NP-MRD: Showing NP-Card for methyl (2e)-3-[3-methyl-5-(3-methylbut-2-en-1-yl)imidazol-4-yl]prop-2-enoate (NP0197304)

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Record Information

Version

2.0

Created at

2022-09-04 15:32:14 UTC

Updated at

2022-09-04 15:32:15 UTC

NP-MRD ID

NP0197304

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (2e)-3-[3-methyl-5-(3-methylbut-2-en-1-yl)imidazol-4-yl]prop-2-enoate

Description

Visoltricin belongs to the class of organic compounds known as imidazolyl carboxylic acids and derivatives. These are organic compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an imidazole ring. methyl (2e)-3-[3-methyl-5-(3-methylbut-2-en-1-yl)imidazol-4-yl]prop-2-enoate is found in Fusarium tricinctum. methyl (2e)-3-[3-methyl-5-(3-methylbut-2-en-1-yl)imidazol-4-yl]prop-2-enoate was first documented in 1992 (PMID: 1610205). Based on a literature review a small amount of articles have been published on Visoltricin (PMID: 8680598) (PMID: 7664951) (PMID: 20692939).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 35 35  0  0  0  0  0  0  0  0999 V2000
    3.0896    3.4179    1.4083 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1238    2.6073    0.7469 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1913    1.2414    0.8861 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1025    0.7518    1.5922 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1983    0.3534    0.2096 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2946   -0.9378    0.3653 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4203   -1.9488   -0.2143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6678   -1.8294   -0.9809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4073   -0.6637   -1.4978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2717    0.0133   -0.5423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4003    1.2879   -0.4055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3442    1.8489    0.6480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7344    2.2997   -1.2381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0817   -3.1319   -1.2511 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2581   -3.9628   -0.6584 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6894   -3.2912   -0.0030 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7868   -3.8112    0.7770 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9785    2.8198    1.6947 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3486    4.2355    0.6805 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6866    3.8608    2.3442 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4343    0.7772   -0.3904 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1441   -1.2671    1.0174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0931   -1.0552   -2.3511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7813    0.0667   -2.0418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8774   -0.6493    0.1321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7579    2.4695    1.3443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1765    2.3993    0.1573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7963    1.0141    1.2109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8371    2.7314   -0.7057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4184    3.1707   -1.4466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4229    1.9175   -2.2219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3410   -5.0549   -0.6988 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7114   -3.3113    0.4292 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8378   -4.8963    0.7169 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6293   -3.4733    1.8281 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  3
 11 12  1  0
 11 13  1  0
  8 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16  7  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  5 21  1  0
  6 22  1  0
  9 23  1  0
  9 24  1  0
 10 25  1  0
 12 26  1  0
 12 27  1  0
 12 28  1  0
 13 29  1  0
 13 30  1  0
 13 31  1  0
 15 32  1  0
 17 33  1  0
 17 34  1  0
 17 35  1  0
M  END


  Mrv1652309042217322D          

 17 17  0  0  0  0            999 V2000
   -0.8612    4.4143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8612    3.5893    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    3.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    3.5893    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0198    0.8843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1913    1.6913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9760    1.9462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1475    2.7532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5891    1.3942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8843    0.8843    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
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
  8 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
  7 16  1  0  0  0  0
 16 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0197304

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)\C=C\C1=C(CC=C(C)C)N=CN1C

> <INCHI_IDENTIFIER>
InChI=1S/C13H18N2O2/c1-10(2)5-6-11-12(15(3)9-14-11)7-8-13(16)17-4/h5,7-9H,6H2,1-4H3/b8-7+

> <INCHI_KEY>
LFPQYOYKAPGCGM-BQYQJAHWSA-N

> <FORMULA>
C13H18N2O2

> <MOLECULAR_WEIGHT>
234.299

> <EXACT_MASS>
234.136827828

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
26.398315734927827

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (2E)-3-[1-methyl-4-(3-methylbut-2-en-1-yl)-1H-imidazol-5-yl]prop-2-enoate

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
6.116356005622666

> <JCHEM_POLAR_SURFACE_AREA>
44.120000000000005

> <JCHEM_REFRACTIVITY>
69.37699999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2E)-3-[3-methyl-5-(3-methylbut-2-en-1-yl)imidazol-4-yl]prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.608   8.240   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.608   6.700   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.274   5.930   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       1.060   6.700   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -0.274   4.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.060   3.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.770   1.651   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.091   3.157   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.555   3.633   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.875   5.139   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.700   2.602   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       1.830  -0.290   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0      -0.186   1.175   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0      -1.651   1.651   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   16                                                  
CONECT    8    7    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    8   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15    7   17                                                  
CONECT   17   16                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

