Anisomycin

Identification

Name
Anisomycin
Accession Number
DB07374
Type
Small Molecule
Groups
Experimental
Description

Anisomycin, also known as flagecidin, is an antibiotic produced by Streptomyces griseolus which inhibits protein synthesis. Partial inhibition of DNA synthesis occurs at anisomycin concentrations that effect 95% inhibition of protein synthesis. Anisomycin can activate stress-activated protein kinases, MAP kinase and other signal transduction pathways.

Structure
Thumb
Synonyms
Not Available
External IDs
NSC-76712
Categories
UNII
6C74YM2NGI
CAS number
22862-76-6
Weight
Average: 265.305
Monoisotopic: 265.131408101
Chemical Formula
C14H19NO4
InChI Key
YKJYKKNCCRKFSL-RDBSUJKOSA-N
InChI
InChI=1S/C14H19NO4/c1-9(16)19-14-12(15-8-13(14)17)7-10-3-5-11(18-2)6-4-10/h3-6,12-15,17H,7-8H2,1-2H3/t12-,13+,14+/m1/s1
IUPAC Name
(2R,3S,4S)-4-hydroxy-2-[(4-methoxyphenyl)methyl]pyrrolidin-3-yl acetate
SMILES
[H][[email protected]]1(O)CN[[email protected]]([H])(CC2=CC=C(OC)C=C2)[[email protected]]1([H])OC(C)=O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
U60S ribosomal protein L10-likeNot AvailableHuman
U60S ribosomal protein L13aNot AvailableHuman
U60S ribosomal protein L23Not AvailableHuman
U60S ribosomal protein L15Not AvailableHuman
U60S ribosomal protein L19Not AvailableHuman
U60S ribosomal protein L23aNot AvailableHuman
UProbable ribosome biogenesis protein RLP24Not AvailableHuman
U60S ribosomal protein L26-like 1Not AvailableHuman
U60S ribosomal protein L8Not AvailableHuman
U60S ribosomal protein L37Not AvailableHuman
U60S ribosomal protein L3Not AvailableHuman
U60S ribosomal protein L11Not AvailableHuman
UNHP2-like protein 1Not AvailableHuman
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
BCG vaccineThe therapeutic efficacy of BCG vaccine can be decreased when used in combination with Anisomycin.Investigational
Picosulfuric acidThe therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with Anisomycin.Approved
Food Interactions
Not Available

References

General References
Not Available
External Links
KEGG Compound
C11281
PubChem Compound
253602
PubChem Substance
99443845
ChemSpider
222267
BindingDB
63919
ChEBI
338412
ChEMBL
CHEMBL423192
HET
ANM
Wikipedia
Anisomycin
PDB Entries
1k73 / 3cc4 / 5fcj

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility2.07 mg/mLALOGPS
logP0.97ALOGPS
logP0.73ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)13.77ChemAxon
pKa (Strongest Basic)9.22ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area67.79 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity69.3 m3·mol-1ChemAxon
Polarizability28.19 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.811
Blood Brain Barrier-0.9275
Caco-2 permeable-0.7046
P-glycoprotein substrateSubstrate0.6533
P-glycoprotein inhibitor INon-inhibitor0.9551
P-glycoprotein inhibitor IINon-inhibitor0.8909
Renal organic cation transporterNon-inhibitor0.8154
CYP450 2C9 substrateNon-substrate0.787
CYP450 2D6 substrateNon-substrate0.6997
CYP450 3A4 substrateNon-substrate0.5
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.907
CYP450 2D6 inhibitorInhibitor0.8932
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.9726
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8681
Ames testNon AMES toxic0.832
CarcinogenicityNon-carcinogens0.9613
BiodegradationNot ready biodegradable0.8313
Rat acute toxicity3.5352 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9043
hERG inhibition (predictor II)Non-inhibitor0.7773
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-00di-3910000000-ee44d251825b41bdcbdd

