NP-MRD: Showing NP-Card for Cystothiazole E (NP0069769)

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Record Information

Version

2.0

Created at

2022-04-28 15:06:49 UTC

Updated at

2022-04-28 15:06:49 UTC

NP-MRD ID

NP0069769

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cystothiazole E

Description

Cystothiazole E belongs to the class of organic compounds known as 2,4-disubstituted thiazoles. 2,4-Disubstituted thiazoles are compounds containing a thiazole ring substituted at the positions 2 and 3. Cystothiazole E is found in Cystobacter fuscus. Cystothiazole E was first documented in 2002 (PMID: 12693040). Based on a literature review very few articles have been published on Cystothiazole E.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 45 46  0  0  0  0  0  0  0  0999 V2000
    5.7113   -1.4019   -0.8827 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8008   -0.7637   -0.0763 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7090   -0.3151   -0.8008 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5253   -1.1270   -0.3164 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3030   -0.6670   -0.3079 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1518   -1.4825    0.1731 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3378   -2.7622    0.6302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2739   -3.2084    1.0401 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0514   -1.7595    0.6073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5009   -1.4304    0.6993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3980   -2.3522    1.1825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8685   -1.4895    1.0754 S   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2590   -0.0322    0.4322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0061    1.2272    0.0666 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.7731    1.7815    1.2190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9211    0.8553   -1.0971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9646   -0.2795    0.3325 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0560   -1.0130    0.1758 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4928    1.1389   -0.5832 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2284    1.3908    0.9051 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7228    1.8876   -0.9075 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0186    1.7211   -0.2024 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7405    2.7290   -1.8221 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0910   -0.7494   -1.6764 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2281   -2.3141   -1.3206 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5651   -1.7160   -0.2304 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8741   -0.5649   -1.8663 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7119   -2.1318    0.0351 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1698    0.3476   -0.6729 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2686   -3.3508    0.7141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1786   -3.3770    1.5380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2609    1.9361   -0.3129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6496    1.2171    2.1613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8580    1.7356    0.9533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5610    2.8746    1.3838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9781    0.9414   -0.8314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7552    1.5535   -1.9597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7276   -0.1637   -1.4699 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6787    1.5534   -1.2140 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5769    2.2784    0.9761 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1824    1.6309    1.4065 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7504    0.4812    1.3227 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8354    1.3735   -0.8705 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3782    2.7214    0.1774 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9887    1.0757    0.6714 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  2  0
  7  8  1  0
  8  9  1  0
  9 18  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 17  2  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
  3 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  2  0
 18  6  1  0
 17 10  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  6
  4 28  1  0
  5 29  1  0
  7 30  1  0
 11 31  1  0
 14 32  1  6
 15 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  0
 16 37  1  0
 16 38  1  0
 19 39  1  6
 20 40  1  0
 20 41  1  0
 20 42  1  0
 22 43  1  0
 22 44  1  0
 22 45  1  0
M  END


  Mrv1652304282217062D          

 23 24  0  0  1  0            999 V2000
    1.5765    9.1173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2439    8.6324    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.9890    7.8478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1640    7.8478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9090    8.6324    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6790    7.1804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9340    6.3957    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2665    5.9108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4009    6.3957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1460    7.1804    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.2665    5.0858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4479    4.6733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4479    3.8483    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1624    3.4358    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1624    2.6108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8769    2.1983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4479    2.1983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8769    3.8483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2665    3.4358    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2665    2.6108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5765    9.9423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8620   10.3548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2909   10.3548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  1  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  6 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 14 18  1  6  0  0  0
 13 19  1  6  0  0  0
 19 20  1  0  0  0  0
  1 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0069769

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@@H](\C=C\C1=CSC(=N1)C1=CSC(=N1)C(C)C)[C@@H](C)C(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C17H22N2O2S2/c1-10(2)16-19-14(9-23-16)17-18-13(8-22-17)6-7-15(21-5)11(3)12(4)20/h6-11,15H,1-5H3/b7-6+/t11-,15-/m0/s1

> <INCHI_KEY>
DYTYLMNUPWHHGQ-GYCFJXGYSA-N

> <FORMULA>
C17H22N2O2S2

> <MOLECULAR_WEIGHT>
350.5

> <EXACT_MASS>
350.112270304

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
38.771203139921305

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R,4S,5E)-4-methoxy-3-methyl-6-{2-[2-(propan-2-yl)-1,3-thiazol-4-yl]-1,3-thiazol-4-yl}hex-5-en-2-one

