NP-MRD: Showing NP-Card for (1r,4r,5r,6r,7s,8r)-6-(acetyloxy)-7-amino-4-hydroxy-4-(c-hydroxycarbonimidoyl)-8-(phosphonooxy)-9-oxa-3-thiabicyclo[3.3.1]nonane-1-carboxylic acid (NP0319635)

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Record Information

Version

1.0

Created at

2022-09-11 20:46:18 UTC

Updated at

2022-09-11 20:46:18 UTC

NP-MRD ID

NP0319635

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,4r,5r,6r,7s,8r)-6-(acetyloxy)-7-amino-4-hydroxy-4-(c-hydroxycarbonimidoyl)-8-(phosphonooxy)-9-oxa-3-thiabicyclo[3.3.1]nonane-1-carboxylic acid

Description

Tagetitoxin belongs to the class of organic compounds known as delta amino acids and derivatives. Delta amino acids and derivatives are compounds containing a carboxylic acid group and an amino group at the C5 carbon atom. In contrast, eukaryotic RNA polymerase I and II as well as single-subunit RNA polymerases of bacteriophage T7 and SP6 are relatively insensitive to the compound. Tagetitoxin is a very strong basic compound (based on its pKa). Tagetitoxin (TGT) is a bacterial phytotoxin produced by Pseudomonas syringae pv. It has been suggested that TGT forms a ternary RNAP-NTP-TGT complex and inhibits phosphodiester bond synthesis either by binding an inhibitory magnesium ion or by trapping a flexible active site domain in an inactive conformation. When TGT was first isolated, it was only partially characterized. Chloroplast RNA polymerase belongs to ubiquitous family of multisubunit RNA polymerases (RNAP) and is most closely related to bacterial enzymes. The absolute configuration remains undetermined, and attempts at confirming the structure by organic synthesis are underway. However, the detailed mechanism of inhibition remains a subject of heated debate. (1r,4r,5r,6r,7s,8r)-6-(acetyloxy)-7-amino-4-hydroxy-4-(c-hydroxycarbonimidoyl)-8-(phosphonooxy)-9-oxa-3-thiabicyclo[3.3.1]nonane-1-carboxylic acid is found in Pseudomonas syringae. TGT interferes with development of chloroplasts in young plant leaves thereby causing chlorosis.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02231217552D          

 26 27  0  0  1  0            999 V2000
   -1.2401    1.0663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1491    0.3140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7551   -0.1411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4420    0.0124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2245   -0.5127    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1079   -1.2493    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6429   -1.6157    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7230   -0.7080    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5981   -1.5034    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6484   -2.4616    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    0.6880   -3.2184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4051   -2.4220    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1085   -2.5012    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4533   -0.8497    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4964   -1.7563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7466   -1.9212    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.1251   -1.3876    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2517   -1.8878    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0687   -0.5120    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5738   -0.1115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3458   -0.8924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4792   -0.7950    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3825    0.0128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2576   -0.5673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0493   -0.5925    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5519    0.2102    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  1  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
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 10 13  2  0  0  0  0
  8 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
  5 19  1  0  0  0  0
 19 20  1  1  0  0  0
 14 20  1  0  0  0  0
 17 21  1  1  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 14 24  1  1  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
M  END

