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Showing NP-Card for 6-Chloro-N-(1-methylethyl)-1,3,5-triazine-2,4-diamine (NP0337216)

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Record Information
Version2.0
Created at2024-09-11 09:51:59 UTC
Updated at2024-09-11 09:52:00 UTC
NP-MRD IDNP0337216
Secondary Accession NumbersNone
Natural Product Identification
Common Name6-Chloro-N-(1-methylethyl)-1,3,5-triazine-2,4-diamine
Description6-Chloro-N-(1-methylethyl)-1,3,5-triazine-2,4-diamine, also known as 4-deethylatrazine or 2-chloro-4-amino-6-(isopropylamino)-S-triazine, belongs to the class of organic compounds known as 1,3,5-triazine-2,4-diamines. These are aromatic compounds containing a 1,3,5-triazine ring which is 2,4-disusbtituted wit amine groups. It was first documented in 2001 (PMID: 11476505). 6-Chloro-N-(1-methylethyl)-1,3,5-triazine-2,4-diamine is a strong basic compound (based on its pKa) (PMID: 15506812) (PMID: 25281136) (PMID: 21541850) (PMID: 21774428).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0337216 (6-Chloro-N-(1-methylethyl)-1,3,5-triazine-2,4-diamine)


  Mrv0541 02241216442D          

 12 12  0  0  0  0            999 V2000
   -0.3927   -0.6553    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3937   -0.2181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3937    0.6555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3927    1.0927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0923    0.6555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0923   -0.2181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8798   -0.6553    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.1803   -0.6553    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1803   -1.5302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8798   -1.9675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3927    1.9675    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6019   -1.8506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  2  0  0  0  0
  2  3  2  0  0  0  0
  2  8  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4 11  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 12  1  0  0  0  0
M  END
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3D MOL for NP0337216 (6-Chloro-N-(1-methylethyl)-1,3,5-triazine-2,4-diamine)

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3D SDF for NP0337216 (6-Chloro-N-(1-methylethyl)-1,3,5-triazine-2,4-diamine)

  Mrv0541 02241216442D          

 12 12  0  0  0  0            999 V2000
   -0.3927   -0.6553    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3937   -0.2181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3937    0.6555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3927    1.0927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0923    0.6555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0923   -0.2181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8798   -0.6553    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.1803   -0.6553    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1803   -1.5302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8798   -1.9675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3927    1.9675    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6019   -1.8506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  2  0  0  0  0
  2  3  2  0  0  0  0
  2  8  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4 11  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0337216

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)NC1=NC(N)=NC(Cl)=N1

> <INCHI_IDENTIFIER>
InChI=1S/C6H10ClN5/c1-3(2)9-6-11-4(7)10-5(8)12-6/h3H,1-2H3,(H3,8,9,10,11,12)

> <INCHI_KEY>
DFWFIQKMSFGDCQ-UHFFFAOYSA-N

> <FORMULA>
C6H10ClN5

> <MOLECULAR_WEIGHT>
187.63

> <EXACT_MASS>
187.062473052

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
18.294466691739903

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-chloro-N2-(propan-2-yl)-1,3,5-triazine-2,4-diamine

> <ALOGPS_LOGP>
1.50

> <JCHEM_LOGP>
1.5390895590000002

> <ALOGPS_LOGS>
-2.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.30261991581657

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.584420013962507

> <JCHEM_PKA_STRONGEST_BASIC>
3.3788663987639214

> <JCHEM_POLAR_SURFACE_AREA>
76.72

> <JCHEM_REFRACTIVITY>
51.973800000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.25e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
desethylatrazine

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0337216 (6-Chloro-N-(1-methylethyl)-1,3,5-triazine-2,4-diamine)
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PDB for NP0337216 (6-Chloro-N-(1-methylethyl)-1,3,5-triazine-2,4-diamine)
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  N   UNK     0      -0.733  -1.223   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       0.735  -0.407   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       0.735   1.224   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      -0.733   2.040   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      -2.039   1.224   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      -2.039  -0.407   0.000  0.00  0.00           C+0
HETATM    7 Cl   UNK     0      -3.509  -1.223   0.000  0.00  0.00          Cl+0
HETATM    8  N   UNK     0       2.203  -1.223   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       2.203  -2.856   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.509  -3.673   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      -0.733   3.673   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       1.124  -3.454   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   11                                                  
CONECT    5    4    6                                                       
CONECT    6    1    5    7                                                  
CONECT    7    6                                                            
CONECT    8    2    9                                                       
CONECT    9    8   10   12                                                  
CONECT   10    9                                                            
CONECT   11    4                                                            
CONECT   12    9                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

