NP-MRD: Showing NP-Card for (2e,4r,5s,6e)-3,5-dimethoxy-4-methyl-7-(2-{2-[(2s,3e,5e)-7-methylocta-3,5-dien-2-yl]-1,3-thiazol-4-yl}-1,3-thiazol-4-yl)hepta-2,6-dienimidic acid (NP0150692)

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Record Information

Version

2.0

Created at

2022-09-02 06:53:12 UTC

Updated at

2022-09-02 06:53:13 UTC

NP-MRD ID

NP0150692

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2e,4r,5s,6e)-3,5-dimethoxy-4-methyl-7-(2-{2-[(2s,3e,5e)-7-methylocta-3,5-dien-2-yl]-1,3-thiazol-4-yl}-1,3-thiazol-4-yl)hepta-2,6-dienimidic acid

Description

Myxothiazol 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. Myxothiazol is a moderately basic compound (based on its pKa). Binding of myxothiazol induces a red-shift to the visible absorption spectrum of reduced haem bl. Movement of the cytoplasmic domain of the Rieske protein is therefore unaffected by the binding of this inhibitor. Myxothiazol (produced by the myxobacterium Myxococcus fulvus) is an inhibitor of the mitochondrial cytochrome bc1 complex (coenzyme Q - cytochrome c reductase). Myxothiazol is a competitive inhibitor of ubiquinol, and binds at the quinol oxidation (Qo) site of the bc1 complex, blocking electron transfer to the Rieske iron-sulfur protein. (2e,4r,5s,6e)-3,5-dimethoxy-4-methyl-7-(2-{2-[(2s,3e,5e)-7-methylocta-3,5-dien-2-yl]-1,3-thiazol-4-yl}-1,3-thiazol-4-yl)hepta-2,6-dienimidic acid is found in Myxococcus fulvus. In contrast to stigmatellin, myxothiazol does not form a hydrogen bond to the Rieske iron-sulfur protein, binding instead in the 'b-proximal' region of the cytochrome b Qo site.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02231217532D          

 33 34  0  0  1  0            999 V2000
    1.2564    2.2948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2564    1.4698    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9709    1.0573    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9709    0.2323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2564   -0.1802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2564   -1.0052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9239   -1.4901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv0541 02231217532D          

 33 34  0  0  1  0            999 V2000
    1.2564    2.2948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2564    1.4698    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0150692

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C25H33N3O3S2/c1-16(2)9-7-8-10-17(3)24-28-20(15-33-24)25-27-19(14-32-25)11-12-21(30-5)18(4)22(31-6)13-23(26)29/h7-18,21H,1-6H3,(H2,26,29)/b9-7+,10-8+,12-11+,22-13+/t17-,18+,21-/m0/s1

> <INCHI_KEY>
XKTFQMCPGMTBMD-FYHMSGCOSA-N

> <FORMULA>
C25H33N3O3S2

> <MOLECULAR_WEIGHT>
487.678

> <EXACT_MASS>
487.196333317

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
55.00961711406345

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E,4R,5S,6E)-3,5-dimethoxy-4-methyl-7-(2-{2-[(2S,3E,5E)-7-methylocta-3,5-dien-2-yl]-1,3-thiazol-4-yl}-1,3-thiazol-4-yl)hepta-2,6-dienamide

> <ALOGPS_LOGP>
5.38

> <JCHEM_LOGP>
4.964887877666666

> <ALOGPS_LOGS>
-5.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.913214384813429

> <JCHEM_PKA_STRONGEST_BASIC>
1.416522788363545

> <JCHEM_POLAR_SURFACE_AREA>
87.33000000000001

> <JCHEM_REFRACTIVITY>
149.96790000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.49e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
myxothiazol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0       2.345   4.284   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.345   2.744   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       3.679   1.974   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.679   0.434   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.345  -0.336   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.345  -1.876   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.591  -2.782   0.000  0.00  0.00           C+0
HETATM    8  S   UNK     0       3.115  -4.246   0.000  0.00  0.00           S+0
HETATM    9  C   UNK     0       1.575  -4.246   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       1.099  -2.782   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       0.670  -5.492   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.146  -6.957   0.000  0.00  0.00           C+0
HETATM   13  S   UNK     0      -0.100  -7.862   0.000  0.00  0.00           S+0
HETATM   14  C   UNK     0      -1.346  -6.957   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0      -0.870  -5.492   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0      -2.810  -7.433   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.955  -6.402   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.131  -8.939   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.595  -9.415   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.915 -10.921   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -6.380 -11.397   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -6.700 -12.904   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -8.165 -13.379   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -5.556 -13.934   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.013   2.744   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.013   4.284   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.346   1.974   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       6.346   0.434   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       7.680  -0.336   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.680   2.744   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.680   4.284   0.000  0.00  0.00           C+0
HETATM   32  N   UNK     0       9.014   5.054   0.000  0.00  0.00           N+0
HETATM   33  O   UNK     0       6.346   5.054   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   25                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   10                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9    6                                                       
CONECT   11    9   12   15                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14   11                                                       
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25    3   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   30                                                  
CONECT   28   27   29                                                       
CONECT   29   28                                                            
CONECT   30   27   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   68    0
END

View in JSmol

Synonyms

Value	Source
(2E,4R,5S,6E)-3,5-Dimethoxy-4-methyl-7-(2-{2-[(2S,3E,5E)-7-methylocta-3,5-dien-2-yl]-1,3-thiazol-4-yl}-1,3-thiazol-4-yl)hepta-2,6-dienimidate	Generator

