sirolimus (Q32089)

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pharmaceutical drug
  • rapamycin
  • WY-090217
  • AY-22989
  • (-)-rapamycin
edit
Language Label Description Also known as
English
sirolimus
pharmaceutical drug
  • rapamycin
  • WY-090217
  • AY-22989
  • (-)-rapamycin

Statements

subclass of
alkaloid
0 references
(32RS)-rapamycin
0 references
mass
913.555142 dalton
1 reference
stated in
PubChem
PubChem CID
5284616
language of work or name
English
title
Rapamycin (English)
retrieved
21 September 2016
chemical formula
C₅₁H₇₉NO₁₃
1 reference
stated in
PubChem
PubChem CID
5284616
language of work or name
English
title
Rapamycin (English)
retrieved
21 September 2016
canonical SMILES
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
1 reference
stated in
PubChem
PubChem CID
5284616
language of work or name
English
title
Rapamycin (English)
retrieved
21 September 2016
isomeric SMILES
CO[C@@H]1C[C@H](C[C@@H](C)[C@@H]2CC(=O)[C@H](C)\C=C(C)\[C@@H](O)[C@@H](OC)C(=O)[C@H](C)C[C@H](C)\C=C\C=C\C=C(C)\[C@H](C[C@@H]3CC[C@@H](C)[C@@](O)(O3)C(=O)C(=O)N4CCCC[C@H]4C(=O)O2)OC)CC[C@H]1O
1 reference
stated in
Global Substance Registration System
UNII
W36ZG6FT64
retrieved
14 February 2018
found in taxon
Streptomyces hygroscopicus
19 references
stated in
Incorporation of acetate, propionate, and methionine into rapamycin by Streptomyces hygroscopicus
stated in
Rapamycin (AY-22,989), a new antifungal antibiotic. II. Fermentation, isolation and characterization.
stated in
Secretion of FK506/FK520 and rapamycin by Streptomyces inhibits the growth of competing Saccharomyces cerevisiae and Cryptococcus neoformans.
stated in
Cytochrome p450 complement (CYPome) of the avermectin-producer Streptomyces avermitilis and comparison to that of Streptomyces coelicolor A3(2).
stated in
Organization of the biosynthetic gene cluster for the macrolide concanamycin A in Streptomyces neyagawaensis ATCC 27449.
stated in
A combined approach of classical mutagenesis and rational metabolic engineering improves rapamycin biosynthesis and provides insights into methylmalonyl-CoA precursor supply pathway in Streptomyces hygroscopicus ATCC 29253.
stated in
Waking up Streptomyces secondary metabolism by constitutive expression of activators or genetic disruption of repressors.
stated in
Effects of dissolved oxygen level on rapamycin production by pellet-form of Streptomyces hygroscopicus
stated in
Studies on process optimization methods for rapamycin production using Streptomyces hygroscopicus ATCC 29253.
stated in
Production of rapamycin in Streptomyces hygroscopicus from glycerol-based media optimized by systemic methodology
stated in
Draft Genome Sequence of Streptomyces iranensis.
stated in
Discovery of actinoplanic acid pathway in reveals a genetically conserved synergism with rapamycin
stated in
Carbon source nutrition of rapamycin biosynthesis in Streptomyces hygroscopicus
stated in
Organisation of the biosynthetic gene cluster for rapamycin in Streptomyces hygroscopicus: analysis of genes flanking the polyketide synthase
stated in
An amplifiable and deletable locus of Streptomyces ambofaciens RP181110 contains a very large gene homologous to polyketide synthase genes
stated in
The pipecolate-incorporating enzyme for the biosynthesis of the immunosuppressant rapamycin--nucleotide sequence analysis, disruption and heterologous expression of rapP from Streptomyces hygroscopicus.
stated in
Effect of nitrogen source on biosynthesis of rapamycin by Streptomyces hygroscopicus
stated in
A second type-I PKS gene cluster isolated from Streptomyces hygroscopicus ATCC 29253, a rapamycin-producing strain
stated in
Isolation and structure of homotemsirolimuses A, B, and C.
Streptomyces iranensis
16 references
stated in
Secretion of FK506/FK520 and rapamycin by Streptomyces inhibits the growth of competing Saccharomyces cerevisiae and Cryptococcus neoformans.
stated in
Cytochrome p450 complement (CYPome) of the avermectin-producer Streptomyces avermitilis and comparison to that of Streptomyces coelicolor A3(2).
stated in
Organization of the biosynthetic gene cluster for the macrolide concanamycin A in Streptomyces neyagawaensis ATCC 27449.
stated in
A combined approach of classical mutagenesis and rational metabolic engineering improves rapamycin biosynthesis and provides insights into methylmalonyl-CoA precursor supply pathway in Streptomyces hygroscopicus ATCC 29253.
stated in
Waking up Streptomyces secondary metabolism by constitutive expression of activators or genetic disruption of repressors.
stated in
Effects of dissolved oxygen level on rapamycin production by pellet-form of Streptomyces hygroscopicus
stated in
Studies on process optimization methods for rapamycin production using Streptomyces hygroscopicus ATCC 29253.
