NP-MRD: Showing NP-Card for 2-Methylthioribosyl-trans-zeatin (NP0045530)

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Record Information

Version

2.0

Created at

2022-03-17 19:25:16 UTC

Updated at

2022-03-17 19:25:16 UTC

NP-MRD ID

NP0045530

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-Methylthioribosyl-trans-zeatin

Description

2-Methylthioribosyl-trans-zeatin is found in Agrobacterium tumefaciens, Bradyrhizobium japonicum, Euglena gracilis, Humulus lupulus and Corynebacterium fascians.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241221302D          

 21 22  0  0  0  0            999 V2000
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    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   -2.8875    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
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 Cl  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
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  2  7  1  0  0  0  0
  4  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  9 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 11 20  1  0  0  0  0
  3 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0045530

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C(C)C(NC2=CC(Cl)=NC(SCC(O)=O)=N2)=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C14H14ClN3O2S/c1-8-4-3-5-10(9(8)2)16-12-6-11(15)17-14(18-12)21-7-13(19)20/h3-6H,7H2,1-2H3,(H,19,20)(H,16,17,18)

> <INCHI_KEY>
SZRPDCCEHVWOJX-UHFFFAOYSA-N

> <FORMULA>
C14H14ClN3O2S

> <MOLECULAR_WEIGHT>
323.798

> <EXACT_MASS>
323.049525104

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
32.072586675753314

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-({4-chloro-6-[(2,3-dimethylphenyl)amino]pyrimidin-2-yl}sulfanyl)acetic acid

> <ALOGPS_LOGP>
3.79

> <JCHEM_LOGP>
4.107006531805247

> <ALOGPS_LOGS>
-4.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.969580694379392

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.2456353039330246

> <JCHEM_PKA_STRONGEST_BASIC>
2.0152231208507883

> <JCHEM_POLAR_SURFACE_AREA>
75.11

> <JCHEM_REFRACTIVITY>
86.40759999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.05e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
pirinixic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       6.668  -5.390   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       6.668 -10.010   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       5.335  -7.700   0.000  0.00  0.00           N+0
HETATM   15  S   UNK     0       4.001 -10.010   0.000  0.00  0.00           S+0
HETATM   16  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       1.334 -11.550   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       0.000  -9.240   0.000  0.00  0.00           O+0
HETATM   20 Cl   UNK     0       9.336 -10.010   0.000  0.00  0.00          Cl+0
HETATM   21  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4   21                                                  
CONECT    4    3    5    8                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    2                                                       
CONECT    8    4    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   20                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13    9                                                       
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   11                                                            
CONECT   21    3                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

View in JSmol

Synonyms

Value	Source
((4-Chloro-6-((2,3-dimethylphenyl)amino)-2-pyrimidinyl)thio)acetic acid	ChEBI
(4-Chloro-6-(2,3-xylidino)-2-pyrimidinylthio)acetic acid	ChEBI
WY-14,643	ChEBI
((4-Chloro-6-((2,3-dimethylphenyl)amino)-2-pyrimidinyl)thio)acetate	Generator
(4-Chloro-6-(2,3-xylidino)-2-pyrimidinylthio)acetate	Generator
4-Chloro-6-(2,3-xylidinyl)-2-pyrimidinylthioacetic acid	MeSH
Wyeth-14643	MeSH
CXPTA	MeSH
Wyeth 14,643	MeSH
4-Chloro-6-(2,3-dimethylphenyl)amino-2-pyrimidinylthioacetic acid	MeSH
Pirinixate	Generator

Chemical Formula

C₁₄H₁₄ClN₃O₂S

Average Mass

323.7980 Da

Monoisotopic Mass

323.04953 Da

IUPAC Name

2-({4-chloro-6-[(2,3-dimethylphenyl)amino]pyrimidin-2-yl}sulfanyl)acetic acid

Traditional Name

pirinixic acid

CAS Registry Number

53274-45-6

SMILES

CC1=C(C)C(NC2=CC(Cl)=NC(SCC(O)=O)=N2)=CC=C1

InChI Identifier

InChI=1S/C14H14ClN3O2S/c1-8-4-3-5-10(9(8)2)16-12-6-11(15)17-14(18-12)21-7-13(19)20/h3-6H,7H2,1-2H3,(H,19,20)(H,16,17,18)

InChI Key

SZRPDCCEHVWOJX-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50.32 MHz, DMSO-d6, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Agrobacterium tumefaciens	Bacteria	KNApSAcK
Bradyrhizobium japonicum	Bacteria	KNApSAcK
Euglena gracilis	Excavata	KNApSAcK
Humulus lupulus	Plant	KNApSAcK
Pisum sativum	FooDB	KNAPSACK
Rhodococcus fascians	Bacteria	KNApSAcK
Triticum aestivum	FooDB	KNAPSACK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aryl thioethers. These are organosulfur compounds containing a thioether group that is substituted by an aryl group.

Kingdom

Organic compounds

Super Class

Organosulfur compounds

Class

Thioethers

Sub Class

Aryl thioethers

Direct Parent

Aryl thioethers

Alternative Parents

Substituents

Aryl thioether
O-xylene
Xylene
Halopyrimidine
Alkylarylthioether
Aryl chloride
Aryl halide
Monocyclic benzene moiety
Hydropyrimidine
Pyrimidine
Benzenoid
Imidolactam
Heteroaromatic compound
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Azacycle
Sulfenyl compound
Organoheterocyclic compound
Organohalogen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organic nitrogen compound
Organochloride
Organonitrogen compound
Organooxygen compound
Organopnictogen compound
Carbonyl group
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

aryl sulfide (CHEBI:32509 )
organochlorine compound (CHEBI:32509 )
pyrimidines (CHEBI:32509 )

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	3.79	ALOGPS
logP	4.11	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	3.25	ChemAxon
pKa (Strongest Basic)	2.02	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.11 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	86.41 m³·mol⁻¹	ChemAxon
Polarizability	32.07 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

FDB001402

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C15617

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Pirinixic_Acid

METLIN ID

Not Available

PubChem Compound

5694

PDB ID

Not Available

ChEBI ID

32509

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 2-Methylthioribosyl-trans-zeatin (NP0045530)

MOL for NP0045530 (2-Methylthioribosyl-trans-zeatin)

3D MOL for NP0045530 (2-Methylthioribosyl-trans-zeatin)

3D SDF for NP0045530 (2-Methylthioribosyl-trans-zeatin)

3D-SDF for NP0045530 (2-Methylthioribosyl-trans-zeatin)

PDB for NP0045530 (2-Methylthioribosyl-trans-zeatin)

3D PDB for NP0045530 (2-Methylthioribosyl-trans-zeatin)

SMILES for NP0045530 (2-Methylthioribosyl-trans-zeatin)

INCHI for NP0045530 (2-Methylthioribosyl-trans-zeatin)

Structure for NP0045530 (2-Methylthioribosyl-trans-zeatin)

3D Structure for NP0045530 (2-Methylthioribosyl-trans-zeatin)