뉴모칸딘B0

(2R,6S,9S,11R,12R,14aS,15S,20S,23S,25aS)-20-(2-Carbamoyl-1(R)-hydroxyethyl)-23-(1(S),2(S)-dihydroxy-2-(4-hydroxyphenyl)ethyl)-9-(10,12-dimethyltetradecanamido)-2,11,12,15-tetrahydroxy-6-(1(R)-hydroxyethyl)perhydrodipyrrolo(2,1-c:2',1'-l)(1,4,7,10,13,16)hexaazacycloheneicosine-5,8,14,19,22,25-hexaone

HCID 5742645

기본 정보

CAS
135575-42-7
표준 SMILES
CCC(C)CC(C)CCCCCCCCC(=O)N[C@H]1C[C@@H](O)[C@@H](O)NC(=O)[C@@H]2[C@@H](O)CCN2C(=O)[C@H]([C@H](O)CC(N)=O)NC(=O)[C@H]([C@H](O)[C@@H](O)c2ccc(O)cc2)NC(=O)[C@@H]2C[C@@H](O)CN2C(=O)[C@H]([C@@H](C)O)NC1=O
InChIKey
DQXPFAADCTZLNL-ZESADUFFSA-N
분자식
C50H80N8O17
평균 분자량
1,065.2 g/mol

이름 및 식별자

우선 이름
(2R,6S,9S,11R,12R,14aS,15S,20S,23S,25aS)-20-(2-Carbamoyl-1(R)-hydroxyethyl)-23-(1(S),2(S)-dihydroxy-2-(4-hydroxyphenyl)ethyl)-9-(10,12-dimethyltetradecanamido)-2,11,12,15-tetrahydroxy-6-(1(R)-hydroxyethyl)perhydrodipyrrolo(2,1-c:2',1'-l)(1,4,7,10,13,16)hexaazacycloheneicosine-5,8,14,19,22,25-hexaone
IUPAC
N-[(3S,6S,9S,11R,15S,18S,20R,21R,24S,25S)-3-[(1R)-3-amino-1-hydroxy-3-oxopropyl]-6-[(1S,2S)-1,2-dihydroxy-2-(4-hydroxyphenyl)ethyl]-11,20,21,25-tetrahydroxy-15-[(1R)-1-hydroxyethyl]-2,5,8,14,17,23-hexaoxo-1,4,7,13,16,22-hexazatricyclo[22.3.0.09,13]heptacosan-18-yl]-10,12-dimethyltetradecanamide
현지명
뉴모칸딘B0
영어명
Pneumocandin B0
분자식
C50H80N8O17
분자량
1065.22

이름 및 동의어

(2R,6S,9S,11R,12R,14aS,15S,20S,23S,25aS)-20-[2-Carbamoyl-1(R)-hydroxyethyl]-23-[1(S),2(S)-dihydroxy-2-(4-hydroxyphenyl)ethyl]-9-(10,12-dimethyltetradecanamido)-2,11,12,15-tetrahydroxy-6-[1(R)-hydroxyethyl]perhydrodipyrrolo[2,1-c:2',1'-l][1,4,7,10,13,16]hexaazacycloheneicosine-5,8,14,19,22,25-hexaone(2R,6S,9S,11R,12R,14aS,15S,20S,23S,25aS)-20-(2-Carbamoyl-1(R)-hydroxyethyl)-23-(1(S),2(S)-dihydroxy-2-(4-hydroxyphenyl)ethyl)-9-(10,12-dimethyltetradecanamido)-2,11,12,15-tetrahydroxy-6-(1(R)-hydroxyethyl)perhydrodipyrrolo(2,1-c:2',1'-l)(1,4,7,10,13,16)hexaazacycloheneicosine-5,8,14,19,22,25-hexaoneRefChem:397684629-746-0Pneumocandin BoCHEMBL269311C50H80N8O17N-[(3S,6S,9S,11R,15S,18S,20R,21R,24S,25S)-3-[(1R)-3-Amino-1-hydroxy-3-oxopropyl]-6-[(1S,2S)-1,2-dihydroxy-2-(4-hydroxyphenyl)ethyl]-11,20,21,25-tetrahydroxy-15-[(1R)-1-hydroxyethyl]-2,5,8,14,17,23-hexaoxo-1,4,7,13,16,22-hexazatricyclo[22.3.0.09,13]heptacosan-18-yl]-10,12-dimethyltetradecanamideHydroxy EchinocandinSCHEMBL8444763DQXPFAADCTZLNL-ZESADUFFSA-NGLXC-20110
이름 더 보기
뉴모칸딘B0CFAPneumocardin B0Caspofungin PneuMocandin B0 IMpurityCS-492L-688786CFA/ CBR01Novocontin B0PneumocandinBoneumocandin B0
EX-A1768BDBM50043897FP76367PD11815310,12-Dimethyl-tetradecanoic acid [3-(2-carbamoyl-1-hydroxy-ethyl)-6-[1,2-dihydroxy-2-(4-hydroxy-phenyl)-ethyl]-11,20,21,25-tetrahydroxy-15-(1-hydroxy-ethyl)-2,5,8,14,17,23-hexaoxo-1,4,7,13,16,22-hexaaza-tricyclo[22.3.0.0*9,13*]heptacos-18-yl]-amide1N-[20-(2-carbamoyl-1-hydroxyethyl)-23-[1,2-dihydroxy-2-(4-hydroxyphenyl)ethyl]-2,11,12,15-tetrahydroxy-6-(1-hydroxyethyl)-5,8,14,19,22,25-hexaoxoperhydrodipyrrolo[2,1-c:2,1-l][1,4,7,10,13,16]hexaazacyclohenicosin-9-yl]-10,12-dimethyltetradecanamN-((2R,6S,9S,11R,12R,14aS,15S,20S,23S,25aS)-20-((R)-3-amino-1-hydroxy-3-oxopropyl)-23-((1S,2S)-1,2-dihydroxy-2-(4-hydroxyphenyl)ethyl)-2,11,12,15-tetrahydroxy-6-((R)-1-hydroxyethyl)-5,8,14,19,22,25-hexaoxotetracosahydro-1H-dipyrrolo[2,1-c:2',1'-l][1,4,7,10,13,16]hexaazacyclohenicosin-9-yl)-10,12-dimethyltetradecanamideN-[(3S,6S,9S,11R,15S,18S,20R,21R,24S,25S)-3-[(1R)-3-amino-1-hydroxy-3-oxo-propyl]-6-[(1S,2S)-1,2-dihydroxy-2-(4-hydroxyphenyl)ethyl]-11,20,21,25-tetrahydroxy-15-[(1R)-1-hydroxyethyl]-2,5,8,14,17,23-hexaoxo-1,4,7,13,16,22-hexazatricyclo[22.3.0.09,13]heptacosan-18-yl]-10,12-dimethyl-tetradecanamide

