NP-MRD: Showing NP-Card for 4-(ethylimino)-6-(isopropylimino)-1,5-dihydro-1,3,5-triazin-2-ol (NP0259878)

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Record Information

Version

2.0

Created at

2022-09-08 01:53:11 UTC

Updated at

2022-09-08 01:53:12 UTC

NP-MRD ID

NP0259878

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-(ethylimino)-6-(isopropylimino)-1,5-dihydro-1,3,5-triazin-2-ol

Description

4-Ethylamino-6-isopropylamino-1,3,5-triazin-2-ol, also known as 2-hydroxyatrazine, belongs to the class of organic compounds known as 1,3,5-triazines. 1,3,5-Triazines are compounds containing a triazine ring, which is a heterocyclic ring, similar to the six-member benzene ring but with three carbons replaced by nitrogen atoms, at ring positions 1, 3, and 5. 4-Ethylamino-6-isopropylamino-1,3,5-triazin-2-ol is a moderately basic compound (based on its pKa). 4-Ethylamino-6-isopropylamino-1,3,5-triazin-2-ol exists in all living organisms, ranging from bacteria to humans. 4-(ethylimino)-6-(isopropylimino)-1,5-dihydro-1,3,5-triazin-2-ol is found in Apis cerana. 4-(ethylimino)-6-(isopropylimino)-1,5-dihydro-1,3,5-triazin-2-ol was first documented in 2001 (PMID: 11476505). A monohydroxy-1,3,5-triazine that is atrazine in which the chloro group has been replaced by a hydroxy group (PMID: 20299293) (PMID: 22153354) (PMID: 24062064).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 29 29  0  0  0  0  0  0  0  0999 V2000
    3.5919   -0.0159   -0.0739 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4912    1.2930    0.6436 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5691    1.1790    1.7385 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2222    0.8222    1.4642 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3378    0.7090    2.4767 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9453    0.3727    2.2515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8320    0.2640    3.3137 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3214    0.1502    0.9636 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4776    0.2525   -0.0591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8489    0.0243   -1.4156 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2352   -0.3389   -1.6600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4819   -0.5492   -3.1380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6549   -1.5536   -0.8622 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7954    0.5907    0.2102 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5577   -0.8796    0.6326 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7998   -0.1811   -0.8149 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6009   -0.0674   -0.5525 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5089    1.5823    1.0343 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1638    2.0882   -0.0677 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8766    1.3524    2.7071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6928   -0.3648    4.0752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1741    0.1110   -2.1845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8508    0.5129   -1.3014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6806    0.4379   -3.6038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3750   -1.1678   -3.2488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5856   -1.0070   -3.6140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4869   -2.0594   -1.4012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8306   -2.2696   -0.7914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0416   -1.2882    0.1375 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
  9 14  2  0
 14  4  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  2 18  1  0
  2 19  1  0
  3 20  1  0
  7 21  1  0
 10 22  1  0
 11 23  1  0
 12 24  1  0
 12 25  1  0
 12 26  1  0
 13 27  1  0
 13 28  1  0
 13 29  1  0
M  END

 
  Mrv1533006041520252D          
 
 14 14  0  0  0  0            999 V2000
   17.7255  -10.8276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0117  -11.2414    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.7255  -10.0035    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.4394  -11.2380    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.2943  -10.8276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0117   -9.5896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1532  -10.8276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2943  -10.0035    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.5805  -11.2414    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.0117   -8.7654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.8670  -11.2380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1532  -10.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8666  -10.8276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1529  -11.2414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  3  6  2  0  0  0  0
  4  7  1  0  0  0  0
  5  8  2  0  0  0  0
  5  9  1  0  0  0  0
  6 10  1  0  0  0  0
  7 11  1  0  0  0  0
  7 12  1  0  0  0  0
  9 13  1  0  0  0  0
 13 14  1  0  0  0  0
  6  8  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0259878

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCNC1=NC(O)=NC(NC(C)C)=N1

> <INCHI_IDENTIFIER>
InChI=1S/C8H15N5O/c1-4-9-6-11-7(10-5(2)3)13-8(14)12-6/h5H,4H2,1-3H3,(H3,9,10,11,12,13,14)

> <INCHI_KEY>
NFMIMWNQWAWNDW-UHFFFAOYSA-N

> <FORMULA>
C8H15N5O

> <MOLECULAR_WEIGHT>
197.242

> <EXACT_MASS>
197.127660123

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
21.260576440727483

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-(ethylamino)-6-[(propan-2-yl)amino]-1,3,5-triazin-2-ol

> <ALOGPS_LOGP>
1.69

> <JCHEM_LOGP>
1.6642719500000005

> <ALOGPS_LOGS>
-2.82

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.557389146465614

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.155091876288893

> <JCHEM_PKA_STRONGEST_BASIC>
2.9870194598360333

> <JCHEM_POLAR_SURFACE_AREA>
82.96000000000001

> <JCHEM_REFRACTIVITY>
58.644099999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.98e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-hydroxyatrazine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-JUN-15   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-JUN-15         0                                  
HETATM    1  C   UNK     0      33.088 -20.212   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      31.755 -20.984   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0      33.088 -18.673   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0      34.420 -20.978   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      30.416 -20.212   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      31.755 -17.901   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      35.753 -20.212   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      30.416 -18.673   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0      29.084 -20.984   0.000  0.00  0.00           N+0
HETATM   10  O   UNK     0      31.755 -16.362   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      37.085 -20.978   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      35.753 -18.667   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      27.751 -20.212   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      26.419 -20.984   0.000  0.00  0.00           C+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5                                                       
CONECT    3    1    6                                                       
CONECT    4    1    7                                                       
CONECT    5    2    8    9                                                  
CONECT    6    3   10    8                                                  
CONECT    7    4   11   12                                                  
CONECT    8    5    6                                                       
CONECT    9    5   13                                                       
CONECT   10    6                                                            
CONECT   11    7                                                            
CONECT   12    7                                                            
CONECT   13    9   14                                                       
CONECT   14   13                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

