Brefeldin A

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
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 rates
Build, train, & validate machine-learning models
with evidence-based and structured datasets.
See how
Build, train, & validate predictive machine-learning models with structured datasets.
See how
Contraindications & Blackbox Warnings
Prevent Adverse Drug Events Today
Tap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.
Learn more
Avoid life-threatening adverse drug events with our Clinical API
Learn more
Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UCytohesin-2Not AvailableHumans
UADP-ribosylation factor 1Not AvailableHumans
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 outcomes
With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!
See the data
Improve decision support & research outcomes with our structured adverse effects data.
See a data sample
Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
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.
DrugInteraction
AbemaciclibThe serum concentration of Abemaciclib can be increased when it is combined with Brefeldin A.
AcalabrutinibThe serum concentration of Acalabrutinib can be increased when it is combined with Brefeldin A.
AcenocoumarolThe serum concentration of Acenocoumarol can be increased when it is combined with Brefeldin A.
AcetyldigitoxinThe serum concentration of Acetyldigitoxin can be increased when it is combined with Brefeldin A.
AfatinibThe serum concentration of Afatinib can be increased when it is combined with Brefeldin A.
Food Interactions
Not Available

Categories

Drug Categories
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
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
PhaseStatusPurposeConditionsCount

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 Solubility0.812 mg/mLALOGPS
logP1.73ALOGPS
logP2.01Chemaxon
logS-2.5ALOGPS
pKa (Strongest Acidic)14.42Chemaxon
pKa (Strongest Basic)-2.7Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area66.76 Å2Chemaxon
Rotatable Bond Count0Chemaxon
Refractivity78.75 m3·mol-1Chemaxon
Polarizability31.04 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9842
Blood Brain Barrier+0.8777
Caco-2 permeable+0.6226
P-glycoprotein substrateSubstrate0.635
P-glycoprotein inhibitor INon-inhibitor0.9534
P-glycoprotein inhibitor IINon-inhibitor0.9416
Renal organic cation transporterNon-inhibitor0.9007
CYP450 2C9 substrateNon-substrate0.7686
CYP450 2D6 substrateNon-substrate0.8602
CYP450 3A4 substrateSubstrate0.5245
CYP450 1A2 substrateInhibitor0.7107
CYP450 2C9 inhibitorNon-inhibitor0.9547
CYP450 2D6 inhibitorNon-inhibitor0.9599
CYP450 2C19 inhibitorNon-inhibitor0.9054
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9773
Ames testNon AMES toxic0.9426
CarcinogenicityNon-carcinogens0.9598
BiodegradationReady biodegradable0.6336
Rat acute toxicity2.1006 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9471
hERG inhibition (predictor II)Non-inhibitor0.893
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-MSsplash10-00dr-0090000000-b818ed7e7f1e7b9f5372
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-01q9-0090000000-baf1fc097727197c14ed
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-0090000000-6300d22accfc951de698
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-03ea-0090000000-7a149556c2f6b9f4f115
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-01t9-0090000000-a69f14648bebc621a05b
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-014r-1090000000-bcccf791a849bd08b6ad
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-01oy-0090000000-5a4e49ac4d66e049657e
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-174.7495066
predicted
DarkChem Lite v0.1.0
[M-H]-167.44423
predicted
DeepCCS 1.0 (2019)
[M+H]+175.5555066
predicted
DarkChem Lite v0.1.0
[M+H]+169.8398
predicted
DeepCCS 1.0 (2019)
[M+Na]+175.1425066
predicted
DarkChem Lite v0.1.0
[M+Na]+175.7523
predicted
DeepCCS 1.0 (2019)

Targets

Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.
Learn more
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
Learn more
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
  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. [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
  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. [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
  1. 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