NP-MRD: Showing NP-Card for (2e,4e)-n-[(1s)-2-{[(2s)-1-[(3r,4s)-5-hydroxy-4-methyl-2-oxo-3,4-dihydropyrrol-3-yl]-3-methyl-1-oxobutan-2-yl]-c-hydroxycarbonimidoyl}-1-phenylethyl]hexa-2,4-dienimidic acid (NP0327052)

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Record Information

Version

2.0

Created at

2022-09-12 09:14:54 UTC

Updated at

2022-09-12 09:14:55 UTC

NP-MRD ID

NP0327052

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2e,4e)-n-[(1s)-2-{[(2s)-1-[(3r,4s)-5-hydroxy-4-methyl-2-oxo-3,4-dihydropyrrol-3-yl]-3-methyl-1-oxobutan-2-yl]-c-hydroxycarbonimidoyl}-1-phenylethyl]hexa-2,4-dienimidic acid

Description

Moiramide B belongs to the class of organic compounds known as beta amino acids and derivatives. These are amino acids having a (-NH2) group attached to the beta carbon atom. (2e,4e)-n-[(1s)-2-{[(2s)-1-[(3r,4s)-5-hydroxy-4-methyl-2-oxo-3,4-dihydropyrrol-3-yl]-3-methyl-1-oxobutan-2-yl]-c-hydroxycarbonimidoyl}-1-phenylethyl]hexa-2,4-dienimidic acid is found in Pseudomonas fluorescens. (2e,4e)-n-[(1s)-2-{[(2s)-1-[(3r,4s)-5-hydroxy-4-methyl-2-oxo-3,4-dihydropyrrol-3-yl]-3-methyl-1-oxobutan-2-yl]-c-hydroxycarbonimidoyl}-1-phenylethyl]hexa-2,4-dienimidic acid was first documented in 2005 (PMID: 15686939). Based on a literature review a small amount of articles have been published on moiramide B (PMID: 29975047) (PMID: 27471863) (PMID: 16870762) (PMID: 15673760).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122211142D          

 33 34  0  0  1  0            999 V2000
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   -3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.7145   -0.4125    0.0000 O   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


  Mrv1652309122211142D          

 33 34  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0327052

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C\C=C\C(O)=N[C@@H](CC(O)=N[C@@H](C(C)C)C(=O)[C@H]1[C@H](C)C(O)=NC1=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C25H31N3O5/c1-5-6-8-13-19(29)26-18(17-11-9-7-10-12-17)14-20(30)27-22(15(2)3)23(31)21-16(4)24(32)28-25(21)33/h5-13,15-16,18,21-22H,14H2,1-4H3,(H,26,29)(H,27,30)(H,28,32,33)/b6-5+,13-8+/t16-,18-,21+,22-/m0/s1

> <INCHI_KEY>
WMLLJSBRSSYYPT-PQUJRENYSA-N

> <FORMULA>
C25H31N3O5

> <MOLECULAR_WEIGHT>
453.539

> <EXACT_MASS>
453.22637111

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
48.20467800707707

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E,4E)-N-[(1S)-2-{[(2S)-1-[(3R,4S)-5-hydroxy-4-methyl-2-oxo-3,4-dihydro-2H-pyrrol-3-yl]-3-methyl-1-oxobutan-2-yl]-C-hydroxycarbonimidoyl}-1-phenylethyl]hexa-2,4-dienimidic acid

> <JCHEM_LOGP>
4.072096977278334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
4.990976148395541

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.233830482964581

> <JCHEM_PKA_STRONGEST_BASIC>
3.5592847759629316

> <JCHEM_POLAR_SURFACE_AREA>
131.91000000000003

> <JCHEM_REFRACTIVITY>
126.78229999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2E,4E)-N-[(1S)-2-{[(2S)-1-[(3R,4S)-5-hydroxy-4-methyl-2-oxo-3,4-dihydropyrrol-3-yl]-3-methyl-1-oxobutan-2-yl]-C-hydroxycarbonimidoyl}-1-phenylethyl]hexa-2,4-dienimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0      -8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0       0.000  -3.080   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   13  N   UNK     0       5.335  -3.080   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       9.336  -2.310   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.756  -5.525   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       5.292  -5.049   0.000  0.00  0.00           O+0
HETATM   20  N   UNK     0       7.232  -6.990   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0       8.772  -6.990   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       9.677  -8.236   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       9.248  -5.525   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.713  -5.049   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.000   1.540   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   28                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   25                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   23                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   17   24                                                  
CONECT   24   23                                                            
CONECT   25   14   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28    9   29   33                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   28                                                       
MASTER        0    0    0    0    0    0    0    0   33    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₁N₃O₅

