기본 정보
- CAS
30562-34-6- 표준 SMILES
COC1=C2C[C@@H](C)C[C@H](OC)[C@H](O)[C@@H](C)/C=C(\C)[C@H](OC(N)=O)[C@@H](OC)/C=C\C=C(/C)C(=O)NC(=CC1=O)C2=O- InChIKey
QTQAWLPCGQOSGP-KSRBKZBZSA-N- 분자식
- C29H40N2O9
- 평균 분자량
- 560.6 g/mol
- 단동위원소 질량
- 560.27338086
개요
Geldanamycin is an ansamycin consisting of a 19-membered macrocyle incorporating a benzoquinone ring and a lactam functionality. It shows antimicrobial activity against many Gram-positive and some Gram-negative bacteria. It has a role as an antiviral agent, an antimicrobial agent, an antineoplastic agent, a Hsp90 inhibitor and a cysteine protease inhibitor. It is a member of 1,4-benzoquinones, an ansamycin, a carbamate ester and an organic heterobicyclic compound.
이름 및 식별자
- 우선 이름
- Geldanamycin
- IUPAC
- [(4E,6Z,8S,9S,10E,12S,13R,14S,16R)-13-hydroxy-8,14,19-trimethoxy-4,10,12,16-tetramethyl-3,20,22-trioxo-2-azabicyclo[16.3.1]docosa-1(21),4,6,10,18-pentaen-9-yl] carbamate
- 영어명
- Geldanamycin
- 분자식
- C29H40N2O9
- 분자량
- 560.64
이름 및 동의어
이름 더 보기
데이터베이스 식별자
- CAS
30562-34-6、368455-10-1- PubChem CID
- 5288382
- DTXSID
DTXSID7042691- ChEMBL
CHEMBL278315- ChEBI
CHEBI:5292- UNII
- Z3K3VJ16KU
- EC Number
- 805-356-8
물성
구조 계산 물성
- XLogP
- 2
- 극성 표면적
- 163 Ų
- 수소 결합 공여자 수
- 3
- 수소 결합 수용자 수
- 9
- 회전 가능 결합 수
- 5
- 무거운 원자 수
- 40
- 형식 전하
- 0
- 복잡도
- 1,150
실험 및 물리화학적 성질
물리화학적 성질
- 녹는점
- 255 °C · 255 °C
- 끓는 점
- 627.87 °C · 627.87°C (rough estimate)
- 밀도
- 1.2443 · 1.2443 (rough estimate)
- 굴절률
- 1.58 · 1.5800 (estimate)
- 인화점
- 87 ℃ · 87℃
- 저장 조건
- -20 °C · -20°C
- 용해도
- DMSO: 용해될 수 있다
- 물리적 상태
- 가루
- 산도 계수 (pKa)
- 8.42 · 8.42±0.70(Predicted)
- 색상
- 노란색에서 주황색으로
- 생물학적 소스
- Streptomyces hygroscopicus
- 안정성
- 2 · 제공된 대로 구매일로부터 2년 동안 안정적입니다. DMSO 용액은 -20°C에서 최대 3개월 동안 보관할 수 있습니다.
- InChIKey
- QTQAWLPCGQOSGP-KSRBKZBZSA-N
- SMILES
- C1(OC)C(=O)C=C2NC(=O)C(C)=CC=C[C@H](OC)[C@@H](OC(=O)N)C(C)=C[C@H](C)[C@@H](O)[C@@H](OC)C[C@H](C)CC=1C2=O |c:13,t:11,24|
화학적 성질
Yellow to Orange Powder
안전 및 규제
GHS 분류
GHS Classification
This chemical does not meet GHS hazard criteria for 100% (3 of 3) of all reports.
Not Classified
Aggregated GHS information provided per 3 reports by companies from 1 notifications to the ECHA C&L Inventory.
유해성 정보
안전 데이터
- wgk
- 2
- rtecs
- LX8920000
- HS 번호
- 29419090
- risk_code
- 36/37/38
- hazard_code
- T,Xi
- safety_code
- 26-27-36/37/39-24/25
- 스토리지 클래스
- 11 - Combustible Solids
화학 및 산업
약리 정보
MeSH Pharmacological Classification
Chemical substances, produced by microorganisms, inhibiting or preventing the proliferation of neoplasms.
Agents used in the prophylaxis or therapy of VIRUS DISEASES. Some of the ways they may act include preventing viral replication by inhibiting viral DNA polymerase; binding to specific cell-surface receptors and inhibiting viral penetration or uncoating; inhibiting viral protein synthesis; or blocking late stages of virus assembly.
Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.
Exogenous and endogenous compounds which inhibit CYSTEINE ENDOPEPTIDASES.
응용 분야
개요Geldanamycin from Streptomyces hygroscopicus. Geldanamycin is a benzoquinone ansamycin antitumor antibiotic. Geldanamycin binds specifically to Hsp90 (Heat Shock Protein 90) and to its endoplasmic reticulum homologue GP96. The Hsp90 chaperone is required for the activation of several families of eukaryotic protein kinases and nuclear hormone receptors, many of which are proto-oncogenic and play a prominent role in cancer. The geldanamycin antibiotic has antiproliferative and antitumor effects, as it binds to Hsp90, inhibits the Hsp90-mediated conformational maturation/refolding reaction, and results in the degradation of Hsp90 substrates. Hsp90 also plays a key role in regulating the physiology of cells exposed to environmental stress and thus, geldanamycin interferes with cellular stress response. Geldanamycin was found to be a potent antibiotic active at nanomolar concentrations against 60 cell lines as well as in mouse tumor models. It is an inhibitor of proto-oncogenic protein kinases, such as erbB22, EFG receptor tyrosine kinases, and non-receptor tyrosine kinases, such as v-src and Raf-1. In addition, it is a potent inhibitor of the nuclear hormone receptor family including the estrogen and androgen hormone receptors.
용도Geldanamycin is a potent antitumor antibiotic active at nanomolar concentration against 60 cell lines. It binds specifically to the heat shock protein Hsp90 and to its endoplasmic reticulum homologue GP96, and thus interferes with conformational maturation of proteins and the cellular stress response. In addition, it is a potent inhibitor of the nuclear hormone receptor family.
일반 설명Chemical structure: benzenoid
상·하류 제품 정보
하류 제품
공급사101 곳
추가 설명
정의ChEBI: An ansamycin consisting of a 19-membered macrocyle incorporating a benzoquinone ring and a lactam functionality. It shows antimicrobial activity against many Gram-positive and some Gram-negative bacteria.
관련 반응
화합물 노트
불러오는 중…