     RDKit          3D

 43 44  0  0  0  0  0  0  0  0999 V2000
   -1.4751    3.8620    2.3818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1343    2.5113    1.9120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9121    1.6036    2.7171 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0249    2.1051    0.6253 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7125    0.8426    0.2174 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7845    1.0380   -0.1801 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8633    1.9953   -1.2608 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4091   -0.2596   -0.5711 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8307   -0.8942    0.6040 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5083   -1.0367    0.6857 P   0  0  0  0  0  5  0  0  0  0  0  0
    3.9725   -0.3103    1.9388 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8691   -2.6927    0.7827 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2224   -0.3335   -0.6660 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4436   -1.1111   -1.3658 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2015   -1.5378   -2.6024 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8335   -1.2918   -3.7572 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3720   -2.2433   -2.4060 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2067   -2.3731   -0.5849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3652   -2.3424    0.3185 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3678   -0.9899   -0.3782 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8792   -1.5556   -1.5839 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4916   -0.6277    0.4495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3266   -0.0711    1.7356 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6736   -0.7907    0.0663 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4622    0.1577   -0.8218 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6447   -0.4499   -1.8118 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9881    3.8842    3.3476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1941    4.2896    1.6230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5947    4.5560    2.3673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6131    0.1875    1.1103 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2750    1.4630    0.6977 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5098    1.6213   -2.0030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0863    2.0287   -1.7089 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3356   -0.0226   -1.1352 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4195   -2.8267    1.6110 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5014    0.5836   -0.4241 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4232   -3.1744   -2.0512 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1764   -3.2789   -1.2364 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9982   -2.5716    0.1660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6308   -0.9525   -1.8358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7848    0.7790    2.0922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6734   -0.5703    2.3968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1209    0.8001   -1.4619 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 12  1  0
 10 13  1  0
 10 11  2  0
  8 14  1  0
 14 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  6
 20 25  1  0
 25 26  1  0
 20 22  1  0
 22 23  1  0
 22 24  2  0
 14 15  1  6
 15 17  1  0
 15 16  2  0
 25  5  1  0
 26 14  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  5 30  1  1
  6 31  1  1
  7 32  1  0
  7 33  1  0
  8 34  1  6
 12 35  1  0
 13 36  1  0
 18 38  1  0
 18 39  1  0
 21 40  1  0
 25 43  1  6
 23 41  1  0
 23 42  1  0
 17 37  1  0
M  END


  Mrv0541 02231217552D          

 26 27  0  0  1  0            999 V2000
   -1.2401    1.0663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1491    0.3140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7551   -0.1411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4420    0.0124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2245   -0.5127    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1079   -1.2493    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6429   -1.6157    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7230   -0.7080    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5981   -1.5034    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6484   -2.4616    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    0.6880   -3.2184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4051   -2.4220    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1085   -2.5012    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4533   -0.8497    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4964   -1.7563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7466   -1.9212    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.1251   -1.3876    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2517   -1.8878    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0687   -0.5120    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5738   -0.1115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3458   -0.8924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4792   -0.7950    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3825    0.0128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2576   -0.5673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0493   -0.5925    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5519    0.2102    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  1  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
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 10 13  2  0  0  0  0
  8 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
  5 19  1  0  0  0  0
 19 20  1  1  0  0  0
 14 20  1  0  0  0  0
 17 21  1  1  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 14 24  1  1  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0319635

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@@H]1[C@H](N)[C@@H](OP(O)(O)=O)[C@]2(CS[C@](O)([C@@H]1O2)C(N)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H17N2O11PS/c1-3(14)22-5-4(12)6(24-25(19,20)21)10(9(16)17)2-26-11(18,8(13)15)7(5)23-10/h4-7,18H,2,12H2,1H3,(H2,13,15)(H,16,17)(H2,19,20,21)/t4-,5+,6+,7+,10+,11+/m0/s1

> <INCHI_KEY>
UVAAUIDYGIWLMB-HGNFPZBQSA-N

> <FORMULA>
C11H17N2O11PS

> <MOLECULAR_WEIGHT>
416.298

> <EXACT_MASS>
416.029066598

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_AVERAGE_POLARIZABILITY>
34.13923674046006

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,4R,5R,6R,7S,8R)-6-(acetyloxy)-7-amino-4-carbamoyl-4-hydroxy-8-(phosphonooxy)-9-oxa-3-thiabicyclo[3.3.1]nonane-1-carboxylic acid

> <ALOGPS_LOGP>
-1.50

> <JCHEM_LOGP>
-3.8289817682571625

> <ALOGPS_LOGS>
-1.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
2.9883645242951746

