Rapamycin - Moligand™, ≥95%(HPLC) , CAS No.53123-88-9

CAS: 53123-88-9 Cat. No.: S293790 分子式: C₅₁H₇₉NO₁₃ 分子量: 914.19 EC番号: 610-965-5

GRADE & PURITY Moligand™, ≥95%(HPLC)

Synonyms

AY 22989 | AY-22989 | CHEBI:9168 | EC 610-965-5 | HMS2089A21 | RAPA | (1R,9S,12S,15R,16E,18R,19R,21R,23S,24E,26E,28E,30S,32S,35R)-1,18-dihydroxy-12-{(2S)-1-[(1S,3R,4R)-4-hydroxy-3-methoxycyclohexyl]propan-2-yl}-19,30-dimethoxy-15,17,21,23,29,35-hexamethyl

Storage

Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

概要

Anti-fungal and immunosuppressant. Selectively inhibits the mammalian target of rapamycin (mTOR) and blocks the subsequent activation of p70 S6 kinase (IC50 = 50 pM). Specifically inhibits mTORC1, but mTORC2 that phosphorylates Akt at Ser473 appears to be insensitive to rapamycin. Prevents the translational activation of IGF-II. Also prevents resting T-cells from entering the cell cycle, but does not directly arrest cell cycle progression. Shown to inhibit later signaling events, such as p110Rb phosphorylation, p34cdc2 kinase activation, and cyclin A synthesis. Exhibits strong binding to FK-506 binding proteins. Also reported to induce apoptosis in a murine B-cell line, to inhibit lymphokine-induced cell proliferation at the G1 phase, and to irreversibly arrest Saccharomyces cerevisiae cells in the G1 phase.

Specifications

同義語

AY 22989 | AY-22989 | CHEBI:9168 | EC 610-965-5 | HMS2089A21 | RAPA | (1R,9S,12S,15R,16E,18R,19R,21R,23S,24E,26E,28E,30S,32S,35R)-1,18-dihydroxy-12-{(2S)-1-[(1S,3R,4R)-4-hydroxy-3-methoxycyclohexyl]propan-2-yl}-19,30-dimethoxy-15,17,21,23,29,35-hexamethyl

仕様と純度

Moligand™, ≥95%(HPLC)

生化学的・生理学的メカニズム

A macrocyclic triene antibiotic that binds to and inhibits the molecular target of rapamycin (mTOR). It forms a complex with FKBP12 that binds to and inhibits the molecular target of rapamycin (mTOR). Rapamycin is a potent immunosuppressant and has antica

保管条件

Store at -20°C,Argon charged

入荷

Ice chest + Ice pads

この製品は冷冷この冷このこの製品の運送が必要です。地上およびその他の経済サービスは利用できません。

等級

Moligand™

純度

≥95%(HPLC)

名前と識別子

パブケム・シド

504763502

パブケム・シド・ウル

https://pubchem.ncbi.nlm.nih.gov/substance/504763502

カノニカル・スマイル

CC1CCC2CC(C(=CC=CC=CC(CC(C(=O)C(C(C(=CC(C(=O)CC(OC(=O)C3CCCCN3C(=O)C(=O)C1(O2)O)C(C)CC4CCC(C(C4)OC)O)C)C)O)OC)C)C)C)OC

IUPAC Name

(1R,9S,12S,15R,16E,18R,19R,21R,23S,24E,26E,28E,30S,32S,35R)-1,18-dihydroxy-12-[(2R)-1-[(1S,3R,4R)-4-hydroxy-3-methoxycyclohexyl]propan-2-yl]-19,30-dimethoxy-15,17,21,23,29,35-hexamethyl-11,36-dioxa-4-azatricyclo[30.3.1.04,9]hexatriaconta-16,24,26,28-tetraene-2,3,10,14,20-pentone

InChIKey

QFJCIRLUMZQUOT-HPLJOQBZSA-N

INCHI

1S/C51H79NO13/c1-30-16-12-11-13-17-31(2)42(61-8)28-38-21-19-36(7)51(60,65-38)48(57)49(58)52-23-15-14-18-39(52)50(59)64-43(33(4)26-37-20-22-40(53)44(27-37)62-9)29-41(54)32(3)25-35(6)46(56)47(63-10)45(55)34(5)24-30/h11-13,16-17,25,30,32-34,36-40,42-44,46-47,53,56,60H,14-15,18-24,26-29H2,1-10H3/b13-11+,16-12+,31-17+,35-25+/t30-,32-,33-,34-,36-,37+,38+,39+,40-,42+,43+,44-,46-,47+,51-/m1/s1

