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(5R,9R,11E,12aS,13S,15S,15aS,16S,18aS)-4,5,6,7,8,9,10,12a,13,14,15,15a,16,17-Tetradecahydro-5,13-dihydroxy-9,15-dimethyl-14-methylene-16-(phenylmethyl)-2H-oxacyclotetradecino(2,3-d)isoindole-2,18(3H)-dione

HCID 6438347
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Grundinformationen

CAS
39156-67-7
Standard-SMILES
C=C1[C@@H](C)[C@H]2[C@H](Cc3ccccc3)NC(=O)[C@]23OC(=O)CC[C@H](O)CCC[C@@H](C)C/C=C/[C@H]3[C@@H]1O
InChIKey
WIULKAASLBZREV-RXPQEOCGSA-N
Summenformel
C29H39NO5
Durchschnittliche Molmasse
481,6 g/mol
Monoisotopische Masse
481,28282334

Überblick

Cytochalasins are mycotoxins that have the ability to bind to actin filaments and block polymerization and the elongation of actin. As a result, they can change cellular morphology, inhibit cellular processes such as cell division, and cause cells to undergo apoptosis. Cytochalasins also have the ability to permeate cell membranes, prevent cellular translocation, cause cells to enucleate, and affect other aspects of biological processes unrelated to actin polymerization. Dihydrocytochalasin B is a semi-synthetic derivative of cytochalasin B and is a useful probe for studying cytochalasin binding sites. (A2910, A2911, L1913, L1916)

Namen und Bezeichner

Bevorzugter Name
(5R,9R,11E,12aS,13S,15S,15aS,16S,18aS)-4,5,6,7,8,9,10,12a,13,14,15,15a,16,17-Tetradecahydro-5,13-dihydroxy-9,15-dimethyl-14-methylene-16-(phenylmethyl)-2H-oxacyclotetradecino(2,3-d)isoindole-2,18(3H)-dione
IUPAC
(1S,6R,10R,12E,14S,15S,17S,18S,19S)-19-benzyl-6,15-dihydroxy-10,17-dimethyl-16-methylidene-2-oxa-20-azatricyclo[12.7.0.01,18]henicos-12-ene-3,21-dione
Englischer Name
Dihydrocytochalasin B
Summenformel
C29H39NO5
Molmasse
481.62

Namen und Synonyme

dihydrocytochalasin B39156-67-721,22-Dihydrophomin21,22-Dihydrochalasin B21,22-Dihydrocytochalasan BL9RT18CY85DTXSID501046323RefChem:404437DTXCID101528151(5R,9R,11E,12aS,13S,15S,15aS,16S,18aS)-4,5,6,7,8,9,10,12a,13,14,15,15a,16,17-Tetradecahydro-5,13-dihydroxy-9,15-dimethyl-14-methylene-16-(phenylmethyl)-2H-oxacyclotetradecino(2,3-d)isoindole-2,18(3H)-dione15-benzyl-4,12-dihydroxy-8,14-dimethyl-13-methylidene-2H,3H,4H,5H,6H,7H,8H,9H,12H,13H,14H,14aH,15H,16H,17H,17bH-oxacyclotrideca(3,2-e)isoindole-2,17-dione254-324-4
Weitere Namen anzeigen
DHCBDihidrocytochalasin BCYTOCHALASIN B, DIHYDRO21,22-Dihydrocytochalalsin BCytochalasin B, Dihydro- - CAS 39156-67-7 - Calbiochem7(S),20(R)-dihydroxy-16(R)-methyl-10-phenyl-24-oxa[14]cytochalasa-6(12),13(E)-diene-1,23-dione(7S,13E,16R,20R)-7,20-Dihydroxy-16-methyl-10-phenyl-24-oxa[14]cytochalasa-6(12),13-diene-1,23-dione(7S,13E,16R,20R)-7β,20-Dihydroxy-16-methyl-10-phenyl-24-oxa[14]cytochalasa-6(12),13-diene-1,23-dione2H-Oxacyclotetradecino[2,3-d]isoindole-2,18(3H)-dione, 4,5,6,7,8,9,10,12a,13,14,15,15a,16,17-tetradecahydro-5,13-dihydroxy-9,15-dimethyl-14-methylene-16-(phenylmethyl)-, (5R,9R,11E,12aS,13S,15S,15aS,16S,18aS)-
Cytochalasin H2BMFCD12910542C29H39NO5WIULKAASLBZREV-RXPQEOCGSA-NEINECS 254-324-4Cytochalasin H(2)BUNII-L9RT18CY8574409-92-0

