NP-MRD: Showing NP-Card for pyrazofurin (NP0166948)

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Record Information

Version

2.0

Created at

2022-09-03 02:25:47 UTC

Updated at

2022-09-03 02:25:47 UTC

NP-MRD ID

NP0166948

Secondary Accession Numbers

None

Natural Product Identification

Common Name

pyrazofurin

Description

Pirazofurin, also known as 47599 or beta-pyrazomycin, belongs to the class of organic compounds known as 3-ribofuranosylpyrazoles. These are nucleoside and nucleotide analogs with a structure that consists of a pyrazole ring system which is N-substituted at the 3-position with a ribose moiety. Nucleotide analogues contain a phosphate group linked to the C5 carbon atom of the furanose. Pirazofurin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. pyrazofurin was first documented in 2016 (PMID: 26513594). Based on a literature review very few articles have been published on pirazofurin.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 31 32  0  0  0  0  0  0  0  0999 V2000
    5.0701    1.1208   -0.0027 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1080    1.3332   -1.0061 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4544    2.0014   -2.0399 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7654    0.8230   -0.8891 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6961    1.1858   -1.7049 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6023    0.6654   -1.2567 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8186   -0.0551   -0.1561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1170   -0.8931    0.6087 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9630   -1.4474   -0.4099 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2208   -0.9904   -0.2824 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0287   -0.6701   -1.5160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3173   -0.2063   -1.0944 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1663    0.3028    0.5858 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3997    0.4947    1.2414 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0650   -0.1276    1.4971 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6241   -1.0515    2.4124 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1948    0.0422    0.0764 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8093   -0.5777    1.1337 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7149    0.3524    0.0174 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0768    1.8489    0.7711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3227    0.8344   -1.7362 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3538   -1.7469    1.0994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7943   -1.6907    0.3688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0736   -1.4361   -2.2837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5818    0.2836   -1.9508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9655   -0.9081   -1.2325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9399    1.1070   -0.0922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1811    1.1777    1.9640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5674    0.6985    2.0145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1709   -1.9327    2.3571 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8345   -0.5382    1.3158 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 10 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
  7 17  2  0
 17 18  1  0
 17  4  1  0
 15  8  1  0
  1 19  1  0
  1 20  1  0
  6 21  1  0
  8 22  1  1
 10 23  1  1
 11 24  1  0
 11 25  1  0
 12 26  1  0
 13 27  1  6
 14 28  1  0
 15 29  1  1
 16 30  1  0
 18 31  1  0
M  END


  Mrv1652309032204252D          

 18 19  0  0  1  0            999 V2000
    1.9709    0.2323    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2564   -0.1802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5420    0.2323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2564   -1.0052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9239   -1.4901    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6689   -2.2748    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8439   -2.2748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3590   -2.9422    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6139   -3.7268    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0535   -4.2117    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0535   -5.0367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6610   -5.4492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7209   -3.7268    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5056   -3.9818    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4660   -2.9422    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9509   -2.2748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5890   -1.4901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1956   -1.2352    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
  8 15  1  0  0  0  0
 15 16  1  1  0  0  0
  7 17  2  0  0  0  0
  4 17  1  0  0  0  0
 17 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0166948

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC(=O)C1=NNC([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C9H13N3O6/c10-9(17)4-6(15)3(11-12-4)8-7(16)5(14)2(1-13)18-8/h2,5,7-8,13-16H,1H2,(H2,10,17)(H,11,12)/t2-,5-,7-,8+/m1/s1

> <INCHI_KEY>
XESARGFCSKSFID-FLLFQEBCSA-N

> <FORMULA>
C9H13N3O6

> <MOLECULAR_WEIGHT>
259.218

> <EXACT_MASS>
259.080435151

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
23.614934118742653

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-[(2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-hydroxy-1H-pyrazole-3-carboxamide

> <ALOGPS_LOGP>
-1.95

> <JCHEM_LOGP>
-2.3466297330000003

> <ALOGPS_LOGS>
-0.70

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.70570613571704

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.442043881641856

> <JCHEM_PKA_STRONGEST_BASIC>
-0.504725962935043

> <JCHEM_POLAR_SURFACE_AREA>
161.92

> <JCHEM_REFRACTIVITY>
57.465999999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.20e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
pyrazofurin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  N   UNK     0       3.679   0.434   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       2.345  -0.336   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.012   0.434   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.345  -1.876   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       3.591  -2.782   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       3.115  -4.246   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       1.575  -4.246   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.670  -5.492   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.146  -6.957   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -0.100  -7.862   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.100  -9.402   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.234 -10.172   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -1.346  -6.957   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -2.810  -7.433   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -0.870  -5.492   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.775  -4.246   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.099  -2.782   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.365  -2.306   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   17                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   17                                                  
CONECT    8    7    9   15                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13   10   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    8   16                                                  
CONECT   16   15                                                            
CONECT   17    7    4   18                                                  
CONECT   18   17                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

