NP-MRD: Showing NP-Card for 3-acetyl-1-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione (NP0218975)

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Record Information

Version

2.0

Created at

2022-09-05 19:48:43 UTC

Updated at

2022-09-05 19:48:43 UTC

NP-MRD ID

NP0218975

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-acetyl-1-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione

Description

3-Acetyl-1-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione belongs to the class of organic compounds known as pyrimidine 2'-deoxyribonucleosides. Pyrimidine 2'-deoxyribonucleosides are compounds consisting of a pyrimidine linked to a ribose which lacks a hydroxyl group at position 2. 3-acetyl-1-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione is found in Streptomyces microflavus. Based on a literature review very few articles have been published on 3-acetyl-1-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309052221482D          

 20 21  0  0  0  0            999 V2000
    1.3222    5.5902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3222    4.7652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6078    4.3527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367    4.3527    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512    4.7652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512    5.5902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4656    4.3527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1801    4.7652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4656    3.5277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512    3.1152    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512    2.2902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4186    1.8053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1637    1.0206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6486    0.3532    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387    1.0206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8538    0.3532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1893   -0.4005    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0837    1.8053    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367    3.5277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3222    3.1152    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  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 15 18  1  0  0  0  0
 11 18  1  0  0  0  0
 10 19  1  0  0  0  0
  4 19  1  0  0  0  0
 19 20  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0218975

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)N1C(=O)N(C=C(C)C1=O)C1CC(O)C(CO)O1

> <INCHI_IDENTIFIER>
InChI=1S/C12H16N2O6/c1-6-4-13(10-3-8(17)9(5-15)20-10)12(19)14(7(2)16)11(6)18/h4,8-10,15,17H,3,5H2,1-2H3

> <INCHI_KEY>
DOYZPOPPDQRFPK-UHFFFAOYSA-N

> <FORMULA>
C12H16N2O6

> <MOLECULAR_WEIGHT>
284.268

> <EXACT_MASS>
284.100836243

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
27.703371894518487

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
-1.1304452836666665

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.787555327664535

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.894924215558088

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9780835910899173

> <JCHEM_POLAR_SURFACE_AREA>
107.38000000000002

> <JCHEM_REFRACTIVITY>
64.97789999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
3-acetyl-1-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       2.468  10.435   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.468   8.895   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.134   8.125   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       3.802   8.125   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       5.136   8.895   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       5.136  10.435   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       6.469   8.125   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.803   8.895   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.469   6.585   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       5.136   5.815   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       5.136   4.275   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.381   3.370   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.906   1.905   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       6.811   0.659   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.366   1.905   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.460   0.659   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       4.087  -0.748   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       3.890   3.370   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       3.802   6.585   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.468   5.815   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   19                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   19                                                  
CONECT   11   10   12   18                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18   15   11                                                       
CONECT   19   10    4   20                                                  
CONECT   20   19                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₂H₁₆N₂O₆

Average Mass

284.2680 Da

Monoisotopic Mass

284.10084 Da

IUPAC Name

3-acetyl-1-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione

Traditional Name

3-acetyl-1-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione

CAS Registry Number

Not Available

SMILES

CC(=O)N1C(=O)N(C=C(C)C1=O)C1CC(O)C(CO)O1

InChI Identifier

InChI=1S/C12H16N2O6/c1-6-4-13(10-3-8(17)9(5-15)20-10)12(19)14(7(2)16)11(6)18/h4,8-10,15,17H,3,5H2,1-2H3

InChI Key

DOYZPOPPDQRFPK-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Streptomyces microflavus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrimidine 2'-deoxyribonucleosides. Pyrimidine 2'-deoxyribonucleosides are compounds consisting of a pyrimidine linked to a ribose which lacks a hydroxyl group at position 2.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Pyrimidine nucleosides

Sub Class

Pyrimidine 2'-deoxyribonucleosides

Direct Parent

Pyrimidine 2'-deoxyribonucleosides

Alternative Parents

Substituents

Pyrimidine 2'-deoxyribonucleoside
N-acyl urea
Pyrimidone
Ureide
Hydropyrimidine
Pyrimidine
Heteroaromatic compound
Acetamide
Tetrahydrofuran
Vinylogous amide
Lactam
Secondary alcohol
Urea
Oxacycle
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Primary alcohol
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Alcohol
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	-1.1	ChemAxon
pKa (Strongest Acidic)	13.89	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	107.38 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	64.98 m³·mol⁻¹	ChemAxon
Polarizability	27.7 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

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

163061682

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-acetyl-1-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione (NP0218975)

MOL for NP0218975 (3-acetyl-1-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione)

3D MOL for NP0218975 (3-acetyl-1-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione)

3D SDF for NP0218975 (3-acetyl-1-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione)

3D-SDF for NP0218975 (3-acetyl-1-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione)

PDB for NP0218975 (3-acetyl-1-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione)

3D PDB for NP0218975 (3-acetyl-1-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione)

SMILES for NP0218975 (3-acetyl-1-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione)

INCHI for NP0218975 (3-acetyl-1-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione)

Structure for NP0218975 (3-acetyl-1-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione)

3D Structure for NP0218975 (3-acetyl-1-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione)