2-Aminoadenosine

HCID 72200

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Basic information

CAS: 2096-10-8
Standard SMILES: Nc1nc(N)c2ncn([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)c2n1
InChIKey: ZDTFMPXQUSBYRL-UUOKFMHZSA-N
Molecular formula: C10H14N6O4
Average molar mass: 282.26 g/mol
Monoisotopic mass: 282.10765295

Names & identifiers

Preferred name: 2-Aminoadenosine
IUPAC: (2R,3R,4S,5R)-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-Aminoadenosine2096-10-8Adenosine, 2-amino-2,6-Diaminonebularine2,6-Diaminopurinosine2,6-Diaminopurine ribosideCCF94TM2UR2,6-Diaminopurine ribonucleoside9-beta-Ribosyl-2,6-diaminopurineDTXSID001346570NSC-7363(2R,3R,4S,5R)-2-(2,6-diaminopurin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol

Show more names

2-NH2-rA2-NH2-AAminoadenosine(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

9H-Purine, 2,6-diamino-9-beta-D-ribofuranosyl-RefChem:85359DTXCID601775236606-677-42-Amine adenosine2-Amino AdenosineMFCD00053556(2R,3R,4S,5R)-2-(2,6-diaminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol

Database identifiers

CAS: 2096-10-8
PubChem CID: 72200
DTXSID: DTXSID001346570
ChEMBL: CHEMBL255442
ChEBI: CHEBI:1014
UNII: CCF94TM2UR
EC Number: 606-677-4
Nikkaji: J616.886H

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

GHS classification

GHS Classification · 5 items

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]；H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]；H335 (50%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Hazard information

Hazard Classes and CategoriesSkin Irrit. 2 (100%)；Eye Irrit. 2 (100%)；STOT SE 3 (50%)

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.