Average Mass

453.5390 Da

Monoisotopic Mass

453.22637 Da

IUPAC Name

(2E,4E)-N-[(1S)-2-{[(2S)-1-[(3R,4S)-5-hydroxy-4-methyl-2-oxo-3,4-dihydro-2H-pyrrol-3-yl]-3-methyl-1-oxobutan-2-yl]-C-hydroxycarbonimidoyl}-1-phenylethyl]hexa-2,4-dienimidic acid

Traditional Name

(2E,4E)-N-[(1S)-2-{[(2S)-1-[(3R,4S)-5-hydroxy-4-methyl-2-oxo-3,4-dihydropyrrol-3-yl]-3-methyl-1-oxobutan-2-yl]-C-hydroxycarbonimidoyl}-1-phenylethyl]hexa-2,4-dienimidic acid

CAS Registry Number

Not Available

SMILES

C\C=C\C=C\C(O)=N[C@@H](CC(O)=N[C@@H](C(C)C)C(=O)[C@H]1[C@H](C)C(O)=NC1=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C25H31N3O5/c1-5-6-8-13-19(29)26-18(17-11-9-7-10-12-17)14-20(30)27-22(15(2)3)23(31)21-16(4)24(32)28-25(21)33/h5-13,15-16,18,21-22H,14H2,1-4H3,(H,26,29)(H,27,30)(H,28,32,33)/b6-5+,13-8+/t16-,18-,21+,22-/m0/s1

InChI Key

WMLLJSBRSSYYPT-PQUJRENYSA-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
Pseudomonas fluorescens	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as beta amino acids and derivatives. These are amino acids having a (-NH2) group attached to the beta carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Beta amino acids and derivatives

Alternative Parents

Substituents

Beta amino acid or derivatives
Monocyclic benzene moiety
Fatty amide
N-acyl-amine
Pyrrolidone
Fatty acyl
2-pyrrolidone
Benzenoid
1,3-dicarbonyl compound
Carboxylic acid imide
Dicarboximide
Carboxylic acid imide, n-unsubstituted
Pyrrolidine
Lactam
Ketone
Carboxamide group
Secondary carboxylic acid amide
Azacycle
Organoheterocyclic compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organic nitrogen 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	4.07	ChemAxon
pKa (Strongest Acidic)	4.23	ChemAxon
pKa (Strongest Basic)	3.56	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	131.91 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	126.78 m³·mol⁻¹	ChemAxon
Polarizability	48.2 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

9919348

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11744644

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wu Y, Seyedsayamdost MR: The Polyene Natural Product Thailandamide A Inhibits Fatty Acid Biosynthesis in Gram-Positive and Gram-Negative Bacteria. Biochemistry. 2018 Jul 24;57(29):4247-4251. doi: 10.1021/acs.biochem.8b00678. Epub 2018 Jul 12. [PubMed:29975047 ]
Silvers MA, Pakhomova S, Neau DB, Silvers WC, Anzalone N, Taylor CM, Waldrop GL: Crystal Structure of Carboxyltransferase from Staphylococcus aureus Bound to the Antibacterial Agent Moiramide B. Biochemistry. 2016 Aug 23;55(33):4666-74. doi: 10.1021/acs.biochem.6b00641. Epub 2016 Aug 10. [PubMed:27471863 ]
Freiberg C, Pohlmann J, Nell PG, Endermann R, Schuhmacher J, Newton B, Otteneder M, Lampe T, Habich D, Ziegelbauer K: Novel bacterial acetyl coenzyme A carboxylase inhibitors with antibiotic efficacy in vivo. Antimicrob Agents Chemother. 2006 Aug;50(8):2707-12. doi: 10.1128/AAC.00012-06. [PubMed:16870762 ]
Pohlmann J, Lampe T, Shimada M, Nell PG, Pernerstorfer J, Svenstrup N, Brunner NA, Schiffer G, Freiberg C: Pyrrolidinedione derivatives as antibacterial agents with a novel mode of action. Bioorg Med Chem Lett. 2005 Feb 15;15(4):1189-92. doi: 10.1016/j.bmcl.2004.12.002. [PubMed:15686939 ]
Freiberg C, Fischer HP, Brunner NA: Discovering the mechanism of action of novel antibacterial agents through transcriptional profiling of conditional mutants. Antimicrob Agents Chemother. 2005 Feb;49(2):749-59. doi: 10.1128/AAC.49.2.749-759.2005. [PubMed:15673760 ]
LOTUS database [Link]

