NP-MRD: Showing NP-Card for 1-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-iminopyrimidin-2-ol (NP0322350)

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Record Information

Version

2.0

Created at

2022-09-12 01:04:35 UTC

Updated at

2022-09-12 01:04:35 UTC

NP-MRD ID

NP0322350

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-iminopyrimidin-2-ol

Description

1-[4-Hydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-imino-1,4-dihydropyrimidin-2-ol 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. 1-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-iminopyrimidin-2-ol is found in Isodictya erinacea. 1-[4-Hydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-imino-1,4-dihydropyrimidin-2-ol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 29 30  0  0  0  0  0  0  0  0999 V2000
   -5.1389    0.1983   -0.6259 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7567   -0.0576   -0.4688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2487   -0.8083    0.5707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9228   -1.0572    0.7266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0491   -0.5498   -0.1746 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3625   -0.7684   -0.0780 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8867   -0.7066    1.3284 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1117    0.1976    1.1687 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1917   -0.2620    1.8979 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3357    0.1039   -0.3246 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2235    1.2128   -0.8379 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7577    2.4516   -0.4820 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0418    0.1984   -0.8158 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5220    0.1860   -1.1975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7534    0.6855   -2.0697 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8376    0.4289   -1.3460 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6818    0.7982    0.0185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6228   -0.2407   -1.4285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9366   -1.2141    1.2896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4937   -1.6391    1.5266 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5836   -1.7691   -0.5054 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2910   -1.6864    1.6731 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2266   -0.2230    2.0405 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8363    1.2436    1.4564 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8739   -0.7138    1.3316 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7379   -0.8942   -0.5496 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2741    1.0577   -0.5400 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1855    1.1464   -1.9574 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0440    2.6814    0.4372 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2 16  2  0
 16 14  1  0
 14 15  2  0
 14  5  1  0
  5  4  1  0
  4  3  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 10 13  1  0
  3  2  1  0
 13  6  1  0
  1 17  1  0
  1 18  1  0
  4 20  1  0
  3 19  1  0
  6 21  1  6
  7 22  1  0
  7 23  1  0
  8 24  1  1
  9 25  1  0
 10 26  1  1
 11 27  1  0
 11 28  1  0
 12 29  1  0
M  END


  Mrv1533004201503102D          

 16 17  0  0  0  0            999 V2000
    0.7145    6.7661    0.0000 N   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 N   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
    2.1434    4.2911    0.0000 O   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
    0.0000    4.7036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    5.5286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.4661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3819    2.9812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    2.1965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6119    1.5291    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    2.1965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1830    1.5291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1526    0.7754    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0470    2.9812    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
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  2  8  1  0  0  0  0
  6  9  1  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
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 13 16  1  0  0  0  0
  9 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0322350

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC1=NC(=O)N(C=C1)C1CC(O)C(CO)O1

> <INCHI_IDENTIFIER>
InChI=1S/C9H13N3O4/c10-7-1-2-12(9(15)11-7)8-3-5(14)6(4-13)16-8/h1-2,5-6,8,13-14H,3-4H2,(H2,10,11,15)

> <INCHI_KEY>
CKTSBUTUHBMZGZ-UHFFFAOYSA-N

> <FORMULA>
C9H13N3O4

> <MOLECULAR_WEIGHT>
227.22

> <EXACT_MASS>
227.090605911

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
21.928854661129755

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-amino-1-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one

> <ALOGPS_LOGP>
-1.93

> <JCHEM_LOGP>
-1.8968792213333328

> <ALOGPS_LOGS>
-1.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.78753514288664

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.894899521324458

> <JCHEM_PKA_STRONGEST_BASIC>
0.3081753362314522

> <JCHEM_POLAR_SURFACE_AREA>
108.38000000000001

> <JCHEM_REFRACTIVITY>
53.0341

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.59e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
deoxycytidine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-15         0                                  
HETATM    1  N   UNK     0       1.334  12.630   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       1.334  11.090   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       2.667  10.320   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       2.667   8.780   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       4.001   8.010   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0       1.334   8.010   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       0.000   8.780   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.000  10.320   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   6.470   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.580   5.565   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.104   4.100   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.009   2.854   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.564   4.100   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.342   2.854   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.285   1.447   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       0.088   5.565   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    9                                                  
CONECT    7    6    8                                                       
CONECT    8    7    2                                                       
CONECT    9    6   10   16                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16   13    9                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

View in JSmol

Synonyms

Value	Source
Cytosine deoxyriboside	MeSH
Deoxyriboside, cytosine	MeSH
Deoxyribonucleoside, cytosine	MeSH
Deoxycytidine	MeSH

Chemical Formula

C₉H₁₃N₃O₄

Average Mass

227.2200 Da

Monoisotopic Mass

227.09061 Da

IUPAC Name

4-amino-1-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one

Traditional Name

deoxycytidine

CAS Registry Number

Not Available

SMILES

NC1=NC(=O)N(C=C1)C1CC(O)C(CO)O1

InChI Identifier

InChI=1S/C9H13N3O4/c10-7-1-2-12(9(15)11-7)8-3-5(14)6(4-13)16-8/h1-2,5-6,8,13-14H,3-4H2,(H2,10,11,15)

InChI Key

CKTSBUTUHBMZGZ-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 22.53 MHz, D₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

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
Isodictya erinacea	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
Aminopyrimidine
Pyrimidone
Hydropyrimidine
Pyrimidine
Imidolactam
Heteroaromatic compound
Tetrahydrofuran
Secondary alcohol
Azacycle
Oxacycle
Organoheterocyclic compound
Alcohol
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Primary amine
Primary alcohol
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Amine
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

a pyrimidine-related compound (DEOXYCYTIDINE )
a deoxynucleoside (DEOXYCYTIDINE )

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	-1.9	ALOGPS
logP	-1.9	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	13.89	ChemAxon
pKa (Strongest Basic)	0.31	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	108.38 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	53.03 m³·mol⁻¹	ChemAxon
Polarizability	21.93 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

637

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-iminopyrimidin-2-ol (NP0322350)

MOL for NP0322350 (1-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-iminopyrimidin-2-ol)

3D MOL for NP0322350 (1-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-iminopyrimidin-2-ol)

3D SDF for NP0322350 (1-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-iminopyrimidin-2-ol)

3D-SDF for NP0322350 (1-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-iminopyrimidin-2-ol)

PDB for NP0322350 (1-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-iminopyrimidin-2-ol)

3D PDB for NP0322350 (1-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-iminopyrimidin-2-ol)

SMILES for NP0322350 (1-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-iminopyrimidin-2-ol)

INCHI for NP0322350 (1-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-iminopyrimidin-2-ol)

Structure for NP0322350 (1-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-iminopyrimidin-2-ol)

3D Structure for NP0322350 (1-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-iminopyrimidin-2-ol)