Chemical Formula

C₂₅H₃₃N₃O₃S₂

Average Mass

487.6780 Da

Monoisotopic Mass

487.19633 Da

IUPAC Name

(2E,4R,5S,6E)-3,5-dimethoxy-4-methyl-7-(2-{2-[(2S,3E,5E)-7-methylocta-3,5-dien-2-yl]-1,3-thiazol-4-yl}-1,3-thiazol-4-yl)hepta-2,6-dienamide

Traditional Name

myxothiazol

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C25H33N3O3S2/c1-16(2)9-7-8-10-17(3)24-28-20(15-33-24)25-27-19(14-32-25)11-12-21(30-5)18(4)22(31-6)13-23(26)29/h7-18,21H,1-6H3,(H2,26,29)/b9-7+,10-8+,12-11+,22-13+/t17-,18+,21-/m0/s1

InChI Key

XKTFQMCPGMTBMD-FYHMSGCOSA-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
Myxococcus fulvus	LOTUS Database	35616633

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
Vinylogous ester
Heteroaromatic compound
Carboxamide group
Primary carboxylic acid amide
Carboxylic acid derivative
Dialkyl ether
Ether
Azacycle
Organooxygen compound
Organonitrogen compound
Carbonyl group
Organic nitrogen compound
Organopnictogen compound
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
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	5.38	ALOGPS
logP	4.96	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Acidic)	15.91	ChemAxon
pKa (Strongest Basic)	1.42	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	87.33 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	149.97 m³·mol⁻¹	ChemAxon
Polarizability	55.01 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

DB04741

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00018319

Chemspider ID

Not Available

KEGG Compound ID

C15674

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Myxothiazol

METLIN ID

Not Available

PubChem Compound

10972974

PDB ID

MYX

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2e,4r,5s,6e)-3,5-dimethoxy-4-methyl-7-(2-{2-[(2s,3e,5e)-7-methylocta-3,5-dien-2-yl]-1,3-thiazol-4-yl}-1,3-thiazol-4-yl)hepta-2,6-dienimidic acid (NP0150692)

MOL for NP0150692 ((2e,4r,5s,6e)-3,5-dimethoxy-4-methyl-7-(2-{2-[(2s,3e,5e)-7-methylocta-3,5-dien-2-yl]-1,3-thiazol-4-yl}-1,3-thiazol-4-yl)hepta-2,6-dienimidic acid)

3D MOL for NP0150692 ((2e,4r,5s,6e)-3,5-dimethoxy-4-methyl-7-(2-{2-[(2s,3e,5e)-7-methylocta-3,5-dien-2-yl]-1,3-thiazol-4-yl}-1,3-thiazol-4-yl)hepta-2,6-dienimidic acid)

3D SDF for NP0150692 ((2e,4r,5s,6e)-3,5-dimethoxy-4-methyl-7-(2-{2-[(2s,3e,5e)-7-methylocta-3,5-dien-2-yl]-1,3-thiazol-4-yl}-1,3-thiazol-4-yl)hepta-2,6-dienimidic acid)

3D-SDF for NP0150692 ((2e,4r,5s,6e)-3,5-dimethoxy-4-methyl-7-(2-{2-[(2s,3e,5e)-7-methylocta-3,5-dien-2-yl]-1,3-thiazol-4-yl}-1,3-thiazol-4-yl)hepta-2,6-dienimidic acid)

PDB for NP0150692 ((2e,4r,5s,6e)-3,5-dimethoxy-4-methyl-7-(2-{2-[(2s,3e,5e)-7-methylocta-3,5-dien-2-yl]-1,3-thiazol-4-yl}-1,3-thiazol-4-yl)hepta-2,6-dienimidic acid)

3D PDB for NP0150692 ((2e,4r,5s,6e)-3,5-dimethoxy-4-methyl-7-(2-{2-[(2s,3e,5e)-7-methylocta-3,5-dien-2-yl]-1,3-thiazol-4-yl}-1,3-thiazol-4-yl)hepta-2,6-dienimidic acid)

SMILES for NP0150692 ((2e,4r,5s,6e)-3,5-dimethoxy-4-methyl-7-(2-{2-[(2s,3e,5e)-7-methylocta-3,5-dien-2-yl]-1,3-thiazol-4-yl}-1,3-thiazol-4-yl)hepta-2,6-dienimidic acid)

INCHI for NP0150692 ((2e,4r,5s,6e)-3,5-dimethoxy-4-methyl-7-(2-{2-[(2s,3e,5e)-7-methylocta-3,5-dien-2-yl]-1,3-thiazol-4-yl}-1,3-thiazol-4-yl)hepta-2,6-dienimidic acid)

Structure for NP0150692 ((2e,4r,5s,6e)-3,5-dimethoxy-4-methyl-7-(2-{2-[(2s,3e,5e)-7-methylocta-3,5-dien-2-yl]-1,3-thiazol-4-yl}-1,3-thiazol-4-yl)hepta-2,6-dienimidic acid)

3D Structure for NP0150692 ((2e,4r,5s,6e)-3,5-dimethoxy-4-methyl-7-(2-{2-[(2s,3e,5e)-7-methylocta-3,5-dien-2-yl]-1,3-thiazol-4-yl}-1,3-thiazol-4-yl)hepta-2,6-dienimidic acid)