NP-MRD: Showing NP-Card for 4-amino-n-{1-[(5s,6r)-5-{[(2r,3r,4s,5s,6r)-3,4-dihydroxy-6-methyl-5-(methylamino)oxan-2-yl]oxy}-6-methyloxan-2-yl]-2-hydroxypyrimidin-4-ylidene}benzamide (NP0156329)

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Record Information

Version

2.0

Created at

2022-09-02 13:31:13 UTC

Updated at

2022-09-02 13:31:13 UTC

NP-MRD ID

NP0156329

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-amino-n-{1-[(5s,6r)-5-{[(2r,3r,4s,5s,6r)-3,4-dihydroxy-6-methyl-5-(methylamino)oxan-2-yl]oxy}-6-methyloxan-2-yl]-2-hydroxypyrimidin-4-ylidene}benzamide

Description

64040-47-7, Also known as norplicacetin, belongs to the class of organic compounds known as aminoglycosides. These are molecules or a portion of a molecule composed of amino-modified sugars. 4-amino-n-{1-[(5s,6r)-5-{[(2r,3r,4s,5s,6r)-3,4-dihydroxy-6-methyl-5-(methylamino)oxan-2-yl]oxy}-6-methyloxan-2-yl]-2-hydroxypyrimidin-4-ylidene}benzamide is found in Streptomyces rochei and Streptomyces vinaceusdrappus. Based on a literature review very few articles have been published on 64040-47-7.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022215312D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309022215312D          

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 24 26  1  0  0  0  0
 26 27  2  0  0  0  0
 21 27  1  0  0  0  0
 17 28  1  0  0  0  0
 28 29  2  0  0  0  0
 14 29  1  0  0  0  0
 29 30  1  0  0  0  0
 13 31  1  0  0  0  0
 31 32  1  0  0  0  0
 10 32  1  0  0  0  0
 32 33  1  6  0  0  0
  8 34  1  0  0  0  0
 34 35  1  0  0  0  0
  3 35  1  0  0  0  0
 35 36  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0156329

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN[C@@H]1[C@@H](C)O[C@H](O[C@H]2CCC(O[C@@H]2C)N2C=CC(=NC(=O)C3=CC=C(N)C=C3)N=C2O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C24H33N5O7/c1-12-16(36-23-21(31)20(30)19(26-3)13(2)35-23)8-9-18(34-12)29-11-10-17(28-24(29)33)27-22(32)14-4-6-15(25)7-5-14/h4-7,10-13,16,18-21,23,26,30-31H,8-9,25H2,1-3H3,(H,27,28,32,33)/t12-,13-,16+,18?,19-,20+,21-,23-/m1/s1

> <INCHI_KEY>
HJFXGPLQIPLHSS-WWYYRNKXSA-N

> <FORMULA>
C24H33N5O7

> <MOLECULAR_WEIGHT>
503.556

> <EXACT_MASS>
503.237998423

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
53.41163489472109

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-amino-N-{1-[(5S,6R)-5-{[(2R,3R,4S,5S,6R)-3,4-dihydroxy-6-methyl-5-(methylamino)oxan-2-yl]oxy}-6-methyloxan-2-yl]-2-hydroxy-1,4-dihydropyrimidin-4-ylidene}benzamide

