NP-MRD: Showing NP-Card for (7s,8s)-11-hydroxy-8-(1h-indol-3-yl)-3,9-diazatricyclo[8.4.0.0³,⁷]tetradeca-1(14),10,12-trien-2-one (NP0257812)

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Record Information

Version

2.0

Created at

2022-09-07 23:02:45 UTC

Updated at

2022-09-07 23:02:45 UTC

NP-MRD ID

NP0257812

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(7s,8s)-11-hydroxy-8-(1h-indol-3-yl)-3,9-diazatricyclo[8.4.0.0³,⁷]tetradeca-1(14),10,12-trien-2-one

Description

Tilivalline belongs to the class of organic compounds known as 1,4-benzodiazepines. These are organic compounds containing a benzene ring fused to a 1,4-azepine. Tilivalline is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. (7s,8s)-11-hydroxy-8-(1h-indol-3-yl)-3,9-diazatricyclo[8.4.0.0³,⁷]tetradeca-1(14),10,12-trien-2-one was first documented in 2017 (PMID: 28972161). Based on a literature review a significant number of articles have been published on tilivalline (PMID: 28993611) (PMID: 29596433) (PMID: 35073747) (PMID: 34851134) (PMID: 34659176) (PMID: 34582979).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082201022D          

 25 29  0  0  1  0            999 V2000
    3.5447    1.2377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5354    0.4127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2747    0.0465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8857    0.6008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6713    0.3489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8459   -0.4575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2349   -1.0118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4094   -1.8181    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4493   -0.7598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9277   -1.3991    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1028   -1.3898    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7365   -2.1291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1193   -2.8599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5426   -3.4498    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8033   -3.0836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0365   -3.3879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3895   -2.8759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5094   -2.0597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2762   -1.7554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9232   -2.2673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5956   -0.7391    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7732   -0.8039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4574   -0.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0847    0.4941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7882    0.0631    0.0000 N   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
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  3  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 12 20  1  0  0  0  0
 15 20  1  0  0  0  0
 11 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
  2 25  1  0  0  0  0
 21 25  1  6  0  0  0
M  END

     RDKit          3D

 44 48  0  0  0  0  0  0  0  0999 V2000
    3.8427    1.7498   -0.8538 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8995    1.1447   -0.3463 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0643   -0.3177   -0.2026 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3899   -0.6808   -0.1323 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7603   -2.0060    0.0237 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8063   -2.9762    0.1110 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4349   -2.6198    0.0406 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5160   -3.6098    0.1260 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0766   -1.2817   -0.1171 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6904   -1.0406   -0.1798 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1155    0.1544   -0.3724 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4180   -0.1523    0.3256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4932   -0.2970    1.7094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7397   -0.7399    2.0349 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4280   -0.8643    0.8995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7453   -1.2133    0.6152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2190   -1.1896   -0.6897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3846   -0.8208   -1.7226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0799   -0.4735   -1.4778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6276   -0.5047   -0.1671 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4154    1.3497    0.3980 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4608    2.5136   -0.1701 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4899    3.6389   -0.4645 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7170    3.2354    0.2986 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7126    1.8015    0.0837 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1419    0.1004   -0.2003 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8135   -2.3130    0.0731 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0631   -4.0168    0.2331 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5794   -3.7178    0.1263 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1343   -1.9102   -0.0525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2978    0.3765   -1.3999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7239   -0.1134    2.4327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0725   -0.9455    2.9798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4011   -1.5097    1.4329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2575   -1.4565   -0.8908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7588   -0.7805   -2.7471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4072   -0.1860   -2.2499 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2666    1.2772    1.4718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2163    2.7519    0.5633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9473    2.1816   -1.1256 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0821    4.6250   -0.1243 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7283    3.7149   -1.5659 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6422    3.7117   -0.0798 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5267    3.4101    1.3532 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 11 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25  2  1  0
  2  1  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
  6  7  1  0
 20 12  1  0
  3  9  1  0
 20 15  1  0
 25 21  1  0
  8 29  1  0
 10 30  1  0
 11 31  1  6
 21 38  1  1
 22 39  1  0
 22 40  1  0
 23 41  1  0
 23 42  1  0
 24 43  1  0
 24 44  1  0
  4 26  1  0
  5 27  1  0
  6 28  1  0
 13 32  1  0
 14 33  1  0
 16 34  1  0
 17 35  1  0
 18 36  1  0
 19 37  1  0
M  END