Showing NP-Card for (2e,4e)-n-[(1s)-2-{[(2s)-1-[(3r,4s)-5-hydroxy-4-methyl-2-oxo-3,4-dihydropyrrol-3-yl]-3-methyl-1-oxobutan-2-yl]-c-hydroxycarbonimidoyl}-1-phenylethyl]hexa-2,4-dienimidic acid (NP0327052)

MOL for NP0327052 ((2e,4e)-n-[(1s)-2-{[(2s)-1-[(3r,4s)-5-hydroxy-4-methyl-2-oxo-3,4-dihydropyrrol-3-yl]-3-methyl-1-oxobutan-2-yl]-c-hydroxycarbonimidoyl}-1-phenylethyl]hexa-2,4-dienimidic acid)

3D MOL for NP0327052 ((2e,4e)-n-[(1s)-2-{[(2s)-1-[(3r,4s)-5-hydroxy-4-methyl-2-oxo-3,4-dihydropyrrol-3-yl]-3-methyl-1-oxobutan-2-yl]-c-hydroxycarbonimidoyl}-1-phenylethyl]hexa-2,4-dienimidic acid)

3D SDF for NP0327052 ((2e,4e)-n-[(1s)-2-{[(2s)-1-[(3r,4s)-5-hydroxy-4-methyl-2-oxo-3,4-dihydropyrrol-3-yl]-3-methyl-1-oxobutan-2-yl]-c-hydroxycarbonimidoyl}-1-phenylethyl]hexa-2,4-dienimidic acid)

3D-SDF for NP0327052 ((2e,4e)-n-[(1s)-2-{[(2s)-1-[(3r,4s)-5-hydroxy-4-methyl-2-oxo-3,4-dihydropyrrol-3-yl]-3-methyl-1-oxobutan-2-yl]-c-hydroxycarbonimidoyl}-1-phenylethyl]hexa-2,4-dienimidic acid)

PDB for NP0327052 ((2e,4e)-n-[(1s)-2-{[(2s)-1-[(3r,4s)-5-hydroxy-4-methyl-2-oxo-3,4-dihydropyrrol-3-yl]-3-methyl-1-oxobutan-2-yl]-c-hydroxycarbonimidoyl}-1-phenylethyl]hexa-2,4-dienimidic acid)

3D PDB for NP0327052 ((2e,4e)-n-[(1s)-2-{[(2s)-1-[(3r,4s)-5-hydroxy-4-methyl-2-oxo-3,4-dihydropyrrol-3-yl]-3-methyl-1-oxobutan-2-yl]-c-hydroxycarbonimidoyl}-1-phenylethyl]hexa-2,4-dienimidic acid)

SMILES for NP0327052 ((2e,4e)-n-[(1s)-2-{[(2s)-1-[(3r,4s)-5-hydroxy-4-methyl-2-oxo-3,4-dihydropyrrol-3-yl]-3-methyl-1-oxobutan-2-yl]-c-hydroxycarbonimidoyl}-1-phenylethyl]hexa-2,4-dienimidic acid)

INCHI for NP0327052 ((2e,4e)-n-[(1s)-2-{[(2s)-1-[(3r,4s)-5-hydroxy-4-methyl-2-oxo-3,4-dihydropyrrol-3-yl]-3-methyl-1-oxobutan-2-yl]-c-hydroxycarbonimidoyl}-1-phenylethyl]hexa-2,4-dienimidic acid)

Structure for NP0327052 ((2e,4e)-n-[(1s)-2-{[(2s)-1-[(3r,4s)-5-hydroxy-4-methyl-2-oxo-3,4-dihydropyrrol-3-yl]-3-methyl-1-oxobutan-2-yl]-c-hydroxycarbonimidoyl}-1-phenylethyl]hexa-2,4-dienimidic acid)

3D Structure for NP0327052 ((2e,4e)-n-[(1s)-2-{[(2s)-1-[(3r,4s)-5-hydroxy-4-methyl-2-oxo-3,4-dihydropyrrol-3-yl]-3-methyl-1-oxobutan-2-yl]-c-hydroxycarbonimidoyl}-1-phenylethyl]hexa-2,4-dienimidic acid)