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Verrucarin A, 7'-Deoxo-7'-(1-hydroxyethyl)-, [7'R(R)]-

Roridin A

HCID 9915017
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Grundinformationen

CAS
14729-29-4
Standard-SMILES
CC1=C[C@H]2O[C@@H]3C[C@H]4OC(=O)/C=C\C=C\[C@H]([C@@H](C)O)OCC[C@@H](C)[C@H](O)C(=O)OC[C@@]2(CC1)[C@]4(C)[C@]31CO1
InChIKey
NSFWWJIQIKBZMJ-PAGWOCKZSA-N
Summenformel
C29H40O9
Durchschnittliche Molmasse
532,6 g/mol

Überblick

roridin A has been reported in Paramyrothecium roridum, Albifimbria verrucaria, and other organisms with data available.

Namen und Bezeichner

Bevorzugter Name
Roridin A
IUPAC
(1R,3R,8R,12S,13R,17R,18E,20Z,24R,25S,26S)-12-hydroxy-17-[(1R)-1-hydroxyethyl]-5,13,25-trimethylspiro[2,10,16,23-tetraoxatetracyclo[22.2.1.03,8.08,25]heptacosa-4,18,20-triene-26,2'-oxirane]-11,22-dione
Lokaler Name
Verrucarin A, 7'-Deoxo-7'-(1-hydroxyethyl)-, [7'R(R)]-
Englischer Name
RORIDIN A
Summenformel
C29H40O9
Molmasse
532.62

Namen und Synonyme

Roridin ARoridine ARoridan AU28899D1U2Verrucarin A, 7'-deoxo-7'-(1-hydroxyethyl)-, (7'R(R))-14729-29-4NSC-200737Verrucarin A, 7'-deoxo-7'-((1R)-1-hydroxyethyl)-, (7'R)-(1R,3R,8R,12S,13R,17R,18E,20Z,24R,25S,26S)-12-hydroxy-17-[(1R)-1-hydroxyethyl]-5,13,25-trimethylspiro[2,10,16,23-tetraoxatetracyclo[22.2.1.03,8.08,25]heptacosa-4,18,20-triene-26,2'-oxirane]-11,22-dioneDTXSID00891839(1R,3R,8R,12S,13R,17R,18E,20Z,24R,25S,26S)-12-hydroxy-17-((1R)-1-hydroxyethyl)-5,13,25-trimethylspiro(2,10,16,23-tetraoxatetracyclo(22.2.1.03,8.08,25)heptacosa-4,18,20-triene-26,2'-oxirane)-11,22-dioneRefChem:179826
Weitere Namen anzeigen
roridanaAi3-29708roridinea(7’r(r))-verrucarinRoridin A, Roridin Croridin a from myrothecium sp.roridin A from myrothecium sp cryst
DTXCID00103126012'-hydroxy-17'-(1-hydroxyethyl)-5',13',25'-trimethyl-2',10',16',23'-tetraoxaspiro(oxirane-2,26'-tetracyclo(22.2.1.03,8.08,25)heptacosane)-4',18',20'-triene-11',22'-dione238-783-8Antibiotic 379XVerrucarin A, 7'-deoxo-7'-(1-hydroxyethyl)-NSC200737EINECS 238-783-8NSC 200737

Eigenschaften

Berechnete Struktureigenschaften

XLogP
2,2
Polarare Oberfläche (TPSA)
124 Ų
H-Brücken-Donoren
2
H-Brücken-Akzeptoren
9
Frei drehbare Bindungen
1
Schwere Atome
38
Formalladung
0
Komplexität
1.040

Physikochemische Eigenschaften

Schmelzpunkt
198 · 198-204 °C
Siedepunkt
752.4 · 752.4±60.0 °C(Predicted)
Dichte
1.29 · 1.29±0.1 g/cm3(Predicted)
storage temp.
20 °C · −20°C
Löslichkeit
10 mg/mL, · chloroform: ≥10 mg/mL, clear, colorless
Aggregatzustand
powder
pka
12.83 · 12.83±0.70(Predicted)
InChIKey
NSFWWJIQIKBZMJ-WZZABFCFNA-N
SMILES
[C@@]12(OC1)C1O[C@@H]3C=C(C)CC[C@]43COC(=O)[C@@H](O)[C@H](C)CCOC(C(O)C)C=CC=CC(=O)O[C@H](C1)C24C |c:31,t:29,&1:0,5,11,16,18,34,r|
CAS Datenbank
14729 · 14729-29-4
EPA chemische Informationen
7 · Verrucarin A, 7'-deoxo-7'-[(1R)-1-hydroxyethyl]-, (7'R)- (14729-29-4)

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]

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.

