Basic information
- CAS
35920-39-9- Standard SMILES
CCNC(=O)[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O- InChIKey
JADDQZYHOWSFJD-FLNNQWSLSA-N- Molecular formula
- C12H16N6O4
- Average molar mass
- 308.29 g/mol
- Monoisotopic mass
- 308.12330299
Overview
N-ethyl-5'-carboxamidoadenosine is a derivative of adenosine in which the 5'-hydroxymethyl group is replaced by an N-ethylcarboxamido group. It has a role as an antineoplastic agent, a vasodilator agent, an EC 3.1.4.* (phosphoric diester hydrolase) inhibitor, an adenosine A1 receptor agonist and an adenosine A2A receptor agonist. It is a member of adenosines and a monocarboxylic acid amide. It is functionally related to an adenosine.
Names & identifiers
- Preferred name
- Neca
- IUPAC
- (2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-N-ethyl-3,4-dihydroxyoxolane-2-carboxamide
- English name
- NECA
- Molecular formula
- C12H16N6O4
- Molecular weight
- 308.29
Names & synonyms
Show more names
Database identifiers
- CAS
35920-39-9、78647-50-4- PubChem CID
- 448222
- DTXSID
DTXSID801017234- ChEMBL
CHEMBL464859- ChEBI
CHEBI:73284- UNII
- 3WC8SJ5ZLJ
- EC Number
- 636-060-5、636-863-0
- Nikkaji
- J260.378K
Properties
Computed structural properties
- XLogP
- -0.7
- Topological polar surface area
- 148 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 8
- Rotatable bonds
- 3
- Heavy atoms
- 22
- Formal charge
- 0
- Complexity
- 426
Experimental & physicochemical properties
Physicochemical properties
- Melting point
- 229 · 229-231°C
- Density
- 1.87 · 1.87±0.1 g/cm3(Predicted)
- storage temp.
- 2 · 2-8°C
- solubility
- 45 % · 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 0.2 mg/mL Solutions may be stored for several days at 4°C.
- pka
- 12.93 · 12.93±0.70(Predicted)
- form
- powder
- color
- white
- Water Solubility
- 45 % · 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 0.2mg/mL (Solutions may be stored for several days at 4 °C.)DMSO: 14mg/mL (Solutions may be stored for several days at 4 °C.)0.1 M HCl: 3.4mg/mL (Solutions may be stored for several days at 4 °C.)H2O: insolubleethanol: soluble (Solutions may be stored for several days at 4 °C.)
- Stability
- Hygroscopic
- InChI
- InChI=1/C12H16N6O4/c1-2-14-11(21)8-6(19)7(20)12(22-8)18-4-17-5-9(13)15-3-16-10(5)18/h3-4,6-8,12,19-20H,2H2,1H3,(H,14,21)(H2,13,15,16)/t6-,7+,8-,12+/s3
- InChIKey
- JADDQZYHOWSFJD-FLNNQWSLSA-N
- SMILES
- N1(C=NC2C(N)=NC=NC1=2)[C@H]1[C@H](O)[C@H](O)[C@@H](C(=O)NCC)O1 |&1:10,11,13,15,r|
- CAS DataBase Reference
- 35920 · 35920-39-9
- UNSPSC Code
- 12352200 · 12352200
- NACRES
- 77 · NA.77
- Symbol(GHS)
- 6 · GHS06
- Signal word
- Danger
- Hazard statements
- 300 · H300
- Precautionary statements
- 264 · P264-P270-P301+P310-P405-P501
- Hazard Codes
- T+
- Risk Statements
- 28 · 28
- Safety Statements
- 22 · 22-26-36-45
- RIDADR
- 2811 · UN 2811 6.1/PG 2
- WGK Germany
- 3 · 3
- RTECS
- 2232000 · VJ2232000
- HazardClass
- 6.1 · 6.1(a)
- PackingGroup
- I
- HS Code
- 29349990 · 29349990
- Storage Class
- 6.1 A · 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
- Hazard Classifications
- 2 Oral · Acute Tox. 2 Oral
Safety & regulation
GHS classification
GHS Classification
Danger
H300 (100%): Fatal 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 39 reports by companies from 1 notifications to the ECHA C&L Inventory.
Danger
H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral]
Hazard information
Hazard Classes and Categories
Acute Tox. 2 (100%)
Acute Tox. 2 (100%)
Safety data
- wgk
- 3
- rtecs
- VJ2232000
- ridadr
- UN 2811 6.1/PG 2
- hs_code
- 29349990
- risk_code
- 28
- Signal word
- Danger
- Symbol(GHS)
- GHS06
- hazard_code
- T+
- safety_code
- 22-26-36-45
- hazard_class
- 6.1(a)
- Storage Class
- 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
- packing_group
- I
- Hazard statements
- H300
- Hazard Classifications
- Acute Tox. 2 Oral
- Precautionary statements
- P264-P270-P301+P310-P405-P501
Chemistry & industry
Applications
UsesA potent adenosine receptor agonist. Inhibits platelet aggregation and is centrally active in vivo
UsesPotent adenosine receptor agonist with some affinity at A1 and A2 receptors
Uses5′-(N-Ethylcarboxamido)adenosine has been used:for the purification of human adenosine A2Areceptor (A2AR) in decylmaltoside (DM)to determine nonspecific binding of adenosine receptorsto investigate adenosine 2B receptor (RA2B) mechanism of action by competition assay
General DescriptionA cell-permeable adenosine analog that acts a potent non-selective agonist of adenosine receptors (Ki = 14 nM, 20 nM, 2.4 μM and 6.2 nM for A1, A2A, A2B, A3, respectively). Increases intracellular cAMP production (EC50 = 3.1 μM in A2B expressing CHO cells). Shown to increase glucagon release in a dose-dependent manner and inhibit insulin release at low concentrations. Although at higher concentration some insulin release is observed. Also, displays a wide range adenosine-dependent effects, such as blocking platelet aggregation and inhibiting DNA synthesis. When administered at reperfusion, it is shown reduce infarction and block the formation of the mitochondrial permeability transition pore by activating p70S6 kinase.
Suppliers70 total
Additional notes
DefinitionChEBI: A derivative of adenosine in which the 5'-hydroxymethyl group is replaced by an N-ethylcarboxamido group.
Related reactions
Compound notes
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