NP-MRD: Showing NP-Card for (2e,4e,6e)-n-[(1s)-2-{[(2s)-1-[(3s,4s)-3,5-dihydroxy-4-methyl-2-oxo-4h-pyrrol-3-yl]-3-methyl-1-oxobutan-2-yl]-c-hydroxycarbonimidoyl}-1-phenylethyl]octa-2,4,6-trienimidic acid (NP0286154)

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Record Information

Version

2.0

Created at

2022-09-09 14:36:34 UTC

Updated at

2022-09-09 14:36:34 UTC

NP-MRD ID

NP0286154

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2e,4e,6e)-n-[(1s)-2-{[(2s)-1-[(3s,4s)-3,5-dihydroxy-4-methyl-2-oxo-4h-pyrrol-3-yl]-3-methyl-1-oxobutan-2-yl]-c-hydroxycarbonimidoyl}-1-phenylethyl]octa-2,4,6-trienimidic acid

Description

Moiramide C 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,6e)-n-[(1s)-2-{[(2s)-1-[(3s,4s)-3,5-dihydroxy-4-methyl-2-oxo-4h-pyrrol-3-yl]-3-methyl-1-oxobutan-2-yl]-c-hydroxycarbonimidoyl}-1-phenylethyl]octa-2,4,6-trienimidic acid is found in Pseudomonas fluorescens. Based on a literature review very few articles have been published on Moiramide C.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092216362D          

 36 37  0  0  1  0            999 V2000
   13.5068    6.0294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9548    5.4163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   10.7888    5.1463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2368    4.5332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4298    4.7047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8778    4.0916    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


  Mrv1652309092216362D          

 36 37  0  0  1  0            999 V2000
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 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 31 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0286154

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C27H33N3O6/c1-5-6-7-8-12-15-21(31)28-20(19-13-10-9-11-14-19)16-22(32)29-23(17(2)3)24(33)27(36)18(4)25(34)30-26(27)35/h5-15,17-18,20,23,36H,16H2,1-4H3,(H,28,31)(H,29,32)(H,30,34,35)/b6-5+,8-7+,15-12+/t18-,20+,23+,27+/m1/s1

> <INCHI_KEY>
MDWPTHONDMTCBU-ZUDAILPZSA-N

> <FORMULA>
C27H33N3O6

> <MOLECULAR_WEIGHT>
495.576

> <EXACT_MASS>
495.236935795

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
52.17954815541206

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E,4E,6E)-N-[(1S)-2-{[(2S)-1-[(3S,4S)-3,5-dihydroxy-4-methyl-2-oxo-3,4-dihydro-2H-pyrrol-3-yl]-3-methyl-1-oxobutan-2-yl]-C-hydroxycarbonimidoyl}-1-phenylethyl]octa-2,4,6-trienimidic acid

> <JCHEM_LOGP>
4.183301249713056

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
5.3684165050575885

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.66710094807044

> <JCHEM_PKA_STRONGEST_BASIC>
3.6197662195846836

> <JCHEM_POLAR_SURFACE_AREA>
152.14000000000001

> <JCHEM_REFRACTIVITY>
138.34689999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2E,4E,6E)-N-[(1S)-2-{[(2S)-1-[(3S,4S)-3,5-dihydroxy-4-methyl-2-oxo-4H-pyrrol-3-yl]-3-methyl-1-oxobutan-2-yl]-C-hydroxycarbonimidoyl}-1-phenylethyl]octa-2,4,6-trienimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0      25.213  11.255   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      24.182  10.111   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      22.676  10.431   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      21.646   9.286   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      20.139   9.606   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      19.109   8.462   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      17.602   8.782   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      16.572   7.638   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      17.048   6.173   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0      15.066   7.958   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      14.035   6.813   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.529   7.134   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.498   5.989   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      11.974   4.525   0.000  0.00  0.00           O+0
HETATM   15  N   UNK     0       9.992   6.309   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       8.961   5.165   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.437   3.700   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      10.944   3.380   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       8.407   2.556   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       7.376   3.700   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       9.653   1.651   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      11.117   2.127   0.000  0.00  0.00           O+0
HETATM   23  N   UNK     0       9.177   0.186   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0       7.637   0.186   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       6.732  -1.060   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       7.161   1.651   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.696   2.127   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.455   5.485   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.425   4.341   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.979   6.950   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      14.511   5.349   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      16.017   5.029   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      16.493   3.564   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      15.463   2.420   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      13.956   2.740   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      13.481   4.204   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                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   31                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   28                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21   26                                             
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   19   27                                                  
CONECT   27   26                                                            
CONECT   28   16   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   11   32   36                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   31                                                       
MASTER        0    0    0    0    0    0    0    0   36    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₃N₃O₆

Average Mass

495.5760 Da

Monoisotopic Mass

495.23694 Da

IUPAC Name

(2E,4E,6E)-N-[(1S)-2-{[(2S)-1-[(3S,4S)-3,5-dihydroxy-4-methyl-2-oxo-3,4-dihydro-2H-pyrrol-3-yl]-3-methyl-1-oxobutan-2-yl]-C-hydroxycarbonimidoyl}-1-phenylethyl]octa-2,4,6-trienimidic acid

