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Showing NP-Card for Arabinosylhypoxanthine (NP0334719)

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Record Information
Version2.0
Created at2024-09-10 19:40:05 UTC
Updated at2024-09-10 19:40:06 UTC
NP-MRD IDNP0334719
Secondary Accession NumbersNone
Natural Product Identification
Common NameArabinosylhypoxanthine
DescriptionArabinosylhypoxanthine, also known as ara-HX or hypoxanthine arabinoside, belongs to the class of organic compounds known as purine nucleosides. Purine nucleosides are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety. Arabinosylhypoxanthine was first documented in 1976 (PMID: 185947). Arabinosylhypoxanthine is a moderately basic compound (based on its pKa) (PMID: 7371366) (PMID: 935646) (PMID: 2423028).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0334719 (Arabinosylhypoxanthine)


  Mrv0541 02231219382D          

 19 21  0  0  1  0            999 V2000
   16.5016  -12.5939    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.5016  -13.4189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2161  -13.8314    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.9306  -13.4189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9306  -12.5939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2161  -12.1814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7152  -13.6738    0.0000 N   0  0  2  0  0  0  0  0  0  0  0  0
   19.2001  -13.0064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7152  -12.3390    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.2161  -11.3564    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9702  -14.4585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4852  -15.1259    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.9702  -15.7934    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   19.7548  -15.5384    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   19.7548  -14.7134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.4222  -16.0233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3359  -16.8438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.7152  -16.5780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6602  -15.1259    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  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  1  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9  5  1  0  0  0  0
  6 10  2  0  0  0  0
  7 11  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 11  1  0  0  0  0
 14 16  1  6  0  0  0
 16 17  1  0  0  0  0
 13 18  1  1  0  0  0
 12 19  1  6  0  0  0
M  END
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3D MOL for NP0334719 (Arabinosylhypoxanthine)

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3D SDF for NP0334719 (Arabinosylhypoxanthine)

  Mrv0541 02231219382D          

 19 21  0  0  1  0            999 V2000
   16.5016  -12.5939    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.5016  -13.4189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2161  -13.8314    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.9306  -13.4189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9306  -12.5939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2161  -12.1814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7152  -13.6738    0.0000 N   0  0  2  0  0  0  0  0  0  0  0  0
   19.2001  -13.0064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7152  -12.3390    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.2161  -11.3564    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9702  -14.4585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4852  -15.1259    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.9702  -15.7934    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   19.7548  -15.5384    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   19.7548  -14.7134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.4222  -16.0233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3359  -16.8438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.7152  -16.5780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6602  -15.1259    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  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  1  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9  5  1  0  0  0  0
  6 10  2  0  0  0  0
  7 11  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 11  1  0  0  0  0
 14 16  1  6  0  0  0
 16 17  1  0  0  0  0
 13 18  1  1  0  0  0
 12 19  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0334719

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1OC([C@@H](O)[C@@H]1O)N1C=NC2=C1NC=NC2=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H12N4O5/c15-1-4-6(16)7(17)10(19-4)14-3-13-5-8(14)11-2-12-9(5)18/h2-4,6-7,10,15-17H,1H2,(H,11,12,18)/t4-,6-,7+,10?/m1/s1

> <INCHI_KEY>
UGQMRVRMYYASKQ-KBNQYOMWSA-N

> <FORMULA>
C10H12N4O5

> <MOLECULAR_WEIGHT>
268.2261

> <EXACT_MASS>
268.080769514

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
24.680920580771456

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
9-[(3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-3H-purin-6-one

> <ALOGPS_LOGP>
-1.74

> <JCHEM_LOGP>
-1.9609272363333337

> <ALOGPS_LOGS>
-1.27

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.456472643759938

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.941792238826917

> <JCHEM_PKA_STRONGEST_BASIC>
2.735737342527512

> <JCHEM_POLAR_SURFACE_AREA>
129.20000000000002

> <JCHEM_REFRACTIVITY>
60.89840000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.43e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9-[(3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-purin-6-one

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0334719 (Arabinosylhypoxanthine)
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PDB for NP0334719 (Arabinosylhypoxanthine)
HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  N   UNK     0      30.803 -23.509   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      30.803 -25.049   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      32.137 -25.819   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      33.470 -25.049   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      33.470 -23.509   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      32.137 -22.739   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      34.935 -25.524   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      35.840 -24.279   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      34.935 -23.033   0.000  0.00  0.00           N+0
HETATM   10  O   UNK     0      32.137 -21.199   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      35.411 -26.989   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      34.506 -28.235   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      35.411 -29.481   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      36.876 -29.005   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      36.876 -27.465   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      38.121 -29.910   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      37.960 -31.442   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      34.935 -30.946   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      32.966 -28.235   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6    9                                                  
CONECT    6    5    1   10                                                  
CONECT    7    4    8   11                                                  
CONECT    8    7    9                                                       
CONECT    9    8    5                                                       
CONECT   10    6                                                            
CONECT   11    7   12   15                                                  
CONECT   12   11   13   19                                                  
CONECT   13   12   14   18                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14   11                                                       
CONECT   16   14   17                                                       
CONECT   17   16                                                            
CONECT   18   13                                                            
CONECT   19   12                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

