NP-MRD: Showing NP-Card for 1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3-hydroxypyrimidine-2,4-dione (NP0170086)

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Record Information

Version

2.0

Created at

2022-09-03 06:09:41 UTC

Updated at

2022-09-03 06:09:41 UTC

NP-MRD ID

NP0170086

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3-hydroxypyrimidine-2,4-dione

Description

3-Hydroxyuridine belongs to the class of organic compounds known as pyrimidine nucleosides. Pyrimidine nucleosides are compounds comprising a pyrimidine base attached to a ribosyl or deoxyribosyl moiety. 1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3-hydroxypyrimidine-2,4-dione is found in Baillonella toxisperma. Based on a literature review very few articles have been published on 3-hydroxyuridine.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 31  0  0  0  0  0  0  0  0999 V2000
    5.1255    0.7019    0.7375 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9357    0.5345    0.3650 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0266    1.5395    0.5603 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7165    1.3454    0.1460 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3127    0.2031   -0.4403 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0493   -0.0266   -0.8828 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8425    1.0022   -0.3796 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1427    0.5282   -0.3501 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9304    1.4234    0.5932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2358    0.9546    0.6284 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0160   -0.8660    0.1687 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0056   -1.6846   -0.3933 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6366   -1.2806   -0.2922 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7273   -2.2612   -1.2762 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2444   -0.7517   -0.6086 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9435   -1.8518   -1.1509 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5258   -0.6069   -0.2225 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4478   -1.6332   -0.4236 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2978    2.4904    1.0319 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9888    2.1176    0.2887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1281   -0.0056   -1.9910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5768    0.5484   -1.3532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4634    1.4694    1.5946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9390    2.4630    0.2077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7984    1.4155   -0.0661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0730   -0.9135    1.2813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7010   -1.1300   -0.8084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0377   -1.6787    0.5507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6413   -2.6215   -1.3764 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3800   -1.4254   -0.7678 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  9  1  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6 13  1  0
 13 14  1  0
 13 11  1  0
 11 12  1  0
  6  5  1  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
  2  1  2  0
  2 17  1  0
 17 18  1  0
 17 15  1  0
 15 16  2  0
 11  8  1  0
 15  5  1  0
 10 25  1  0
  9 23  1  0
  9 24  1  0
  8 22  1  6
  6 21  1  6
 13 28  1  1
 14 29  1  0
 11 26  1  1
 12 27  1  0
  4 20  1  0
  3 19  1  0
 18 30  1  0
M  END


  Mrv1652309032208092D          

 18 19  0  0  1  0            999 V2000
    0.7145    6.7661    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    5.9411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    5.5286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.7036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.2911    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.4661    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3819    2.9812    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    2.1965    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6119    1.5291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4324    1.6153    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    2.1965    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1830    1.5291    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0470    2.9812    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7376    3.2361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.7036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.2911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    5.5286    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    5.9411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
  6 13  1  0  0  0  0
 13 14  1  1  0  0  0
  5 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
  2 17  1  0  0  0  0
 17 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0170086

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=CC(=O)N(O)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C9H12N2O7/c12-3-4-6(14)7(15)8(18-4)10-2-1-5(13)11(17)9(10)16/h1-2,4,6-8,12,14-15,17H,3H2/t4-,6-,7-,8-/m1/s1

> <INCHI_KEY>
RSDVTBJFCGBNOI-XVFCMESISA-N

> <FORMULA>
C9H12N2O7

> <MOLECULAR_WEIGHT>
260.202

> <EXACT_MASS>
260.064450734

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
22.83478143535482

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-1.59

> <JCHEM_LOGP>
-2.418423869

> <ALOGPS_LOGS>
-0.13

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.553864809914494

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.5214886198239554

> <JCHEM_PKA_STRONGEST_BASIC>
-2.980299645944836

> <JCHEM_POLAR_SURFACE_AREA>
130.77

> <JCHEM_REFRACTIVITY>
54.33019999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.93e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3-hydroxypyrimidine-2,4-dione

> <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  O   UNK     0       1.334  12.630   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.334  11.090   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667  10.320   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   8.780   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       1.334   8.010   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       1.334   6.470   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.580   5.565   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.104   4.100   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.009   2.854   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.540   3.015   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.564   4.100   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.342   2.854   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.088   5.565   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.377   6.041   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.000   8.780   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.334   8.010   0.000  0.00  0.00           O+0
HETATM   17  N   UNK     0      -0.000  10.320   0.000  0.00  0.00           N+0
HETATM   18  O   UNK     0      -1.334  11.090   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   17                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   15                                                  
CONECT    6    5    7   13                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    8   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11    6   14                                                  
CONECT   14   13                                                            
CONECT   15    5   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15    2   18                                                  
CONECT   18   17                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₉H₁₂N₂O₇

Average Mass

260.2020 Da

Monoisotopic Mass

260.06445 Da

IUPAC Name

1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3-hydroxy-1,2,3,4-tetrahydropyrimidine-2,4-dione

Traditional Name

1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3-hydroxypyrimidine-2,4-dione

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=CC(=O)N(O)C1=O

InChI Identifier

InChI=1S/C9H12N2O7/c12-3-4-6(14)7(15)8(18-4)10-2-1-5(13)11(17)9(10)16/h1-2,4,6-8,12,14-15,17H,3H2/t4-,6-,7-,8-/m1/s1

InChI Key

RSDVTBJFCGBNOI-XVFCMESISA-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
Baillonella toxisperma	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrimidine nucleosides. Pyrimidine nucleosides are compounds comprising a pyrimidine base attached to a ribosyl or deoxyribosyl moiety.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Pyrimidine nucleosides

Sub Class

Not Available

Direct Parent

Pyrimidine nucleosides

Alternative Parents

Substituents

Pyrimidine nucleoside
Glycosyl compound
N-glycosyl compound
Pentose monosaccharide
Pyrimidone
Hydropyrimidine
Monosaccharide
Pyrimidine
Vinylogous amide
Tetrahydrofuran
Heteroaromatic compound
Secondary alcohol
Lactam
Organoheterocyclic compound
Oxacycle
Azacycle
Hydrocarbon derivative
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Primary alcohol
Alcohol
Organic oxygen compound
Organic oxide
Organic nitrogen compound
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	-1.6	ALOGPS
logP	-2.4	ChemAxon
logS	-0.13	ALOGPS
pKa (Strongest Acidic)	5.52	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	130.77 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	54.33 m³·mol⁻¹	ChemAxon
Polarizability	22.83 Å³	ChemAxon
Number of Rings	2	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

C00000143

Chemspider ID

66000994

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14330990

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3-hydroxypyrimidine-2,4-dione (NP0170086)

MOL for NP0170086 (1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3-hydroxypyrimidine-2,4-dione)

3D MOL for NP0170086 (1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3-hydroxypyrimidine-2,4-dione)

3D SDF for NP0170086 (1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3-hydroxypyrimidine-2,4-dione)

3D-SDF for NP0170086 (1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3-hydroxypyrimidine-2,4-dione)

PDB for NP0170086 (1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3-hydroxypyrimidine-2,4-dione)

3D PDB for NP0170086 (1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3-hydroxypyrimidine-2,4-dione)

SMILES for NP0170086 (1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3-hydroxypyrimidine-2,4-dione)

INCHI for NP0170086 (1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3-hydroxypyrimidine-2,4-dione)

Structure for NP0170086 (1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3-hydroxypyrimidine-2,4-dione)

3D Structure for NP0170086 (1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3-hydroxypyrimidine-2,4-dione)