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서베린

Cerberin

HCID 10031063
노트반응
기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
25633-33-4
표준 SMILES
CO[C@@H]1[C@@H](O)[C@H](C)O[C@@H](O[C@H]2CC[C@@]3(C)[C@H](CC[C@@H]4[C@@H]3CC[C@]3(C)[C@@H](C5=CC(=O)OC5)CC[C@]43O)C2)[C@H]1OC(C)=O
InChIKey
UYQMTWMXBKEHJQ-IVHDSYOHSA-N
분자식
C32H48O9
평균 분자량
576.7 g/mol
단동위원소 질량
576.3298331

개요

Cerberin is a cardenolide glycoside that is the 2'-acetyl derivative of neriifolin. It has a role as a metabolite and an antineoplastic agent. It is a cardenolide glycoside, an acetate ester and a monosaccharide derivative. It is functionally related to a neriifolin.

이름 및 식별자

우선 이름
Cerberin
IUPAC
[(2R,3S,4R,5S,6S)-5-hydroxy-2-[[(3S,5R,8R,9S,10S,13R,14S,17R)-14-hydroxy-10,13-dimethyl-17-(5-oxo-2H-furan-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-yl]oxy]-4-methoxy-6-methyloxan-3-yl] acetate
현지명
서베린
영어명
cerberin
분자식
C32H48O9
분자량
576.72

이름 및 동의어

Cerberin25633-33-42'-acetylneriifolinVeneniferinKW5A155S64[(2R,3S,4R,5S,6S)-5-hydroxy-2-[[(3S,5R,8R,9S,10S,13R,14S,17R)-14-hydroxy-10,13-dimethyl-17-(5-oxo-2H-furan-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-yl]oxy]-4-methoxy-6-methyloxan-3-yl] acetateCHEBI:75049DTXSID30893922((2R,3S,4R,5S,6S)-5-hydroxy-2-(((3S,5R,8R,9S,10S,13R,14S,17R)-14-hydroxy-10,13-dimethyl-17-(5-oxo-2H-furan-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta(a)phenanthren-3-yl)oxy)-4-methoxy-6-methyloxan-3-yl) acetateRefChem:918244DTXCID3013239613-((4-0-acetyl-6-deoxy-3-0-methyl-alpha-L-glucopyranosyl)oxy)-14-hydroxy-(3 beta,5 beta)-card-20(22)-enolide
이름 더 보기
서베린Vaneferine3β-(2-O-Acetyl-6-deoxy-3-O-methyl-α-L-glucopyranosyloxy)-14-hydroxy-5β-card-20(22)-enolide3β-[(2-O-Acetyl-3-O-methyl-6-deoxy-α-L-glucopyranosyl)oxy]-14-hydroxy-5β-card-20(22)-enolide3β-(2-O-Acetyl-3-O-methyl-6-deoxy-α-L-glucopyranosyloxy)-14β-hydroxy-5β-carda-20(22)-enolide

물성

구조 계산 물성

XLogP
2.7
극성 표면적
121 Ų
수소 결합 공여자 수
2
수소 결합 수용자 수
9
회전 가능 결합 수
6
무거운 원자 수
41
형식 전하
0
복잡도
1,080

물리화학적 성질

녹는점
212 · 212-215 °C
끓는 점
693.7 · 693.7±55.0 °C(Predicted)
밀도
1.26 · 1.26±0.1 g/cm3(Predicted)
저장 조건
Hygroscopic, Refrigerator, under inert atmosphere
용해도
클로로포름(약간 용해됨), 메탄올(약간 용해됨)
물리적 상태
고체
산도 계수 (pKa)
13.06 · 13.06±0.70(Predicted)
색상
흰색에서 연한 노란색
안정성
흡습성

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

독성 정보

Toxicity Summary · 1건

Cerbera odollam is a plant species of the Apocynaceae family and te common names include Pong-Pong and Othalanga. The poison rich part is the kernel, which is present at the core of its fruit, and the bioactive toxin is cerberin, a cardiac glycoside. Cerberin has a mechanism of action similar to digoxin, and the signs of toxicity are similar to acute digoxin poisoning. Ingestion of the kernel causes nausea, vomiting, hyperkalemia, thrombocytopenia, and ECG abnormalities, and exposure to high doses can be fatal. The initial management includes supportive therapy and the administration of atropine, followed by temporary pacemaker insertion. Administration of digoxin immune Fab can be considered in severe cases, although the authors noted hat the efficacy is variable and the data are limited to isolated case reports.

화학 및 산업

약리 정보

Mechanism of Action · 2건

Cerberin has a mechanism of action similar to digoxin. Thus, cerbera odollam's signs of toxicity are similar to acute digoxin poisoning. The ingestion of its kernel causes nausea, vomiting, hyperkalemia, thrombocytopenia, and ECG abnormalities.

Cerberin (CR) was found to potently inhibit cancer cell growth, colony formation and migration. Also, CR significantly increased the generation of reactive oxygen species (ROS) producing DNA double strand breaks. Preliminary in silico biopharmaceutical assessment of CR predicted >60% bioavailability and rapid absorption. The authors noted that CR's potent and selective anti-tumour activity, and its targeting of key signalling mechanisms pertinent to tumourigenesis support further preclinical evaluation of this cardiac glycoside.

공급사6 곳

安耐吉化学&3A(安徽泽升科技有限公司)021-58432009 400-005-6266 · [email protected]
TargetMol 中国(陶术生物)400-821-0310 15002144251 · [email protected]
艾吉析科技(上海)有限公司17717235263 17717235263 · [email protected]
成都标样生物科技有限公司028-81700200 13308200041 · [email protected]
河南天孚化工有限公司+86-0371-55170693 +86-19937530512 · [email protected]
上海一飞生物科技有限公司021-65675885 18964387627 · [email protected]

추가 설명

정의ChEBI: A cardenolide glycoside that is the 2'-acetyl derivative of neriifolin.

관련 반응

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화합물 노트

불러오는 중…

이 페이지에서기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
Card-20(22)-enolide, 3-[(2-O-acetyl-6-deoxy-3-O-methyl-α-L-glucopyranosyl)oxy]-14-hydroxy-, (3β,5β)-
[(2S,3S,4S,5S,6R)-5-Hydroxy-6-[[(3S,5R,8R,9S,10S,13R,14S,17R)-14-hydroxy-10,13-dimethyl-17-(5-oxo-2H-furan-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-yl]oxy]-4-methoxy-2-methyloxan-3-yl] acetatePveneniferinAcetylneriifolinCard-20(22)-enolide, 3-[(2-O-acetyl-6-deoxy-3-O-methyl-.alpha.-L-glucopyranosyl)oxy]-14-hydroxy-, (3.beta.,5.beta.)-Neriifolin-monoacetatPveneniferin [German]Acetylneriifolin [German]UNII-KW5A155S64

데이터베이스 식별자

CAS
25633-33-4
PubChem CID
10031063
DTXSID
DTXSID30893922
ChEMBL
CHEMBL554969
ChEBI
CHEBI:75049
UNII
KW5A155S64
Nikkaji
J18.711I