NP-MRD: Showing NP-Card for 2-[(2s,4z)-4-(11-chloro-1-hydroxydodeca-2,4,6,8,10-pentaen-1-ylidene)-3,5-dioxo-1-[(2r,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]pyrrolidin-2-yl]ethanimidic acid (NP0191424)

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Record Information

Version

2.0

Created at

2022-09-04 08:22:46 UTC

Updated at

2022-09-04 08:22:46 UTC

NP-MRD ID

NP0191424

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-[(2s,4z)-4-(11-chloro-1-hydroxydodeca-2,4,6,8,10-pentaen-1-ylidene)-3,5-dioxo-1-[(2r,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]pyrrolidin-2-yl]ethanimidic acid

Description

2-[(2S,4Z)-4-(11-chloro-1-hydroxydodeca-2,4,6,8,10-pentaen-1-ylidene)-3,5-dioxo-1-[(2R,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]pyrrolidin-2-yl]ethanimidic acid belongs to the class of organic compounds known as glycosylamines. Glycosylamines are compounds consisting of an amine with a beta-N-glycosidic bond to a carbohydrate, thus forming a cyclic hemiaminal ether bond (alpha-amino ether). 2-[(2s,4z)-4-(11-chloro-1-hydroxydodeca-2,4,6,8,10-pentaen-1-ylidene)-3,5-dioxo-1-[(2r,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]pyrrolidin-2-yl]ethanimidic acid is found in Theonella swinhoei. Based on a literature review very few articles have been published on 2-[(2S,4Z)-4-(11-chloro-1-hydroxydodeca-2,4,6,8,10-pentaen-1-ylidene)-3,5-dioxo-1-[(2R,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]pyrrolidin-2-yl]ethanimidic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042210222D          

 34 35  0  0  1  0            999 V2000
    5.0013    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    6.1875    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    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


  Mrv1652309042210222D          

 34 35  0  0  1  0            999 V2000
    5.0013    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0191424

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(Cl)=CC=CC=CC=CC=C\C(O)=C1/C(=O)[C@H](CC(O)=N)N([C@@H]2OC[C@@H](O)[C@H](O)[C@H]2O)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C23H27ClN2O8/c1-13(24)9-7-5-3-2-4-6-8-10-15(27)18-19(30)14(11-17(25)29)26(22(18)33)23-21(32)20(31)16(28)12-34-23/h2-10,14,16,20-21,23,27-28,31-32H,11-12H2,1H3,(H2,25,29)/b3-2?,6-4?,7-5?,10-8?,13-9?,18-15-/t14-,16+,20-,21+,23+/m0/s1

> <INCHI_KEY>
VRZYXKVDNUBKHN-LEPDXFRDSA-N

> <FORMULA>
C23H27ClN2O8

> <MOLECULAR_WEIGHT>
494.93

> <EXACT_MASS>
494.1455935

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
50.81513774693117

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(2S,4Z)-4-(11-chloro-1-hydroxydodeca-2,4,6,8,10-pentaen-1-ylidene)-3,5-dioxo-1-[(2R,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]pyrrolidin-2-yl]ethanimidic acid

> <JCHEM_LOGP>
-2.344158645454477

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
5.1903453644404705

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.3477073598910918

> <JCHEM_PKA_STRONGEST_BASIC>
14.011971903483802

> <JCHEM_POLAR_SURFACE_AREA>
171.60999999999999

> <JCHEM_REFRACTIVITY>
141.06700000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
2-[(2S,4Z)-4-(11-chloro-1-hydroxydodeca-2,4,6,8,10-pentaen-1-ylidene)-3,5-dioxo-1-[(2R,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]pyrrolidin-2-yl]ethanimidic acid

> <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       9.336  11.550   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002  10.780   0.000  0.00  0.00           C+0
HETATM    3 Cl   UNK     0       6.668  11.550   0.000  0.00  0.00          Cl+0
HETATM    4  C   UNK     0       8.002   9.240   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668   8.470   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.580  -3.215   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       4.044  -2.739   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.104  -4.680   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.009  -5.926   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.540  -5.765   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       5.167  -4.358   0.000  0.00  0.00           N+0
HETATM   22  O   UNK     0       5.446  -7.011   0.000  0.00  0.00           O+0
HETATM   23  N   UNK     0       0.564  -4.680   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0      -0.342  -5.926   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       0.285  -7.333   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -0.620  -8.578   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.152  -8.417   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -3.057  -9.663   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -2.778  -7.011   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -4.310  -6.850   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -1.873  -5.765   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -2.499  -4.358   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       0.088  -3.215   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -1.377  -2.739   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   33                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   18   24   33                                                  
CONECT   24   23   25   31                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   24   32                                                  
CONECT   32   31                                                            
CONECT   33   23   15   34                                                  
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   70    0
END

View in JSmol

Synonyms

Value	Source
2-[(2S,4Z)-4-(11-Chloro-1-hydroxydodeca-2,4,6,8,10-pentaen-1-ylidene)-3,5-dioxo-1-[(2R,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]pyrrolidin-2-yl]ethanimidate	Generator

Chemical Formula

C₂₃H₂₇ClN₂O₈

Average Mass

494.9300 Da

Monoisotopic Mass

494.14559 Da

IUPAC Name

2-[(2S,4Z)-4-(11-chloro-1-hydroxydodeca-2,4,6,8,10-pentaen-1-ylidene)-3,5-dioxo-1-[(2R,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]pyrrolidin-2-yl]ethanimidic acid

