Np mrd loader

Record Information
Version2.0
Created at2022-04-28 06:57:38 UTC
Updated at2022-04-28 06:57:38 UTC
NP-MRD IDNP0062278
Secondary Accession NumbersNone
Natural Product Identification
Common Name(-)-Aristeromycin
DescriptionAristeromycin, also known as cycloadenosine, belongs to the class of organic compounds known as 1,3-substituted cyclopentyl purine nucleosides. These are nucleoside analogues with a structure that consists of a cyclobutane that is substituted a the 1-position with a hydroxyl group and at the 3-position with either a purine base. (-)-Aristeromycin is found in Streptomyces citricolor and Streptomyces citricolor nov. sp.. (-)-Aristeromycin was first documented in 2020 (PMID: 33479662). Based on a literature review a small amount of articles have been published on aristeromycin (PMID: 33792325) (PMID: 33396631) (PMID: 32854369) (PMID: 31841728).
Structure
Thumb
Synonyms
ValueSource
Aristeromycin, (1alpha,2alpha,3beta,5beta)-(+-)-isomerMeSH
Aristeromycin, (1alpha,2beta,3beta,5beta)-(+-)-isomerMeSH
Carbocyclic adenosineMeSH
CycloadenosineMeSH
Chemical FormulaC11H15N5O3
Average Mass265.2730 Da
Monoisotopic Mass265.11749 Da
IUPAC Name(1R,2S,3R,5R)-3-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)cyclopentane-1,2-diol
Traditional Name(1R,2S,3R,5R)-3-(6-aminopurin-9-yl)-5-(hydroxymethyl)cyclopentane-1,2-diol
CAS Registry NumberNot Available
SMILES
NC1=C2N=CN([C@@H]3C[C@H](CO)[C@@H](O)[C@H]3O)C2=NC=N1
InChI Identifier
InChI=1S/C11H15N5O3/c12-10-7-11(14-3-13-10)16(4-15-7)6-1-5(2-17)8(18)9(6)19/h3-6,8-9,17-19H,1-2H2,(H2,12,13,14)/t5-,6-,8-,9+/m1/s1
InChI KeyUGRNVLGKAGREKS-GCXDCGAKSA-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
Streptomyces citricolorLOTUS Database
Streptomyces citricolor nov. sp.Bacteria
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 1,3-substituted cyclopentyl purine nucleosides. These are nucleoside analogues with a structure that consists of a cyclobutane that is substituted a the 1-position with a hydroxyl group and at the 3-position with either a purine base.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassNucleoside and nucleotide analogues
Sub ClassCyclopentyl nucleosides
Direct Parent1,3-substituted cyclopentyl purine nucleosides
Alternative Parents
Substituents
  • 1,3-substituted cyclopentyl purine nucleoside
  • 6-aminopurine
  • Imidazopyrimidine
  • Purine
  • Aminopyrimidine
  • Cyclopentanol
  • N-substituted imidazole
  • Pyrimidine
  • Imidolactam
  • Azole
  • Cyclic alcohol
  • Imidazole
  • Heteroaromatic compound
  • Secondary alcohol
  • Azacycle
  • Organoheterocyclic compound
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Amine
  • Organopnictogen compound
  • Alcohol
  • Organic nitrogen compound
  • Primary amine
  • 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-0.84ALOGPS
logP-2.1ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)13.34ChemAxon
pKa (Strongest Basic)4.11ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area130.31 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity66.93 m³·mol⁻¹ChemAxon
Polarizability26.17 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00017104
Chemspider ID58761
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound65269
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Vendola AJ, Allais C, Dechert-Schmitt AR, Lee JT, Singer RA, Morken JP: Diastereoselective Diboration of Cyclic Alkenes: Application to the Synthesis of Aristeromycin. Org Lett. 2021 Apr 16;23(8):2863-2867. doi: 10.1021/acs.orglett.1c00353. Epub 2021 Apr 1. [PubMed:33792325 ]
  2. Samunuri R, Toyama M, Pallaka RS, Neeladri S, Jha AK, Baba M, Bal C: Synthesis and anti-HBV activity of carbocyclic nucleoside hybrids with salient features of entecavir and aristeromycin. RSC Med Chem. 2020 May 15;11(5):597-601. doi: 10.1039/d0md00059k. eCollection 2020 May 1. [PubMed:33479662 ]
  3. Santana AC, Silva Filho RC, Menezes JCJMDS, Allonso D, Campos VR: Nitrogen-Based Heterocyclic Compounds: A Promising Class of Antiviral Agents against Chikungunya Virus. Life (Basel). 2020 Dec 30;11(1):16. doi: 10.3390/life11010016. [PubMed:33396631 ]
  4. Chen Q, Schneller SW, Liu C, Jones KL, Singer T: 5'-Nor-3-Deaza-1',6'-Isoneplanocin, the Synthesis and Antiviral Study. Molecules. 2020 Aug 25;25(17):3865. doi: 10.3390/molecules25173865. [PubMed:32854369 ]
  5. Shin YS, Jarhad DB, Jang MH, Kovacikova K, Kim G, Yoon JS, Kim HR, Hyun YE, Tipnis AS, Chang TS, van Hemert MJ, Jeong LS: Identification of 6'-beta-fluoro-homoaristeromycin as a potent inhibitor of chikungunya virus replication. Eur J Med Chem. 2020 Feb 1;187:111956. doi: 10.1016/j.ejmech.2019.111956. Epub 2019 Dec 9. [PubMed:31841728 ]