Identification
- Generic Name
- Brefeldin A
- DrugBank Accession Number
- DB07348
- Background
A metabolite from Penicillium brefeldianum that exhibits a wide range of antibiotic activity.
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for Brefeldin A (DB07348)
- Weight
- Average: 280.3594
Monoisotopic: 280.167459256 - Chemical Formula
- C16H24O4
- Synonyms
- (+)-brefeldin A
- Ascotoxin
- Cyanein
- Decumbin
- Nectrolide
- Synergisidin
- External IDs
- NSC-107456
- NSC-244390
- NSC-56310
- NSC-89671
Pharmacology
- Indication
Not Available
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UCytohesin-2 Not Available Humans UADP-ribosylation factor 1 Not Available Humans - 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
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbemaciclib The serum concentration of Abemaciclib can be increased when it is combined with Brefeldin A. Acalabrutinib The serum concentration of Acalabrutinib can be increased when it is combined with Brefeldin A. Acenocoumarol The serum concentration of Acenocoumarol can be increased when it is combined with Brefeldin A. Acetyldigitoxin The serum concentration of Acetyldigitoxin can be increased when it is combined with Brefeldin A. Afatinib The serum concentration of Afatinib can be increased when it is combined with Brefeldin A. - Food Interactions
- Not Available
Categories
- Drug Categories
- Anti-Bacterial Agents
- Anti-Infective Agents
- Cytochrome P-450 CYP3A Inhibitors
- Cytochrome P-450 CYP3A4 Inhibitors
- Cytochrome P-450 CYP3A4 Inhibitors (strength unknown)
- Cytochrome P-450 Enzyme Inhibitors
- Enzyme Inhibitors
- Lactones
- Macrolides
- P-glycoprotein inhibitors
- Polyketides
- Protein Synthesis Inhibitors
- Chemical TaxonomyProvided by Classyfire
- 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
- Enoate esters / Secondary alcohols / Lactones / Cyclic alcohols and derivatives / Oxacyclic compounds / Monocarboxylic acids and derivatives / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
- Substituents
- Alcohol / Aliphatic heteropolycyclic compound / Alpha,beta-unsaturated carboxylic ester / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Cyclic alcohol / Enoate ester / Hydrocarbon derivative / Lactone
- Molecular Framework
- Aliphatic heteropolycyclic compounds
- External Descriptors
- macrolide antibiotic (CHEBI:48080)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- XG0D35F9K6
- CAS number
- 20350-15-6
- InChI Key
- KQNZDYYTLMIZCT-KQPMLPITSA-N
- InChI
- InChI=1S/C16H24O4/c1-11-5-3-2-4-6-12-9-13(17)10-14(12)15(18)7-8-16(19)20-11/h4,6-8,11-15,17-18H,2-3,5,9-10H2,1H3/b6-4+,8-7+/t11-,12+,13-,14+,15+/m0/s1
- IUPAC Name
- (1R,6S,11aS,13S,14aR)-1,13-dihydroxy-6-methyl-1H,4H,6H,7H,8H,9H,11aH,12H,13H,14H,14aH-cyclopenta[f]oxacyclotridecan-4-one
- SMILES
- [H][C@]1(O)C[C@@]2([H])\C=C\CCC[C@]([H])(C)OC(=O)\C=C\[C@@]([H])(O)[C@]2([H])C1
References
- General References
- Not Available
- External Links
- PubChem Compound
- 5287620
- PubChem Substance
- 99443819
- ChemSpider
- 4449949
- BindingDB
- 97307
- ChEBI
- 48080
- ChEMBL
- CHEMBL19980
- ZINC
- ZINC000012371944
- PDBe Ligand
- AFB
- Wikipedia
- Brefeldin_A
- PDB Entries
- 1r8q / 1re0 / 1s9d
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count
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
Property Value Source Water Solubility 0.812 mg/mL ALOGPS logP 1.73 ALOGPS logP 2.01 Chemaxon logS -2.5 ALOGPS pKa (Strongest Acidic) 14.42 Chemaxon pKa (Strongest Basic) -2.7 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 66.76 Å2 Chemaxon Rotatable Bond Count 0 Chemaxon Refractivity 78.75 m3·mol-1 Chemaxon Polarizability 31.04 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9842 Blood Brain Barrier + 0.8777 Caco-2 permeable + 0.6226 P-glycoprotein substrate Substrate 0.635 P-glycoprotein inhibitor I Non-inhibitor 0.9534 P-glycoprotein inhibitor II Non-inhibitor 0.9416 Renal organic cation transporter Non-inhibitor 0.9007 CYP450 2C9 substrate Non-substrate 0.7686 CYP450 2D6 substrate Non-substrate 0.8602 CYP450 3A4 substrate Substrate 0.5245 CYP450 1A2 substrate Inhibitor 0.7107 CYP450 2C9 inhibitor Non-inhibitor 0.9547 CYP450 2D6 inhibitor Non-inhibitor 0.9599 CYP450 2C19 inhibitor Non-inhibitor 0.9054 CYP450 3A4 inhibitor Non-inhibitor 0.8309 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9773 Ames test Non AMES toxic 0.9426 Carcinogenicity Non-carcinogens 0.9598 Biodegradation Ready biodegradable 0.6336 Rat acute toxicity 2.1006 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9471 hERG inhibition (predictor II) Non-inhibitor 0.893
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-00dr-0090000000-b818ed7e7f1e7b9f5372 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-01q9-0090000000-baf1fc097727197c14ed Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-004i-0090000000-6300d22accfc951de698 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-03ea-0090000000-7a149556c2f6b9f4f115 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-01t9-0090000000-a69f14648bebc621a05b Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-014r-1090000000-bcccf791a849bd08b6ad Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-01oy-0090000000-5a4e49ac4d66e049657e Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 174.7495066 predictedDarkChem Lite v0.1.0 [M-H]- 167.44423 predictedDeepCCS 1.0 (2019) [M+H]+ 175.5555066 predictedDarkChem Lite v0.1.0 [M+H]+ 169.8398 predictedDeepCCS 1.0 (2019) [M+Na]+ 175.1425066 predictedDarkChem Lite v0.1.0 [M+Na]+ 175.7523 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Lipid binding
- Specific Function
- Acts as a guanine-nucleotide exchange factor (GEF). Promotes guanine-nucleotide exchange on ARF1, ARF3 and ARF6. Promotes the activation of ARF factors through replacement of GDP with GTP. The cell...
- Gene Name
- CYTH2
- Uniprot ID
- Q99418
- Uniprot Name
- Cytohesin-2
- Molecular Weight
- 46545.725 Da
References
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Receptor signaling protein activity
- Specific Function
- GTP-binding protein that functions as an allosteric activator of the cholera toxin catalytic subunit, an ADP-ribosyltransferase. Involved in protein trafficking among different compartments. Modula...
- Gene Name
- ARF1
- Uniprot ID
- P84077
- Uniprot Name
- ADP-ribosylation factor 1
- Molecular Weight
- 20696.62 Da
References
- 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. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Inhibitor
- General Function
- Vitamin d3 25-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- Kuper JI, D'Aprile M: Drug-Drug interactions of clinical significance in the treatment of patients with Mycobacterium avium complex disease. Clin Pharmacokinet. 2000 Sep;39(3):203-14. doi: 10.2165/00003088-200039030-00003. [Article]
Drug created at September 15, 2010 21:20 / Updated at June 12, 2020 16:52