> <ALOGPS_LOGP>
0.43

> <JCHEM_LOGP>
-2.05590916597567

> <ALOGPS_LOGS>
-3.63

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
12.36349203705888

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.701752151999632

> <JCHEM_PKA_STRONGEST_BASIC>
8.941177947728471

> <JCHEM_POLAR_SURFACE_AREA>
171.45999999999995

> <JCHEM_REFRACTIVITY>
129.69510000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.18e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-amino-N-{1-[(5S,6R)-5-{[(2R,3R,4S,5S,6R)-3,4-dihydroxy-6-methyl-5-(methylamino)oxan-2-yl]oxy}-6-methyloxan-2-yl]-2-hydroxypyrimidin-4-ylidene}benzamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       5.335 -12.320   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       5.335 -13.860   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668 -14.630   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       8.002 -13.860   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       6.668 -16.170   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       8.002 -16.940   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       5.335 -16.940   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.335 -18.480   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.001 -19.250   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001 -20.790   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667 -21.560   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334 -20.790   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       0.000 -21.560   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       0.000 -23.100   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.334 -23.870   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.667 -23.100   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0      -4.001 -23.870   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0      -4.001 -25.410   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -2.667 -26.180   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -5.335 -26.180   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -5.335 -27.720   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -6.668 -28.490   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -8.002 -27.720   0.000  0.00  0.00           C+0
HETATM   25  N   UNK     0      -9.336 -28.490   0.000  0.00  0.00           N+0
HETATM   26  C   UNK     0      -8.002 -26.180   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -6.668 -25.410   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0      -2.667 -21.560   0.000  0.00  0.00           N+0
HETATM   29  C   UNK     0      -1.334 -20.790   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -1.334 -19.250   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       1.334 -19.250   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       2.667 -18.480   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.667 -16.940   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       4.001 -16.170   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       4.001 -14.630   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       2.667 -13.860   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   35                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   34                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   32                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   31                                                  
CONECT   14   13   15   29                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   28                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   27                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   21                                                       
CONECT   28   17   29                                                       
CONECT   29   28   14   30                                                  
CONECT   30   29                                                            
CONECT   31   13   32                                                       
CONECT   32   31   10   33                                                  
CONECT   33   32                                                            
CONECT   34    8   35                                                       
CONECT   35   34    3   36                                                  
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   78    0
END

View in JSmol

Synonyms

Value	Source
Norplicacetin	MeSH

Chemical Formula

C₂₄H₃₃N₅O₇

Average Mass

503.5560 Da

Monoisotopic Mass

503.23800 Da

IUPAC Name

4-amino-N-{1-[(5S,6R)-5-{[(2R,3R,4S,5S,6R)-3,4-dihydroxy-6-methyl-5-(methylamino)oxan-2-yl]oxy}-6-methyloxan-2-yl]-2-hydroxy-1,4-dihydropyrimidin-4-ylidene}benzamide

Traditional Name

4-amino-N-{1-[(5S,6R)-5-{[(2R,3R,4S,5S,6R)-3,4-dihydroxy-6-methyl-5-(methylamino)oxan-2-yl]oxy}-6-methyloxan-2-yl]-2-hydroxypyrimidin-4-ylidene}benzamide

CAS Registry Number

Not Available

SMILES

CN[C@@H]1[C@@H](C)O[C@H](O[C@H]2CCC(O[C@@H]2C)N2C=CC(=NC(=O)C3=CC=C(N)C=C3)N=C2O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C24H33N5O7/c1-12-16(36-23-21(31)20(30)19(26-3)13(2)35-23)8-9-18(34-12)29-11-10-17(28-24(29)33)27-22(32)14-4-6-15(25)7-5-14/h4-7,10-13,16,18-21,23,26,30-31H,8-9,25H2,1-3H3,(H,27,28,32,33)/t12-,13-,16+,18?,19-,20+,21-,23-/m1/s1

InChI Key

HJFXGPLQIPLHSS-WWYYRNKXSA-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
Streptomyces rochei	LOTUS Database	35616633
Streptomyces vinaceusdrappus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aminoglycosides. These are molecules or a portion of a molecule composed of amino-modified sugars.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Aminoglycosides

Alternative Parents

Substituents

Aminoglycoside core
Aminobenzoic acid or derivatives
Benzamide
Benzoic acid or derivatives
Benzoyl
Aniline or substituted anilines
Pyrimidone
Monocyclic benzene moiety
Hydropyrimidine
Monosaccharide
Oxane
Primary aromatic amine
Pyrimidine
Benzenoid
Imidolactam
Heteroaromatic compound
Amino acid or derivatives
Secondary carboxylic acid amide
Secondary alcohol
1,2-aminoalcohol
Carboxamide group
1,2-diol
Azacycle
Organoheterocyclic compound
Secondary amine
Oxacycle
Acetal
Carboxylic acid derivative
Secondary aliphatic amine
Organic nitrogen compound
Organic oxide
Alcohol
Hydrocarbon derivative
Organonitrogen compound
Amine
Organopnictogen compound
Primary amine
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	0.43	ALOGPS
logP	-2.1	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	5.7	ChemAxon
pKa (Strongest Basic)	8.94	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	171.46 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	129.7 m³·mol⁻¹	ChemAxon
Polarizability	53.41 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	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

