CAS 16373-93-6 Deoxyadenosine (HCID 13730)

Overview

2'-deoxyadenosine is a purine 2'-deoxyribonucleoside having adenine as the nucleobase. It has a role as a mouse metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a human metabolite. It is a purines 2'-deoxy-D-ribonucleoside and a purine 2'-deoxyribonucleoside.

Names & identifiers

Preferred name: Deoxyadenosine
IUPAC: (2R,3S,5R)-5-(6-aminopurin-9-yl)-2-(hydroxymethyl)oxolan-3-ol
English name: 2'-Deoxyadenosine monohydrate
Molecular formula: C10H15N5O4
Molecular weight: 269.26

Names & synonyms

2'-deoxyadenosinedeoxyadenosine958-09-82-DeoxyadenosineDesoxyadenosineAdenyldeoxyribosideADENOSINE, 2'-DEOXY-Adenine deoxyribose(2R,3S,5R)-5-(6-Aminopurin-9-yl)-2-(hydroxymethyl)oxolan-3-olCHEBI:17256Adenine deoxy nucleosideP582C98ULC

Show more names

2-DEOXYADENOSINE MONOHYDRATE2′-DaAdenyldeoxy2'-Deoxyadenosine moADENINE DEOXYRIBOSIDE2'-DEOXYADENOSINE:H2ODEOXYADENOSINE HYDRATE2'-Deoxy-adenosine ,98%2-DEOXYADENOSINE H2O D22-deoxyadenosine 99-100%

DTXSID10883624(2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-2-(hydroxymethyl)oxolan-3-ol9H-Purin-6-amine, 9-(2-deoxy-beta-D-ribofuranosyl)-9-(2-Deoxy-beta-D-erythro-pentofuranosyl)adenine9H-Purin-6-amine, 9-(2-deoxy-beta-D-erythro-pentofuranosyl)-beta-D-Ribofuranose, 1-(6-amino-9H-purin-9-yl)-1,2-dideoxy-9-(2-deoxy-beta-D-ribofuranosyl)-9H-purin-6-amineNSC-83258

Database identifiers

CAS: 16373-93-6、40627-14-3、958-09-8
PubChem CID: 13730
DTXSID: DTXSID10883624
ChEMBL: CHEMBL449329
ChEBI: CHEBI:17256
UNII: P582C98ULC
EC Number: 213-488-7、683-408-7
Nikkaji: J80.042B

Properties

Computed structural properties

XLogP: -0.5
Topological polar surface area: 119 Å²
Hydrogen bond donors: 3
Hydrogen bond acceptors: 7
Rotatable bonds: 2
Heavy atoms: 18
Formal charge: 0
Complexity: 307

Experimental & physicochemical properties

Chemical ClassesBiological Agents -> Nucleic Acids and Derivatives

SpringerMaterials PropertiesAngular frequency

LogP · 2 items

-0.55

-0.68

Melting Point189 °C

Physical Description · 2 items

White odorless crystals; [La-Mar-Ka MSDS]

Solid

Collision Cross Section · 6 items

152.3 Å² [M+H]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

154.6 Å² [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

160.57 Å² [M-H]- [CCS Type: DT; Method: stepped-field]

151.59 Å² [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

155.3 Å² [M-H]- [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]

