NP-MRD: Showing NP-Card for (2z,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 (NP0215673)

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Record Information

Version

2.0

Created at

2022-09-05 15:21:53 UTC

Updated at

2022-09-05 15:21:54 UTC

NP-MRD ID

NP0215673

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2z,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. (2z,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. (2z,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 was first documented in 2022 (PMID: 35748215). Based on a literature review a small amount of articles have been published on Myxothiazol (PMID: 35660297) (PMID: 35657511) (PMID: 35413622).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052217212D          

 33 34  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309052217212D          

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    1.2564    2.2948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0215673

> <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(O)=N

> <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-ZDBABOMLSA-N

> <FORMULA>
C25H33N3O3S2

> <MOLECULAR_WEIGHT>
487.68

> <EXACT_MASS>
487.196334283

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
55.94262061901735

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2Z,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

> <JCHEM_LOGP>
3.1396094153514102

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.2429529612679993

> <JCHEM_PKA_STRONGEST_BASIC>
12.023021034823161

> <JCHEM_POLAR_SURFACE_AREA>
88.32000000000001

> <JCHEM_REFRACTIVITY>
160.9045

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2Z,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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       2.345   4.284   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       3.679   5.054   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       5.013   4.284   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.346   5.054   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.346   6.594   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       7.680   7.364   0.000  0.00  0.00           N+0
HETATM    7  O   UNK     0       5.013   7.364   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       5.013   2.744   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.346   1.974   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.679   1.974   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.679   0.434   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.345  -0.336   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.345  -1.876   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.591  -2.782   0.000  0.00  0.00           C+0
HETATM   15  S   UNK     0       3.115  -4.246   0.000  0.00  0.00           S+0
HETATM   16  C   UNK     0       1.575  -4.246   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.670  -5.492   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.146  -6.957   0.000  0.00  0.00           C+0
HETATM   19  S   UNK     0      -0.100  -7.862   0.000  0.00  0.00           S+0
HETATM   20  C   UNK     0      -1.346  -6.957   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.810  -7.433   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -3.955  -6.402   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -3.131  -8.939   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -4.595  -9.415   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -4.915 -10.921   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -6.380 -11.397   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -6.700 -12.903   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -5.556 -13.934   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -8.165 -13.379   0.000  0.00  0.00           C+0
HETATM   30  N   UNK     0      -0.870  -5.492   0.000  0.00  0.00           N+0
HETATM   31  N   UNK     0       1.099  -2.782   0.000  0.00  0.00           N+0
HETATM   32  O   UNK     0       2.345   2.744   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       1.012   1.974   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    3    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   32                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   31                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   31                                                  
CONECT   17   16   18   30                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   30                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   20   17                                                       
CONECT   31   16   13                                                       
CONECT   32   10   33                                                       
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₃N₃O₃S₂

Average Mass

487.6800 Da

Monoisotopic Mass

487.19633 Da

IUPAC Name

(2Z,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

Traditional Name

(2Z,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

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(O)=N

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-ZDBABOMLSA-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
Organonitrogen compound
Carbonyl group
Organic nitrogen compound
Organooxygen compound
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

monocarboxylic acid amide (CHEBI:44129 )
bi-1,3-thiazole (CHEBI:44129 )

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	3.14	ChemAxon
pKa (Strongest Acidic)	-1.2	ChemAxon
pKa (Strongest Basic)	12.02	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	88.32 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	160.9 m³·mol⁻¹	ChemAxon
Polarizability	55.94 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

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00018319

Chemspider ID

17346993

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Myxothiazol

METLIN ID

Not Available

PubChem Compound

16219676

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Li J, Chang WT, Qin G, Wojcik KR, Li CQ, Hsu CW, Han M, Zhu X, Vanden Hoek TL, Shao ZH: Baicalein Preconditioning Cardioprotection Involves Pro-Oxidant Signaling and Activation of Pyruvate Dehydrogenase. Am J Chin Med. 2022;50(5):1255-1267. doi: 10.1142/S0192415X22500513. Epub 2022 Jun 23. [PubMed:35748215 ]
F Turrens J, Alexandre A, L Lehninger A: Reprint of: Ubisemiquinone Is the Electron Donor for Superoxide Formation by Complex III of Heart Mitochondria. Arch Biochem Biophys. 2022 Sep 15;726:109232. doi: 10.1016/j.abb.2022.109232. Epub 2022 Jun 2. [PubMed:35660297 ]
Shapiguzov A, Kangasjarvi J: Studying Plant Stress Reactions In Vivo by PAM Chlorophyll Fluorescence Imaging. Methods Mol Biol. 2022;2526:43-61. doi: 10.1007/978-1-0716-2469-2_4. [PubMed:35657511 ]
Wang Y, Chi H, Xu F, He Z, Li Z, Wu F, Li Y, Zhang G, Peng X, Yu S, Yang J, Zhang W, Yang X: Cadmium chloride-induced apoptosis of HK-2 cells via interfering with mitochondrial respiratory chain. Ecotoxicol Environ Saf. 2022 May 1;236:113494. doi: 10.1016/j.ecoenv.2022.113494. Epub 2022 Apr 9. [PubMed:35413622 ]
LOTUS database [Link]

Showing NP-Card for (2z,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 (NP0215673)

MOL for NP0215673 ((2z,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 NP0215673 ((2z,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 NP0215673 ((2z,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 NP0215673 ((2z,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 NP0215673 ((2z,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 NP0215673 ((2z,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 NP0215673 ((2z,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 NP0215673 ((2z,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 NP0215673 ((2z,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 NP0215673 ((2z,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)