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.8531402067437499

> <JCHEM_PKA_STRONGEST_BASIC>
8.717465201976024

> <JCHEM_POLAR_SURFACE_AREA>
228.92999999999998

> <JCHEM_REFRACTIVITY>
80.57669999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.75e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tagetitoxin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      -2.315   1.990   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.145   0.586   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -3.276  -0.263   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -0.825   0.023   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.419  -0.957   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.201  -2.332   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      -1.200  -3.016   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       1.350  -1.322   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.116  -2.806   0.000  0.00  0.00           O+0
HETATM   10  P   UNK     0       1.210  -4.595   0.000  0.00  0.00           P+0
HETATM   11  O   UNK     0       1.284  -6.008   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       2.623  -4.521   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -0.203  -4.669   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.713  -1.586   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.793  -3.278   0.000  0.00  0.00           C+0
HETATM   16  S   UNK     0       1.394  -3.586   0.000  0.00  0.00           S+0
HETATM   17  C   UNK     0       2.100  -2.590   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.470  -3.524   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       1.995  -0.956   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.938  -0.208   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       0.645  -1.666   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0      -0.895  -1.484   0.000  0.00  0.00           N+0
HETATM   23  O   UNK     0       0.714   0.024   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       4.214  -1.059   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       5.692  -1.106   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       4.764   0.392   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   19                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12   13                                             
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13   10                                                            
CONECT   14    8   15   20   24                                             
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19   21                                             
CONECT   18   17                                                            
CONECT   19   17    5   20                                                  
CONECT   20   19   14                                                       
CONECT   21   17   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   14   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   54    0
END

View in JSmol

Synonyms

Value	Source
(1R,4R,5R,6R,7S,8R)-6-(Acetyloxy)-7-amino-4-hydroxy-4-(C-hydroxycarbonimidoyl)-8-(phosphonooxy)-9-oxa-3-thiabicyclo[3.3.1]nonane-1-carboxylate	Generator

Chemical Formula

C₁₁H₁₇N₂O₁₁PS

Average Mass

416.2980 Da

Monoisotopic Mass

416.02907 Da

IUPAC Name

(1R,4R,5R,6R,7S,8R)-6-(acetyloxy)-7-amino-4-carbamoyl-4-hydroxy-8-(phosphonooxy)-9-oxa-3-thiabicyclo[3.3.1]nonane-1-carboxylic acid

Traditional Name

tagetitoxin

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@@H]1[C@H](N)[C@@H](OP(O)(O)=O)[C@]2(CS[C@](O)([C@@H]1O2)C(N)=O)C(O)=O

InChI Identifier

InChI=1S/C11H17N2O11PS/c1-3(14)22-5-4(12)6(24-25(19,20)21)10(9(16)17)2-26-11(18,8(13)15)7(5)23-10/h4-7,18H,2,12H2,1H3,(H2,13,15)(H,16,17)(H2,19,20,21)/t4-,5+,6+,7+,10+,11+/m0/s1

InChI Key

UVAAUIDYGIWLMB-HGNFPZBQSA-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 syringae	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as delta amino acids and derivatives. Delta amino acids and derivatives are compounds containing a carboxylic acid group and an amino group at the C5 carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Delta amino acids and derivatives

Alternative Parents

Substituents

Delta amino acid or derivatives
Gamma amino acid or derivatives
Monoalkyl phosphate
Dicarboxylic acid or derivatives
Monosaccharide
Organic phosphoric acid derivative
Oxane
1,4-oxathiane
Phosphoric acid ester
Pyran
Alkyl phosphate
Primary carboxylic acid amide
Amino acid
Carboxylic acid ester
Carboxamide group
Carboxylic acid
Oxacycle
Organoheterocyclic compound
Dialkyl ether
Ether
Organic oxide
Primary aliphatic amine
Organic oxygen compound
Amine
Organic nitrogen compound
Carbonyl group
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Primary amine
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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	-1.5	ALOGPS
logP	-3.8	ChemAxon
logS	-1	ALOGPS
pKa (Strongest Acidic)	0.85	ChemAxon
pKa (Strongest Basic)	8.72	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	228.93 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	80.58 m³·mol⁻¹	ChemAxon
Polarizability	34.14 Å³	ChemAxon
Number of Rings	2	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