158.2 Å² [M+H]+

Physicochemical properties

Melting point: 187 · 187-189 °C
refractive index: -25.5 ° · -25.5 ° (C=0.5, H2O)
storage temp.: 2 · 2-8°C
solubility: 2 O: · H2O: soluble50mg/mL, clear, colorless
form: powder
color: White to light beige
biological source: synthetic (organic)
Water Solubility: 0.3 g/100 · 0.3 g/100 mL (20 ºC)
BRN: 5191174 · 5191174
Stability: Stable, but air sensitive. Incompatible with strong oxidizing agents.
Cosmetics Ingredients Functions: HAIR CONDITIONING
InChI: InChI=1/C10H13N5O3.H2O/c11-9-8-10(13-3-12-9)15(4-14-8)7-1-5(17)6(2-16)18-7;/h3-7,16-17H,1-2H2,(H2,11,12,13);1H2/t5-,6+,7+;/s3
InChIKey: WZJWHIMNXWKNTO-VWZUFWLJSA-N
SMILES: NC1=NC=NC2N([C@H]3C[C@H](O)[C@@H](CO)O3)C=NC1=2.O |&1:7,9,11,r|
CAS DataBase Reference: 16373 · 16373-93-6(CAS DataBase Reference)
FDA UNII: 79 D3BS9UH · F79D3BS9UH
UNSPSC Code: 41106305 · 41106305
NACRES: 75 · NA.75
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 302 · H302
Precautionary statements: 264 b-P270-P301+P312-P330-P403-P501c · P264b-P270-P301+P312-P330-P403-P501c
PPE: 95 · dust mask type N95 (US), Eyeshields, Faceshields, Gloves
Hazard Codes: Xn,Xi
Risk Statements: 22 · 22-36/37/38-20/21/22
Safety Statements: 24 · 24/25-37/39-36-26
RIDADR: 2811 · UN2811 6.1/PG 3
WGK Germany: 3 · 3
RTECS: 7358600 · AU7358600
F: 10 · 10-23
TSCA: Yes
HazardClass: 6.1 · 6.1
HS Code: 29349990 · 29349990
Storage Class: 11 · 11 - Combustible Solids
Limited Quantities: 5 kg · 5.0 kg (11 lbs) (solid)
Excepted Quantities: Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)

Safety & regulation

GHS classification

GHS Classification · 6 items

Danger

H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]

P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 38 reports by companies from 1 notifications to the ECHA C&L Inventory.

This chemical does not meet GHS hazard criteria for 25% (1 of 4) of reports.

Warning

Hazard information

Regulatory InformationAdenosine, 2'-deoxy-: Does not have an individual approval but may be used under an appropriate group standard

Hazards SummaryIntraperitoneal LD50 (rat) > 800 mg/kg; [RTECS]

Hazard Classes and Categories · 2 items

Skin Irrit. 2 (75%)

Acute Tox. 3 (100%)

Toxicology

Health EffectsChronically high levels of deoxyadenosine are associated Adenosine Deaminase Deficiency.

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

Safety data

F: 10-23
PPE: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
wgk: 3
tsca: Yes
rtecs: AU7358600
ridadr: UN2811 6.1/PG 3
hs_code: 29349990
risk_code: 22-36/37/38-20/21/22
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xn,Xi
safety_code: 24/25-37/39-36-26
hazard_class: 6.1
Storage Class: 11 - Combustible Solids
Hazard statements: H302
Limited Quantities: 5.0 kg (11 lbs) (solid)
Excepted Quantities: Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
Precautionary statements: P264b-P270-P301+P312-P330-P403-P501c

Chemistry & industry

Pharmacology

MeSH Pharmacological Classification · 2 items

Agents used in the prophylaxis or therapy of VIRUS DISEASES. Some of the ways they may act include preventing viral replication by inhibiting viral DNA polymerase; binding to specific cell-surface receptors and inhibiting viral penetration or uncoating; inhibiting viral protein synthesis; or blocking late stages of virus assembly.

Chemical agents that increase the rate of genetic mutation by interfering with the function of nucleic acids. A clastogen is a specific mutagen that causes breaks in chromosomes.

Tissue LocationsAll Tissues

Cellular LocationsCytoplasm

Metabolite PathwaysAdenine phosphoribosyltransferase deficiency (APRT)

Uses & manufacturing

General Manufacturing InformationAdenosine, 2'-deoxy-: INACTIVE

Applications · 4 items

Description2'-Deoxyadenosine monohydrate is an adenosine nucleotide, which can be synthesized by the enzyme adenosine kinase. 2'-Deoxyadenosine monohydrate is a competitive inhibitor of phosphodiesterase, which breaks down cyclic nucleotides to their corresponding monophosphate form. This leads to elevated levels of cAMP, which can cause neuronal death by apoptosis.

Uses2'-Deoxyadenosineise is used by some cells as an energy source under energy stress conditions and to affect cAMP levels. 2'-dAdo is used in comparison studies of the functions of adenosine analogues on various biological processes.

Uses2′-Deoxyadenosine monohydrate has been used: as a component for nucleoside supplementationas a standard for to estimate DNA global methylation rate in proliferating oil palm embryogenic suspensionsto reverse sterile alpha motif (SAM) and histidine-aspartate (HD) domain-containing protein (SAMHD1) inhibition of human immunodeficiency virus (HIV-1) and hepatitis B virus (HBV)

Uses2'-Deoxyadenosine monohydrate is used in the synthesis of 5'-modified 2'-deoxyadenosine analogues as anti-hepatitis C virus agents.