NP-MRD: Showing NP-Card for Pyrimethanil (NP0336540)

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Record Information

Version

2.0

Created at

2024-09-11 06:46:45 UTC

Updated at

2024-09-11 06:46:45 UTC

NP-MRD ID

NP0336540

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Pyrimethanil

Description

Pyrimethanil, also known as mythos or scala, belongs to the class of organic compounds known as aniline and substituted anilines. These are organic compounds containing an aminobenzene moiety. Pyrimethanil is a strong basic compound (based on its pKa). Pyrimethanil is a potentially toxic compound. Pyrimethanil was first documented in 2013 (PMID: 22949075). Pyrimethanil is a broad spectrum fungicide often applied to seeds (PMID: 23246620) (PMID: 23258318) (PMID: 23410121) (PMID: 23436777).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061306562D          

 15 16  0  0  0  0            999 V2000
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
  9  1  1  0  0  0  0
  9  8  2  0  0  0  0
 10  2  1  0  0  0  0
 10  8  1  0  0  0  0
 11  6  2  0  0  0  0
 11  7  1  0  0  0  0
 13  9  1  0  0  0  0
 13 12  2  0  0  0  0
 14 10  2  0  0  0  0
 14 12  1  0  0  0  0
 15 11  1  0  0  0  0
 15 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0336540

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC(C)=NC(NC2=CC=CC=C2)=N1

> <INCHI_IDENTIFIER>
InChI=1S/C12H13N3/c1-9-8-10(2)14-12(13-9)15-11-6-4-3-5-7-11/h3-8H,1-2H3,(H,13,14,15)

> <INCHI_KEY>
ZLIBICFPKPWGIZ-UHFFFAOYSA-N

> <FORMULA>
C12H13N3

> <MOLECULAR_WEIGHT>
199.2517

> <EXACT_MASS>
199.110947431

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
22.501304289230383

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,6-dimethyl-N-phenylpyrimidin-2-amine

> <ALOGPS_LOGP>
3.02

> <JCHEM_LOGP>
2.431187591333333

> <ALOGPS_LOGS>
-3.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.674460548809744

> <JCHEM_PKA_STRONGEST_BASIC>
3.959545507169305

> <JCHEM_POLAR_SURFACE_AREA>
37.81

> <JCHEM_REFRACTIVITY>
60.3375

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.91e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
pyrimethanil

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001   8.470   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       4.001   3.850   0.000  0.00  0.00           N+0
HETATM   14  N   UNK     0       5.335   6.160   0.000  0.00  0.00           N+0
HETATM   15  N   UNK     0       6.668   3.850   0.000  0.00  0.00           N+0
CONECT    1    9                                                            
CONECT    2   10                                                            
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    3    7                                                       
CONECT    6    4   11                                                       
CONECT    7    5   11                                                       
CONECT    8    9   10                                                       
CONECT    9    1    8   13                                                  
CONECT   10    2    8   14                                                  
CONECT   11    6    7   15                                                  
CONECT   12   13   14   15                                                  
CONECT   13    9   12                                                       
CONECT   14   10   12                                                       
CONECT   15   11   12                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

View in JSmol

Synonyms

Value	Source
2-Anilino-4,6-dimethylpyrimidine	ChEBI
4,6-Dimethyl-N-phenyl-2-pyrimidinamine	ChEBI
N-(4,6-Dimethylpyrimidin-2-yl)aniline	ChEBI
4,6-Dimethyl-N-phenylpyrimidin-2-amine	HMDB
Mythos	HMDB
Pyrimethanil, bsi	HMDB
Scala	HMDB
sn 100309	HMDB
ZK 100309	HMDB

Chemical Formula

C₁₂H₁₃N₃

Average Mass

199.2517 Da

Monoisotopic Mass

199.11095 Da

IUPAC Name

4,6-dimethyl-N-phenylpyrimidin-2-amine

Traditional Name

pyrimethanil

CAS Registry Number

Not Available

SMILES

CC1=CC(C)=NC(NC2=CC=CC=C2)=N1

InChI Identifier

InChI=1S/C12H13N3/c1-9-8-10(2)14-12(13-9)15-11-6-4-3-5-7-11/h3-8H,1-2H3,(H,13,14,15)

