Geldanamycin

HCID 5288382

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

geldanamycin30562-34-6geldanomycinZ3K3VJ16KUNSC-122750CHEBI:5292DTXSID7042691[(3R,5S,6R,7S,8E,10S,11S,12Z,14E)-6-hydroxy-5,11,21-trimethoxy-3,7,9,15-tetramethyl-16,20,22-trioxo-17-azabicyclo[16.3.1]docosa-1(21),8,12,14,18-pentaen-10-yl] carbamateAntibiotic U 29135[(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] carbamateAntibiotic (U-29,135)NSC212518
이름 더 보기
GAStreptomyces hygroscopicus[(4Z,6E,8R,9R,10Z,12R,13R,14R,16R)-13-Hydroxy-8,14,19-trimethoxy-4,10,12,16-tetramethyl-3,20,22-trioxo-2-azabicyclo[16.3.1]docosa-4,6,10,18,21-pentaen-9-yl] carbamate(4E,6Z,8S,9S,10E,12S,13R,14S,16R)-9-[(Aminocarbonyl)oxy]-13-hydroxy-8,14,19-trimethoxy-4,10,12,16-tetramethyl-2-azabicyclo[16.3.1]docosa-4,6,10,18,21(1)-pentene-3,20,22-trioneCS-503CP-122634NSC 212518GeldamycinGeldanamyCln
((3R,5S,6R,7S,8E,10S,11S,12Z,14E)-6-hydroxy-5,11,21-trimethoxy-3,7,9,15-tetramethyl-16,20,22-trioxo-17-azabicyclo(16.3.1)docosa-1(21),8,12,14,18-pentaen-10-yl) carbamate((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) carbamateRefChem:142823DTXCID5022691805-356-8NSC122750MFCD00274570U-29135

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

실험 및 물리화학적 성질

DrugsPharmaceuticals -> Antibiotics

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

화학적 성질

Yellow to Orange Powder

안전 및 규제

GHS 분류

GHS Classification · 3건

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

Hazard Classes and CategoriesNot Classified

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

화학 및 산업

약리 정보

MeSH Pharmacological Classification · 4건

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 · 3건

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

공급사101 곳

北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
Baoji Guokang Healthchem co.,ltd+8615604608665 15604608665 · [email protected]
上海如吉生物科技发展有限公司+86-21-65211385-8001 36031160 · [email protected]

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

22건

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