> <ALOGPS_LOGP>
4.37

> <JCHEM_LOGP>
4.434767241

> <ALOGPS_LOGS>
-4.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.002442248047842

> <JCHEM_PKA_STRONGEST_BASIC>
1.5995418123620884

> <JCHEM_POLAR_SURFACE_AREA>
52.08

> <JCHEM_REFRACTIVITY>
104.86489999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.08e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R,4S,5E)-6-[2-(2-isopropyl-1,3-thiazol-4-yl)-1,3-thiazol-4-yl]-4-methoxy-3-methylhex-5-en-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       2.943  17.019   0.000  0.00  0.00           C+0
HETATM    2  S   UNK     0       4.189  16.114   0.000  0.00  0.00           S+0
HETATM    3  C   UNK     0       3.713  14.649   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.173  14.649   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       1.697  16.114   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       1.268  13.403   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       1.743  11.939   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       0.498  11.034   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.748  11.939   0.000  0.00  0.00           C+0
HETATM   10  S   UNK     0      -0.272  13.403   0.000  0.00  0.00           S+0
HETATM   11  C   UNK     0       0.498   9.494   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.836   8.724   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.836   7.184   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.170   6.414   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.170   4.874   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -3.504   4.104   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -0.836   4.104   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.504   7.184   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       0.498   6.414   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       0.498   4.874   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.943  18.559   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.609  19.329   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.276  19.329   0.000  0.00  0.00           C+0
CONECT    1    2    5   21                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4    1                                                       
CONECT    6    4    7   10                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9    6                                                       
CONECT   11    8   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   19                                                  
CONECT   14   13   15   18                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   14                                                            
CONECT   19   13   20                                                       
CONECT   20   19                                                            
CONECT   21    1   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₂₂N₂O₂S₂

Average Mass

350.5000 Da

Monoisotopic Mass

350.11227 Da

IUPAC Name

(3R,4S,5E)-4-methoxy-3-methyl-6-{2-[2-(propan-2-yl)-1,3-thiazol-4-yl]-1,3-thiazol-4-yl}hex-5-en-2-one

Traditional Name

(3R,4S,5E)-6-[2-(2-isopropyl-1,3-thiazol-4-yl)-1,3-thiazol-4-yl]-4-methoxy-3-methylhex-5-en-2-one

CAS Registry Number

Not Available

SMILES

CO[C@@H](\C=C\C1=CSC(=N1)C1=CSC(=N1)C(C)C)[C@@H](C)C(C)=O

InChI Identifier

InChI=1S/C17H22N2O2S2/c1-10(2)16-19-14(9-23-16)17-18-13(8-22-17)6-7-15(21-5)11(3)12(4)20/h6-11,15H,1-5H3/b7-6+/t11-,15-/m0/s1

InChI Key

DYTYLMNUPWHHGQ-GYCFJXGYSA-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, 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
Cystobacter fuscus	Bacteria	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2,4-disubstituted thiazoles. 2,4-Disubstituted thiazoles are compounds containing a thiazole ring substituted at the positions 2 and 3.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azoles

Sub Class

Thiazoles

Direct Parent

2,4-disubstituted thiazoles

Alternative Parents

Substituents

2,4-disubstituted 1,3-thiazole
Heteroaromatic compound
Ketone
Azacycle
Ether
Dialkyl ether
Organic nitrogen compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

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	4.37	ALOGPS
logP	4.43	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	19	ChemAxon
pKa (Strongest Basic)	1.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	52.08 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	104.86 m³·mol⁻¹	ChemAxon
Polarizability	38.77 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

C00028124

Chemspider ID

9327414

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11152306

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Bach T, Heuser S: Synthesis of cystothiazole E and formal syntheses of cystothiazoles A and C by Pd0-catalyzed cross-coupling reactions. Chemistry. 2002 Dec 16;8(24):5585-92. doi: 10.1002/1521-3765(20021216)8:24<5585::AID-CHEM5585>3.0.CO;2-1. [PubMed:12693040 ]

Showing NP-Card for Cystothiazole E (NP0069769)

MOL for NP0069769 (Cystothiazole E)

3D MOL for NP0069769 (Cystothiazole E)

3D SDF for NP0069769 (Cystothiazole E)

3D-SDF for NP0069769 (Cystothiazole E)

PDB for NP0069769 (Cystothiazole E)

3D PDB for NP0069769 (Cystothiazole E)

SMILES for NP0069769 (Cystothiazole E)

INCHI for NP0069769 (Cystothiazole E)

Structure for NP0069769 (Cystothiazole E)

3D Structure for NP0069769 (Cystothiazole E)