Traditional Name

2-[(2S,4Z)-4-(11-chloro-1-hydroxydodeca-2,4,6,8,10-pentaen-1-ylidene)-3,5-dioxo-1-[(2R,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]pyrrolidin-2-yl]ethanimidic acid

CAS Registry Number

Not Available

SMILES

CC(Cl)=CC=CC=CC=CC=C\C(O)=C1/C(=O)[C@H](CC(O)=N)N([C@@H]2OC[C@@H](O)[C@H](O)[C@H]2O)C1=O

InChI Identifier

InChI=1S/C23H27ClN2O8/c1-13(24)9-7-5-3-2-4-6-8-10-15(27)18-19(30)14(11-17(25)29)26(22(18)33)23-21(32)20(31)16(28)12-34-23/h2-10,14,16,20-21,23,27-28,31-32H,11-12H2,1H3,(H2,25,29)/b3-2?,6-4?,7-5?,10-8?,13-9?,18-15-/t14-,16+,20-,21+,23+/m0/s1

InChI Key

VRZYXKVDNUBKHN-LEPDXFRDSA-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
Theonella swinhoei	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as glycosylamines. Glycosylamines are compounds consisting of an amine with a beta-N-glycosidic bond to a carbohydrate, thus forming a cyclic hemiaminal ether bond (alpha-amino ether).

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Glycosylamines

Alternative Parents

Substituents

N-glycosyl compound
N-alkylpyrrolidine
3-pyrrolidone
2-pyrrolidone
Pyrrolidone
Oxane
Monosaccharide
Vinylogous acid
Tertiary carboxylic acid amide
Pyrrolidine
Cyclic ketone
Secondary alcohol
Lactam
Ketone
Carboxamide group
Oxacycle
Azacycle
Chloroalkene
Haloalkene
Organoheterocyclic compound
Vinyl halide
Vinyl chloride
Polyol
Enol
Carboxylic acid derivative
Carboximidic acid derivative
Carboximidic acid
Organic nitrogen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organonitrogen compound
Organochloride
Organohalogen compound
Carbonyl group
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic 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	-2.3	ChemAxon
pKa (Strongest Acidic)	-1.3	ChemAxon
pKa (Strongest Basic)	14.01	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	171.61 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	141.07 m³·mol⁻¹	ChemAxon
Polarizability	50.82 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

162971168

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-[(2s,4z)-4-(11-chloro-1-hydroxydodeca-2,4,6,8,10-pentaen-1-ylidene)-3,5-dioxo-1-[(2r,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]pyrrolidin-2-yl]ethanimidic acid (NP0191424)

MOL for NP0191424 (2-[(2s,4z)-4-(11-chloro-1-hydroxydodeca-2,4,6,8,10-pentaen-1-ylidene)-3,5-dioxo-1-[(2r,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]pyrrolidin-2-yl]ethanimidic acid)

3D MOL for NP0191424 (2-[(2s,4z)-4-(11-chloro-1-hydroxydodeca-2,4,6,8,10-pentaen-1-ylidene)-3,5-dioxo-1-[(2r,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]pyrrolidin-2-yl]ethanimidic acid)

3D SDF for NP0191424 (2-[(2s,4z)-4-(11-chloro-1-hydroxydodeca-2,4,6,8,10-pentaen-1-ylidene)-3,5-dioxo-1-[(2r,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]pyrrolidin-2-yl]ethanimidic acid)

3D-SDF for NP0191424 (2-[(2s,4z)-4-(11-chloro-1-hydroxydodeca-2,4,6,8,10-pentaen-1-ylidene)-3,5-dioxo-1-[(2r,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]pyrrolidin-2-yl]ethanimidic acid)

PDB for NP0191424 (2-[(2s,4z)-4-(11-chloro-1-hydroxydodeca-2,4,6,8,10-pentaen-1-ylidene)-3,5-dioxo-1-[(2r,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]pyrrolidin-2-yl]ethanimidic acid)

3D PDB for NP0191424 (2-[(2s,4z)-4-(11-chloro-1-hydroxydodeca-2,4,6,8,10-pentaen-1-ylidene)-3,5-dioxo-1-[(2r,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]pyrrolidin-2-yl]ethanimidic acid)

SMILES for NP0191424 (2-[(2s,4z)-4-(11-chloro-1-hydroxydodeca-2,4,6,8,10-pentaen-1-ylidene)-3,5-dioxo-1-[(2r,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]pyrrolidin-2-yl]ethanimidic acid)

INCHI for NP0191424 (2-[(2s,4z)-4-(11-chloro-1-hydroxydodeca-2,4,6,8,10-pentaen-1-ylidene)-3,5-dioxo-1-[(2r,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]pyrrolidin-2-yl]ethanimidic acid)

Structure for NP0191424 (2-[(2s,4z)-4-(11-chloro-1-hydroxydodeca-2,4,6,8,10-pentaen-1-ylidene)-3,5-dioxo-1-[(2r,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]pyrrolidin-2-yl]ethanimidic acid)

3D Structure for NP0191424 (2-[(2s,4z)-4-(11-chloro-1-hydroxydodeca-2,4,6,8,10-pentaen-1-ylidene)-3,5-dioxo-1-[(2r,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]pyrrolidin-2-yl]ethanimidic acid)