DB04788

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Tagetitoxin

METLIN ID

Not Available

PubChem Compound

5327077

PDB ID

TGT

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,4r,5r,6r,7s,8r)-6-(acetyloxy)-7-amino-4-hydroxy-4-(c-hydroxycarbonimidoyl)-8-(phosphonooxy)-9-oxa-3-thiabicyclo[3.3.1]nonane-1-carboxylic acid (NP0319635)

MOL for NP0319635 ((1r,4r,5r,6r,7s,8r)-6-(acetyloxy)-7-amino-4-hydroxy-4-(c-hydroxycarbonimidoyl)-8-(phosphonooxy)-9-oxa-3-thiabicyclo[3.3.1]nonane-1-carboxylic acid)

3D MOL for NP0319635 ((1r,4r,5r,6r,7s,8r)-6-(acetyloxy)-7-amino-4-hydroxy-4-(c-hydroxycarbonimidoyl)-8-(phosphonooxy)-9-oxa-3-thiabicyclo[3.3.1]nonane-1-carboxylic acid)

3D SDF for NP0319635 ((1r,4r,5r,6r,7s,8r)-6-(acetyloxy)-7-amino-4-hydroxy-4-(c-hydroxycarbonimidoyl)-8-(phosphonooxy)-9-oxa-3-thiabicyclo[3.3.1]nonane-1-carboxylic acid)

3D-SDF for NP0319635 ((1r,4r,5r,6r,7s,8r)-6-(acetyloxy)-7-amino-4-hydroxy-4-(c-hydroxycarbonimidoyl)-8-(phosphonooxy)-9-oxa-3-thiabicyclo[3.3.1]nonane-1-carboxylic acid)

PDB for NP0319635 ((1r,4r,5r,6r,7s,8r)-6-(acetyloxy)-7-amino-4-hydroxy-4-(c-hydroxycarbonimidoyl)-8-(phosphonooxy)-9-oxa-3-thiabicyclo[3.3.1]nonane-1-carboxylic acid)

3D PDB for NP0319635 ((1r,4r,5r,6r,7s,8r)-6-(acetyloxy)-7-amino-4-hydroxy-4-(c-hydroxycarbonimidoyl)-8-(phosphonooxy)-9-oxa-3-thiabicyclo[3.3.1]nonane-1-carboxylic acid)

SMILES for NP0319635 ((1r,4r,5r,6r,7s,8r)-6-(acetyloxy)-7-amino-4-hydroxy-4-(c-hydroxycarbonimidoyl)-8-(phosphonooxy)-9-oxa-3-thiabicyclo[3.3.1]nonane-1-carboxylic acid)

INCHI for NP0319635 ((1r,4r,5r,6r,7s,8r)-6-(acetyloxy)-7-amino-4-hydroxy-4-(c-hydroxycarbonimidoyl)-8-(phosphonooxy)-9-oxa-3-thiabicyclo[3.3.1]nonane-1-carboxylic acid)

Structure for NP0319635 ((1r,4r,5r,6r,7s,8r)-6-(acetyloxy)-7-amino-4-hydroxy-4-(c-hydroxycarbonimidoyl)-8-(phosphonooxy)-9-oxa-3-thiabicyclo[3.3.1]nonane-1-carboxylic acid)

3D Structure for NP0319635 ((1r,4r,5r,6r,7s,8r)-6-(acetyloxy)-7-amino-4-hydroxy-4-(c-hydroxycarbonimidoyl)-8-(phosphonooxy)-9-oxa-3-thiabicyclo[3.3.1]nonane-1-carboxylic acid)