NP-MRD: Showing NP-Card for n-[(3r,4r,5s,6r)-2,5-dihydroxy-6-(hydroxymethyl)-4-[(1-oxopropan-2-yl)oxy]oxan-3-yl]ethanimidic acid (NP0251729)

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Record Information

Version

2.0

Created at

2022-09-07 15:00:43 UTC

Updated at

2022-09-07 15:00:43 UTC

NP-MRD ID

NP0251729

Secondary Accession Numbers

None

Natural Product Identification

Common Name

n-[(3r,4r,5s,6r)-2,5-dihydroxy-6-(hydroxymethyl)-4-[(1-oxopropan-2-yl)oxy]oxan-3-yl]ethanimidic acid

Description

Muracein C belongs to the class of organic compounds known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group. n-[(3r,4r,5s,6r)-2,5-dihydroxy-6-(hydroxymethyl)-4-[(1-oxopropan-2-yl)oxy]oxan-3-yl]ethanimidic acid was first documented in 1984 (PMID: 6327591). Based on a literature review very few articles have been published on Muracein C.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 38 38  0  0  0  0  0  0  0  0999 V2000
    4.1272    1.1138    0.4807 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0082    0.2549   -0.0064 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3494   -0.8316   -0.8007 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7757    0.4972    0.2881 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7473   -0.3612   -0.2079 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6720   -1.6892    0.4983 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7213   -1.7617    1.4140 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5087   -1.8647    1.2008 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6353   -1.8691    0.4221 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9981   -3.2264   -0.1230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2319   -4.1300    0.8842 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5604   -0.8432   -0.6756 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8007   -0.3309   -1.0194 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6276    0.2533   -0.1527 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7467    1.4172   -0.8521 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1428    2.4467   -0.0089 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1686    3.6051   -0.0353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4736    2.9970   -0.3996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0071    3.9061    0.2071 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6794    1.5222   -0.4024 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8306    0.4292    1.0148 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7613    1.9193    1.1419 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9625   -1.5339   -0.3978 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9657   -0.5614   -1.2920 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8150   -2.5364   -0.2126 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4636   -1.4594    2.3173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4918   -1.5515    1.0867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2647   -3.5703   -0.8639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9625   -3.0938   -0.6850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3979   -4.5662    1.1887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1015   -1.3389   -1.5568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8340    0.0302   -1.9226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8756    0.3928    0.9385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2526    2.0287    1.0095 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5306    3.4494    0.8128 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3514    3.7081   -0.9991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6898    4.5684    0.1504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9895    2.5802   -1.2494 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 16  1  0
 16 15  1  0
 15 14  1  0
 14 12  1  0
 12 13  1  0
 12  9  1  0
  9 10  1  0
 10 11  1  0
  9  8  1  0
  8  6  1  0
  6  7  1  0
  6  5  1  0
  5  4  1  0
  4  2  2  0
  2  1  1  0
  2  3  1  0
 16 18  1  0
 18 19  2  0
  5 14  1  0
 17 35  1  0
 17 36  1  0
 17 37  1  0
 16 34  1  1
 14 33  1  1
 12 31  1  6
 13 32  1  0
  9 27  1  1
 10 28  1  0
 10 29  1  0
 11 30  1  0
  6 25  1  6
  7 26  1  0
  5 24  1  6
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
 18 38  1  0
M  END


  Mrv1652309072217002D          

 19 19  0  0  1  0            999 V2000
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  1  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
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  4  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
  5 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0251729

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(O[C@H]1[C@H](O)[C@@H](CO)OC(O)[C@@H]1N=C(C)O)C=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H19NO7/c1-5(3-13)18-10-8(12-6(2)15)11(17)19-7(4-14)9(10)16/h3,5,7-11,14,16-17H,4H2,1-2H3,(H,12,15)/t5?,7-,8-,9-,10-,11?/m1/s1

> <INCHI_KEY>
QWRYRQKHCGBRGW-NJJVJDFKSA-N

> <FORMULA>
C11H19NO7

> <MOLECULAR_WEIGHT>
277.273

> <EXACT_MASS>
277.116151956

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
26.902857635525947

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-[(3R,4R,5S,6R)-2,5-dihydroxy-6-(hydroxymethyl)-4-[(1-oxopropan-2-yl)oxy]oxan-3-yl]ethanimidic acid

> <JCHEM_LOGP>
-1.8697124826666671

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.721157291498995

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.751438563509071

> <JCHEM_PKA_STRONGEST_BASIC>
1.483242706081323

> <JCHEM_POLAR_SURFACE_AREA>
128.81000000000003

> <JCHEM_REFRACTIVITY>
61.9507

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
N-[(3R,4R,5S,6R)-2,5-dihydroxy-6-(hydroxymethyl)-4-[(1-oxopropan-2-yl)oxy]oxan-3-yl]ethanimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       1.334   3.850   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       0.000   6.160   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   14                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    9   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    5   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   38    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₁H₁₉NO₇

