2-(2,6-Diaminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol

HCID 222076

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Basic information

CAS: 2096-10-8
Standard SMILES: Nc1nc(N)c2ncn(C3OC(CO)C(O)C3O)c2n1
InChIKey: ZDTFMPXQUSBYRL-UHFFFAOYSA-N
Molecular formula: C10H14N6O4
Average molar mass: 282.26 g/mol

Overview

2,6-Diaminopurine riboside is a purine nucleoside.

Names & identifiers

Preferred name: 2-(2,6-Diaminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
IUPAC: 2-(2,6-diaminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
English name: 2-Aminoadenosine
Molecular formula: C10H14N6O4
Molecular weight: 282.26

Names & synonyms

2-(2,6-diaminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol24649-67-0araDAPR9-.beta.-Ribosyl-2,6-diaminopurine9H-Purine-2,6-diamine, 9-.beta.-D-ribofuranosyl-(2R,3S,4S,5R)-2-(2,6-diaminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol9H-Purine, 2,6-diamino-9-.beta.-D-ribofuranosyl-2.6-diaminopurine ribosideSCHEMBL22559823SCHEMBL300751232,6-Diaminopurine-9-arabinosideNSC7363

Show more names

2-NH2-rA2-NH2-AAminoadenosine2-AMINE ADENOSINE2,6-DIAMINOPURINE RIBOSIDE(2R,3R,4S,5R)-2-(2,6-Diamino-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol0/8/962-NH2-ArNSC 73632-NH?-rA

(2R,3S,4S,5R)-2-(2,6-diamino-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diolCHEBI:182533NSC122197AKOS001705159EBC-277073NSC-122197LS-13816PD200218

Database identifiers

CAS: 2096-10-8、24649-67-0
PubChem CID: 222076
ChEBI: CHEBI:182533

Properties

Computed structural properties

XLogP: -1.4
Topological polar surface area: 166 Å²
Hydrogen bond donors: 5
Hydrogen bond acceptors: 9
Rotatable bonds: 2
Heavy atoms: 20
Formal charge: 0
Complexity: 363

Physicochemical properties

Melting point: 241 · 241-243°C (dec.)
storage temp.: Keep in dark place,Sealed in dry,Room Temperature
solubility: Aqueous Acid (Slightly, Heated, Sonicated), DMSO (Slightly, Sonicated), Ethanol
form: Powder
Boiling point: 798.5 · 798.5±70.0 °C(Predicted)
Density: 2.25 · 2.25±0.1 g/cm3(Predicted)
pka: 13.1 · 13.10±0.70(Predicted)
color: White to Off-White
InChI: InChI=1S/C10H14N6O4/c11-7-4-8(15-10(12)14-7)16(2-13-4)9-6(19)5(18)3(1-17)20-9/h2-3,5-6,9,17-19H,1H2,(H4,11,12,14,15)/t3-,5-,6-,9-/m1/s1
InChIKey: ZDTFMPXQUSBYRL-UUOKFMHZSA-N
SMILES: OC[C@H]1O[C@@H](N2C3C(=C(N=C(N)N=3)N)N=C2)[C@H](O)[C@@H]1O
CAS DataBase Reference: 2096 · 2096-10-8(CAS DataBase Reference)
FDA UNII: 94 TM2UR · CCF94TM2UR
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 315 · H315-H319
Precautionary statements: 264 · P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313
Safety Statements: 24 · 24/25
HS Code: 29389090 · 29389090

Safety & regulation

Safety data

hs_code: 29389090
Signal word: Warning
Symbol(GHS): GHS07
safety_code: 24/25
Hazard statements: H315-H319
Precautionary statements: P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313

Chemistry & industry

Applications

Description2-Aminoadenosine is a known analogue of adenosine that engages in three hydrogen bonds of the W-C type, adding considerable stability to the double helix.

Uses2-Aminoadenosine is a nucleoside analog as inhibitor or substrate of adenosine kinase from M. tuberculosis. It is also used to synthesize 2′-O-methyl and 3′-O-methyl Guanosine.