  Mrv1652309082201022D          

 25 29  0  0  1  0            999 V2000
    3.5447    1.2377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5354    0.4127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2747    0.0465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8857    0.6008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6713    0.3489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8459   -0.4575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2349   -1.0118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4094   -1.8181    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4493   -0.7598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9277   -1.3991    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1028   -1.3898    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7365   -2.1291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1193   -2.8599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5426   -3.4498    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8033   -3.0836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0365   -3.3879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3895   -2.8759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5094   -2.0597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2762   -1.7554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9232   -2.2673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5956   -0.7391    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7732   -0.8039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4574   -0.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0847    0.4941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7882    0.0631    0.0000 N   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
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  3  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 12 20  1  0  0  0  0
 15 20  1  0  0  0  0
 11 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
  2 25  1  0  0  0  0
 21 25  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0257812

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=C2N[C@H]([C@@H]3CCCN3C(=O)C2=CC=C1)C1=CNC2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C20H19N3O2/c24-17-9-3-6-13-19(17)22-18(16-8-4-10-23(16)20(13)25)14-11-21-15-7-2-1-5-12(14)15/h1-3,5-7,9,11,16,18,21-22,24H,4,8,10H2/t16-,18-/m0/s1

> <INCHI_KEY>
AJZNARCWDDMOPL-WMZOPIPTSA-N

> <FORMULA>
C20H19N3O2

> <MOLECULAR_WEIGHT>
333.391

> <EXACT_MASS>
333.147726864

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
35.4056385014813

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(7S,8S)-11-hydroxy-8-(1H-indol-3-yl)-3,9-diazatricyclo[8.4.0.0^{3,7}]tetradeca-1(10),11,13-trien-2-one

> <JCHEM_LOGP>
3.2674928209999994

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.874978265681815

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.605276572851084

> <JCHEM_PKA_STRONGEST_BASIC>
1.9695434722913845

> <JCHEM_POLAR_SURFACE_AREA>
68.36000000000001

> <JCHEM_REFRACTIVITY>
97.71599999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(7S,8S)-11-hydroxy-8-(1H-indol-3-yl)-3,9-diazatricyclo[8.4.0.0^{3,7}]tetradeca-1(10),11,13-trien-2-one

> <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  O   UNK     0       6.617   2.310   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       6.599   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.979   0.087   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.120   1.122   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.586   0.651   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.912  -0.854   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.772  -1.889   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      10.098  -3.394   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       8.305  -1.418   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       7.332  -2.612   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       5.792  -2.594   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.108  -3.974   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.823  -5.338   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       4.746  -6.440   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       3.366  -5.756   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.935  -6.324   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.727  -5.368   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.951  -3.845   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.382  -3.277   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.590  -4.232   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.845  -1.380   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.310  -1.501   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.721  -0.078   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.892   0.922   0.000  0.00  0.00           C+0
HETATM   25  N   UNK     0       5.205   0.118   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3   25                                                  
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7    3   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   21                                                  
CONECT   12   11   13   20                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   12   15                                                  
CONECT   21   11   22   25                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24    2   21                                                  
MASTER        0    0    0    0    0    0    0    0   25    0   58    0
END

View in JSmol

Synonyms

Value	Source
(7S,8S)-11-Hydroxy-8-(1H-indol-3-yl)-3,9-diazatricyclo[8.4.0.0(3,7)]tetradeca-1(10),11,13-trien-2-one	ChEBI
Epitilivalline	ChEBI

Chemical Formula

C₂₀H₁₉N₃O₂

Average Mass

333.3910 Da

Monoisotopic Mass

333.14773 Da

IUPAC Name

(7S,8S)-11-hydroxy-8-(1H-indol-3-yl)-3,9-diazatricyclo[8.4.0.0^{3,7}]tetradeca-1(10),11,13-trien-2-one