데이터베이스 식별자

CAS
135575-42-7
PubChem CID
5742645
ChEMBL
CHEMBL269311
Nikkaji
J613.168I

물성

구조 계산 물성

XLogP
0.5
극성 표면적
411 Ų
수소 결합 공여자 수
15
수소 결합 수용자 수
17
회전 가능 결합 수
20
무거운 원자 수
75

물리화학적 성질

녹는점
230 °C · >230°C (dec.)
끓는 점
1442.9 · 1442.9±65.0 °C(Predicted)
밀도
1.41 · 1.41±0.1 g/cm3(Predicted)
저장 조건
-20 °C · Sealed in dry,Store in freezer, under -20°C
용해도
DMSO(약간 용해됨), 메탄올(약간 용해됨)
산도 계수 (pKa)
9.86 · 9.86±0.26(Predicted)

안전 및 규제

안전 데이터

HS 번호
2941.90.3000

화학 및 산업

응용 분야 · 3건

개요Pneumocandin B0 is an antifungal lipopeptide that acts by inhibiting the synthesis of β-(1,3)-D-glucan, a component of fungal cell walls (IC50s = 70 and 67 ng/ml for inhibiting glucan synthase in C. albicans and A. fumigatus, respectively). It can be used to synthesize the echinocandin caspofungin acetate .

용도Pneumocandin B0 is the major analogue of a family of lipopeptides isolated from several species of several different genera, such as Cryptosporiopsis, Glarea and Pezicula. Pneumocandin B0 is a potent antifungal and acts by inhibition of the synthesis of β-(1,3)-D-glucan, an essential component of the cell wall of susceptible fungi.

일반 설명Pneumocandin B0, the precursor of the antifungal drug caspofungin, is a lipohexapeptide produced by the fungus Glarea lozoyensis. Oxidative stress and the resulting reactive oxygen species (ROS) are involved in regulating the biosynthesis of it. Acetyl-CoA and NADPH are major factors limiting the biosynthesis of pneumocandin B0. Other metabolites, such as pyruvate, α-ketoglutaric acid, lactate, unsaturated fatty acids, and metabolite γ-aminobutyric acid, also play an important role in the biosynthesis of pneumocandin B0 and cell growth[1-2].

공급사100 곳

北京华美互利生物化工010-56205725 · [email protected]
Shandong chuangyingchemical Co., Ltd.18853181302 · [email protected]
HubeiwidelychemicaltechnologyCo.,Ltd18627774460 · [email protected]
合肥翰刚医药科技有限公司+8618062405514 · [email protected]
广州隽沐生物科技股份有限公司020-36607679; 13502246435 · [email protected]
추가 설명 · 1건

정의ChEBI: An echinocandin initially isolated as a very minor bioactive fermentation product of Glarea lozoyensis (originally known as Zalerion arboricola). Subsequent random mutagenesis work and optimisation of the fermentation medium permi ted the industrial production of pneumocandin B0, which is used as the starting point for the synthesis of the antifungal drug caspofungin.

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