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Showing NP-Card for 2-Hydroxyadenine (NP0086575)

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Record Information
Version2.0
Created at2022-05-11 16:24:55 UTC
Updated at2022-05-11 16:24:55 UTC
NP-MRD IDNP0086575
Secondary Accession NumbersNone
Natural Product Identification
Common Name2-Hydroxyadenine
Description2-Hydroxyadenine, also known as isoguanine or 2-OH-ade, belongs to the class of organic compounds known as 6-aminopurines. These are purines that carry an amino group at position 6. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring. 2-Hydroxyadenine was first documented in 1976 (PMID: 1018622). 2-Hydroxyadenine is a moderately basic compound (based on its pKa) (PMID: 14615972) (PMID: 14709079) (PMID: 8841637) (PMID: 9726918) (PMID: 1324197) (PMID: 9726022).
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0086575 (2-Hydroxyadenine)

2-Hydroxyadenine.mol
  Mrv0541 02231218302D          

 11 12  0  0  0  0            999 V2000
   -0.6638    0.4466    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0507    0.8591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7652    0.4466    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7652   -0.3784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0507   -0.7909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6638   -0.3784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3783   -0.7909    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3783   -0.9304    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0427   -1.6841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2222   -1.5979    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0507    1.6841    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
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  1  6  2  0  0  0  0
  4  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  5 10  1  0  0  0  0
  2 11  1  0  0  0  0
M  END
Download

3D MOL for NP0086575 (2-Hydroxyadenine)

     RDKit          3D

 16 17  0  0  0  0  0  0  0  0999 V2000
   -0.8487    2.1912    0.2849 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0177    1.0664    0.0092 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2827    1.2205   -0.2974 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1095    0.1946   -0.5656 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4606    0.4052   -0.8809 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5828   -1.0419   -0.5179 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2934   -1.2846   -0.2198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4752   -2.3767   -0.1038 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7391   -2.0488    0.2254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7801   -0.7126    0.3225 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5414   -0.2194    0.0530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0726    2.3500    1.3007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2169    2.8213   -0.4532 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1150    0.2978   -0.0962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5594   -2.7379    0.3802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5930   -0.1251    0.5587 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  6  7  1  0
  7 11  2  0
 11 10  1  0
 10  9  1  0
  9  8  2  0
 11  2  1  0
  8  7  1  0
  1 12  1  0
  1 13  1  0
  5 14  1  0
 10 16  1  0
  9 15  1  0
M  END
Download

3D SDF for NP0086575 (2-Hydroxyadenine)

2-Hydroxyadenine.mol
  Mrv0541 02231218302D          

 11 12  0  0  0  0            999 V2000
   -0.6638    0.4466    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0507    0.8591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7652    0.4466    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7652   -0.3784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0507   -0.7909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6638   -0.3784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3783   -0.7909    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3783   -0.9304    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0427   -1.6841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2222   -1.5979    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0507    1.6841    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
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  1  6  2  0  0  0  0
  4  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  5 10  1  0  0  0  0
  2 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0086575

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC1=NC(O)=NC2=C1NC=N2

> <INCHI_IDENTIFIER>
InChI=1S/C5H5N5O/c6-3-2-4(8-1-7-2)10-5(11)9-3/h1H,(H4,6,7,8,9,10,11)

> <INCHI_KEY>
DRAVOWXCEBXPTN-UHFFFAOYSA-N

> <FORMULA>
C5H5N5O

> <MOLECULAR_WEIGHT>
151.1261

> <EXACT_MASS>
151.049409807

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
13.361417514029057

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-amino-7H-purin-2-ol

> <ALOGPS_LOGP>
-0.65

> <JCHEM_LOGP>
-0.1982495303333333

> <ALOGPS_LOGS>
-1.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.811865928730988

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.775155616350027

> <JCHEM_PKA_STRONGEST_BASIC>
2.017194790434338

> <JCHEM_POLAR_SURFACE_AREA>
100.71

> <JCHEM_REFRACTIVITY>
40.14639999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.06e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-hydroxy-6-aminopurine

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0086575 (2-Hydroxyadenine)

Download
PDB for NP0086575 (2-Hydroxyadenine)
HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 2-Hydroxyadenine.mol                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  N   UNK     0      -1.239   0.834   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       0.095   1.604   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       1.428   0.834   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       1.428  -0.706   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.095  -1.476   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.239  -0.706   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      -2.573  -1.476   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0       2.573  -1.737   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       1.946  -3.144   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       0.415  -2.983   0.000  0.00  0.00           N+0
HETATM   11  O   UNK     0       0.095   3.144   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    8                                                  
CONECT    5    4    6   10                                                  
CONECT    6    5    7    1                                                  
CONECT    7    6                                                            
CONECT    8    4    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    5                                                       
CONECT   11    2                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   24    0
END