InChI Key

ZLIBICFPKPWGIZ-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aniline and substituted anilines. These are organic compounds containing an aminobenzene moiety.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Aniline and substituted anilines

Direct Parent

Aniline and substituted anilines

Alternative Parents

Substituents

Aniline or substituted anilines
Aminopyrimidine
Pyrimidine
Heteroaromatic compound
Azacycle
Organoheterocyclic compound
Secondary amine
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Amine
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

aminopyrimidine (CHEBI:8674 )
secondary amino compound (CHEBI:8674 )
anilinopyrimidine fungicide (CHEBI:8674 )
Pyrimidine fungicides (C11180 )

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	3.02	ALOGPS
logP	2.43	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	13.67	ChemAxon
pKa (Strongest Basic)	3.96	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.81 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	60.34 m³·mol⁻¹	ChemAxon
Polarizability	22.5 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0033135

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB011136

KNApSAcK ID

Not Available

Chemspider ID

82753

KEGG Compound ID

C11180

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Pyrimethanil

METLIN ID

Not Available

PubChem Compound

91650

PDB ID

Not Available

ChEBI ID

8674

Good Scents ID

Not Available

References

General References

Park JH, Park JS, Abd El-Aty AM, Rahman MM, Na TW, Shim JH: Analysis of imidacloprid and pyrimethanil in shallot (Allium ascalonicum) grown under greenhouse conditions using tandem mass spectrometry: establishment of pre-harvest residue limits. Biomed Chromatogr. 2013 Apr;27(4):451-7. doi: 10.1002/bmc.2812. Epub 2012 Sep 4. [PubMed:22949075 ]
Seeland A, Albrand J, Oehlmann J, Muller R: Life stage-specific effects of the fungicide pyrimethanil and temperature on the snail Physella acuta (Draparnaud, 1805) disclose the pitfalls for the aquatic risk assessment under global climate change. Environ Pollut. 2013 Mar;174:1-9. doi: 10.1016/j.envpol.2012.10.020. Epub 2012 Dec 13. [PubMed:23246620 ]
Vaquero-Fernandez L, Sanz-Asensio J, Fernandez-Zurbano P, Lopez-Alonso M, Martinez-Soria MT: Determination of fungicide pyrimethanil in grapes, must, fermenting must and wine. J Sci Food Agric. 2013 Jun;93(8):1960-6. doi: 10.1002/jsfa.5998. Epub 2012 Dec 19. [PubMed:23258318 ]
Liang X, Liu X, Dong F, Xu J, Qin D, Li Y, Tian Y, Zhang Y, Han Y, Zheng Y: Simultaneous determination of pyrimethanil, cyprodinil, mepanipyrim and its metabolite in fresh and home-processed fruit and vegetables by a QuEChERS method coupled with UPLC-MS/MS. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2013;30(4):713-21. doi: 10.1080/19440049.2013.768777. Epub 2013 Feb 14. [PubMed:23410121 ]
Medjakovic S, Zoechling A, Gerster P, Ivanova MM, Teng Y, Klinge CM, Schildberger B, Gartner M, Jungbauer A: Effect of nonpersistent pesticides on estrogen receptor, androgen receptor, and aryl hydrocarbon receptor. Environ Toxicol. 2014 Oct;29(10):1201-16. doi: 10.1002/tox.21852. Epub 2013 Feb 23. [PubMed:23436777 ]

Showing NP-Card for Pyrimethanil (NP0336540)

MOL for NP0336540 (Pyrimethanil)

3D MOL for NP0336540 (Pyrimethanil)

3D SDF for NP0336540 (Pyrimethanil)

3D-SDF for NP0336540 (Pyrimethanil)

PDB for NP0336540 (Pyrimethanil)

3D PDB for NP0336540 (Pyrimethanil)

SMILES for NP0336540 (Pyrimethanil)

INCHI for NP0336540 (Pyrimethanil)

Structure for NP0336540 (Pyrimethanil)

3D Structure for NP0336540 (Pyrimethanil)