Traditional Name

(7S,8S)-11-hydroxy-8-(1H-indol-3-yl)-3,9-diazatricyclo[8.4.0.0^{3,7}]tetradeca-1(10),11,13-trien-2-one

CAS Registry Number

Not Available

SMILES

OC1=C2N[C@H]([C@@H]3CCCN3C(=O)C2=CC=C1)C1=CNC2=CC=CC=C12

InChI Identifier

InChI=1S/C20H19N3O2/c24-17-9-3-6-13-19(17)22-18(16-8-4-10-23(16)20(13)25)14-11-21-15-7-2-1-5-12(14)15/h1-3,5-7,9,11,16,18,21-22,24H,4,8,10H2/t16-,18-/m0/s1

InChI Key

AJZNARCWDDMOPL-WMZOPIPTSA-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 1,4-benzodiazepines. These are organic compounds containing a benzene ring fused to a 1,4-azepine.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzodiazepines

Sub Class

1,4-benzodiazepines

Direct Parent

1,4-benzodiazepines

Alternative Parents

Substituents

1,4-benzodiazepine
3-alkylindole
Indole
Indole or derivatives
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Secondary aliphatic/aromatic amine
Aralkylamine
Substituted pyrrole
Benzenoid
Pyrrole
Pyrrolidine
Tertiary carboxylic acid amide
Heteroaromatic compound
Vinylogous amide
Amino acid or derivatives
Lactam
Carboxamide group
Secondary amine
Carboxylic acid derivative
Azacycle
Organic oxide
Organopnictogen compound
Amine
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	3.27	ChemAxon
pKa (Strongest Acidic)	9.61	ChemAxon
pKa (Strongest Basic)	1.97	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	68.36 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	97.72 m³·mol⁻¹	ChemAxon
Polarizability	35.41 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