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3D PDB for NP0086575 (2-Hydroxyadenine)
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SMILES for NP0086575 (2-Hydroxyadenine)
NC1=NC(O)=NC2=C1NC=N2
Download
INCHI for NP0086575 (2-Hydroxyadenine)
InChI=1S/C5H5N5O/c6-3-2-4(8-1-7-2)10-5(11)9-3/h1H,(H4,6,7,8,9,10,11)
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View in JSmol
Synonyms
ValueSource
2-OxoadenineChEBI
6-Amino-1,3-dihydro-2H-purin-2-oneChEBI
6-Amino-3,7-dihydro-purin-2-oneChEBI
6-Amino-3,9-dihydro-2H-purin-2-oneChEBI
6-Amino-7H-purin-2-olChEBI
6-Amino-9H-purin-2-olChEBI
2-Hydroxy-6-aminopurineHMDB
2-OxyadenineHMDB
6-Amino-2-hydroxypurineHMDB
6-Amino-3,7(9)-dihydro-purin-2-oneHMDB
IsoguanineHMDB
2-OH-AdeHMDB
CrotonosideHMDB
2-HydroxyadenineChEBI
Chemical FormulaC5H5N5O
Average Mass151.1261 Da
Monoisotopic Mass151.04941 Da
IUPAC Name6-amino-7H-purin-2-ol
Traditional Name2-hydroxy-6-aminopurine
CAS Registry NumberNot Available
SMILES
NC1=NC(O)=NC2=C1NC=N2
InChI Identifier
InChI=1S/C5H5N5O/c6-3-2-4(8-1-7-2)10-5(11)9-3/h1H,(H4,6,7,8,9,10,11)
InChI KeyDRAVOWXCEBXPTN-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 6-aminopurines. These are purines that carry an amino group at position 6. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassImidazopyrimidines  
Sub ClassPurines and purine derivatives  
Direct Parent6-aminopurines  
Alternative Parents
Substituents
  • 6-aminopurine
    • 

  • Aminopyrimidine
    • 

  • Hydroxypyrimidine
    • 

  • Pyrimidine
    • 

  • Imidolactam
    • 

  • Azole
    • 

  • Imidazole
    • 

  • Heteroaromatic compound
    • 

  • Azacycle
    • 

  • Organopnictogen compound
    • 

  • Primary amine
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Amine
    • 

  • Organic nitrogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxygen compound
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
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-0.65ALOGPS
logP-0.2ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)10.78ChemAxon
pKa (Strongest Basic)2.02ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area100.71 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity40.15 m³·mol⁻¹ChemAxon
Polarizability13.36 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000403  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022019  
KNApSAcK IDNot Available
Chemspider ID69351  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkIsoguanine  
METLIN ID5392  
PubChem Compound76900  
PDB IDNot Available
ChEBI ID62462  
Good Scents IDNot Available
References
General References
  1. Pettit GR, Ode RH, Coomes RM, Ode SL: Antineoplastic agents. 42. The butterfly, Prioneris thestylis. Lloydia. 1976 Sep-Oct;39(5):363-7. [PubMed:1018622  ] 
  2. Rogstad KN, Jang YH, Sowers LC, Goddard WA 3rd: First principles calculations of the pKa values and tautomers of isoguanine and xanthine. Chem Res Toxicol. 2003 Nov;16(11):1455-62. doi: 10.1021/tx034068e. [PubMed:14615972  ] 
  3. Blas JR, Luque FJ, Orozco M: Unique tautomeric properties of isoguanine. J Am Chem Soc. 2004 Jan 14;126(1):154-64. doi: 10.1021/ja036806r. [PubMed:14709079  ] 
  4. Kamiya H, Kasai H: 2-Hydroxyadenine (isoguanine) as oxidative DNA damage: its formation and mutation inducibility. Nucleic Acids Symp Ser. 1995;(34):233-4. [PubMed:8841637  ] 
  5. Yang XL, Sugiyama H, Ikeda S, Saito I, Wang AH: Structural studies of a stable parallel-stranded DNA duplex incorporating isoguanine:cytosine and isocytosine:guanine basepairs by nuclear magnetic resonance spectroscopy. Biophys J. 1998 Sep;75(3):1163-71. doi: 10.1016/S0006-3495(98)74035-4. [PubMed:9726918  ] 
  6. Olinski R, Zastawny T, Budzbon J, Skokowski J, Zegarski W, Dizdaroglu M: DNA base modifications in chromatin of human cancerous tissues. FEBS Lett. 1992 Sep 7;309(2):193-8. doi: 10.1016/0014-5793(92)81093-2. [PubMed:1324197  ] 
  7. Arashidani K, Iwamoto-Tanaka N, Muraoka M, Kasai H: Genotoxicity of ribo- and deoxyribonucleosides of 8-hydroxyguanine, 5-hydroxycytosine, and 2-hydroxyadenine: induction of SCE in human lymphocytes and mutagenicity in Salmonella typhimurium TA 100. Mutat Res. 1998 Jul 17;403(1-2):223-7. doi: 10.1016/s0027-5107(98)00086-4. [PubMed:9726022  ]