Basic information
- CAS
16373-93-6- Standard SMILES
Nc1ncnc2c1ncn2[C@H]1C[C@H](O)[C@@H](CO)O1.O- InChIKey
WZJWHIMNXWKNTO-VWZUFWLJSA-N- Molecular formula
- C10H15N5O4
- Average molar mass
- 269.26 g/mol
- Monoisotopic mass
- 269.11240396
Overview
See also: Deoxyadenosine (annotation moved to); Adenine Deoxyribonucleoside (annotation moved to).
Names & identifiers
- Preferred name
- 2'-Deoxyadenosine monohydrate
- IUPAC
- (2R,3S,5R)-5-(6-aminopurin-9-yl)-2-(hydroxymethyl)oxolan-3-ol;hydrate
- English name
- 2'-Deoxyadenosine monohydrate
- Molecular formula
- C10H15N5O4
- Molecular weight
- 269.26
Names & synonyms
2'-Deoxyadenosine monohydrate16373-93-6F79D3BS9UHDTXSID801036040RefChem:1058625DTXCID901520268Adenosine, 2'-deoxy-, hydrate (1:1)(2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-2-(hydroxymethyl)tetrahydrofuran-3-ol hydrateAdenosine, 2'-deoxy-, monohydrateMFCD001493642'-Deoxyadenosine Hydrate2'-dA
Show more names
2′-DaAdenyldeoxy2'-Deoxyadenosine moADENINE DEOXYRIBOSIDE2'-DEOXYADENOSINE:H2O2'-Deoxy-adenosine ,98%2-DEOXYADENOSINE H2O D22-deoxyadenosine 99-100%
Deoxyadenosine Hydratedeoxyadenosine monohydrate2-Deoxyadenosine monohydrate(2R,3S,5R)-5-(6-aminopurin-9-yl)-2-(hydroxymethyl)oxolan-3-ol;hydrate2 inverted exclamation mark -Deoxyadenosine monohydrate9-(2'-Deoxy-beta-D-eryth9-(2'-Deoxy-beta-D-erythro-pentofuranosyl)adenineHY-W011683
Database identifiers
- CAS
16373-93-6
Properties
Computed structural properties
- Topological polar surface area
- 120 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 8
- Rotatable bonds
- 2
- Heavy atoms
- 19
- Formal charge
- 0
- Complexity
- 307
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
Safety & regulation
GHS classification
GHS Classification
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.
Hazard information
Hazard Classes and CategoriesAcute Tox. 3 (100%)
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
Applications
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.
Suppliers100 total
国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
T&W GROUP021-61551611 13296011611 · [email protected]
上海如吉生物科技发展有限公司+86-21-65211385-8001 36031160 · [email protected]
韶远科技（上海）有限公司021-50795510 4000665055 · [email protected]
Related reactions
9 records
Compound notes
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