113792

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Tilivalline

METLIN ID

Not Available

PubChem Compound

128363

PDB ID

Not Available

ChEBI ID

156292

Good Scents ID

Not Available

References

General References

Tse H, Gu Q, Sze KH, Chu IK, Kao RY, Lee KC, Lam CW, Yang D, Tai SS, Ke Y, Chan E, Chan WM, Dai J, Leung SP, Leung SY, Yuen KY: A tricyclic pyrrolobenzodiazepine produced by Klebsiella oxytoca is associated with cytotoxicity in antibiotic-associated hemorrhagic colitis. J Biol Chem. 2017 Nov 24;292(47):19503-19520. doi: 10.1074/jbc.M117.791558. Epub 2017 Sep 26. [PubMed:28972161 ]
Tobias NJ, Wolff H, Djahanschiri B, Grundmann F, Kronenwerth M, Shi YM, Simonyi S, Grun P, Shapiro-Ilan D, Pidot SJ, Stinear TP, Ebersberger I, Bode HB: Natural product diversity associated with the nematode symbionts Photorhabdus and Xenorhabdus. Nat Microbiol. 2017 Dec;2(12):1676-1685. doi: 10.1038/s41564-017-0039-9. Epub 2017 Oct 9. [PubMed:28993611 ]
Wolff H, Bode HB: The benzodiazepine-like natural product tilivalline is produced by the entomopathogenic bacterium Xenorhabdus eapokensis. PLoS One. 2018 Mar 29;13(3):e0194297. doi: 10.1371/journal.pone.0194297. eCollection 2018. [PubMed:29596433 ]
Ledala N, Malik M, Rezaul K, Paveglio S, Provatas A, Kiel A, Caimano M, Zhou Y, Lindgren J, Krasulova K, Illes P, Dvorak Z, Kortagere S, Kienesberger S, Cosic A, Poltl L, Zechner EL, Ghosh S, Mani S, Radolf JD, Matson AP: Bacterial Indole as a Multifunctional Regulator of Klebsiella oxytoca Complex Enterotoxicity. mBio. 2022 Feb 22;13(1):e0375221. doi: 10.1128/mbio.03752-21. Epub 2022 Jan 25. [PubMed:35073747 ]
Yang J, Long H, Hu Y, Feng Y, McNally A, Zong Z: Klebsiella oxytoca Complex: Update on Taxonomy, Antimicrobial Resistance, and Virulence. Clin Microbiol Rev. 2022 Jan 19;35(1):e0000621. doi: 10.1128/CMR.00006-21. Epub 2021 Dec 1. [PubMed:34851134 ]
Rodriguez-Valverde D, Leon-Montes N, Soria-Bustos J, Martinez-Cruz J, Gonzalez-Ugalde R, Rivera-Gutierrez S, Gonzalez-Y-Merchand JA, Rosales-Reyes R, Garcia-Morales L, Hirakawa H, Fox JG, Giron JA, De la Cruz MA, Ares MA: cAMP Receptor Protein Positively Regulates the Expression of Genes Involved in the Biosynthesis of Klebsiella oxytoca Tilivalline Cytotoxin. Front Microbiol. 2021 Sep 30;12:743594. doi: 10.3389/fmicb.2021.743594. eCollection 2021. [PubMed:34659176 ]
Leitner E, Bozic M, Kienesberger S, Cosic A, Landt O, Hogenauer C, Kessler HH: Improved diagnosis of antibiotic-associated haemorrhagic colitis (AAHC) in faecal specimens by a new qualitative real-time PCR assay detecting relevant toxin genes of Klebsiella oxytoca sensu lato. Clin Microbiol Infect. 2022 May;28(5):690-694. doi: 10.1016/j.cmi.2021.09.017. Epub 2021 Sep 25. [PubMed:34582979 ]
Greimel TM, Stampfer L, Leitner E, Kienesberger S, Zechner EL, Bozic M, Wagner GE, Unterhauser K, Kitsera M, Hauer AC, Gorkiewicz G, Wurm P, Valitutti F, Hogenauer C, Hoffmann KM: Toxin-Producing Klebsiella oxytoca in Healthy Infants: Commensal or Pathobiont? J Pediatr Gastroenterol Nutr. 2022 Jan 1;74(1):e1-e7. doi: 10.1097/MPG.0000000000003299. [PubMed:34520403 ]
Neog N, Phukan U, Puzari M, Sharma M, Chetia P: Klebsiella oxytoca and Emerging Nosocomial Infections. Curr Microbiol. 2021 Apr;78(4):1115-1123. doi: 10.1007/s00284-021-02402-2. Epub 2021 Mar 3. [PubMed:33656584 ]
Glabonjat RA, Kitsera M, Unterhauser K, Lembacher-Fadum C, Hogenauer C, Raber G, Breinbauer R, Zechner EL: Simultaneous quantification of enterotoxins tilimycin and tilivalline in biological matrices using HPLC high resolution ESMS(2) based on isotopically (15)N-labeled internal standards. Talanta. 2021 Jan 15;222:121677. doi: 10.1016/j.talanta.2020.121677. Epub 2020 Sep 17. [PubMed:33167283 ]
Hering NA, Fromm A, Bucker R, Gorkiewicz G, Zechner E, Hogenauer C, Fromm M, Schulzke JD, Troeger H: Tilivalline- and Tilimycin-Independent Effects of Klebsiella oxytoca on Tight Junction-Mediated Intestinal Barrier Impairment. Int J Mol Sci. 2019 Nov 8;20(22):5595. doi: 10.3390/ijms20225595. [PubMed:31717457 ]
Unterhauser K, Poltl L, Schneditz G, Kienesberger S, Glabonjat RA, Kitsera M, Pletz J, Josa-Prado F, Dornisch E, Lembacher-Fadum C, Roier S, Gorkiewicz G, Lucena D, Barasoain I, Kroutil W, Wiedner M, Loizou JI, Breinbauer R, Diaz JF, Schild S, Hogenauer C, Zechner EL: Klebsiella oxytoca enterotoxins tilimycin and tilivalline have distinct host DNA-damaging and microtubule-stabilizing activities. Proc Natl Acad Sci U S A. 2019 Feb 26;116(9):3774-3783. doi: 10.1073/pnas.1819154116. Epub 2019 Feb 11. [PubMed:30808763 ]
Pavlikova M, Kamenik Z, Janata J, Kadlcik S, Kuzma M, Najmanova L: Novel pathway of 3-hydroxyanthranilic acid formation in limazepine biosynthesis reveals evolutionary relation between phenazines and pyrrolobenzodiazepines. Sci Rep. 2018 May 17;8(1):7810. doi: 10.1038/s41598-018-26179-w. [PubMed:29773836 ]
von Tesmar A, Hoffmann M, Abou Fayad A, Huttel S, Schmitt V, Herrmann J, Muller R: Biosynthesis of the Klebsiella oxytoca Pathogenicity Factor Tilivalline: Heterologous Expression, in Vitro Biosynthesis, and Inhibitor Development. ACS Chem Biol. 2018 Mar 16;13(3):812-819. doi: 10.1021/acschembio.7b00990. Epub 2018 Feb 13. [PubMed:29389112 ]
Dornisch E, Pletz J, Glabonjat RA, Martin F, Lembacher-Fadum C, Neger M, Hogenauer C, Francesconi K, Kroutil W, Zangger K, Breinbauer R, Zechner EL: Biosynthesis of the Enterotoxic Pyrrolobenzodiazepine Natural Product Tilivalline. Angew Chem Int Ed Engl. 2017 Nov 13;56(46):14753-14757. doi: 10.1002/anie.201707737. Epub 2017 Oct 18. [PubMed:28977734 ]
LOTUS database [Link]