異性体SMILES

C[C@@H]1CC[C@H]2C[C@@H](/C(=C/C=C/C=C/[C@H](C[C@H](C(=O)[C@@H]([C@@H](/C(=C/[C@H](C(=O)C[C@H](OC(=O)[C@@H]3CCCCN3C(=O)C(=O)[C@@]1(O2)O)[C@H](C)C[C@@H]4CC[C@H]([C@@H](C4)OC)O)C)/C)O)OC)C)C)/C)OC

RTECS

VE6250000

分子量

914.19

Reaxy-Rn

5848501

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • 分類 Macrolide lactams

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• 分類: Macrolide lactams
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Macrolide lactams
• Alternative Parents: Alpha amino acid esters Macrolides and analogues Cyclohexanols Piperidines Oxanes Tertiary carboxylic acid amides Carboxylic acid esters Cyclic alcohols and derivatives Cyclic ketones Hemiacetals Lactams Lactones Azacyclic compounds Dialkyl ethers Oxacyclic compounds Monocarboxylic acids and derivatives Hydrocarbon derivatives Organopnictogen compounds Organonitrogen compounds Organic oxides
• Molecular Framework: Aliphatic heteropolycyclic compounds
• Substituents: Macrolide lactam - Alpha-amino acid ester - Macrolide - Alpha-amino acid or derivatives - Cyclohexanol - Oxane - Piperidine - Cyclic alcohol - Tertiary carboxylic acid amide - Cyclic ketone - Secondary alcohol - Carboxamide group - Carboxylic acid ester - Hemiacetal - Ketone - Lactam - Lactone - Organoheterocyclic compound - Azacycle - Carboxylic acid derivative - Oxacycle - Dialkyl ether - Ether - Monocarboxylic acid or derivatives - Organopnictogen compound - Alcohol - Organic oxygen compound - Carbonyl group - Organooxygen compound - Organonitrogen compound - Organic nitrogen compound - Hydrocarbon derivative - Organic oxide - Aliphatic heteropolycyclic compound
• 説明: This compound belongs to the class of organic compounds known as macrolide lactams. These are cyclic polyketides containing both a cyclic amide and a cyclic ester group.
• External Descriptors: Plyenes

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

関連ターゲット（人間）

FKBP1A Tclin Peptidyl-prolyl cis-trans isomerase FKBP1A (10 Activities)

Discover Target: FKBP1A

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

FKBP1B Tchem Peptidyl-prolyl cis-trans isomerase FKBP1B (1 Activities)

Discover Target: FKBP1B

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

FKBP5 Tchem Peptidyl-prolyl cis-trans isomerase FKBP5 (1 Activities)

Discover Target: FKBP5

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

EIF4E Tchem Eukaryotic translation initiation factor 4E (1 Activities)

Discover Target: EIF4E

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

PDCD4 Tchem Programmed cell death protein 4 (1 Activities)

Discover Target: PDCD4

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

MTOR Tclin Serine/threonine-protein kinase mTOR (7 Activities)

Discover Target: MTOR

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

化学的性質と物理的性質

• 溶解度: Soluble in DMSO at 50mg/ml or methanol at 25mg/mlSoluble in alcohol, dimethyl sulfoxide and dimethyl formamide. Insoluble in water.
• 感度: Heat sensitive.
• 比旋光度［α］: -150° (C=0.2,MeOH)
• 融点（°C）: 177 °C(dec.)
• 分子量: 914.200 g/mol
• XLogP3: 6.000
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 13
• Rotatable Bond Count: 6
• Exact Mass: 913.555 Da
• Monoisotopic Mass: 913.555 Da
• Topological Polar Surface Area: 195.000 Ų
• Heavy Atom Count: 65
• Formal Charge: 0
• Complexity: 1760.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 15
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 4
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 4
• Covalently-Bonded Unit Count: 1