C00018139

Chemspider ID

166454

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

191715

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-amino-n-{1-[(5s,6r)-5-{[(2r,3r,4s,5s,6r)-3,4-dihydroxy-6-methyl-5-(methylamino)oxan-2-yl]oxy}-6-methyloxan-2-yl]-2-hydroxypyrimidin-4-ylidene}benzamide (NP0156329)

MOL for NP0156329 (4-amino-n-{1-[(5s,6r)-5-{[(2r,3r,4s,5s,6r)-3,4-dihydroxy-6-methyl-5-(methylamino)oxan-2-yl]oxy}-6-methyloxan-2-yl]-2-hydroxypyrimidin-4-ylidene}benzamide)

3D MOL for NP0156329 (4-amino-n-{1-[(5s,6r)-5-{[(2r,3r,4s,5s,6r)-3,4-dihydroxy-6-methyl-5-(methylamino)oxan-2-yl]oxy}-6-methyloxan-2-yl]-2-hydroxypyrimidin-4-ylidene}benzamide)

3D SDF for NP0156329 (4-amino-n-{1-[(5s,6r)-5-{[(2r,3r,4s,5s,6r)-3,4-dihydroxy-6-methyl-5-(methylamino)oxan-2-yl]oxy}-6-methyloxan-2-yl]-2-hydroxypyrimidin-4-ylidene}benzamide)

3D-SDF for NP0156329 (4-amino-n-{1-[(5s,6r)-5-{[(2r,3r,4s,5s,6r)-3,4-dihydroxy-6-methyl-5-(methylamino)oxan-2-yl]oxy}-6-methyloxan-2-yl]-2-hydroxypyrimidin-4-ylidene}benzamide)

PDB for NP0156329 (4-amino-n-{1-[(5s,6r)-5-{[(2r,3r,4s,5s,6r)-3,4-dihydroxy-6-methyl-5-(methylamino)oxan-2-yl]oxy}-6-methyloxan-2-yl]-2-hydroxypyrimidin-4-ylidene}benzamide)

3D PDB for NP0156329 (4-amino-n-{1-[(5s,6r)-5-{[(2r,3r,4s,5s,6r)-3,4-dihydroxy-6-methyl-5-(methylamino)oxan-2-yl]oxy}-6-methyloxan-2-yl]-2-hydroxypyrimidin-4-ylidene}benzamide)

SMILES for NP0156329 (4-amino-n-{1-[(5s,6r)-5-{[(2r,3r,4s,5s,6r)-3,4-dihydroxy-6-methyl-5-(methylamino)oxan-2-yl]oxy}-6-methyloxan-2-yl]-2-hydroxypyrimidin-4-ylidene}benzamide)

INCHI for NP0156329 (4-amino-n-{1-[(5s,6r)-5-{[(2r,3r,4s,5s,6r)-3,4-dihydroxy-6-methyl-5-(methylamino)oxan-2-yl]oxy}-6-methyloxan-2-yl]-2-hydroxypyrimidin-4-ylidene}benzamide)

Structure for NP0156329 (4-amino-n-{1-[(5s,6r)-5-{[(2r,3r,4s,5s,6r)-3,4-dihydroxy-6-methyl-5-(methylamino)oxan-2-yl]oxy}-6-methyloxan-2-yl]-2-hydroxypyrimidin-4-ylidene}benzamide)

3D Structure for NP0156329 (4-amino-n-{1-[(5s,6r)-5-{[(2r,3r,4s,5s,6r)-3,4-dihydroxy-6-methyl-5-(methylamino)oxan-2-yl]oxy}-6-methyloxan-2-yl]-2-hydroxypyrimidin-4-ylidene}benzamide)