View in JSmol

Synonyms

Value	Source
3-(1-Methyl-4-(3-methyl-2-butenyl)imidazol-5-yl)-2-propenoic acid methyl ester	MeSH

Chemical Formula

C₁₃H₁₈N₂O₂

Average Mass

234.2990 Da

Monoisotopic Mass

234.13683 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC(=O)\C=C\C1=C(CC=C(C)C)N=CN1C

InChI Identifier

InChI=1S/C13H18N2O2/c1-10(2)5-6-11-12(15(3)9-14-11)7-8-13(16)17-4/h5,7-9H,6H2,1-4H3/b8-7+

InChI Key

LFPQYOYKAPGCGM-BQYQJAHWSA-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
Fusarium tricinctum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as imidazolyl carboxylic acids and derivatives. These are organic compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an imidazole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azoles

Sub Class

Imidazoles

Direct Parent

Imidazolyl carboxylic acids and derivatives

Alternative Parents

Substituents

Imidazolyl carboxylic acid derivative
Fatty acid ester
N-substituted imidazole
Fatty acyl
Methyl ester
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Heteroaromatic compound
Carboxylic acid ester
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Azacycle
Carbonyl group
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organic oxide
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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4534848

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5388713

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Solfrizzo M, Visconti A: Simultaneous high-performance liquid chromatographic determination of visoltricin, acuminatopyrone and chlamydosporols in Fusarium cultures on maize. J Chromatogr A. 1996 Apr 12;730(1-2):69-73. doi: 10.1016/0021-9673(95)00899-3. [PubMed:8680598 ]
Visconti A, Solfrizzo M: Visoltricin, a novel biologically active compound produced by Fusarium tricinctum. Food Addit Contam. 1995 May-Jun;12(3):515-9. doi: 10.1080/02652039509374338. [PubMed:7664951 ]
Solfrizzo M, Visconti A: Anticholinesterase activity of the fusarium metabolite visoltricin and its N-methyl derivative. Toxicol In Vitro. 1994 Jun;8(3):461-5. doi: 10.1016/0887-2333(94)90169-4. [PubMed:20692939 ]
Visconti A, Minervini F, Solfrizzo M, Bottalico C, Lucivero G: Toxicity of some Fusarium section Sporotrichiella strains in relation to mycotoxin production. Appl Environ Microbiol. 1992 Feb;58(2):769-72. doi: 10.1128/aem.58.2.769-772.1992. [PubMed:1610205 ]
LOTUS database [Link]

Showing NP-Card for methyl (2e)-3-[3-methyl-5-(3-methylbut-2-en-1-yl)imidazol-4-yl]prop-2-enoate (NP0197304)

MOL for NP0197304 (methyl (2e)-3-[3-methyl-5-(3-methylbut-2-en-1-yl)imidazol-4-yl]prop-2-enoate)

3D MOL for NP0197304 (methyl (2e)-3-[3-methyl-5-(3-methylbut-2-en-1-yl)imidazol-4-yl]prop-2-enoate)

3D SDF for NP0197304 (methyl (2e)-3-[3-methyl-5-(3-methylbut-2-en-1-yl)imidazol-4-yl]prop-2-enoate)

3D-SDF for NP0197304 (methyl (2e)-3-[3-methyl-5-(3-methylbut-2-en-1-yl)imidazol-4-yl]prop-2-enoate)

PDB for NP0197304 (methyl (2e)-3-[3-methyl-5-(3-methylbut-2-en-1-yl)imidazol-4-yl]prop-2-enoate)

3D PDB for NP0197304 (methyl (2e)-3-[3-methyl-5-(3-methylbut-2-en-1-yl)imidazol-4-yl]prop-2-enoate)

SMILES for NP0197304 (methyl (2e)-3-[3-methyl-5-(3-methylbut-2-en-1-yl)imidazol-4-yl]prop-2-enoate)

INCHI for NP0197304 (methyl (2e)-3-[3-methyl-5-(3-methylbut-2-en-1-yl)imidazol-4-yl]prop-2-enoate)

Structure for NP0197304 (methyl (2e)-3-[3-methyl-5-(3-methylbut-2-en-1-yl)imidazol-4-yl]prop-2-enoate)

3D Structure for NP0197304 (methyl (2e)-3-[3-methyl-5-(3-methylbut-2-en-1-yl)imidazol-4-yl]prop-2-enoate)