Adenosine

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Adenosine are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the Adenosine?

The molecule Adenosine presents a molecular formula of C10H13N5O4 and its IUPAC name is (2R,3R,4S,5R)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol.

Adenosine is a nucleoside that is composed of a molecule of adenine attached to a ribose sugar molecule (ribofuranose) moiety. It is also a purine nucleoside.Adenosine belongs in all living cells and is an important component of RNA. It is also a precursor of the nucleotides adenosine monophosphate (AMP), adenosine diphosphate (ADP), and adenosine triphosphate (ATP). These nucleotides are important in cellular metabolism and are components of the energy-carrying molecule ATP..

Adenosine is an important neuromodulator and has a variety of effects on the brain. It is a potent agonist of the A1 receptor and has sedative effects. It also inhibits the release of neurotransmitters such as glutamate and noradrenaline..

Adenosine is also a potent vasodilator and can be used to treat heart conditions such as heart failure and angina. It is also being investigated as a treatment for other conditions such as Alzheimer's disease, Parkinson's disease, and stroke..

3D structure

Cartesian coordinates

Geometry of Adenosine in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

Adenosine OIRDTQYFTABQOQ-KQYNXXCUSA-N chemical compound 2D structure molecule svg
Adenosine

 

Molecule descriptors

 
IUPAC name(2R,3R,4S,5R)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
InChI codeInChI=1S/C10H13N5O4/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(18)6(17)4(1-16)19-10/h2-4,6-7,10,16-18H,1H2,(H2,11,12,13)/t4-,6-,7-,10-/m1/s1
InChI KeyOIRDTQYFTABQOQ-KQYNXXCUSA-N
SMILESNc1ncnc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • (2R,3R,4S,5R)-2-(6-Aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
  • (2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
  • (2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol
  • (2R,3R,4S,5R)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol
  • .beta.-D-Adenosine
  • .beta.-D-Ribofuranose, 1-(6-amino-9H-purin-9-yl)-1-deoxy-
  • .beta.-D-Ribofuranoside, adenine-9
  • 1-(6-amino-9H-purin-9-yl)-1-deoxy-beta-D-Ribofuranose
  • 1-(6-amino-9H-purin-9-yl)-1-deoxy-beta-delta-Ribofuranose
  • 109767-06-8
  • 133248-01-8
  • 142796-17-6
  • 158749-77-0
  • 177030-94-3
  • 1dgm
  • 1odi
  • 244769-76-4
  • 2fqy
  • 2gl0
  • 2ydo
  • 3H-adenosine
  • 3axz
  • 3ay0
  • 4-Aminopyrazolo[3,4-d]pyrimidine ribonucleoside
  • 41547-82-4
  • 4cki
  • 4ckj
  • 4pd9
  • 58-61-7
  • 6-AMINO-9-.BETA.-D-RIBOFURANOSYL-9H-PURINE
  • 6-Amino-9-.beta.-ribofuranosyl-9H-purine
  • 6-Amino-9-beta-D-ribofuranosyl-9H-purine
  • 6-Amino-9.beta.-D-ribofuranosyl-9H-purine
  • 6-Amino-9beta-D-ribofuranosyl-9H-purine
  • 6-Amino-9beta-delta-ribofuranosyl-9H-purine
  • 9-.alpha.-D-Arabinofuranosyladenine
  • 9-.beta.-D-Ribofuranosidoadenine
  • 9-.beta.-D-Ribofuranosyl-9H-purin-6-amine
  • 9-.beta.-d-Ribofuranosyladenine
  • 9-? -D-Ribofuranosyl-9H-purin-6-amine
  • 9-?-D-Ribofuranosyl-9H-purin-6-amine
  • 9-beta-D-Ribofuranosidoadenine
  • 9-beta-D-Ribofuranosyl-9H-purin-6-amine