Datenbank-Bezeichner

CAS
39156-67-7
PubChem CID
6438347
DTXSID
DTXSID501046323
ChEMBL
CHEMBL2074735
UNII
L9RT18CY85
EC Number
254-324-4
Nikkaji
J261.323I

Eigenschaften

Berechnete Struktureigenschaften

XLogP
3,4
Polarare Oberfläche (TPSA)
95,9 Ų
H-Brücken-Donoren
3
H-Brücken-Akzeptoren
5
Frei drehbare Bindungen
2
Schwere Atome
35
Formalladung
0
Komplexität
818

Physikochemische Eigenschaften

Schmelzpunkt
203 · 203-205 °C
Siedepunkt
727.5 · 727.5±60.0 °C(Predicted)
Dichte
1.19 · 1.19±0.1 g/cm3(Predicted)
storage temp.
-20 °C · -20°C
Löslichkeit
30 mg/ml; · DMF: 30 mg/ml; DMF:PBS (pH 7.2) (1:20): 0.05 mg/ml; DMSO: 20 mg/ml; Ethanol: 20 mg/ml
pka
13.65 · 13.65±0.70(Predicted)
Aggregatzustand
White solid
Farbe
white
InChIKey
WIULKAASLBZREV-PEVBMUQXNA-N
SMILES
[C@H]1(C(=C)[C@H]([C@]2([C@]3(OC(CC[C@H](O)CCC[C@@H](C)CC=C2)=O)C(=O)N[C@@H](CC2C=CC=CC=2)[C@]13[H])[H])O)C |t:18,&1:0,3,4,5,10,15,24,32,r|

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 4 Einträge

Danger

H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral]

P203, P260, P262, P264, P270, P271, P280, P284, P301+P316, P302+P352, P304+P340, P316, P318, P320, P321, P330, P361+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Hazard Classes and CategoriesAcute Tox. 2 (100%)

Toxikologische Informationen

Treatment · 1 Eintrag

Consider activated charcoal after gastrointestinal absportion. Nitroprusside is recommended to reverse peripheral ischemia secondary to vasoconstriction and for the treatment of hypertension. Anticoagulant therapy with intravenous heparin is also recommended. (A704)

Health Effects · 1 Eintrag

Major biological effects of cytochalasins include inhibition of the division of cytoplasm, reversible inhibition of cell movement, induction of nuclear extrusion, inhibition of such processes as phagocytosis, platelet aggregation and clot retraction, glucose transport, thyroid secretion, and release of growth hormone. Some cytochalasins have been shown to have developmental effects. (L1916)

Exposure RoutesOral, dermal, inhalation, and parenteral (contaminated drugs). (A3101)
Toxicity Summary · 1 Eintrag

Cytochalasins are known to bind to the barbed, fast growing plus ends of microfilaments, which then blocks both the assembly and disassembly of individual actin monomers from the bound end. Once bound, cytochalasin essentially caps the end of the new actin filament. One cytochalasin will bind to one actin filament. By blocking the polymerization and elongation of actin, cytochalasins can change cellular morphology, inhibit cellular processes such as cell division, and cause cells to undergo apoptosis. (A2910, A2911, L1913)

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

Sicherheitsdaten

wgk
3
ridadr
UN 2811 6.1/PG 2
hs_code
29349990
RTECS-Nr.
RO0205000
risk_code
26/27/28-40
hazard_code
T+,T
safety_code
22-36/37/39-45
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 DermalAcute Tox. 2 InhalationAcute Tox. 2 OralCarc. 2

Chemie und Industrie

Verwendung und Herstellung

UsesDihydrocytochalasin B is a semi-synthetic derivative of cytochalasin B and is a useful probe for studying cytochalasin binding sites. (L1916)

Anwendungen

VerwendenDihydrocytochalasin B is a cell morphology and motility and inducer.

Anbieter32 Anbieter

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