stated in
Production of rapamycin in Streptomyces hygroscopicus from glycerol-based media optimized by systemic methodology
stated in
Draft Genome Sequence of Streptomyces iranensis.
stated in
Discovery of actinoplanic acid pathway in reveals a genetically conserved synergism with rapamycin
stated in
Carbon source nutrition of rapamycin biosynthesis in Streptomyces hygroscopicus
stated in
Organisation of the biosynthetic gene cluster for rapamycin in Streptomyces hygroscopicus: analysis of genes flanking the polyketide synthase
stated in
An amplifiable and deletable locus of Streptomyces ambofaciens RP181110 contains a very large gene homologous to polyketide synthase genes
stated in
The pipecolate-incorporating enzyme for the biosynthesis of the immunosuppressant rapamycin--nucleotide sequence analysis, disruption and heterologous expression of rapP from Streptomyces hygroscopicus.
stated in
Effect of nitrogen source on biosynthesis of rapamycin by Streptomyces hygroscopicus
stated in
A second type-I PKS gene cluster isolated from Streptomyces hygroscopicus ATCC 29253, a rapamycin-producing strain
Streptomyces rapamycinicus
16 references
stated in
Secretion of FK506/FK520 and rapamycin by Streptomyces inhibits the growth of competing Saccharomyces cerevisiae and Cryptococcus neoformans.
stated in
Cytochrome p450 complement (CYPome) of the avermectin-producer Streptomyces avermitilis and comparison to that of Streptomyces coelicolor A3(2).
stated in
Organization of the biosynthetic gene cluster for the macrolide concanamycin A in Streptomyces neyagawaensis ATCC 27449.
stated in
A combined approach of classical mutagenesis and rational metabolic engineering improves rapamycin biosynthesis and provides insights into methylmalonyl-CoA precursor supply pathway in Streptomyces hygroscopicus ATCC 29253.
stated in
Waking up Streptomyces secondary metabolism by constitutive expression of activators or genetic disruption of repressors.
stated in
Effects of dissolved oxygen level on rapamycin production by pellet-form of Streptomyces hygroscopicus
stated in
Studies on process optimization methods for rapamycin production using Streptomyces hygroscopicus ATCC 29253.
stated in
Production of rapamycin in Streptomyces hygroscopicus from glycerol-based media optimized by systemic methodology
stated in
Draft Genome Sequence of Streptomyces iranensis.
stated in
Discovery of actinoplanic acid pathway in reveals a genetically conserved synergism with rapamycin
stated in
Carbon source nutrition of rapamycin biosynthesis in Streptomyces hygroscopicus
stated in
Organisation of the biosynthetic gene cluster for rapamycin in Streptomyces hygroscopicus: analysis of genes flanking the polyketide synthase
stated in
An amplifiable and deletable locus of Streptomyces ambofaciens RP181110 contains a very large gene homologous to polyketide synthase genes
stated in
The pipecolate-incorporating enzyme for the biosynthesis of the immunosuppressant rapamycin--nucleotide sequence analysis, disruption and heterologous expression of rapP from Streptomyces hygroscopicus.
stated in
Effect of nitrogen source on biosynthesis of rapamycin by Streptomyces hygroscopicus
stated in
A second type-I PKS gene cluster isolated from Streptomyces hygroscopicus ATCC 29253, a rapamycin-producing strain
significant drug interaction
legal status (medicine)
boxed warning
1 reference
reference URL
https://nctr-crs.fda.gov/fdalabel/ui/spl-summaries/criteria/343802
title
FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links. (English)
has part(s)
carbon
0 references
hydrogen
0 references
oxygen
0 references
nitrogen
0 references
Commons category
Sirolimus
0 references

Identifiers

HSDB ID
7284
1 reference
stated in
Hazardous Substances Data Bank
HSDB ID
7284
publication date
28 October 2019
title
SIROLIMUS (English)
retrieved
10 May 2021
NSC number
226080
0 references
758664
0 references
EC number
610-965-5
1 reference
stated in
ECHA Substance Infocard database
ECHA Substance Infocard ID
100.107.147
retrieved
27 December 2018
title
(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 (English)
quotation
CAS no.: 53123-88-9 (English)
ECHA Substance Infocard ID
100.107.147
1 reference
stated in
ECHA Substance Infocard database
ECHA Substance Infocard ID
100.107.147
retrieved
27 December 2018
title
(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 (English)
quotation
CAS no.: 53123-88-9 (English)
Nikkaji ID
J137.896A
0 references
ATC code
S01XA23
0 references
KNApSAcK ID
C00018055
0 references
PDB ligand ID
RAP
0 references
DeCS ID
33809
0 references
NE.se ID
sirolimus
0 references
rapamycin
0 references
UNSPSC Code
51201515
0 references
 
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