1-(6-Amino-9H-purin-9-yl)-1-deoxy-N-ethyl-beta-D-ribofuranuronamid

Neca

HCID 448222CAS 35920-39-9

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Grundinformationen

Standard-SMILES: CCNC(=O)[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O
InChIKey: JADDQZYHOWSFJD-FLNNQWSLSA-N
Summenformel: C12H16N6O4
Durchschnittliche Molmasse: 308,29 g/mol
Monoisotopische Masse: 308,12330299

Überblick

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.

Namen und Bezeichner

Bevorzugter Name: Neca
IUPAC: (2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-N-ethyl-3,4-dihydroxyoxolane-2-carboxamide
Lokaler Name: 1-(6-Amino-9H-purin-9-yl)-1-deoxy-N-ethyl-beta-D-ribofuranuronamid
Englischer Name: NECA
Summenformel: C12H16N6O4
Molmasse: 308.29

Namen und Synonyme

NECAN-ethyl-5'-carboxamidoadenosine(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-N-ethyl-3,4-dihydroxyoxolane-2-carboxamide3WC8SJ5ZLJCHEBI:73284RefChem:109229935920-39-95'-N-Ethylcarboxamidoadenosine5'-Ethylcarboxamido AdenosineAdenosine-5'-(N-ethylcarboxamide)N-Ethylcarboxamidoadenosine[3H]NECA

Weitere Namen anzeigen

D-NECA744-96765-21B-744-96NECA USP/EP/BPNECA, adenosine agonist5'-ETHYLCARBOXAMIDOADENOSINE5’-EthylcarboxamidoAdenosineAdenosine-5'-ethylcarboxamide

MFCD000691951-(6-Amino-9H-purin-9-yl)-1-deoxy-N-ethyl-beta-D-ribofuranuronamide(2S,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-N-ethyl-3,4-dihydroxytetrahydrofuran-2-carboxamideMLS000069759CHEMBL464859Adenosine-5-(N-ethylcarboxamide)AC-27392C12H16N6O4

Datenbank-Bezeichner

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

Eigenschaften

Berechnete Struktureigenschaften

XLogP: -0,7
Polarare Oberfläche (TPSA): 148 Å²
H-Brücken-Donoren: 4
H-Brücken-Akzeptoren: 8
Frei drehbare Bindungen: 3
Schwere Atome: 22
Formalladung: 0
Komplexität: 426

Experimentelle und physikochemische Eigenschaften

Solubility>46.2 [ug/mL] (The mean of the results at pH 7.4)

Physikochemische Eigenschaften

Schmelzpunkt: 229 · 229-231°C
Dichte: 1.87 · 1.87±0.1 g/cm3(Predicted)
storage temp.: 2 · 2-8°C
Löslichkeit: 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)
Aggregatzustand: powder
Farbe: white
Wasserlöslichkeit: 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.)
Stabilität: 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 Datenbank: 35920 · 35920-39-9

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 6 Einträge

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]

Gefahrenhinweise

Hazard Classes and Categories · 2 Einträge

Acute Tox. 2 (100%)

Sicherheitsdaten

wgk: 3
ridadr: UN 2811 6.1/PG 2
hs_code: 29349990
RTECS-Nr.: VJ2232000
risk_code: 28
hazard_code: T+
safety_code: 22-26-36-45
hazard_class: 6.1(a)
packing_group: I
Speicherklasse: 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
Hazard Classifications: Acute Tox. 2 Oral