NP-MRD: Showing NP-Card for (-)-Aristeromycin (NP0062278)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-28 06:57:38 UTC

Updated at

2022-04-28 06:57:38 UTC

NP-MRD ID

NP0062278

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Aristeromycin

Description

Aristeromycin, 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

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 34 36  0  0  0  0  0  0  0  0999 V2000
    5.3930    0.4127    0.0747 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1325   -0.2234   -0.0231 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9672   -1.5454   -0.2038 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7535   -2.1182   -0.2926 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6620   -1.3441   -0.1978 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7443   -0.0215   -0.0179 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9998    0.5424    0.0701 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8156    1.8539    0.2461 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5009    2.0816    0.2647 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8182    0.9331    0.1028 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6025    0.8300    0.0757 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1130   -0.4006    0.8378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5871   -0.3364    0.4411 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3235   -1.5853    0.8467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2132   -1.6931    2.2427 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4867   -0.1656   -1.0478 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5687    0.5288   -1.5792 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1850    0.5986   -1.2832 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4176    1.8069   -1.9391 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8428    0.8179   -0.7692 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8500    0.4625    1.0008 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6825   -3.2014   -0.4400 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0560    3.0744    0.3951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1028    1.6956    0.5597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6565   -1.3003    0.4089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9678   -0.2876    1.9176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0289    0.5146    0.9639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9631   -2.4930    0.3334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3875   -1.4305    0.6298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8459   -0.8697    2.6470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3810   -1.1743   -1.5029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3905    1.5042   -1.5987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4698   -0.0203   -1.8673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5273    2.5536   -1.2962 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 13 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 10  6  1  0
  6  5  2  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
  6  7  1  0
 18 11  1  0
  1 20  1  0
  1 21  1  0
  9 23  1  0
 11 24  1  1
 12 25  1  0
 12 26  1  0
 13 27  1  1
 14 28  1  0
 14 29  1  0
 15 30  1  0
 16 31  1  6
 17 32  1  0
 18 33  1  6
 19 34  1  0
  4 22  1  0
M  END


  Mrv1652304282208572D          

 19 21  0  0  1  0            999 V2000
    3.3523    1.9354    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.0709    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3687   -0.5966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -1.2640    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0992   -1.0091    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0992   -0.1841    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5683    0.3009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5683   -1.4940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -2.0486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9457   -2.2201    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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
 11 10  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
 11 15  1  0  0  0  0
 15 16  1  1  0  0  0
 14 17  1  1  0  0  0
 13 18  1  6  0  0  0
 18 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0062278

> <DATABASE_NAME>
NP-MRD

> <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_KEY>
UGRNVLGKAGREKS-GCXDCGAKSA-N

> <FORMULA>
C11H15N5O3

> <MOLECULAR_WEIGHT>
265.273

> <EXACT_MASS>
265.117489363

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
26.167596299597694

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,3R,5R)-3-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)cyclopentane-1,2-diol

> <ALOGPS_LOGP>
-0.84

> <JCHEM_LOGP>
-2.1325910750000006

> <ALOGPS_LOGS>
-1.42

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.7287417505743

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.33665377902551

> <JCHEM_PKA_STRONGEST_BASIC>
4.105935818518656

> <JCHEM_POLAR_SURFACE_AREA>
130.31

> <JCHEM_REFRACTIVITY>
66.9337

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.98e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,3R,5R)-3-(6-aminopurin-9-yl)-5-(hydroxymethyl)cyclopentane-1,2-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  N   UNK     0       6.258   3.613   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       4.924   1.303   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       4.924   5.923   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0       2.126   4.089   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       2.126   1.597   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       1.650   0.132   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.555  -1.114   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.650  -2.359   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.185  -1.884   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.185  -0.344   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.061   0.562   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -1.061  -2.789   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.126  -3.824   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.632  -4.144   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6    8                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    5    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    4   11                                                  
CONECT   11   10   12   15                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15   17                                                  
CONECT   15   14   11   16                                                  
CONECT   16   15                                                            
CONECT   17   14                                                            
CONECT   18   13   19                                                       
CONECT   19   18                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

View in JSmol

Synonyms

Value	Source
Aristeromycin, (1alpha,2alpha,3beta,5beta)-(+-)-isomer	MeSH
Aristeromycin, (1alpha,2beta,3beta,5beta)-(+-)-isomer	MeSH
Carbocyclic adenosine	MeSH
Cycloadenosine	MeSH

Chemical Formula

C₁₁H₁₅N₅O₃

Average Mass

265.2730 Da

Monoisotopic Mass

265.11749 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 Number

Not 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 Key

UGRNVLGKAGREKS-GCXDCGAKSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Streptomyces citricolor	LOTUS Database	35616633
Streptomyces citricolor nov. sp.	Bacteria	KNApSAcK

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.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Nucleoside and nucleotide analogues

Sub Class

Cyclopentyl nucleosides

Direct Parent

1,3-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 Framework

Aromatic heteropolycyclic 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	-0.84	ALOGPS
logP	-2.1	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	13.34	ChemAxon
pKa (Strongest Basic)	4.11	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	130.31 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	66.93 m³·mol⁻¹	ChemAxon
Polarizability	26.17 Å³	ChemAxon
Number of Rings	3	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

C00017104

Chemspider ID

58761

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

65269

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

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 ]
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 ]
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 ]
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 ]
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 ]

Showing NP-Card for (-)-Aristeromycin (NP0062278)

MOL for NP0062278 ((-)-Aristeromycin)

3D MOL for NP0062278 ((-)-Aristeromycin)

3D SDF for NP0062278 ((-)-Aristeromycin)

3D-SDF for NP0062278 ((-)-Aristeromycin)

PDB for NP0062278 ((-)-Aristeromycin)

3D PDB for NP0062278 ((-)-Aristeromycin)

SMILES for NP0062278 ((-)-Aristeromycin)

INCHI for NP0062278 ((-)-Aristeromycin)

Structure for NP0062278 ((-)-Aristeromycin)

3D Structure for NP0062278 ((-)-Aristeromycin)