Traditional Name

(2E,4E,6E)-N-[(1S)-2-{[(2S)-1-[(3S,4S)-3,5-dihydroxy-4-methyl-2-oxo-4H-pyrrol-3-yl]-3-methyl-1-oxobutan-2-yl]-C-hydroxycarbonimidoyl}-1-phenylethyl]octa-2,4,6-trienimidic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C27H33N3O6/c1-5-6-7-8-12-15-21(31)28-20(19-13-10-9-11-14-19)16-22(32)29-23(17(2)3)24(33)27(36)18(4)25(34)30-26(27)35/h5-15,17-18,20,23,36H,16H2,1-4H3,(H,28,31)(H,29,32)(H,30,34,35)/b6-5+,8-7+,15-12+/t18-,20+,23+,27+/m1/s1

InChI Key

MDWPTHONDMTCBU-ZUDAILPZSA-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
Alpha-hydroxy ketone
Carboxylic acid imide
Dicarboximide
Carboxylic acid imide, n-unsubstituted
Pyrrolidine
Tertiary alcohol
Lactam
Ketone
Carboxamide group
Secondary carboxylic acid amide
Azacycle
Organoheterocyclic compound
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Alcohol
Organooxygen compound
Organic oxygen 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	4.18	ChemAxon
pKa (Strongest Acidic)	4.67	ChemAxon
pKa (Strongest Basic)	3.62	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	152.14 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	138.35 m³·mol⁻¹	ChemAxon
Polarizability	52.18 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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101663895

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2e,4e,6e)-n-[(1s)-2-{[(2s)-1-[(3s,4s)-3,5-dihydroxy-4-methyl-2-oxo-4h-pyrrol-3-yl]-3-methyl-1-oxobutan-2-yl]-c-hydroxycarbonimidoyl}-1-phenylethyl]octa-2,4,6-trienimidic acid (NP0286154)

MOL for NP0286154 ((2e,4e,6e)-n-[(1s)-2-{[(2s)-1-[(3s,4s)-3,5-dihydroxy-4-methyl-2-oxo-4h-pyrrol-3-yl]-3-methyl-1-oxobutan-2-yl]-c-hydroxycarbonimidoyl}-1-phenylethyl]octa-2,4,6-trienimidic acid)

3D MOL for NP0286154 ((2e,4e,6e)-n-[(1s)-2-{[(2s)-1-[(3s,4s)-3,5-dihydroxy-4-methyl-2-oxo-4h-pyrrol-3-yl]-3-methyl-1-oxobutan-2-yl]-c-hydroxycarbonimidoyl}-1-phenylethyl]octa-2,4,6-trienimidic acid)

3D SDF for NP0286154 ((2e,4e,6e)-n-[(1s)-2-{[(2s)-1-[(3s,4s)-3,5-dihydroxy-4-methyl-2-oxo-4h-pyrrol-3-yl]-3-methyl-1-oxobutan-2-yl]-c-hydroxycarbonimidoyl}-1-phenylethyl]octa-2,4,6-trienimidic acid)

3D-SDF for NP0286154 ((2e,4e,6e)-n-[(1s)-2-{[(2s)-1-[(3s,4s)-3,5-dihydroxy-4-methyl-2-oxo-4h-pyrrol-3-yl]-3-methyl-1-oxobutan-2-yl]-c-hydroxycarbonimidoyl}-1-phenylethyl]octa-2,4,6-trienimidic acid)

PDB for NP0286154 ((2e,4e,6e)-n-[(1s)-2-{[(2s)-1-[(3s,4s)-3,5-dihydroxy-4-methyl-2-oxo-4h-pyrrol-3-yl]-3-methyl-1-oxobutan-2-yl]-c-hydroxycarbonimidoyl}-1-phenylethyl]octa-2,4,6-trienimidic acid)

3D PDB for NP0286154 ((2e,4e,6e)-n-[(1s)-2-{[(2s)-1-[(3s,4s)-3,5-dihydroxy-4-methyl-2-oxo-4h-pyrrol-3-yl]-3-methyl-1-oxobutan-2-yl]-c-hydroxycarbonimidoyl}-1-phenylethyl]octa-2,4,6-trienimidic acid)

SMILES for NP0286154 ((2e,4e,6e)-n-[(1s)-2-{[(2s)-1-[(3s,4s)-3,5-dihydroxy-4-methyl-2-oxo-4h-pyrrol-3-yl]-3-methyl-1-oxobutan-2-yl]-c-hydroxycarbonimidoyl}-1-phenylethyl]octa-2,4,6-trienimidic acid)

INCHI for NP0286154 ((2e,4e,6e)-n-[(1s)-2-{[(2s)-1-[(3s,4s)-3,5-dihydroxy-4-methyl-2-oxo-4h-pyrrol-3-yl]-3-methyl-1-oxobutan-2-yl]-c-hydroxycarbonimidoyl}-1-phenylethyl]octa-2,4,6-trienimidic acid)

Structure for NP0286154 ((2e,4e,6e)-n-[(1s)-2-{[(2s)-1-[(3s,4s)-3,5-dihydroxy-4-methyl-2-oxo-4h-pyrrol-3-yl]-3-methyl-1-oxobutan-2-yl]-c-hydroxycarbonimidoyl}-1-phenylethyl]octa-2,4,6-trienimidic acid)

3D Structure for NP0286154 ((2e,4e,6e)-n-[(1s)-2-{[(2s)-1-[(3s,4s)-3,5-dihydroxy-4-methyl-2-oxo-4h-pyrrol-3-yl]-3-methyl-1-oxobutan-2-yl]-c-hydroxycarbonimidoyl}-1-phenylethyl]octa-2,4,6-trienimidic acid)