View in JSmol

Synonyms

Value	Source
2-Hydroxyatrazine	ChEBI
4-(Ethylamino)-2-hydroxy-6-(isopropylamino)-1,3,5-triazine	ChEBI
4-(Ethylamino)-6-(isopropylamino)-S-triazin-2-ol	ChEBI
Hydroxyatrazine	ChEBI
Hydroxydechloroatrazine	ChEBI
2-Hydroxy-4-(ethylamino)-6-(isopropylamino)-S-triazine	MeSH, HMDB

Chemical Formula

C₈H₁₅N₅O

Average Mass

197.2420 Da

Monoisotopic Mass

197.12766 Da

IUPAC Name

4-(ethylamino)-6-[(propan-2-yl)amino]-1,3,5-triazin-2-ol

Traditional Name

2-hydroxyatrazine

CAS Registry Number

Not Available

SMILES

CCNC1=NC(O)=NC(NC(C)C)=N1

InChI Identifier

InChI=1S/C8H15N5O/c1-4-9-6-11-7(10-5(2)3)13-8(14)12-6/h5H,4H2,1-3H3,(H3,9,10,11,12,13,14)

InChI Key

NFMIMWNQWAWNDW-UHFFFAOYSA-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

Species Name	Source	Reference
Apis cerana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1,3,5-triazines. 1,3,5-Triazines are compounds containing a triazine ring, which is a heterocyclic ring, similar to the six-member benzene ring but with three carbons replaced by nitrogen atoms, at ring positions 1, 3, and 5.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Triazines

Sub Class

1,3,5-triazines

Direct Parent

1,3,5-triazines

Alternative Parents

Substituents

1,3,5-triazine
Heteroaromatic compound
Azacycle
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

diamino-1,3,5-triazine (CHEBI:18316 )
monohydroxy-1,3,5-triazine (CHEBI:18316 )
a small molecule (HYDROXYATRAZINE )

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	1.69	ALOGPS
logP	1.66	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	14.16	ChemAxon
pKa (Strongest Basic)	2.99	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	82.96 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	58.64 m³·mol⁻¹	ChemAxon
Polarizability	21.26 Å³	ChemAxon
Number of Rings	1	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

HMDB0062766

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

C06552

BioCyc ID

HYDROXYATRAZINE

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16553

PDB ID

Not Available

ChEBI ID

18316

Good Scents ID

Not Available

References

General References

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 ]
Panuwet P, Restrepo PA, Magsumbol M, Jung KY, Montesano MA, Needham LL, Barr DB: An improved high-performance liquid chromatography-tandem mass spectrometric method to measure atrazine and its metabolites in human urine. J Chromatogr B Analyt Technol Biomed Life Sci. 2010 Apr 15;878(13-14):957-62. doi: 10.1016/j.jchromb.2010.02.025. Epub 2010 Mar 1. [PubMed:20299293 ]
Baranda AB, Barranco A, de Maranon IM: Fast atrazine photodegradation in water by pulsed light technology. Water Res. 2012 Mar 1;46(3):669-78. doi: 10.1016/j.watres.2011.11.034. Epub 2011 Nov 25. [PubMed:22153354 ]
Kolekar PD, Phugare SS, Jadhav JP: Biodegradation of atrazine by Rhodococcus sp. BCH2 to N-isopropylammelide with subsequent assessment of toxicity of biodegraded metabolites. Environ Sci Pollut Res Int. 2014 Feb;21(3):2334-2345. doi: 10.1007/s11356-013-2151-6. Epub 2013 Sep 24. [PubMed:24062064 ]
LOTUS database [Link]

Showing NP-Card for 4-(ethylimino)-6-(isopropylimino)-1,5-dihydro-1,3,5-triazin-2-ol (NP0259878)

MOL for NP0259878 (4-(ethylimino)-6-(isopropylimino)-1,5-dihydro-1,3,5-triazin-2-ol)

3D MOL for NP0259878 (4-(ethylimino)-6-(isopropylimino)-1,5-dihydro-1,3,5-triazin-2-ol)

3D SDF for NP0259878 (4-(ethylimino)-6-(isopropylimino)-1,5-dihydro-1,3,5-triazin-2-ol)

3D-SDF for NP0259878 (4-(ethylimino)-6-(isopropylimino)-1,5-dihydro-1,3,5-triazin-2-ol)

PDB for NP0259878 (4-(ethylimino)-6-(isopropylimino)-1,5-dihydro-1,3,5-triazin-2-ol)

3D PDB for NP0259878 (4-(ethylimino)-6-(isopropylimino)-1,5-dihydro-1,3,5-triazin-2-ol)

SMILES for NP0259878 (4-(ethylimino)-6-(isopropylimino)-1,5-dihydro-1,3,5-triazin-2-ol)

INCHI for NP0259878 (4-(ethylimino)-6-(isopropylimino)-1,5-dihydro-1,3,5-triazin-2-ol)

Structure for NP0259878 (4-(ethylimino)-6-(isopropylimino)-1,5-dihydro-1,3,5-triazin-2-ol)

3D Structure for NP0259878 (4-(ethylimino)-6-(isopropylimino)-1,5-dihydro-1,3,5-triazin-2-ol)