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3D PDB for NP0337216 (6-Chloro-N-(1-methylethyl)-1,3,5-triazine-2,4-diamine)
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SMILES for NP0337216 (6-Chloro-N-(1-methylethyl)-1,3,5-triazine-2,4-diamine)
CC(C)NC1=NC(N)=NC(Cl)=N1
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INCHI for NP0337216 (6-Chloro-N-(1-methylethyl)-1,3,5-triazine-2,4-diamine)
InChI=1S/C6H10ClN5/c1-3(2)9-6-11-4(7)10-5(8)12-6/h3H,1-2H3,(H3,8,9,10,11,12)
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Synonyms
ValueSource
2-Amino-4-chloro-6-(isopropylamino)-S-triazineChEBI
2-Chloro-4-amino-6-(isopropylamino)-S-triazineChEBI
4-DeethylatrazineChEBI
6-Chloro-N-isopropyl-1,3,5-triazine-2,4-diamineChEBI
DeethylatrazinChEBI
Desethyl atrazineChEBI
2-Amino-4-chloro-6-(isopropylamino)-1,3,5-triazineHMDB
2-Amino-4-chloro-6-isopropylamino-1,3,5-triazineHMDB
2-Amino-4-isopropylamino-6-chloro-S-triazineHMDB
2-Chloro-4-amino-6-isopropylamino-S-triazineHMDB
2-Chloro-4-isopropylamino-6-amino-S-triazineHMDB
6-Chloro-N-(1-methylethyl)-1,3,5-triazine-2,4-diamine, 9ciHMDB
6-Chloro-N-(propan-2-yl)-1,3,5-triazine-2,4-diamineHMDB
Atrazine desethylHMDB
Atrazine m (des-ethyl)HMDB
Atrazine-desethylHMDB
CIATHMDB
DeethyatrazineHMDB
DeethylatrazineHMDB
Des-ethyl atrazineHMDB
Desethyl-atrazineHMDB
DesethylatrazineHMDB
Desisopropyl propazineHMDB
2-CIATHMDB
6-Chloro-N-(1-methylethyl)-1,3,5-triazine-2,4-diamineChEBI
Chemical FormulaC6H10ClN5
Average Mass187.6300 Da
Monoisotopic Mass187.06247 Da
IUPAC Name6-chloro-N2-(propan-2-yl)-1,3,5-triazine-2,4-diamine
Traditional Namedesethylatrazine
CAS Registry NumberNot Available
SMILES
CC(C)NC1=NC(N)=NC(Cl)=N1
InChI Identifier
InChI=1S/C6H10ClN5/c1-3(2)9-6-11-4(7)10-5(8)12-6/h3H,1-2H3,(H3,8,9,10,11,12)
InChI KeyDFWFIQKMSFGDCQ-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 1,3,5-triazine-2,4-diamines. These are aromatic compounds containing a 1,3,5-triazine ring which is 2,4-disusbtituted wit amine groups.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassTriazines  
Sub ClassAminotriazines  
Direct Parent1,3,5-triazine-2,4-diamines  
Alternative Parents
Substituents
  • 2,4-diamine-s-triazine
    • 

  • Chloro-s-triazine
    • 

  • Halo-s-triazine
    • 

  • Secondary aliphatic/aromatic amine
    • 

  • N-aliphatic s-triazine
    • 

  • Aryl chloride
    • 

  • Aryl halide
    • 

  • 1,3,5-triazine
    • 

  • Heteroaromatic compound
    • 

  • Azacycle
    • 

  • Secondary amine
    • 

  • Amine
    • 

  • Hydrocarbon derivative
    • 

  • Primary amine
    • 

  • Organonitrogen compound
    • 

  • Organochloride
    • 

  • Organohalogen compound
    • 

  • Organopnictogen compound
    • 

  • Organic nitrogen compound
    • 

  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
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
logP1.5ALOGPS
logP1.54ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)14.58ChemAxon
pKa (Strongest Basic)3.38ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area76.72 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity51.97 m³·mol⁻¹ChemAxon
Polarizability18.29 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0033249  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB011269  
KNApSAcK IDNot Available
Chemspider ID21157  
KEGG Compound IDC06559  
BioCyc IDCPD-801  
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound22563  
PDB IDNot Available
ChEBI ID28212  
Good Scents IDNot Available
References
General References
  1. Seybold CA, Mersie W, McNamee C: Anaerobic degradation of atrazine and metolachlor and metabolite formation in wetland soil and water microcosms. J Environ Qual. 2001 Jul-Aug;30(4):1271-7. doi: 10.2134/jeq2001.3041271x. [PubMed:11476505  ] 
  2. Abate G, Penteado JC, Cuzzi JD, Vitti GC, Lichtig J, Masini JC: Influence of humic acid on adsorption and desorption of atrazine, hydroxyatrazine, deethylatrazine, and deisopropylatrazine onto a clay-rich soil sample. J Agric Food Chem. 2004 Nov 3;52(22):6747-54. doi: 10.1021/jf049229e. [PubMed:15506812  ] 
  3. de Pra Urio R, Masini JC: Evaluation of sequential injection chromatography for reversed phase separation of triazine herbicides exploiting monolithic and core-shell columns. Talanta. 2015 Jan;131:528-34. doi: 10.1016/j.talanta.2014.08.020. Epub 2014 Aug  19. [PubMed:25281136  ] 
  4. Schulte-Oehlmann U, Oehlmann J, Keil F: Before the curtain falls: endocrine-active pesticides--a German contamination legacy. Rev Environ Contam Toxicol. 2011;213:137-59. doi: 10.1007/978-1-4419-9860-6_5. [PubMed:21541850  ] 
  5. Schotthoefer AM, Rohr JR, Cole RA, Koehler AV, Johnson CM, Johnson LB, Beasley VR: Effects of wetland vs. landscape variables on parasite communities of Rana pipiens: links to anthropogenic factors. Ecol Appl. 2011 Jun;21(4):1257-71. doi: 10.1890/10-0374.1. [PubMed:21774428  ]