NP-MRD: Showing NP-Card for (2e)-3-(3-bromo-4-methoxyphenyl)-2-(n-hydroxyimino)-n-[2-(3h-imidazol-4-yl)ethyl]propanimidic acid (NP0225890)

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Record Information

Version

2.0

Created at

2022-09-06 04:45:17 UTC

Updated at

2022-09-06 04:45:18 UTC

NP-MRD ID

NP0225890

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2e)-3-(3-bromo-4-methoxyphenyl)-2-(n-hydroxyimino)-n-[2-(3h-imidazol-4-yl)ethyl]propanimidic acid

Description

Verongamine belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof. Verongamine is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. (2e)-3-(3-bromo-4-methoxyphenyl)-2-(n-hydroxyimino)-n-[2-(3h-imidazol-4-yl)ethyl]propanimidic acid is found in Aiolochroia crassa and Verongula gigantea. (2e)-3-(3-bromo-4-methoxyphenyl)-2-(n-hydroxyimino)-n-[2-(3h-imidazol-4-yl)ethyl]propanimidic acid was first documented in 1994 (PMID: 8158162). Based on a literature review a small amount of articles have been published on verongamine (PMID: 11325276) (PMID: 9871722).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062206452D          

 23 24  0  0  0  0            999 V2000
    1.4289   14.6036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   14.1911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   13.3661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   12.9536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   12.1286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   11.7161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   10.8911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   10.4786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   10.8911    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   11.7161    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    9.6536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    9.2411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    9.2411    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    8.4161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    8.0036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    7.1786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0964    6.6937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414    5.9090    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164    5.9090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7615    6.6937    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   12.1286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   12.9536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   13.3661    0.0000 Br  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
  5  6  2  0  0  0  0
  6  7  1  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
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
 13 14  1  4  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 16 20  1  0  0  0  0
  6 21  1  0  0  0  0
 21 22  2  0  0  0  0
  3 22  1  0  0  0  0
 22 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0225890

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(C\C(=N/O)C(O)=NCCC2=CN=CN2)C=C1Br

> <INCHI_IDENTIFIER>
InChI=1S/C15H17BrN4O3/c1-23-14-3-2-10(6-12(14)16)7-13(20-22)15(21)18-5-4-11-8-17-9-19-11/h2-3,6,8-9,22H,4-5,7H2,1H3,(H,17,19)(H,18,21)/b20-13+

> <INCHI_KEY>
MFMMJKGZEGTTSV-DEDYPNTBSA-N

> <FORMULA>
C15H17BrN4O3

> <MOLECULAR_WEIGHT>
381.23

> <EXACT_MASS>
380.048403

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
34.637006600156155

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-3-(3-bromo-4-methoxyphenyl)-2-(N-hydroxyimino)-N-[2-(1H-imidazol-5-yl)ethyl]propanimidic acid

> <JCHEM_LOGP>
1.5039481448770293

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.234991832280771

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.7816408304480849

> <JCHEM_PKA_STRONGEST_BASIC>
6.757374857084564

> <JCHEM_POLAR_SURFACE_AREA>
103.09

> <JCHEM_REFRACTIVITY>
90.17020000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-3-(3-bromo-4-methoxyphenyl)-2-(N-hydroxyimino)-N-[2-(3H-imidazol-4-yl)ethyl]propanimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       2.667  27.260   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.001  26.490   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.001  24.950   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335  24.180   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335  22.640   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  21.870   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  20.330   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  19.560   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       1.334  20.330   0.000  0.00  0.00           N+0
HETATM   10  O   UNK     0       1.334  21.870   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.667  18.020   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       4.001  17.250   0.000  0.00  0.00           O+0
HETATM   13  N   UNK     0       1.334  17.250   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       1.334  15.710   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667  14.940   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667  13.400   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.913  12.495   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       3.437  11.030   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0       1.897  11.030   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0       1.421  12.495   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0       2.667  22.640   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.667  24.180   0.000  0.00  0.00           C+0
HETATM   23 Br   UNK     0       1.334  24.950   0.000  0.00  0.00          Br+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   22                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   21                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    8   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   20                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   16                                                       
CONECT   21    6   22                                                       
CONECT   22   21    3   23                                                  
CONECT   23   22                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

View in JSmol

Synonyms

Value	Source
(e)-3-Bromo-alpha-(hydroxyimino)-N-(2-(1H-imidazol-4-yl)ethyl)-4-methoxy-benzenepropanamide	ChEBI
(e)-3-Bromo-a-(hydroxyimino)-N-(2-(1H-imidazol-4-yl)ethyl)-4-methoxy-benzenepropanamide	Generator
(e)-3-Bromo-α-(hydroxyimino)-N-(2-(1H-imidazol-4-yl)ethyl)-4-methoxy-benzenepropanamide	Generator

Chemical Formula

C₁₅H₁₇BrN₄O₃

Average Mass

381.2300 Da

Monoisotopic Mass

380.04840 Da

IUPAC Name

(2E)-3-(3-bromo-4-methoxyphenyl)-2-(N-hydroxyimino)-N-[2-(1H-imidazol-5-yl)ethyl]propanimidic acid

Traditional Name

(2E)-3-(3-bromo-4-methoxyphenyl)-2-(N-hydroxyimino)-N-[2-(3H-imidazol-4-yl)ethyl]propanimidic acid

