NP-MRD: Showing NP-Card for typhon (NP0145586)

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Record Information

Version

2.0

Created at

2022-09-02 00:49:02 UTC

Updated at

2022-09-02 00:49:02 UTC

NP-MRD ID

NP0145586

Secondary Accession Numbers

None

Natural Product Identification

Common Name

typhon

Description

Triadimefon belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring. Triadimefon is a moderately basic compound (based on its pKa). As a seed treatment, it is used on barley, corn, cotton, oats, rye, sorghum, and wheat. In fruit it is used on pineapple and banana. Its mode of action is systemic with protective, curative and eradicant action. Triadimefon is a potentially toxic compound. Non-food uses include pine seedlings, Christmas trees, turf, ornamental plants, and landscaping. It disrupts membrane function. It is also a pesticide transformation product. typhon is found in Colletotrichum gloeosporioides. Triadimefon is a fungicide used to control powdery mildew, rusts, and other infections in many crops.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 08291403462D          

 20 21  0  0  0  0            999 V2000
    0.7145    2.6411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414    2.3391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164    3.7680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    3.0536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.8161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    3.4661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.2286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454    0.9590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5253    1.7437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.2286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.0536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.4661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.0536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.0536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.8161    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.2704    0.9590    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1904    1.7437    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.2286    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.2911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.4661    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
 10  4  2  0  0  0  0
 10  5  1  0  0  0  0
 11  6  2  0  0  0  0
 11  7  1  0  0  0  0
 13 12  1  0  0  0  0
 14  1  1  0  0  0  0
 14  2  1  0  0  0  0
 14  3  1  0  0  0  0
 14 12  1  0  0  0  0
 15 10  1  0  0  0  0
 16  8  1  0  0  0  0
 16  9  2  0  0  0  0
 17  8  2  0  0  0  0
 18  9  1  0  0  0  0
 18 13  1  0  0  0  0
 18 17  1  0  0  0  0
 19 12  2  0  0  0  0
 20 11  1  0  0  0  0
 20 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0145586

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)(C)C(=O)C(OC1=CC=C(Cl)C=C1)N1C=NC=N1

> <INCHI_IDENTIFIER>
InChI=1S/C14H16ClN3O2/c1-14(2,3)12(19)13(18-9-16-8-17-18)20-11-6-4-10(15)5-7-11/h4-9,13H,1-3H3

> <INCHI_KEY>
WURBVZBTWMNKQT-UHFFFAOYSA-N

> <FORMULA>
C14H16ClN3O2

> <MOLECULAR_WEIGHT>
293.749

> <EXACT_MASS>
293.093104478

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
29.226757093230347

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)butan-2-one

> <ALOGPS_LOGP>
2.66

> <JCHEM_LOGP>
3.971188098666668

> <ALOGPS_LOGS>
-3.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.62281607343005

> <JCHEM_PKA_STRONGEST_BASIC>
1.929936694907393

> <JCHEM_POLAR_SURFACE_AREA>
57.010000000000005

> <JCHEM_REFRACTIVITY>
87.73670000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.25e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
typhon

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-AUG-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-AUG-14         0                                  
HETATM    1  C   UNK     0       1.334   4.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.437   4.366   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.897   7.034   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.669   5.700   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.336   3.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.336   6.470   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.002   4.160   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.565   1.790   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.581   3.255   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.669   4.160   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.002   5.700   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001   6.470   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335   5.700   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   5.700   0.000  0.00  0.00           C+0
HETATM   15 Cl   UNK     0      12.003   3.390   0.000  0.00  0.00          Cl+0
HETATM   16  N   UNK     0       6.105   1.790   0.000  0.00  0.00           N+0
HETATM   17  N   UNK     0       4.089   3.255   0.000  0.00  0.00           N+0
HETATM   18  N   UNK     0       5.335   4.160   0.000  0.00  0.00           N+0
HETATM   19  O   UNK     0       4.001   8.010   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       6.668   6.470   0.000  0.00  0.00           O+0
CONECT    1   14                                                            
CONECT    2   14                                                            
CONECT    3   14                                                            
CONECT    4    6   10                                                       
CONECT    5    7   10                                                       
CONECT    6    4   11                                                       
CONECT    7    5   11                                                       
CONECT    8   16   17                                                       
CONECT    9   16   18                                                       
CONECT   10    4    5   15                                                  
CONECT   11    6    7   20                                                  
CONECT   12   13   14   19                                                  
CONECT   13   12   18   20                                                  
CONECT   14    1    2    3   12                                             
CONECT   15   10                                                            
CONECT   16    8    9                                                       
CONECT   17    8   18                                                       
CONECT   18    9   13   17                                                  
CONECT   19   12                                                            
CONECT   20   11   13                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

View in JSmol

Synonyms

Value	Source
Bayleton	MeSH
Azocene	MeSH
Triadimefon nitrate	MeSH
Tripinacloraz	MeSH
Triadimefon sulfate	MeSH
1-(1,2,4-Triazolyl)-1-(4-chlorophenoxy)-3,3-dimethylbutan-2-one	MeSH
Triadimenol	MeSH

Chemical Formula

C₁₄H₁₆ClN₃O₂

Average Mass

293.7490 Da

Monoisotopic Mass

293.09310 Da

IUPAC Name

1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)butan-2-one

Traditional Name

typhon

CAS Registry Number

Not Available

SMILES

CC(C)(C)C(=O)C(OC1=CC=C(Cl)C=C1)N1C=NC=N1

InChI Identifier

InChI=1S/C14H16ClN3O2/c1-14(2,3)12(19)13(18-9-16-8-17-18)20-11-6-4-10(15)5-7-11/h4-9,13H,1-3H3

InChI Key

WURBVZBTWMNKQT-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100.40 MHz, CDCl₃, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Colletotrichum gloeosporioides	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenol ethers

Sub Class

Not Available

Direct Parent

Phenol ethers

Alternative Parents

Substituents

Phenoxy compound
Phenol ether
Chlorobenzene
Halobenzene
Aryl chloride
Aryl halide
Monocyclic benzene moiety
Azole
Heteroaromatic compound
1,2,4-triazole
Ketone
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Organochloride
Organohalogen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organopnictogen compound
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

aromatic ether (CHEBI:84002 )
monochlorobenzenes (CHEBI:84002 )
ketone (CHEBI:84002 )
triazoles (CHEBI:84002 )
Conazole fungicides (C11156 )

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	2.66	ALOGPS
logP	3.97	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	18.62	ChemAxon
pKa (Strongest Basic)	1.93	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	57.01 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	87.74 m³·mol⁻¹	ChemAxon
Polarizability	29.23 Å³	ChemAxon
Number of Rings	2	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

Not Available

KEGG Compound ID

C11156

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Triadimefon

METLIN ID

Not Available

PubChem Compound

39385

PDB ID

Not Available

ChEBI ID

84002

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for typhon (NP0145586)

MOL for NP0145586 (typhon)

3D MOL for NP0145586 (typhon)

3D SDF for NP0145586 (typhon)

3D-SDF for NP0145586 (typhon)

PDB for NP0145586 (typhon)

3D PDB for NP0145586 (typhon)

SMILES for NP0145586 (typhon)

INCHI for NP0145586 (typhon)

Structure for NP0145586 (typhon)

3D Structure for NP0145586 (typhon)