View in JSmol

Synonyms

Value	Source
3-(beta-D-Ribofuranosyl)-4-hydroxypyrazole-5-carboxamide	ChEBI
3-beta-D-Ribofuranosyl-4-hydroxypyrazole-5-carboxamide	ChEBI
4-Hydroxy-3-(beta-D-ribofuranosyl)-1H-pyrazole-5-carboxamide	ChEBI
4-Hydroxy-3-beta-D-ribofuranosyl-1H-pyrazole-5-carboxamide	ChEBI
4-Hydroxy-3-beta-D-ribofuranosylpyrazole-5-carboxamide	ChEBI
47599	ChEBI
Antibiotic a 23813	ChEBI
beta-Pyrazomycin	ChEBI
Compound 47599	ChEBI
PF	ChEBI
Pirazofurina	ChEBI
Pirazofurine	ChEBI
Pirazofurinum	ChEBI
Pyrazofurin	ChEBI
Pyrazomycin	ChEBI
PZF	ChEBI
3-(b-D-Ribofuranosyl)-4-hydroxypyrazole-5-carboxamide	Generator
3-(Β-D-ribofuranosyl)-4-hydroxypyrazole-5-carboxamide	Generator
3-b-D-Ribofuranosyl-4-hydroxypyrazole-5-carboxamide	Generator
3-Β-D-ribofuranosyl-4-hydroxypyrazole-5-carboxamide	Generator
4-Hydroxy-3-(b-D-ribofuranosyl)-1H-pyrazole-5-carboxamide	Generator
4-Hydroxy-3-(β-D-ribofuranosyl)-1H-pyrazole-5-carboxamide	Generator
4-Hydroxy-3-b-D-ribofuranosyl-1H-pyrazole-5-carboxamide	Generator
4-Hydroxy-3-β-D-ribofuranosyl-1H-pyrazole-5-carboxamide	Generator
4-Hydroxy-3-b-D-ribofuranosylpyrazole-5-carboxamide	Generator
4-Hydroxy-3-β-D-ribofuranosylpyrazole-5-carboxamide	Generator
b-Pyrazomycin	Generator
Β-pyrazomycin	Generator

Chemical Formula

C₉H₁₃N₃O₆

Average Mass

259.2180 Da

Monoisotopic Mass

259.08044 Da

IUPAC Name

5-[(2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-hydroxy-1H-pyrazole-3-carboxamide

Traditional Name

pyrazofurin

CAS Registry Number

Not Available

SMILES

NC(=O)C1=NNC([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)=C1O

InChI Identifier

InChI=1S/C9H13N3O6/c10-9(17)4-6(15)3(11-12-4)8-7(16)5(14)2(1-13)18-8/h2,5,7-8,13-16H,1H2,(H2,10,17)(H,11,12)/t2-,5-,7-,8+/m1/s1

InChI Key

XESARGFCSKSFID-FLLFQEBCSA-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 3-ribofuranosylpyrazoles. These are nucleoside and nucleotide analogs with a structure that consists of a pyrazole ring system which is N-substituted at the 3-position with a ribose moiety. Nucleotide analogues contain a phosphate group linked to the C5 carbon atom of the furanose.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Nucleoside and nucleotide analogues

Sub Class

3-ribofuranosylpyrazoles

Direct Parent

3-ribofuranosylpyrazoles

Alternative Parents

Substituents

3-ribofuranosylpyrazole
C-glycosyl compound
Glycosyl compound
Pentose monosaccharide
2-heteroaryl carboxamide
Pyrazole-5-carboxamide
Monosaccharide
Azole
Heteroaromatic compound
Pyrazole
Vinylogous acid
Tetrahydrofuran
Carboxamide group
Primary carboxylic acid amide
Secondary alcohol
Carboxylic acid derivative
Dialkyl ether
Ether
Oxacycle
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Primary alcohol
Organopnictogen compound
Alcohol
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	-2	ALOGPS
logP	-2.3	ChemAxon
logS	-0.7	ALOGPS
pKa (Strongest Acidic)	5.44	ChemAxon
pKa (Strongest Basic)	-0.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	161.92 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	57.47 m³·mol⁻¹	ChemAxon
Polarizability	23.61 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

10570780

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

35595

PDB ID

Not Available

ChEBI ID

90284

Good Scents ID

Not Available

References

General References

De Clercq E: C-Nucleosides To Be Revisited. J Med Chem. 2016 Mar 24;59(6):2301-11. doi: 10.1021/acs.jmedchem.5b01157. Epub 2015 Oct 29. [PubMed:26513594 ]
LOTUS database [Link]

Showing NP-Card for pyrazofurin (NP0166948)

MOL for NP0166948 (pyrazofurin)

3D MOL for NP0166948 (pyrazofurin)

3D SDF for NP0166948 (pyrazofurin)

3D-SDF for NP0166948 (pyrazofurin)

PDB for NP0166948 (pyrazofurin)

3D PDB for NP0166948 (pyrazofurin)

SMILES for NP0166948 (pyrazofurin)

INCHI for NP0166948 (pyrazofurin)

Structure for NP0166948 (pyrazofurin)

3D Structure for NP0166948 (pyrazofurin)