Identification

Name
Bafilomycin A1
Accession Number
DB06733
Type
Small Molecule
Groups
Experimental
Description

The bafilomycins are a family of toxic macrolide antibiotic derived from Streptomyces griseus. These compounds all appear in the same fermentation and have quite similar biological activity. Bafilomycins are specific inhibitors of vacuolar-type H+-ATPase. (V-ATPase). The most used bafilomycin is bafilomycin A1. This is a useful tool as it can prevent the re-acidification of synaptic vesicles once they have undergone exocytosis. [Wikipedia]

Structure
Thumb
Synonyms
Not Available
Categories
UNII
Not Available
CAS number
88899-55-2
Weight
Average: 622.84
Monoisotopic: 622.408083448
Chemical Formula
C35H58O9
InChI Key
XDHNQDDQEHDUTM-JQWOJBOSSA-N
InChI
InChI=1S/C35H58O9/c1-19(2)32-24(7)27(36)18-35(40,44-32)26(9)31(38)25(8)33-28(41-10)14-12-13-20(3)15-22(5)30(37)23(6)16-21(4)17-29(42-11)34(39)43-33/h12-14,16-17,19,22-28,30-33,36-38,40H,15,18H2,1-11H3/b14-12+,20-13+,21-16+,29-17-/t22-,23+,24-,25-,26-,27+,28-,30-,31+,32+,33+,35+/m0/s1
IUPAC Name
(3Z,5E,7R,8S,9S,11E,13E,15S,16R)-16-[(2S,3R,4S)-4-[(2R,4R,5S,6R)-2,4-dihydroxy-5-methyl-6-(propan-2-yl)oxan-2-yl]-3-hydroxypentan-2-yl]-8-hydroxy-3,15-dimethoxy-5,7,9,11-tetramethyl-1-oxacyclohexadeca-3,5,11,13-tetraen-2-one
SMILES
CO[C@H]1\C=C\C=C(C)\C[C@H](C)[C@H](O)[C@H](C)\C=C(/C)\C=C(OC)\C(=O)O[C@@H]1[C@@H](C)[C@@H](O)[C@H](C)[C@@]1(O)C[C@@H](O)[C@H](C)[C@H](O1)C(C)C

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action

The bafilomycins are a family of toxic macrolide antibiotic derived from Streptomyces griseus. These compounds all appear in the same fermentation and have quite similar biological activity. Bafilomycins are specific inhibitors of vacuolar-type H+-ATPase. (V-ATPase).

TargetActionsOrganism
AV-type proton ATPase catalytic subunit A
inhibitor
Human
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
DrugInteraction
AcebutololThe serum concentration of Acebutolol can be increased when it is combined with Bafilomycin A1.
Acetylsalicylic acidThe serum concentration of Acetylsalicylic acid can be increased when it is combined with Bafilomycin A1.
AlitretinoinThe serum concentration of Alitretinoin can be increased when it is combined with Bafilomycin A1.
AmitriptylineThe serum concentration of Amitriptyline can be increased when it is combined with Bafilomycin A1.
AmrinoneThe therapeutic efficacy of Bafilomycin A1 can be increased when used in combination with Amrinone.
Ascorbic acidThe serum concentration of Ascorbic acid can be increased when it is combined with Bafilomycin A1.
AzimilideThe therapeutic efficacy of Bafilomycin A1 can be increased when used in combination with Azimilide.
BetamethasoneThe serum concentration of Betamethasone can be increased when it is combined with Bafilomycin A1.
CarbamazepineThe serum concentration of Carbamazepine can be increased when it is combined with Bafilomycin A1.
ChlorambucilThe serum concentration of Chlorambucil can be increased when it is combined with Bafilomycin A1.
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
6436223
PubChem Substance
347827783
ChemSpider
4642865
BindingDB
50064186
ChEBI
22689
ChEMBL
CHEMBL290814
Wikipedia
Bafilomycin
MSDS
Download (48 KB)

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 Solubility0.0155 mg/mLALOGPS
logP3.89ALOGPS
logP5.08ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)11.69ChemAxon
pKa (Strongest Basic)-0.73ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area134.91 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity174.53 m3·mol-1ChemAxon
Polarizability69.33 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
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

Taxonomy

Description
This compound belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members.
Kingdom
Organic compounds
Super Class
Phenylpropanoids and polyketides
Class
Macrolides and analogues
Sub Class
Not Available
Direct Parent
Macrolides and analogues
Alternative Parents
Oxanes / Enoate esters / Secondary alcohols / Lactones / Hemiacetals / Oxacyclic compounds / Monocarboxylic acids and derivatives / Dialkyl ethers / Organic oxides / Hydrocarbon derivatives
show 1 more
Substituents
Macrolide / Oxane / Alpha,beta-unsaturated carboxylic ester / Enoate ester / Carboxylic acid ester / Hemiacetal / Lactone / Secondary alcohol / Carboxylic acid derivative / Dialkyl ether
show 11 more
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
macrolide antibiotic, cyclic hemiketal, oxanes (CHEBI:22689)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Proton-transporting atpase activity, rotational mechanism
Specific Function
Catalytic subunit of the peripheral V1 complex of vacuolar ATPase. V-ATPase vacuolar ATPase is responsible for acidifying a variety of intracellular compartments in eukaryotic cells.
Gene Name
ATP6V1A
Uniprot ID
P38606
Uniprot Name
V-type proton ATPase catalytic subunit A
Molecular Weight
68303.5 Da
References
  1. Takami M, Suda K, Sahara T, Itoh K, Nagai K, Sasaki T, Udagawa N, Takahashi N: Involvement of vacuolar H+ -ATPase in incorporation of risedronate into osteoclasts. Bone. 2003 Apr;32(4):341-9. [PubMed:12689676]

Drug created on August 25, 2010 14:38 / Updated on October 01, 2018 14:11