Showing NP-Card for (7s,8s)-11-hydroxy-8-(1h-indol-3-yl)-3,9-diazatricyclo[8.4.0.0³,⁷]tetradeca-1(14),10,12-trien-2-one (NP0257812)

MOL for NP0257812 ((7s,8s)-11-hydroxy-8-(1h-indol-3-yl)-3,9-diazatricyclo[8.4.0.0³,⁷]tetradeca-1(14),10,12-trien-2-one)

3D MOL for NP0257812 ((7s,8s)-11-hydroxy-8-(1h-indol-3-yl)-3,9-diazatricyclo[8.4.0.0³,⁷]tetradeca-1(14),10,12-trien-2-one)

3D SDF for NP0257812 ((7s,8s)-11-hydroxy-8-(1h-indol-3-yl)-3,9-diazatricyclo[8.4.0.0³,⁷]tetradeca-1(14),10,12-trien-2-one)

3D-SDF for NP0257812 ((7s,8s)-11-hydroxy-8-(1h-indol-3-yl)-3,9-diazatricyclo[8.4.0.0³,⁷]tetradeca-1(14),10,12-trien-2-one)

PDB for NP0257812 ((7s,8s)-11-hydroxy-8-(1h-indol-3-yl)-3,9-diazatricyclo[8.4.0.0³,⁷]tetradeca-1(14),10,12-trien-2-one)

3D PDB for NP0257812 ((7s,8s)-11-hydroxy-8-(1h-indol-3-yl)-3,9-diazatricyclo[8.4.0.0³,⁷]tetradeca-1(14),10,12-trien-2-one)

SMILES for NP0257812 ((7s,8s)-11-hydroxy-8-(1h-indol-3-yl)-3,9-diazatricyclo[8.4.0.0³,⁷]tetradeca-1(14),10,12-trien-2-one)

INCHI for NP0257812 ((7s,8s)-11-hydroxy-8-(1h-indol-3-yl)-3,9-diazatricyclo[8.4.0.0³,⁷]tetradeca-1(14),10,12-trien-2-one)

Structure for NP0257812 ((7s,8s)-11-hydroxy-8-(1h-indol-3-yl)-3,9-diazatricyclo[8.4.0.0³,⁷]tetradeca-1(14),10,12-trien-2-one)

3D Structure for NP0257812 ((7s,8s)-11-hydroxy-8-(1h-indol-3-yl)-3,9-diazatricyclo[8.4.0.0³,⁷]tetradeca-1(14),10,12-trien-2-one)