Gefahrenhinweise

Hazard Classes and CategoriesAcute Tox. 2 (100%)

Toxikologische Informationen

Treatment · 1 Eintrag

There are no known antidotes to trichothecene mycotoxins. Treatments are directed at supporting hemopoietic abnormalities, gastrointestinal damage, and skin damage. Administer charcoal as a slurry in case of acute oral exposure. In case of inhalation: Move patient to fresh air. Monitor for respiratory distress. If cough or difficulty breathing develops, evaluate for respiratory tract irritation, bronchitis, or pneumonitis. Administer oxygen and assist ventilation as required. Treat bronchospasm with inhaled beta2 agonist and oral or parenteral corticosteroids. In case of eye exposure, Irrigate exposed eyes with copious amounts of room temperature water for at least 15 minutes. In case of dermal exposure, Remove contaminated clothing and wash exposed area thoroughly with soap and water. (A704)

Health Effects · 1 Eintrag

Trichothecenes have multiorgan effects including anoerxia and weight loss, growth retardation, nervous disorders, cardiovascular alterations, immunodepression, hemostatic derangements, skin toxicity, decreased reproductive capacity, bone marrow damage, and alimentary toxic aleukia. (L1948, L1949, A2964)

Exposure Routes

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites · 1 Eintrag

Trichothecenes are lipophilic and thus easily absorbed through the skin, gut, and pulmonary mucosa. They are metabolized mainly by cytochrome P-450 and trichothecene-specific carboxylesterase activity in the liver, although other tissues such as the kidney, spleen, and intestine also show some metabolic activity. Trichothecenes are metabolically transformed to less toxic metabolites by such reactions as hydrolysis, hydroxylation, de-epoxidation, and glucuronidation. Metabolites are excreted in the urine and feces. (L1910, L1949)

Verwendung und Herstellung

Uses · 1 Eintrag

Trichothecenes are a very large family of chemically related mycotoxins produced by various species of Fusarium, Myrothecium, Trichoderma, Trichothecium, Cephalosporium, Verticimonosporium, and Stachybotrys. They are produced on many different grains like wheat, oats or maize by various Fusarium species such as F. graminearum, F. sporotrichioides, F. poae and F. equiseti. Some molds that produce trichothecene mycotoxins, such as Stachybotrys chartarum, can grow in damp indoor environments and may contribute to health problems among building occupants. (L1948)

Anbieter11 Anbieter

陕西缔都新材料有限公司029-63373950 17392216152 · [email protected]
武汉丰泰威远科技有限公司+86-27-8746-5837 +86-18627785180 · [email protected]
武汉丰泰威远科技有限公司027-87465837 19945049750 · [email protected]
池州凯隆进出口贸易有限公司[email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]

Zugehörige Reaktionen

3
Reaktionsaufzeichnung erstellen
Reaktionsgleichung von HRID 975270
HRID 975270als Eduktuspto-grants-1997_03
Reaktionsgleichung von HRID 1780539
HRID 1780539als Eduktuspto-grants-1997_05
Reaktionsgleichung von HRID 1792736
HRID 1792736als Eduktuspto-grants-2006_07

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Datenbank-Bezeichner

CAS
14729-29-4
PubChem CID
9915017
ChEMBL
CHEMBL334648
UNII
U28899D1U2
EC Number
238-783-8
Oral, dermal, inhalation, and parenteral (contaminated drugs). (A3101)
Toxicity Summary · 1 Eintrag

Unlike many other mycotoxins, trichothecenes do not require metabolic activation to exert their biological activity, instead directly reacting with cellular components. Trichothecenes are cytotoxic to most eukaryotic cells due to their powerful ability to inhibit protein synthesis. They do this by freely moving across the plasma membrane and binding specifically to ribosomes with high-affinity. Specifically, they interfere with the active site of peptidyl transferase at the 3'-end of large 28S ribosomal RNA and inhibit the initiation, elongation or termination step of protein synthesis, as well as cause polyribosomal disaggregation. Protein synthesis is an essential function in all tissues, but tissues where cells are actively and rapidly growing and dividing are very susceptible to the toxins. Additionally, binding to ribosomes is thought to activate proteins in downstream signalling events related to immune response and apoptosis, such as mitogen-activated protein kinases. This is known as ribotoxic stress response. Trichothecenes may also induce some alterations in membrane structure, leading to increased lipid peroxidation and inhibition of electron transport activity in the mitochondria. They can further induce apoptosis through generation of reactive oxygen species. Further secondary effects of trichothecenes include inhibition of RNA and DNA synthesis, and also inhibition of mitosis. (L1948, L1949, A2962, A2963, A2964, A2980)

Signs and Symptoms · 1 Eintrag

After direct dermal application or oral ingestion, the trichothecene mycotoxins can cause rapid irritation to the skin or intestinal mucosa, including skin irritation, burning and itching, rash or blisters, and bleeding. Eye contact can cause tearing, eye pain, conjunctivitis, burning sensations about the eyes, and blurred vision for up to 1 week. Symptoms also include nausea, vomiting, fatigue, dyspnea, and acute vascular effects leading to hypotension and shock. (L1948, L1949)

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Toxicity DataLD50: 1.0 mg/kg (Intravenous, Mouse) (L1949)

Sicherheitsdaten

wgk
3
ridadr
UN 3462 6.1/PG 1
RTECS-Nr.
VL0355000
risk_code
28
hazard_code
T+
safety_code
28-36/37-45
hazard_class
6.1(a)
packing_group
I
BOC Sciences16314854226; +8616314854226 · [email protected]
浙江珲达生物科技有限公司0571-89903022 18679456698 · [email protected]
青岛贞开生物医药技术有限公司0532-58268781 18561687109 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354 · [email protected]
AFINE CHEMICALS LIMITED+86-571-85134551 +86-18958018566 · [email protected]
武汉丽合智造生物科技有限公司18971458902 · [email protected]