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3D PDB for NP0334719 (Arabinosylhypoxanthine)
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SMILES for NP0334719 (Arabinosylhypoxanthine)
OC[C@H]1OC([C@@H](O)[C@@H]1O)N1C=NC2=C1NC=NC2=O
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INCHI for NP0334719 (Arabinosylhypoxanthine)
InChI=1S/C10H12N4O5/c15-1-4-6(16)7(17)10(19-4)14-3-13-5-8(14)11-2-12-9(5)18/h2-4,6-7,10,15-17H,1H2,(H,11,12,18)/t4-,6-,7+,10?/m1/s1
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Synonyms
ValueSource
Ara-HXHMDB
9 beta-D-Arabinofuranosyl-1,9-dihydro-6H-purin-6-oneHMDB
Hypoxanthine arabinosideHMDB
9 beta-D-ArabinofuranosylhypoxanthineHMDB
AraHxHMDB
Ara-HHMDB
Chemical FormulaC10H12N4O5
Average Mass268.2261 Da
Monoisotopic Mass268.08077 Da
IUPAC Name9-[(3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-3H-purin-6-one
Traditional Name9-[(3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-purin-6-one
CAS Registry NumberNot Available
SMILES
OC[C@H]1OC([C@@H](O)[C@@H]1O)N1C=NC2=C1NC=NC2=O
InChI Identifier
InChI=1S/C10H12N4O5/c15-1-4-6(16)7(17)10(19-4)14-3-13-5-8(14)11-2-12-9(5)18/h2-4,6-7,10,15-17H,1H2,(H,11,12,18)/t4-,6-,7+,10?/m1/s1
InChI KeyUGQMRVRMYYASKQ-KBNQYOMWSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as purine nucleosides. Purine nucleosides are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety.
KingdomOrganic compounds  
Super ClassNucleosides, nucleotides, and analogues  
ClassPurine nucleosides  
Sub ClassNot Available
Direct ParentPurine nucleosides  
Alternative Parents
Substituents
  • Purine nucleoside
    • 

  • Glycosyl compound
    • 

  • N-glycosyl compound
    • 

  • 6-oxopurine
    • 

  • Hypoxanthine
    • 

  • Pentose monosaccharide
    • 

  • Purinone
    • 

  • Imidazopyrimidine
    • 

  • Purine
    • 

  • Pyrimidone
    • 

  • Pyrimidine
    • 

  • Monosaccharide
    • 

  • N-substituted imidazole
    • 

  • Vinylogous amide
    • 

  • Tetrahydrofuran
    • 

  • Heteroaromatic compound
    • 

  • Azole
    • 

  • Imidazole
    • 

  • Secondary alcohol
    • 

  • Oxacycle
    • 

  • Azacycle
    • 

  • Organoheterocyclic compound
    • 

  • Alcohol
    • 

  • Organonitrogen compound
    • 

  • Organic nitrogen compound
    • 

  • Organooxygen compound
    • 

  • Organic oxide
    • 

  • Organopnictogen compound
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Primary alcohol
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-1.7ALOGPS
logP-2ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)6.94ChemAxon
pKa (Strongest Basic)2.74ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area129.2 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity60.9 m³·mol⁻¹ChemAxon
Polarizability24.68 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0003040  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023100  
KNApSAcK IDNot Available
Chemspider ID24654354  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID3022  
PubChem Compound46874582  
PDB IDNot Available
ChEBI ID705435  
Good Scents IDNot Available
References
General References
  1. Schwartz PM, Shipman C Jr, Drach JC: Antiviral activity of arabinosyladenine and arabinosylhypoxanthine in herpes simplex virus-infected KB cells: selective inhibition of viral deoxyribonucleic acid synthesis in the presence of an adenosine deaminase inhibitor. Antimicrob Agents Chemother. 1976 Jul;10(1):64-74. doi: 10.1128/AAC.10.1.64. [PubMed:185947  ] 
  2. Buchanan RA, Kinkel AW, Alford CA Jr, Whitley RJ: Plasma levels and urinary excretion of vidarabine after repeated dosing. Clin Pharmacol Ther. 1980 May;27(5):690-6. doi: 10.1038/clpt.1980.98. [PubMed:7371366  ] 
  3. Chang T, Glazko AJ: Effect of an adenosine deaminase inhibitor on the uptake and metabolism of arabinosyl adenine (Vidarabine) by intact human erythrocytes. Res Commun Chem Pathol Pharmacol. 1976 May;14(1):127-40. [PubMed:935646  ] 
  4. McCann WP, Hall LM, Siler W, Barton N, Whitley RJ: High-pressure liquid chromatographic methods for determining arabinosyladenine-5'-monophosphate, arabinosyladenine, and arabinosylhypoxanthine in plasma and urine. Antimicrob Agents Chemother. 1985 Aug;28(2):265-73. doi: 10.1128/AAC.28.2.265. [PubMed:2423028  ]