NP-MRD: Showing NP-Card for n-[(2s,4r)-5-[6-(dimethylamino)purin-9-yl]-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]-2-[(1-hydroxyethylidene)amino]-3-(4-methoxyphenyl)propanimidic acid (NP0199269)

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Record Information

Version

2.0

Created at

2022-09-04 17:52:39 UTC

Updated at

2022-09-04 17:52:39 UTC

NP-MRD ID

NP0199269

Secondary Accession Numbers

None

Natural Product Identification

Common Name

n-[(2s,4r)-5-[6-(dimethylamino)purin-9-yl]-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]-2-[(1-hydroxyethylidene)amino]-3-(4-methoxyphenyl)propanimidic acid

Description

N-[(2S,4R)-5-[6-(dimethylamino)-9H-purin-9-yl]-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]-2-[(1-hydroxyethylidene)amino]-3-(4-methoxyphenyl)propanimidic acid belongs to the class of organic compounds known as purine 3'-deoxyribonucleosides. Purine 3'-deoxyribonucleosides are compounds consisting of a purine linked to a ribose which lacks a hydroxyl group at position 3. n-[(2s,4r)-5-[6-(dimethylamino)purin-9-yl]-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]-2-[(1-hydroxyethylidene)amino]-3-(4-methoxyphenyl)propanimidic acid is found in Streptomyces alboniger. Based on a literature review very few articles have been published on N-[(2S,4R)-5-[6-(dimethylamino)-9H-purin-9-yl]-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]-2-[(1-hydroxyethylidene)amino]-3-(4-methoxyphenyl)propanimidic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042219522D          

 37 40  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309042219522D          

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 17 18  1  1  0  0  0
 18 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 26 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 25 33  1  0  0  0  0
 22 33  1  0  0  0  0
 21 34  1  0  0  0  0
 16 34  1  0  0  0  0
 34 35  1  6  0  0  0
  6 36  1  0  0  0  0
 36 37  2  0  0  0  0
  3 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0199269

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(CC(N=C(C)O)C(O)=NC2[C@@H](CO)OC([C@@H]2O)N2C=NC3=C(N=CN=C23)N(C)C)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C24H31N7O6/c1-13(33)28-16(9-14-5-7-15(36-4)8-6-14)23(35)29-18-17(10-32)37-24(20(18)34)31-12-27-19-21(30(2)3)25-11-26-22(19)31/h5-8,11-12,16-18,20,24,32,34H,9-10H2,1-4H3,(H,28,33)(H,29,35)/t16?,17-,18?,20-,24?/m1/s1

> <INCHI_KEY>
LADKVYSQIGJMFP-CKHJIVCFSA-N

> <FORMULA>
C24H31N7O6

> <MOLECULAR_WEIGHT>
513.555

> <EXACT_MASS>
513.233581746

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
52.32701126469716

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-[(2S,4R)-5-[6-(dimethylamino)-9H-purin-9-yl]-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]-2-[(1-hydroxyethylidene)amino]-3-(4-methoxyphenyl)propanimidic acid

> <JCHEM_LOGP>
0.3631908320492071

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
5.766938588933317

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.310192596084754

> <JCHEM_PKA_STRONGEST_BASIC>
3.9046691921046177

> <JCHEM_POLAR_SURFACE_AREA>
170.93999999999997

> <JCHEM_REFRACTIVITY>
133.44809999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
N-[(2S,4R)-5-[6-(dimethylamino)purin-9-yl]-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]-2-[(1-hydroxyethylidene)amino]-3-(4-methoxyphenyl)propanimidic 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       3.950 -17.902   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.444 -17.582   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.968 -16.117   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.462 -15.797   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.014 -14.332   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.016 -13.188   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.541 -11.723   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.571 -10.579   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       3.077 -10.899   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       4.108  -9.755   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.614 -10.075   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.632  -8.290   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.095  -9.114   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -0.411  -8.794   0.000  0.00  0.00           O+0
HETATM   15  N   UNK     0       2.126  -7.970   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       1.650  -6.505   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.185  -6.029   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.061  -6.934   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -2.468  -6.308   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       0.185  -4.489   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.650  -4.013   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0       2.126  -2.549   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0       2.126  -0.057   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   27  N   UNK     0       4.924   1.777   0.000  0.00  0.00           N+0
HETATM   28  C   UNK     0       3.590   2.547   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.258   2.547   0.000  0.00  0.00           C+0
HETATM   30  N   UNK     0       6.258  -0.533   0.000  0.00  0.00           N+0
HETATM   31  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   32  N   UNK     0       4.924  -2.843   0.000  0.00  0.00           N+0
HETATM   33  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.555  -5.259   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       4.095  -5.259   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       2.523 -13.508   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       2.999 -14.973   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   37                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   36                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    8   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   34                                                  
CONECT   17   16   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20   17   21                                                       
CONECT   21   20   22   34                                                  
CONECT   22   21   23   33                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   33                                                  
CONECT   26   25   27   30                                                  
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   26   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   25   22                                                  
CONECT   34   21   16   35                                                  
CONECT   35   34                                                            
CONECT   36    6   37                                                       
CONECT   37   36    3                                                       
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Value	Source
N-[(2S,4R)-5-[6-(Dimethylamino)-9H-purin-9-yl]-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]-2-[(1-hydroxyethylidene)amino]-3-(4-methoxyphenyl)propanimidate	Generator

