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Showing NP-Card for Tentoxin (NP0050705)

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Record Information
Version2.0
Created at2022-04-27 22:02:53 UTC
Updated at2022-04-27 22:02:53 UTC
NP-MRD IDNP0050705
Secondary Accession NumbersNone
Natural Product Identification
Common NameTentoxin
DescriptionTentoxin belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds. Tentoxin has also been used in recent research to eliminate the polyphenol oxidase (PPO) activity from seedlings of higher plants. It selectively induces chlorosis in several germinating seedling plants. Tentoxin is a strong basic compound (based on its pKa). Tentoxin is a potentially toxic compound. Tentoxin was first isolated from Alternaria alternata (syn. Tenuis) and characterized by George Templeton et al. In 1967. Therefore, tentoxin may be used as a potential natural herbicide. Tentoxin is found in Alternaria tenuis and Alternaria porri. Tentoxin is a natural cyclic tetrapeptide produced by phytopathogenic fungus Alternaria alternata.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0050705 (Tentoxin)


  Mrv0541 05041412202D          

 33 34  0  0  1  0            999 V2000
    4.7208   -1.0812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7801   -2.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6749    0.5585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9945    2.1773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2001    1.3470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1717   -1.2563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8862   -0.8438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4573   -0.8438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8862   -0.0188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4573   -0.0188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3189   -0.8044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1717    1.6716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5561    2.7099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9399   -1.3475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4557    0.8248    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1717    0.3937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4787    0.0050    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7982    1.6237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3963    1.9005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0768    0.2817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9580    2.4331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2595    0.2713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3370    2.9762    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8576    0.5480    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6155    1.6342    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4193    1.0807    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0174    1.3574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9170   -0.5276    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7388    2.6994    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8805   -0.2718    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6110    2.2767    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2959    0.0154    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0997   -0.5381    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  2  0  0  0  0
  8  6  1  0  0  0  0
  9  7  1  0  0  0  0
 10  8  2  0  0  0  0
 14  1  1  0  0  0  0
 14  2  1  0  0  0  0
 14 11  1  0  0  0  0
 15  3  1  6  0  0  0
 16  9  2  0  0  0  0
 16 10  1  0  0  0  0
 16 12  1  0  0  0  0
 17 11  1  6  0  0  0
 18 12  2  0  0  0  0
 19 13  1  0  0  0  0
 20 15  1  0  0  0  0
 21 18  1  0  0  0  0
 22 17  1  0  0  0  0
 23 13  1  4  0  0  0
 23 21  2  0  0  0  0
 24 17  1  0  0  0  0
 24 20  2  0  0  0  0
 25  4  1  0  0  0  0
 25 15  1  0  0  0  0
 25 19  1  0  0  0  0
 26  5  1  0  0  0  0
 26 18  1  0  0  0  0
 26 22  1  0  0  0  0
 27 19  2  0  0  0  0
 20 28  1  4  0  0  0
 29 21  1  0  0  0  0
 30 22  2  0  0  0  0
 31 12  1  0  0  0  0
 15 32  1  1  0  0  0
 17 33  1  1  0  0  0
M  END
Download

3D MOL for NP0050705 (Tentoxin)

Download
3D SDF for NP0050705 (Tentoxin)

  Mrv0541 05041412202D          

 33 34  0  0  1  0            999 V2000
    4.7208   -1.0812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7801   -2.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6749    0.5585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9945    2.1773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2001    1.3470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1717   -1.2563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8862   -0.8438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4573   -0.8438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8862   -0.0188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4573   -0.0188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3189   -0.8044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1717    1.6716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5561    2.7099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9399   -1.3475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4557    0.8248    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1717    0.3937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4787    0.0050    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7982    1.6237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3963    1.9005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0768    0.2817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9580    2.4331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2595    0.2713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3370    2.9762    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8576    0.5480    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6155    1.6342    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4193    1.0807    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0174    1.3574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9170   -0.5276    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7388    2.6994    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8805   -0.2718    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6110    2.2767    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2959    0.0154    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0997   -0.5381    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  2  0  0  0  0
  8  6  1  0  0  0  0
  9  7  1  0  0  0  0
 10  8  2  0  0  0  0
 14  1  1  0  0  0  0
 14  2  1  0  0  0  0
 14 11  1  0  0  0  0
 15  3  1  6  0  0  0
 16  9  2  0  0  0  0
 16 10  1  0  0  0  0
 16 12  1  0  0  0  0
 17 11  1  6  0  0  0
 18 12  2  0  0  0  0
 19 13  1  0  0  0  0
 20 15  1  0  0  0  0
 21 18  1  0  0  0  0
 22 17  1  0  0  0  0
 23 13  1  4  0  0  0
 23 21  2  0  0  0  0
 24 17  1  0  0  0  0
 24 20  2  0  0  0  0
 25  4  1  0  0  0  0
 25 15  1  0  0  0  0
 25 19  1  0  0  0  0
 26  5  1  0  0  0  0
 26 18  1  0  0  0  0
 26 22  1  0  0  0  0
 27 19  2  0  0  0  0
 20 28  1  4  0  0  0
 29 21  1  0  0  0  0
 30 22  2  0  0  0  0
 31 12  1  0  0  0  0
 15 32  1  1  0  0  0
 17 33  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0050705

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]\C(C1=CC=CC=C1)=C1\N(C)C(=O)[C@]([H])(CC(C)C)N=C(O)[C@]([H])(C)N(C)C(=O)CN=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C22H30N4O4/c1-14(2)11-17-22(30)26(5)18(12-16-9-7-6-8-10-16)21(29)23-13-19(27)25(4)15(3)20(28)24-17/h6-10,12,14-15,17H,11,13H2,1-5H3,(H,23,29)(H,24,28)/b18-12-/t15-,17-/m0/s1

