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IdentificationPharmacologyInteractionsReferencesTrialsEconomicsPropertiesSpectraTaxonomyBrefeldin A
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
- 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
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
- Toxicity
- Not Available
- Affected organisms
- Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
Drug Interaction (R)-warfarin The serum concentration of (R)-warfarin can be increased when it is combined with Brefeldin A. (S)-Warfarin The serum concentration of (S)-Warfarin can be increased when it is combined with Brefeldin A. 3-isobutyl-1-methyl-7H-xanthine The metabolism of 3-isobutyl-1-methyl-7H-xanthine can be decreased when combined with Brefeldin A. 3,5-diiodothyropropionic acid The metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Brefeldin A. 4-hydroxycoumarin The metabolism of 4-hydroxycoumarin can be decreased when combined with Brefeldin A. 5-androstenedione The metabolism of 5-androstenedione can be decreased when combined with Brefeldin A. 6-O-benzylguanine The metabolism of 6-O-benzylguanine can be decreased when combined with Brefeldin A. 7-Deazaguanine The metabolism of 7-Deazaguanine can be decreased when combined with Brefeldin A. 7-ethyl-10-hydroxycamptothecin The metabolism of 7-ethyl-10-hydroxycamptothecin can be decreased when combined with Brefeldin A. 7,9-Dimethylguanine The metabolism of 7,9-Dimethylguanine 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
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 30.85 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 Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not 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
- 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. [PubMed:10592235]
- 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. [PubMed:10592235]
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. [PubMed:11020135]
Drug created on September 15, 2010 15:20 / Updated on November 02, 2018 06:31