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아르글라빈

(3aR,4aS,6aS,9aS,9bS)-1,4a-Dimethyl-7-methylidene-5,6,6a,7,9a,9b-hexahydro-3H-oxireno[8,8a]azuleno[4,5-b]furan-8(4aH)-one

HCID 636760
노트반응
기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
84692-91-1
표준 SMILES
C=C1C(=O)O[C@H]2[C@H]1CC[C@]1(C)O[C@@]13CC=C(C)[C@@H]23
InChIKey
UVJYAKBJSGRTHA-ZCRGAIPPSA-N
분자식
C15H18O3
평균 분자량
246.3 g/mol
단동위원소 질량
246.12559443

개요

arglabin has been reported in Artemisia myriantha and Pentzia with data available.

이름 및 식별자

우선 이름
(3aR,4aS,6aS,9aS,9bS)-1,4a-Dimethyl-7-methylidene-5,6,6a,7,9a,9b-hexahydro-3H-oxireno[8,8a]azuleno[4,5-b]furan-8(4aH)-one
IUPAC
(1R,3S,6S,10S,11S)-3,12-dimethyl-7-methylidene-2,9-dioxatetracyclo[9.3.0.01,3.06,10]tetradec-12-en-8-one
현지명
아르글라빈
영어명
arglabin
분자식
C15H18O3
분자량
246.3

이름 및 동의어

SCHEMBL15527919HB4630(3aR,4aS,6aS,9aS,9bS)-1,4a-Dimethyl-7-methylidene-5,6,6a,7,9a,9b-hexahydro-3H-oxireno[8,8a]azuleno[4,5-b]furan-8(4aH)-one아르글라빈CS-1320arglabinArglabineArglabin, BR(+)-ArglabinArglabin 84692-91-1Arglabin ((+)-Arglabin)Arglabin, 10 mM in DMSO
이름 더 보기
(3aS)-2,3,3aβ,4,5β,6,6a,7,9aβ,9bα-Decahydro-6α,6aα-epoxy-6,9-dimethyl-3-methyleneazuleno[4,5-b]furan-2-one(3aR,4aS)-1,4aα-Dimethyl-7-methylene-4a,5,6,6aα,9aβ,9bα-hexahydro-3H-oxireno[8,8a]azuleno[4,5-b]furan-8(7H)-one

데이터베이스 식별자

CAS
84692-91-1
PubChem CID
636760
DTXSID
DTXSID30233687

물성

구조 계산 물성

XLogP
1.7
극성 표면적
38.8 Ų
수소 결합 공여자 수
0
수소 결합 수용자 수
3
회전 가능 결합 수
0
무거운 원자 수
18
형식 전하
0
복잡도
506

물리화학적 성질

녹는점
100 · 100-102 °C
끓는 점
404.6 · 404.6±45.0 °C(Predicted)
밀도
1.22 · 1.22±0.1 g/cm3(Predicted)
저장 조건
-20 °C · Amber Vial, -20°C Freezer, Under inert atmosphere
용해도
클로로포름(약간 용해됨)
물리적 상태
고체
색상
회백색
생물학적 소스
semisynthetic (from parthenolide)
InChI
1S/C15H18O3/c1-8-4-7-15-11(8)12-10(9(2)13(16)17-12)5-6-14(15,3)18-15/h4,10-12H,2,5-7H2,1,3H3/t10-,11-,12-,14-,15+/m0/s1
InChIKey
UVJYAKBJSGRTHA-ZCRGAIPPSA-N
SMILES
O1[C@@]32[C@@]1(CC[C@@H]4[C@H](OC(=O)C4=C)[C@@H]3C(=CC2)C)C

안전 및 규제

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

안전 데이터

wgk
WGK 3
Hazard Classifications
Acute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
스토리지 클래스
11 - Combustible Solids

화학 및 산업

응용 분야 · 1건

개요Arglabin is a new antineoplastic agent launched in Russia for the treatment of a variety of cancers. It is a sesquiterpene gamma-lactone extracted from Artemisia glabella, a plant from Kazakstan; it was first developed in Kazakstan followed by US and other countries as an ethical pharmaceutical. Arglabin can be obtained by resin extraction from A.glabella, purification by chromatography and finally recrystallization. Arglabin is a potent and selective inhibitor of farnesyl transferase, an enzyme critical to the function of the Ras oncogene in cancer cell reproduction. It showed a strong Inhibitory effect against tumor cells proliferation in in vitro models of transformed mouse hepatocytes and splenocytes. This cytotoxic effect against tumor cells was 50-100 times higher than that on intact cells. In many patients with various cancers, Arglabin was shown to stop or inhibit the tumour development, alone or in combination with other anticancer agents, and was reportedly well tolerated with few sideeffects. Promising response rates were also reported with Arglabin after treating other 《difficult-to-treat cancers》 such as breast, ovarian, lung or colon cancers.

공급사100 곳

南京世洲生物科技有限公司025-85560043 15850508050 · [email protected]
成都普瑞法科技开发有限公司+86-028-82633397 18982077548 · [email protected]
湖北永阔科技有限公司027-59223108 15972152991 · [email protected]
成都乐美天医药科技有限公司17308096051 17308096051 · [email protected]
湖北万得化工有限公司15377098680 15377098680 · [email protected]
上海纯优生物科技有限公司15921393123 18302135232 · [email protected]
成都埃法生物科技有限公司028-028-85142057 19983342022 · [email protected]

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추가 설명 · 1건

정의ChEBI: An organic heterotetracyclic compound and guaianolide sesquiterpene lactone that is acrylic acid which is substituted at position 2 by a 4-hydroxy-3,8-dimethyl-1,3a,4,5,6,7-hexahydroazulen-5-yl group in which the double bond in the 7-membered ring has been epoxidised and in which the hydroxy group and the carboxy group have undergone formal condensation to give the corresponding gamma-lactone. It is found in Artemisia glabella. Arglabin-DMA HCl, the hydrochloride salt of the add ct resulting from the conjugate addition of dimethylamine to the ene-lactone moiety, has been successfully used in Khazakhstan for the treatment of breast, colon, ovarian and lung cancers.