18;7(15):e01227-18. doi: 10.1128/MRA.01227-18. eCollection 2018 Oct. [PubMed:30533731 ]
Hollensteiner J, Wemheuer F, Harting R, Kolarzyk AM, Diaz Valerio SM, Poehlein A, Brzuszkiewicz EB, Nesemann K, Braus-Stromeyer SA, Braus GH, Daniel R, Liesegang H: Bacillus thuringiensis and Bacillus weihenstephanensis Inhibit the Growth of Phytopathogenic Verticillium Species. Front Microbiol. 2017 Jan 18;7:2171. doi: 10.3389/fmicb.2016.02171. eCollection 2016. [PubMed:28149292 ]
Shi D, Allewell NM, Tuchman M: From Genome to Structure and Back Again: A Family Portrait of the Transcarbamylases. Int J Mol Sci. 2015 Aug 12;16(8):18836-64. doi: 10.3390/ijms160818836. [PubMed:26274952 ]
Zhu L, Tian LJ, Zheng J, Gao QL, Wang YY, Peng DH, Ruan LF, Sun M: Complete genome sequence of Bacillus thuringiensis serovar galleriae strain HD-29, a typical strain of commercial biopesticide. J Biotechnol. 2015 Feb 10;195:108-9. doi: 10.1016/j.jbiotec.2014.12.021. Epub 2014 Dec 30. [PubMed:25556027 ]
Park H, Kevany BM, Dyer DH, Thomas MG, Forest KT: A polyketide synthase acyltransferase domain structure suggests a recognition mechanism for its hydroxymalonyl-acyl carrier protein substrate. PLoS One. 2014 Oct 23;9(10):e110965. doi: 10.1371/journal.pone.0110965. eCollection 2014. [PubMed:25340352 ]
Hao Z, Yan L, Liu J, Song F, Zhang J, Li X: Extraction of antibiotic zwittermicin A from Bacillus thuringiensis by macroporous resin and silica gel column chromatography. Biotechnol Appl Biochem. 2015 May-Jun;62(3):369-74. doi: 10.1002/bab.1277. Epub 2014 Sep 5. [PubMed:25099664 ]
Jain S, Vaishnav A, Kasotia A, Kumari S, Gaur RK, Choudhary DK: Rhizobacterium-mediated growth promotion and expression of stress enzymes in Glycine max L. Merrill against Fusarium wilt upon challenge inoculation. World J Microbiol Biotechnol. 2014 Feb;30(2):399-406. doi: 10.1007/s11274-013-1455-5. Epub 2013 Aug 11. [PubMed:23933805 ]
Luo Y, Ruan LF, Zhao CM, Wang CX, Peng DH, Sun M: Validation of the intact zwittermicin A biosynthetic gene cluster and discovery of a complementary resistance mechanism in Bacillus thuringiensis. Antimicrob Agents Chemother. 2011 Sep;55(9):4161-9. doi: 10.1128/AAC.00111-11. Epub 2011 Jul 5. [PubMed:21730118 ]
Muchalski H, Hong KB, Johnston JN: Bronsted acid-promoted azide-olefin [3 + 2] cycloadditions for the preparation of contiguous aminopolyols: The importance of disiloxane ring size to a diastereoselective, bidirectional approach to zwittermicin A. Beilstein J Org Chem. 2010 Dec 20;6:1206-10. doi: 10.3762/bjoc.6.138. [PubMed:21283562 ]
Chan YA, Thomas MG: Recognition of (2S)-aminomalonyl-acyl carrier protein (ACP) and (2R)-hydroxymalonyl-ACP by acyltransferases in zwittermicin A biosynthesis. Biochemistry. 2010 May 4;49(17):3667-77. doi: 10.1021/bi100141n. [PubMed:20353188 ]
Rogers EW, Dalisay DS, Molinski TF: Zwittermicin A: synthesis of analogs and structure-activity studies. Bioorg Med Chem Lett. 2010 Apr 1;20(7):2183-5. doi: 10.1016/j.bmcl.2010.02.032. Epub 2010 Feb 11. [PubMed:20189808 ]
Athukorala SN, Fernando WG, Rashid KY: Identification of antifungal antibiotics of Bacillus species isolated from different microhabitats using polymerase chain reaction and MALDI-TOF mass spectrometry. Can J Microbiol. 2009 Sep;55(9):1021-32. doi: 10.1139/w09-067. [PubMed:19898544 ]
Bumpus SB, Evans BS, Thomas PM, Ntai I, Kelleher NL: A proteomics approach to discovering natural products and their biosynthetic pathways. Nat Biotechnol. 2009 Oct;27(10):951-6. doi: 10.1038/nbt.1565. Epub 2009 Sep 20. [PubMed:19767731 ]
Rogers EW, Molinski TF: (+)-Zwittermicin A. Rapid assembly of C9-C15 and a formal total synthesis. J Org Chem. 2009 Oct 16;74(20):7660-4. doi: 10.1021/jo901007v. [PubMed:19746943 ]
Chan YA, Thomas MG: Formation and characterization of acyl carrier protein-linked polyketide synthase extender units. Methods Enzymol. 2009;459:143-63. doi: 10.1016/S0076-6879(09)04607-2. [PubMed:19362639 ]
Zhang X, Liang Z, Siddiqui ZA, Gong Y, Yu Z, Chen S: Efficient screening and breeding of Bacillus thuringiensis subsp. kurstaki for high toxicity against Spodoptera exigua and Heliothis armigera. J Ind Microbiol Biotechnol. 2009 Jun;36(6):815-20. doi: 10.1007/s10295-009-0556-5. Epub 2009 Apr 1. [PubMed:19337765 ]
Kevany BM, Rasko DA, Thomas MG: Characterization of the complete zwittermicin A biosynthesis gene cluster from Bacillus cereus. Appl Environ Microbiol. 2009 Feb;75(4):1144-55. doi: 10.1128/AEM.02518-08. Epub 2008 Dec 19. [PubMed:19098220 ]
LOTUS database [Link]