Average Mass

277.2730 Da

Monoisotopic Mass

277.11615 Da

IUPAC Name

N-[(3R,4R,5S,6R)-2,5-dihydroxy-6-(hydroxymethyl)-4-[(1-oxopropan-2-yl)oxy]oxan-3-yl]ethanimidic acid

Traditional Name

N-[(3R,4R,5S,6R)-2,5-dihydroxy-6-(hydroxymethyl)-4-[(1-oxopropan-2-yl)oxy]oxan-3-yl]ethanimidic acid

CAS Registry Number

Not Available

SMILES

CC(O[C@H]1[C@H](O)[C@@H](CO)OC(O)[C@@H]1N=C(C)O)C=O

InChI Identifier

InChI=1S/C11H19NO7/c1-5(3-13)18-10-8(12-6(2)15)11(17)19-7(4-14)9(10)16/h3,5,7-11,14,16-17H,4H2,1-2H3,(H,12,15)/t5?,7-,8-,9-,10-,11?/m1/s1

InChI Key

QWRYRQKHCGBRGW-NJJVJDFKSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Acylaminosugars

Alternative Parents

Substituents

Acylaminosugar
N-acyl-alpha-hexosamine
Monosaccharide
Oxane
Acetamide
Carboxamide group
Hemiacetal
Secondary alcohol
Secondary carboxylic acid amide
Oxacycle
Ether
Dialkyl ether
Carboxylic acid derivative
Organoheterocyclic compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Alcohol
Organic nitrogen compound
Carbonyl group
Primary alcohol
Aldehyde
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	-1.9	ChemAxon
pKa (Strongest Acidic)	5.75	ChemAxon
pKa (Strongest Basic)	1.48	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	128.81 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	61.95 m³·mol⁻¹	ChemAxon
Polarizability	26.9 Å³	ChemAxon
Number of Rings	1	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

2342978

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3086323

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Singh PD, Johnson JH: Muraceins--muramyl peptides produced by Nocardia orientalis as angiotensin-converting enzyme inhibitors. II. Isolation and structure determination. J Antibiot (Tokyo). 1984 Apr;37(4):336-43. doi: 10.7164/antibiotics.37.336. [PubMed:6327591 ]
LOTUS database [Link]

Showing NP-Card for n-[(3r,4r,5s,6r)-2,5-dihydroxy-6-(hydroxymethyl)-4-[(1-oxopropan-2-yl)oxy]oxan-3-yl]ethanimidic acid (NP0251729)

MOL for NP0251729 (n-[(3r,4r,5s,6r)-2,5-dihydroxy-6-(hydroxymethyl)-4-[(1-oxopropan-2-yl)oxy]oxan-3-yl]ethanimidic acid)

3D MOL for NP0251729 (n-[(3r,4r,5s,6r)-2,5-dihydroxy-6-(hydroxymethyl)-4-[(1-oxopropan-2-yl)oxy]oxan-3-yl]ethanimidic acid)

3D SDF for NP0251729 (n-[(3r,4r,5s,6r)-2,5-dihydroxy-6-(hydroxymethyl)-4-[(1-oxopropan-2-yl)oxy]oxan-3-yl]ethanimidic acid)

3D-SDF for NP0251729 (n-[(3r,4r,5s,6r)-2,5-dihydroxy-6-(hydroxymethyl)-4-[(1-oxopropan-2-yl)oxy]oxan-3-yl]ethanimidic acid)

PDB for NP0251729 (n-[(3r,4r,5s,6r)-2,5-dihydroxy-6-(hydroxymethyl)-4-[(1-oxopropan-2-yl)oxy]oxan-3-yl]ethanimidic acid)

3D PDB for NP0251729 (n-[(3r,4r,5s,6r)-2,5-dihydroxy-6-(hydroxymethyl)-4-[(1-oxopropan-2-yl)oxy]oxan-3-yl]ethanimidic acid)

SMILES for NP0251729 (n-[(3r,4r,5s,6r)-2,5-dihydroxy-6-(hydroxymethyl)-4-[(1-oxopropan-2-yl)oxy]oxan-3-yl]ethanimidic acid)

INCHI for NP0251729 (n-[(3r,4r,5s,6r)-2,5-dihydroxy-6-(hydroxymethyl)-4-[(1-oxopropan-2-yl)oxy]oxan-3-yl]ethanimidic acid)

Structure for NP0251729 (n-[(3r,4r,5s,6r)-2,5-dihydroxy-6-(hydroxymethyl)-4-[(1-oxopropan-2-yl)oxy]oxan-3-yl]ethanimidic acid)

3D Structure for NP0251729 (n-[(3r,4r,5s,6r)-2,5-dihydroxy-6-(hydroxymethyl)-4-[(1-oxopropan-2-yl)oxy]oxan-3-yl]ethanimidic acid)