  • 9-beta-D-Ribofuranosyladenine
  • 9-beta-delta-Arabinofuranosyladenine
  • 9-beta-delta-Ribofuranosidoadenine
  • 9-beta-delta-Ribofuranosyl-9H-purin-6-amine
  • 9-beta-delta-Ribofuranosyladenine
  • 9-ss-D-Ribofuranosyladenine
  • 9H-Purin-6-amine, 9-.beta.-d-ribofuranosyl-
  • 9H-Purin-6-amine, 9beta-D-ribofuranosyl-
  • 9beta-D-Ribofuranosyladenine
  • 9beta-D-ribofuranosyl-9H-Purin-6-amine
  • 9beta-delta-Ribofuranosyladenine
  • 9beta-delta-ribofuranosyl-9H-Purin-6-amine
  • A0152
  • AB00384349-11
  • AB00384349_13
  • AB00384349_14
  • AC-27494
  • AC-8229
  • AC7861
  • ACT02616
  • AI3-52413
  • AM83931
  • AMY30083
  • AS-12664
  • Ade-Rib
  • Adenin riboside
  • Adenine nucleoside
  • Adenine riboside
  • Adenine-9-ss-D-ribofuranoside
  • Adenine-beta-D-arabinofuranoside
  • Adenocard
  • Adenocor
  • Adenogesic
  • Adenoscan
  • Adenosin
  • Adenosine
  • Adenosine (Adenocard)
  • Adenosine (JAN/USP)
  • Adenosine,(S)
  • BDBM14487
  • BSPBio_001796
  • Bio1_000437
  • Bio1_000926
  • Bio1_001415
  • Boniton
  • C00212
  • CCG-38824
  • CCRIS 2557
  • Caswell No. 010B
  • D-Adenosine
  • D00045
  • DB-022408
  • DB00640
  • DSSTox_CID_2558
  • DSSTox_GSID_22558
  • DSSTox_RID_76628
  • Dehydran 240
  • EA6C60C2-6AFB-4264-A2F0-541373DB950E
  • Epitope ID:140947
  • GTPL2844
  • HMS1920A13
  • HMS2091G13
  • HMS2235E24
  • HMS3884O04
  • HSDB 7774
  • K72T3FS567
  • KBio3_001296
  • MEDR-640
  • MFCD00005752
  • MLS000069638
  • MLS002153227
  • MLS006010946
  • Myocol
  • N6-Methylado
  • NCGC00023673-03
  • NCGC00023673-04
  • NCGC00023673-05
  • NCGC00023673-06
  • NCGC00023673-07
  • NCGC00023673-10
  • NCGC00023673-20
  • NCGC00178869-03
  • NSC 627048
  • NSC 7652
  • NSC-755857
  • NSC-7652
  • NSC627048
  • NSC755857
  • NSC7652
  • Nucleocardyl
  • Pallacor
  • Pharmakon1600-01500107
  • Q190012
  • Quinquefolan B
  • REGID_for_CID_60961
  • SBI-0206673.P002
  • SDCCGMLS-0003108.P003
  • SMR000058216
  • SPECTRUM1500107
  • SR 96225
  • SR-05000001981
  • SR-05000001981-1
  • SR-05000001981-2
  • SR-96225
  • SUN-Y4001
  • Sandesin
  • USAF CB-10
  • XYA
  • Z1741978458
  • [U-14C]adenosine
  • adenine-9beta-D-Ribofuranoside
  • adenine-9beta-delta-Ribofuranoside
  • adenine-D-ribose
  • adenosine
  • adenosine-2-13C-N,1,3-15N3
  • adenosine-8-13C
  • adenosine-9-15N
  • adenosine-N-15N
  • b-D-Adenosine
  • beta-Adenosine
  • beta-D-Adenosine
  • beta-D-Ribofuranose, 1-(6-amino-9H-purin-9-yl)-1-deoxy-
  • beta-D-Ribofuranoside, adenine-9
  • beta-delta-Adenosine
  • bmse000061
  • bmse000996
  • cid_191
  • cid_60961
  • s1647

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC2169830
  • CAS-58-61-7
  • UNII-K72T3FS567
  • AKOS015888594
  • ALBB-032827
  • DTXSID1022558
  • CHEMBL477
  • CHEBI:16335
  • Tox21_110891
  • Tox21_110891_1
  • EINECS 200-389-9
  • SPBio_001194
  • SCHEMBL731
  • Spectrum2_001257
  • Spectrum3_000288

Physico-Chemical properties

IUPAC name(2R,3R,4S,5R)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
Molecular formulaC10H13N5O4
Molecular weight267.241
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity62.67
LogP-1.4
Topological polar surface area139.5

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.