Brefeldin A

Targets (2)Enzymes (1)Biointeractions (1)

Identification

Name
Brefeldin A
Accession Number
DB07348
Type
Small Molecule
Groups
Experimental
Description

A metabolite from Penicillium brefeldianum that exhibits a wide range of antibiotic activity.

Structure
Thumb
3D
Similar Structures
Synonyms
  • (+)-brefeldin A
  • Ascotoxin
  • Cyanein
  • Decumbin
  • Nectrolide
  • Synergisidin
External IDs
NSC-107456 / NSC-244390 / NSC-56310 / NSC-89671
Categories
UNII
XG0D35F9K6
CAS number
20350-15-6
Weight
Average: 280.3594
Monoisotopic: 280.167459256
Chemical Formula
C16H24O4
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

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UCytohesin-2Not AvailableHuman
UADP-ribosylation factor 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
DrugInteraction
(R)-warfarinThe serum concentration of (R)-warfarin can be increased when it is combined with Brefeldin A.
(S)-WarfarinThe serum concentration of (S)-Warfarin can be increased when it is combined with Brefeldin A.
3-isobutyl-1-methyl-7H-xanthineThe metabolism of 3-isobutyl-1-methyl-7H-xanthine can be decreased when combined with Brefeldin A.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Brefeldin A.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with Brefeldin A.
5-androstenedioneThe metabolism of 5-androstenedione can be decreased when combined with Brefeldin A.
6-O-benzylguanineThe metabolism of 6-O-benzylguanine can be decreased when combined with Brefeldin A.
7-DeazaguanineThe metabolism of 7-Deazaguanine can be decreased when combined with Brefeldin A.
7,9-DimethylguanineThe metabolism of 7,9-Dimethylguanine can be decreased when combined with Brefeldin A.
8-azaguanineThe metabolism of 8-azaguanine can be decreased when combined with Brefeldin A.
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
5287620
PubChem Substance
99443819
ChemSpider
4449949
BindingDB
97307
ChEBI
48080
ChEMBL
CHEMBL19980
HET
AFB
Wikipedia
Brefeldin_A
PDB Entries
1r8q / 1re0 / 1s9d

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 Solubility0.812 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
Polarizability30.85 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-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

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
Enoate esters / Secondary alcohols / Lactones / Cyclic alcohols and derivatives / Oxacyclic compounds / Monocarboxylic acids and derivatives / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Macrolide / Cyclic alcohol / Alpha,beta-unsaturated carboxylic ester / Enoate ester / Carboxylic acid ester / Lactone / Secondary alcohol / Carboxylic acid derivative / Oxacycle / Monocarboxylic acid or derivatives
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
macrolide antibiotic (CHEBI:48080)

Targets

Details1. Cytohesin-2
Kind
Protein
Organism
Human
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. [PubMed:10592235]
Details2. ADP-ribosylation factor 1
Kind
Protein
Organism
Human
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. [PubMed:10592235]

Enzymes

Details1. Cytochrome P450 3A4
Kind
Protein
Organism
Human
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. [PubMed:11020135]

Drug created on September 15, 2010 15:20 / Updated on November 02, 2018 06:31