> <INCHI_KEY>
SIIRBDOFKDACOK-LFXZBHHUSA-N

> <FORMULA>
C22H30N4O4

> <MOLECULAR_WEIGHT>
414.498

> <EXACT_MASS>
414.226705468

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
43.74693717565856

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,6S,12Z)-5,11-dihydroxy-1,6,7-trimethyl-3-(2-methylpropyl)-12-(phenylmethylidene)-1,4,7,10-tetraazacyclododeca-4,10-diene-2,8-dione

> <ALOGPS_LOGP>
2.01

> <JCHEM_LOGP>
1.9812847686897337

> <ALOGPS_LOGS>
-3.98

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
8.26969692821632

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.316958833031537

> <JCHEM_PKA_STRONGEST_BASIC>
4.589908468397472

> <JCHEM_POLAR_SURFACE_AREA>
105.80000000000001

> <JCHEM_REFRACTIVITY>
115.39359999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.31e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tentoxin

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0050705 (Tentoxin)
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PDB for NP0050705 (Tentoxin)
HEADER    PROTEIN                                 04-MAY-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-MAY-14         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   23  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   24  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   25  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   26  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   27  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   31  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   32  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   33  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1   14                                                            
CONECT    2   14                                                            
CONECT    3   15                                                            
CONECT    4   25                                                            
CONECT    5   26                                                            
CONECT    6    7    8                                                       
CONECT    7    6    9                                                       
CONECT    8    6   10                                                       
CONECT    9    7   16                                                       
CONECT   10    8   16                                                       
CONECT   11   14   17                                                       
CONECT   12   16   18   31                                                  
CONECT   13   19   23                                                       
CONECT   14    1    2   11                                                  
CONECT   15    3   20   25   32                                             
CONECT   16    9   10   12                                                  
CONECT   17   11   22   24   33                                             
CONECT   18   12   21   26                                                  
CONECT   19   13   25   27                                                  
CONECT   20   15   24   28                                                  
CONECT   21   18   23   29                                                  
CONECT   22   17   26   30                                                  
CONECT   23   13   21                                                       
CONECT   24   17   20                                                       
CONECT   25    4   15   19                                                  
CONECT   26    5   18   22                                                  
CONECT   27   19                                                            
CONECT   28   20                                                            
CONECT   29   21                                                            
CONECT   30   22                                                            
CONECT   31   12                                                            
CONECT   32   15                                                            
CONECT   33   17                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   68    0
END

Download
3D PDB for NP0050705 (Tentoxin)
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SMILES for NP0050705 (Tentoxin)
[H]\C(C1=CC=CC=C1)=C1\N(C)C(=O)[C@]([H])(CC(C)C)N=C(O)[C@]([H])(C)N(C)C(=O)CN=C1O
Download
INCHI for NP0050705 (Tentoxin)
InChI=1S/C22H30N4O4/c1-14(2)11-17-22(30)26(5)18(12-16-9-7-6-8-10-16)21(29)23-13-19(27)25(4)15(3)20(28)24-17/h6-10,12,14-15,17H,11,13H2,1-5H3,(H,23,29)(H,24,28)/b18-12-/t15-,17-/m0/s1
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View in JSmol
Synonyms
ValueSource
Cycloleucyl-N-methylalanylglycyl-N-methyl dehydrophenylalanineMeSH
Chemical FormulaC22H30N4O4
Average Mass414.4980 Da
Monoisotopic Mass414.22671 Da
IUPAC Name(3S,6S,12Z)-5,11-dihydroxy-1,6,7-trimethyl-3-(2-methylpropyl)-12-(phenylmethylidene)-1,4,7,10-tetraazacyclododeca-4,10-diene-2,8-dione
Traditional Nametentoxin
CAS Registry NumberNot Available
SMILES
[H]\C(C1=CC=CC=C1)=C1\N(C)C(=O)[C@]([H])(CC(C)C)N=C(O)[C@]([H])(C)N(C)C(=O)CN=C1O
InChI Identifier
InChI=1S/C22H30N4O4/c1-14(2)11-17-22(30)26(5)18(12-16-9-7-6-8-10-16)21(29)23-13-19(27)25(4)15(3)20(28)24-17/h6-10,12,14-15,17H,11,13H2,1-5H3,(H,23,29)(H,24,28)/b18-12-/t15-,17-/m0/s1
InChI KeySIIRBDOFKDACOK-LFXZBHHUSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Alternaria alternataFungi
Alternaria porriFungi
Chemical Taxonomy
Description Belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassCarboxylic acids and derivatives  
Sub ClassAmino acids, peptides, and analogues  
Direct ParentOligopeptides  
Alternative Parents
Substituents
  • Alpha-oligopeptide
    • 

  • Macrolactam
    • 

  • Alpha-amino acid or derivatives
    • 

  • Monocyclic benzene moiety
    • 

  • Benzenoid
    • 

  • Tertiary carboxylic acid amide
    • 

  • Carboxamide group
    • 

  • Lactam
    • 

  • Secondary carboxylic acid amide
    • 

  • Organoheterocyclic compound
    • 

  • Azacycle
    • 

  • Organic oxide
    • 

  • Organic oxygen compound
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Organopnictogen compound
    • 

  • Organic nitrogen compound
    • 

  • Carbonyl group
    • 

  • Hydrocarbon derivative
    • 

  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.01ALOGPS
logP1.98ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)6.32ChemAxon
pKa (Strongest Basic)4.59ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area105.8 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity115.39 m³·mol⁻¹ChemAxon
Polarizability43.75 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00001521  
Chemspider IDNot Available
KEGG Compound IDC08441  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTentoxin  
METLIN IDNot Available
PubChem Compound5281143  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available