5-(Methylamino)-2-((3,9,11-trime-thyl-8-(1-methyl-2-oxo-2-(1H-pyrrol-2-yl)ethyl)-1,7-dioxaspiro(5.5)undec-2-yl)methyl)-4-benzoxazolcarbonsäure, (6S-(6 alpha(2S,3S), 8 beta(R*),9 beta, 11 alpha))-

Calcimycin

HCID 11957499

Notizen Reaktionen

Teilstruktursuche Ähnliche Strukturen suchen

Grundinformationen

CAS: 52665-69-7
Standard-SMILES: CNc1ccc2oc(C[C@H]3O[C@@]4(CC[C@H]3C)O[C@H]([C@H](C)C(=O)c3ccc[nH]3)[C@H](C)C[C@H]4C)nc2c1C(=O)O
InChIKey: HIYAVKIYRIFSCZ-CYEMHPAKSA-N
Summenformel: C29H37N3O6
Durchschnittliche Molmasse: 523,6 g/mol
Monoisotopische Masse: 523,26823591

Namen und Bezeichner

Bevorzugter Name: Calcimycin
IUPAC: 5-(methylamino)-2-[[(2S,3R,5R,6S,8R,9R)-3,5,9-trimethyl-2-[(2S)-1-oxo-1-(1H-pyrrol-2-yl)propan-2-yl]-1,7-dioxaspiro[5.5]undecan-8-yl]methyl]-1,3-benzoxazole-4-carboxylic acid
Lokaler Name: 5-(Methylamino)-2-((3,9,11-trime-thyl-8-(1-methyl-2-oxo-2-(1H-pyrrol-2-yl)ethyl)-1,7-dioxaspiro(5.5)undec-2-yl)methyl)-4-benzoxazolcarbonsäure, (6S-(6 alpha(2S*,3S*), 8 beta(R*),9 beta, 11 alpha))-
Englischer Name: A23187
Summenformel: C29H37N3O6
Molmasse: 523.62

Namen und Synonyme

Calcimycin52665-69-7antibiotic A-23187A2318737H9VM9WZLAntibiotic A23187DTXSID1040405A-23187A 231874-Benzoxazolecarboxylic acid, 5-(methylamino)-2-((3,9,11-trimethyl-8-(1-methyl-2-oxo-2-(1H-pyrrol-2-yl)ethyl)-1,7-dioxaspiro(5.5)undec-2-yl)methyl)-, (6S-(6alpha(2S*,3S*),8beta(R*),9beta,11alpha))-5-(Methylamino)-2-[[(2R,3R,6S,8S,9R,11R)-3,9,11-trimethyl-8-[(1S)-1-methyl-2-oxo-2-(1H-pyrrol-2-yl)ethyl]-1,7-dioxaspiro[5.5]undec-2-yl]methyl]-4-benzoxazolecarboxylic acid5-(methylamino)-2-[[(2S,3R,5R,6S,8R,9R)-3,5,9-trimethyl-2-[(2S)-1-oxo-1-(1H-pyrrol-2-yl)propan-2-yl]-1,7-dioxaspiro[5.5]undecan-8-yl]methyl]-1,3-benzoxazole-4-carboxylic acid

Weitere Namen anzeigen

SBE-β-CDCALCIUM IONOPHORE A23187A23187, 98%, FREE ACID5-(Methylamino)-2-[[(2R,3R,6S,8S,9R,11R)-3,9,11-trimethyl-8-[(1S)-1-methyl-2-oxo-2-(1H-pyrrol-2-yl)-ethyl]-1,7-dioxaspiro[5.5]undec-2-yl]methyl]-4-benzoxazolecarboxylic acid11B1(R*),9B2Calimycin(2S*,3S*),8B2