Taxonomy

Description
This compound belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Phenol ethers
Sub Class
Anisoles
Direct Parent
Anisoles
Alternative Parents
Phenoxy compounds / Methoxybenzenes / Alkyl aryl ethers / Aralkylamines / Pyrrolidines / Secondary alcohols / 1,2-aminoalcohols / Amino acids and derivatives / Carboxylic acid esters / Monocarboxylic acids and derivatives
show 6 more
Substituents
Phenoxy compound / Anisole / Methoxybenzene / Alkyl aryl ether / Aralkylamine / Monocyclic benzene moiety / Pyrrolidine / Amino acid or derivatives / 1,2-aminoalcohol / Carboxylic acid ester
show 19 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
organonitrogen heterocyclic antibiotic, monohydroxypyrrolidine (CHEBI:338412)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Structural constituent of ribosome
Specific Function
May play a role in compensating for the inactivated X-linked gene during spermatogenesis.
Gene Name
RPL10L
Uniprot ID
Q96L21
Uniprot Name
60S ribosomal protein L10-like
Molecular Weight
24518.595 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Structural constituent of ribosome
Specific Function
Associated with ribosomes but is not required for canonical ribosome function and has extra-ribosomal functions. Component of the GAIT (gamma interferon-activated inhibitor of translation) complex ...
Gene Name
RPL13A
Uniprot ID
P40429
Uniprot Name
60S ribosomal protein L13a
Molecular Weight
23577.11 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Structural constituent of ribosome
Specific Function
Not Available
Gene Name
RPL23
Uniprot ID
P62829
Uniprot Name
60S ribosomal protein L23
Molecular Weight
14865.335 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Structural constituent of ribosome
Specific Function
Not Available
Gene Name
RPL15
Uniprot ID
P61313
Uniprot Name
60S ribosomal protein L15
Molecular Weight
24145.945 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Structural constituent of ribosome
Specific Function
Not Available
Gene Name
RPL19
Uniprot ID
P84098
Uniprot Name
60S ribosomal protein L19
Molecular Weight
23465.775 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Structural constituent of ribosome
Specific Function
This protein binds to a specific region on the 26S rRNA.
Gene Name
RPL23A
Uniprot ID
P62750
Uniprot Name
60S ribosomal protein L23a
Molecular Weight
17694.885 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Structural constituent of ribosome
Specific Function
Involved in the biogenesis of the 60S ribosomal subunit. Ensures the docking of GTPBP4/NOG1 to pre-60S particles (By similarity).
Gene Name
RSL24D1
Uniprot ID
Q9UHA3
Uniprot Name
Probable ribosome biogenesis protein RLP24
Molecular Weight
19621.02 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Structural constituent of ribosome
Specific Function
Not Available
Gene Name
RPL26L1
Uniprot ID
Q9UNX3
Uniprot Name
60S ribosomal protein L26-like 1
Molecular Weight
17256.2 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Structural constituent of ribosome
Specific Function
Not Available
Gene Name
RPL8
Uniprot ID
P62917
Uniprot Name
60S ribosomal protein L8
Molecular Weight
28024.52 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Structural constituent of ribosome
Specific Function
Binds to the 23S rRNA.
Gene Name
RPL37
Uniprot ID
P61927
Uniprot Name
60S ribosomal protein L37
Molecular Weight
11077.81 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Structural constituent of ribosome
Specific Function
The L3 protein is a component of the large subunit of cytoplasmic ribosomes.
Gene Name
RPL3
Uniprot ID
P39023
Uniprot Name
60S ribosomal protein L3
Molecular Weight
46108.72 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Structural constituent of ribosome
Specific Function
Binds to 5S ribosomal RNA (By similarity). Required for rRNA maturation and formation of the 60S ribosomal subunits. Promotes nucleolar location of PML (By similarity).
Gene Name
RPL11
Uniprot ID
P62913
Uniprot Name
60S ribosomal protein L11
Molecular Weight
20252.235 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
U4atac snrna binding
Specific Function
Binds to the 5'-stem-loop of U4 snRNA and may play a role in the late stage of spliceosome assembly. The protein undergoes a conformational change upon RNA-binding.
Gene Name
SNU13
Uniprot ID
P55769
Uniprot Name
NHP2-like protein 1
Molecular Weight
14173.405 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]

Drug created on September 15, 2010 15:20 / Updated on December 01, 2017 15:50