Chemical Formula

C₂₄H₃₁N₇O₆

Average Mass

513.5550 Da

Monoisotopic Mass

513.23358 Da

IUPAC Name

N-[(2S,4R)-5-[6-(dimethylamino)-9H-purin-9-yl]-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]-2-[(1-hydroxyethylidene)amino]-3-(4-methoxyphenyl)propanimidic acid

Traditional Name

N-[(2S,4R)-5-[6-(dimethylamino)purin-9-yl]-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]-2-[(1-hydroxyethylidene)amino]-3-(4-methoxyphenyl)propanimidic acid

CAS Registry Number

Not Available

SMILES

COC1=CC=C(CC(N=C(C)O)C(O)=NC2[C@@H](CO)OC([C@@H]2O)N2C=NC3=C(N=CN=C23)N(C)C)C=C1

InChI Identifier

InChI=1S/C24H31N7O6/c1-13(33)28-16(9-14-5-7-15(36-4)8-6-14)23(35)29-18-17(10-32)37-24(20(18)34)31-12-27-19-21(30(2)3)25-11-26-22(19)31/h5-8,11-12,16-18,20,24,32,34H,9-10H2,1-4H3,(H,28,33)(H,29,35)/t16?,17-,18?,20-,24?/m1/s1

InChI Key

LADKVYSQIGJMFP-CKHJIVCFSA-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 alboniger	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as purine 3'-deoxyribonucleosides. Purine 3'-deoxyribonucleosides are compounds consisting of a purine linked to a ribose which lacks a hydroxyl group at position 3.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Purine nucleosides

Sub Class

Purine 3'-deoxyribonucleosides

Direct Parent

Purine 3'-deoxyribonucleosides

Alternative Parents

Substituents

Purine 3'-deoxyribonucleoside
Phenylalanine or derivatives
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
Glycosyl compound
N-glycosyl compound
6-alkylaminopurine
6-aminopurine
N-substituted-alpha-amino acid
Amphetamine or derivatives
Pentose monosaccharide
Alpha-amino acid or derivatives
Imidazopyrimidine
Purine
Dialkylarylamine
Anisole
Phenoxy compound
Phenol ether
Methoxybenzene
Alkyl aryl ether
Aminopyrimidine
Imidolactam
Benzenoid
Fatty amide
Fatty acyl
Monosaccharide
N-substituted imidazole
Pyrimidine
Monocyclic benzene moiety
Heteroaromatic compound
Azole
Imidazole
Oxolane
Acetamide
Secondary carboxylic acid amide
Secondary alcohol
Carboxamide group
Carboxylic acid derivative
Ether
Oxacycle
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Carbonyl group
Organonitrogen compound
Organooxygen compound
Amine
Primary alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	0.36	ChemAxon
pKa (Strongest Acidic)	3.31	ChemAxon
pKa (Strongest Basic)	3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	170.94 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	133.45 m³·mol⁻¹	ChemAxon
Polarizability	52.33 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	Yes	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

25244345

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for n-[(2s,4r)-5-[6-(dimethylamino)purin-9-yl]-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]-2-[(1-hydroxyethylidene)amino]-3-(4-methoxyphenyl)propanimidic acid (NP0199269)

MOL for NP0199269 (n-[(2s,4r)-5-[6-(dimethylamino)purin-9-yl]-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]-2-[(1-hydroxyethylidene)amino]-3-(4-methoxyphenyl)propanimidic acid)

3D MOL for NP0199269 (n-[(2s,4r)-5-[6-(dimethylamino)purin-9-yl]-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]-2-[(1-hydroxyethylidene)amino]-3-(4-methoxyphenyl)propanimidic acid)

3D SDF for NP0199269 (n-[(2s,4r)-5-[6-(dimethylamino)purin-9-yl]-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]-2-[(1-hydroxyethylidene)amino]-3-(4-methoxyphenyl)propanimidic acid)

3D-SDF for NP0199269 (n-[(2s,4r)-5-[6-(dimethylamino)purin-9-yl]-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]-2-[(1-hydroxyethylidene)amino]-3-(4-methoxyphenyl)propanimidic acid)

PDB for NP0199269 (n-[(2s,4r)-5-[6-(dimethylamino)purin-9-yl]-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]-2-[(1-hydroxyethylidene)amino]-3-(4-methoxyphenyl)propanimidic acid)

3D PDB for NP0199269 (n-[(2s,4r)-5-[6-(dimethylamino)purin-9-yl]-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]-2-[(1-hydroxyethylidene)amino]-3-(4-methoxyphenyl)propanimidic acid)

SMILES for NP0199269 (n-[(2s,4r)-5-[6-(dimethylamino)purin-9-yl]-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]-2-[(1-hydroxyethylidene)amino]-3-(4-methoxyphenyl)propanimidic acid)

INCHI for NP0199269 (n-[(2s,4r)-5-[6-(dimethylamino)purin-9-yl]-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]-2-[(1-hydroxyethylidene)amino]-3-(4-methoxyphenyl)propanimidic acid)

Structure for NP0199269 (n-[(2s,4r)-5-[6-(dimethylamino)purin-9-yl]-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]-2-[(1-hydroxyethylidene)amino]-3-(4-methoxyphenyl)propanimidic acid)

3D Structure for NP0199269 (n-[(2s,4r)-5-[6-(dimethylamino)purin-9-yl]-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]-2-[(1-hydroxyethylidene)amino]-3-(4-methoxyphenyl)propanimidic acid)