4-BENZOXAZOLECARBOXYLIC ACID, 5-(METHYLAMINO)-2-(((2R,3R,6S,8S,9R,11R)-3,9,11-TRIMETHYL-8-((1S)-1-METHYL-2-OXO-2-(1H-PYRROL-2-YL)ETHYL)-1,7-DIOXASPIRO(5.5)UNDEC-2-YL)METHYL)-5-(METHYLAMINO)-2-(((2R,3R,6S,8S,9R,11R)-3,9,11-TRIMETHYL-8-((1S)-1-METHYL-2-OXO-2-(1H-PYRROL-2-YL)ETHYL)-1,7-DIOXASPIRO(5.5)UNDEC-2-YL)METHYL)-4-BENZOXAZOLECARBOXYLIC ACIDA23187, Antibiotic4-Benzoxazolecarboxylic acid, 5-(methylamino)-2-[[(2R,3R,6S,8S,9R,11R)-3,9,11-trimethyl-8-[(1S)-1-methyl-2-oxo-2-(1H-pyrrol-2-yl)ethyl]-1,7-dioxaspiro[5.5]undec-2-yl]methyl]-5-(methylamino)-2-(((2S,3R,5R,6S,8R,9R)-3,5,9-trimethyl-2-((2S)-1-oxo-1-(1H-pyrrol-2-yl)propan-2-yl)-1,7-dioxaspiro(5.5)undecan-8-yl)methyl)-1,3-benzoxazole-4-carboxylic acidRefChem:122739DTXCID1014761205-(methylamino)-2-(((2S,3R,5R,8S,9S)-3,5,9-trimethyl-2-(1-methyl-2-oxo-2-(1H-pyrrol-2-yl)ethyl)-1,7-dioxaspiro(5.5)undecan-8-yl)methyl)-1,3-benzoxazole-4-carboxylic acid

Datenbank-Bezeichner

CAS: 52665-69-7
PubChem CID: 11957499
DTXSID: DTXSID1040405
ChEMBL: CHEMBL1256686
ChEBI: CHEBI:107643
UNII: 37H9VM9WZL
EC Number: 258-084-1
Nikkaji: J22.635A

Eigenschaften

Berechnete Struktureigenschaften

XLogP: 5,9
Polarare Oberfläche (TPSA): 127 Å²
H-Brücken-Donoren: 3
H-Brücken-Akzeptoren: 8
Frei drehbare Bindungen: 7
Schwere Atome: 38
Formalladung: 0
Komplexität: 873

Physikochemische Eigenschaften

Schmelzpunkt: 187 · 187-190 °C
Siedepunkt: 710.3 · 710.3±55.0 °C(Predicted)
Dichte: 1.28 · 1.28±0.1 g/cm3(Predicted)
storage temp.: 2 · 2-8°C
Löslichkeit: Soluble in DMSO with warming or sonication. Also soluble in ethanol or ethyl acetate
Aggregatzustand: Solid
pka: 1 · pKa1 6.9 in 90% DMSO
Farbe: white to light yellow
Merck: 13 · 13,1639
BRN: 1096801 · 1096801
Stabilität: 2 years · Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 4 months.
InChIKey: HIYAVKIYRIFSCZ-CYEMHPAKSA-N
SMILES: [H][C@@]1(O[C@@]2(CC[C@@H](C)[C@@H](Cc3nc4c(C(O)=O)c(NC)ccc4o3)O2)[C@H](C)C[C@H]1C)[C@H](C)C(=O)c5ccc[nH]5

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 5 Einträge

Warning

H315 (95.2%): Causes skin irritation [Warning Skin corrosion/irritation]；H319 (95.2%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]；H335 (95.2%): 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 42 reports by companies from 4 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.

Gefahrenhinweise

Hazard Classes and CategoriesSkin Irrit. 2 (95.2%)；Eye Irrit. 2 (95.2%)；STOT SE 3 (95.2%)

Sicherheitsdaten

F: 8
wgk: 3
hs_code: 29349990
RTECS-Nr.: DM4676000
risk_code: 36/37/38-20/21/22
Toxizität: LD50 i.p. in mice: 10 mg/kg (Gale)
hazard_code: Xi,Xn
safety_code: 26-36
Speicherklasse: 11 - Combustible Solids

Chemie und Industrie

Pharmakologische Informationen

MeSH Pharmacological Classification · 2 Einträge

Substances that inhibit the growth or reproduction of BACTERIA.

Chemical agents that increase the permeability of CELL MEMBRANES to CALCIUM ions.

Anwendungen · 1 Eintrag

VerwendenA23187 (Mixed Calcium-Magnesium Salt) is used in cell activation experiments when calcium dose-response data are not required. Ca-Mg ratio ~ 1:1. it is widely used as a compound in cell activation. It is used as a highly selective Ca2+ ionophore. it is used in studies of intracellular Ca2+ mediated events. A23187 has been observed to induce cell activation, differentiation or proliferation. In vitro experimentation has shown A23187 to boost ROS generation and platelet fragmentation. A23187 is a widely used ionophore. It has the ability to increase the intracellular concentrations of cations and is widely used to increase the intracellular levels of calcium. Visualization of Synaptic Ca2+ Calmodulin-Dependent Protein Kinase II Activity in Living Neurons.