Showing NP-Card for (2s,3r,4r)-4,8-diamino-2,3,5,7,9-pentahydroxy-n-[1-(c-hydroxycarbonimidoyl)-2-(c-hydroxycarbonimidoylamino)ethyl]nonanimidic acid (NP0142572)

MOL for NP0142572 ((2s,3r,4r)-4,8-diamino-2,3,5,7,9-pentahydroxy-n-[1-(c-hydroxycarbonimidoyl)-2-(c-hydroxycarbonimidoylamino)ethyl]nonanimidic acid)

3D MOL for NP0142572 ((2s,3r,4r)-4,8-diamino-2,3,5,7,9-pentahydroxy-n-[1-(c-hydroxycarbonimidoyl)-2-(c-hydroxycarbonimidoylamino)ethyl]nonanimidic acid)

3D SDF for NP0142572 ((2s,3r,4r)-4,8-diamino-2,3,5,7,9-pentahydroxy-n-[1-(c-hydroxycarbonimidoyl)-2-(c-hydroxycarbonimidoylamino)ethyl]nonanimidic acid)

3D-SDF for NP0142572 ((2s,3r,4r)-4,8-diamino-2,3,5,7,9-pentahydroxy-n-[1-(c-hydroxycarbonimidoyl)-2-(c-hydroxycarbonimidoylamino)ethyl]nonanimidic acid)

PDB for NP0142572 ((2s,3r,4r)-4,8-diamino-2,3,5,7,9-pentahydroxy-n-[1-(c-hydroxycarbonimidoyl)-2-(c-hydroxycarbonimidoylamino)ethyl]nonanimidic acid)

3D PDB for NP0142572 ((2s,3r,4r)-4,8-diamino-2,3,5,7,9-pentahydroxy-n-[1-(c-hydroxycarbonimidoyl)-2-(c-hydroxycarbonimidoylamino)ethyl]nonanimidic acid)

SMILES for NP0142572 ((2s,3r,4r)-4,8-diamino-2,3,5,7,9-pentahydroxy-n-[1-(c-hydroxycarbonimidoyl)-2-(c-hydroxycarbonimidoylamino)ethyl]nonanimidic acid)

INCHI for NP0142572 ((2s,3r,4r)-4,8-diamino-2,3,5,7,9-pentahydroxy-n-[1-(c-hydroxycarbonimidoyl)-2-(c-hydroxycarbonimidoylamino)ethyl]nonanimidic acid)

Structure for NP0142572 ((2s,3r,4r)-4,8-diamino-2,3,5,7,9-pentahydroxy-n-[1-(c-hydroxycarbonimidoyl)-2-(c-hydroxycarbonimidoylamino)ethyl]nonanimidic acid)

3D Structure for NP0142572 ((2s,3r,4r)-4,8-diamino-2,3,5,7,9-pentahydroxy-n-[1-(c-hydroxycarbonimidoyl)-2-(c-hydroxycarbonimidoylamino)ethyl]nonanimidic acid)