CAS Registry Number

Not Available

SMILES

COC1=CC=C(C\C(=N/O)C(O)=NCCC2=CN=CN2)C=C1Br

InChI Identifier

InChI=1S/C15H17BrN4O3/c1-23-14-3-2-10(6-12(14)16)7-13(20-22)15(21)18-5-4-11-8-17-9-19-11/h2-3,6,8-9,22H,4-5,7H2,1H3,(H,17,19)(H,18,21)/b20-13+

InChI Key

MFMMJKGZEGTTSV-DEDYPNTBSA-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
Aiolochroia crassa	LOTUS Database	35616633
Verongula gigantea	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Phenoxy compound
Anisole
Methoxybenzene
Alkyl aryl ether
Halobenzene
Bromobenzene
Aryl bromide
Aryl halide
Fatty amide
Fatty acyl
Monocyclic benzene moiety
Azole
Heteroaromatic compound
Imidazole
Ketoxime
Secondary carboxylic acid amide
Carboxamide group
Carboxylic acid derivative
Ether
Organoheterocyclic compound
Azacycle
Oxime
Organic nitrogen compound
Organohalogen compound
Organobromide
Carbonyl group
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

monocarboxylic acid amide (CHEBI:66355 )
imidazoles (CHEBI:66355 )
monomethoxybenzene (CHEBI:66355 )
bromobenzenes (CHEBI:66355 )
ketoxime (CHEBI:66355 )

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	1.5	ChemAxon
pKa (Strongest Acidic)	1.78	ChemAxon
pKa (Strongest Basic)	6.76	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	103.09 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	90.17 m³·mol⁻¹	ChemAxon
Polarizability	34.64 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

Not Available

Chemspider ID

7852427

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9578063

PDB ID

Not Available

ChEBI ID

66355

Good Scents ID

Not Available

References

General References

Boehlow TR, Harburn JJ, Spilling CD: Approaches to the synthesis of some tyrosine-derived marine sponge metabolites: synthesis of verongamine and purealidin N. J Org Chem. 2001 May 4;66(9):3111-8. doi: 10.1021/jo010015v. [PubMed:11325276 ]
Ali SM, Tedford CE, Gregory R, Yates SL, Phillips JG: New acetylene based histamine H3 receptor antagonists derived from the marine natural product verongamine. Bioorg Med Chem Lett. 1998 May 19;8(10):1133-8. doi: 10.1016/s0960-894x(98)00181-4. [PubMed:9871722 ]
Mierzwa R, King A, Conover MA, Tozzi S, Puar MS, Patel M, Coval SJ, Pomponi SA: Verongamine, a novel bromotyrosine-derived histamine H3-antagonist from the marine sponge Verongula gigantea. J Nat Prod. 1994 Jan;57(1):175-7. doi: 10.1021/np50103a029. [PubMed:8158162 ]
LOTUS database [Link]

Showing NP-Card for (2e)-3-(3-bromo-4-methoxyphenyl)-2-(n-hydroxyimino)-n-[2-(3h-imidazol-4-yl)ethyl]propanimidic acid (NP0225890)

MOL for NP0225890 ((2e)-3-(3-bromo-4-methoxyphenyl)-2-(n-hydroxyimino)-n-[2-(3h-imidazol-4-yl)ethyl]propanimidic acid)

3D MOL for NP0225890 ((2e)-3-(3-bromo-4-methoxyphenyl)-2-(n-hydroxyimino)-n-[2-(3h-imidazol-4-yl)ethyl]propanimidic acid)

3D SDF for NP0225890 ((2e)-3-(3-bromo-4-methoxyphenyl)-2-(n-hydroxyimino)-n-[2-(3h-imidazol-4-yl)ethyl]propanimidic acid)

3D-SDF for NP0225890 ((2e)-3-(3-bromo-4-methoxyphenyl)-2-(n-hydroxyimino)-n-[2-(3h-imidazol-4-yl)ethyl]propanimidic acid)

PDB for NP0225890 ((2e)-3-(3-bromo-4-methoxyphenyl)-2-(n-hydroxyimino)-n-[2-(3h-imidazol-4-yl)ethyl]propanimidic acid)

3D PDB for NP0225890 ((2e)-3-(3-bromo-4-methoxyphenyl)-2-(n-hydroxyimino)-n-[2-(3h-imidazol-4-yl)ethyl]propanimidic acid)

SMILES for NP0225890 ((2e)-3-(3-bromo-4-methoxyphenyl)-2-(n-hydroxyimino)-n-[2-(3h-imidazol-4-yl)ethyl]propanimidic acid)

INCHI for NP0225890 ((2e)-3-(3-bromo-4-methoxyphenyl)-2-(n-hydroxyimino)-n-[2-(3h-imidazol-4-yl)ethyl]propanimidic acid)

Structure for NP0225890 ((2e)-3-(3-bromo-4-methoxyphenyl)-2-(n-hydroxyimino)-n-[2-(3h-imidazol-4-yl)ethyl]propanimidic acid)

3D Structure for NP0225890 ((2e)-3-(3-bromo-4-methoxyphenyl)-2-(n-hydroxyimino)-n-[2-(3h-imidazol-4-yl)ethyl]propanimidic acid)