6-Deoxyerythronolide B

Targets (1)Enzymes (1)

Identification

Name
6-Deoxyerythronolide B
Accession Number
DB04070  (EXPT01153)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
3D
Similar Structures
Synonyms
Not Available
Categories
UNII
Not Available
CAS number
Not Available
Weight
Average: 386.5228
Monoisotopic: 386.266838948
Chemical Formula
C21H38O6
InChI Key
HQZOLNNEQAKEHT-IBBGRPSASA-N
InChI
InChI=1S/C21H38O6/c1-8-16-12(4)19(24)13(5)17(22)10(2)9-11(3)18(23)14(6)20(25)15(7)21(26)27-16/h10-16,18-20,23-25H,8-9H2,1-7H3/t10-,11+,12+,13+,14-,15-,16-,18+,19+,20+/m1/s1
IUPAC Name
(3R,4S,5R,6S,7S,9R,11R,12S,13R,14R)-14-ethyl-4,6,12-trihydroxy-3,5,7,9,11,13-hexamethyl-1-oxacyclotetradecane-2,10-dione
SMILES
[H][C@@]1(C)C[C@]([H])(C)[C@]([H])(O)[C@@]([H])(C)[C@]([H])(O)[C@@]([H])(C)C(=O)O[C@]([H])(CC)[C@]([H])(C)[C@]([H])(O)[C@@]([H])(C)C1=O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
U6-deoxyerythronolide B hydroxylaseNot AvailableSaccharopolyspora erythraea (strain NRRL 23338)
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 6-Deoxyerythronolide B.
(S)-WarfarinThe serum concentration of (S)-Warfarin can be increased when it is combined with 6-Deoxyerythronolide B.
3-isobutyl-1-methyl-7H-xanthineThe metabolism of 3-isobutyl-1-methyl-7H-xanthine can be decreased when combined with 6-Deoxyerythronolide B.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with 6-Deoxyerythronolide B.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with 6-Deoxyerythronolide B.
5-androstenedioneThe metabolism of 5-androstenedione can be decreased when combined with 6-Deoxyerythronolide B.
6-O-benzylguanineThe metabolism of 6-O-benzylguanine can be decreased when combined with 6-Deoxyerythronolide B.
7-DeazaguanineThe metabolism of 7-Deazaguanine can be decreased when combined with 6-Deoxyerythronolide B.
7-ethyl-10-hydroxycamptothecinThe metabolism of 7-ethyl-10-hydroxycamptothecin can be decreased when combined with 6-Deoxyerythronolide B.
7,9-DimethylguanineThe metabolism of 7,9-Dimethylguanine can be decreased when combined with 6-Deoxyerythronolide B.
Food Interactions
Not Available

References

Synthesis Reference

Robert McDaniel, "Production of 8,8a-dihydroxy-6-deoxyerythronolide B." U.S. Patent US20010034046, issued October 25, 2001.

US20010034046
General References
Not Available
External Links
KEGG Compound
C03240
PubChem Compound
121904
PubChem Substance
46508714
ChemSpider
108752
ChEBI
16089
HET
DEB
PDB Entries
1jio / 1oxa / 1z8o / 1z8p / 1z8q / 5mns / 5mnv

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 Solubility1.12 mg/mLALOGPS
logP1.8ALOGPS
logP2.87ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)14ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area104.06 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity102.94 m3·mol-1ChemAxon
Polarizability42.94 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.8891
Blood Brain Barrier+0.8618
Caco-2 permeable-0.5356
P-glycoprotein substrateSubstrate0.5407
P-glycoprotein inhibitor INon-inhibitor0.8554
P-glycoprotein inhibitor IINon-inhibitor0.7101
Renal organic cation transporterNon-inhibitor0.9497
CYP450 2C9 substrateNon-substrate0.8196
CYP450 2D6 substrateNon-substrate0.8539
CYP450 3A4 substrateNon-substrate0.5317
CYP450 1A2 substrateNon-inhibitor0.8867
CYP450 2C9 inhibitorNon-inhibitor0.8888
CYP450 2D6 inhibitorNon-inhibitor0.9394
CYP450 2C19 inhibitorNon-inhibitor0.8459
CYP450 3A4 inhibitorNon-inhibitor0.5415
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9514
Ames testNon AMES toxic0.6607
CarcinogenicityNon-carcinogens0.8856
BiodegradationNot ready biodegradable0.8668
Rat acute toxicity2.6539 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9771
hERG inhibition (predictor II)Non-inhibitor0.9444
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
Secondary alcohols / Lactones / Cyclic ketones / Carboxylic acid esters / Polyols / Oxacyclic compounds / Monocarboxylic acids and derivatives / Organic oxides / Hydrocarbon derivatives
Substituents
Macrolide / Carboxylic acid ester / Ketone / Lactone / Secondary alcohol / Cyclic ketone / Carboxylic acid derivative / Oxacycle / Monocarboxylic acid or derivatives / Polyol
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
erythronolide (CHEBI:16089) / Macrolides and lactone polyketides (C03240) / Macrolides and lactone polyketides (LMPK04000002)

Targets

Details1. 6-deoxyerythronolide B hydroxylase
Kind
Protein
Organism
Saccharopolyspora erythraea (strain NRRL 23338)
Pharmacological action
Unknown
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen
Specific Function
Catalyzes the NADPH-dependent conversion of 6-deoxyerythronolide B (6-DEB) to erythronolide B (EB) by the insertion of an oxygen at the 6S position of 6-DEB. Requires the participation of a ferredo...
Gene Name
eryF
Uniprot ID
Q00441
Uniprot Name
6-deoxyerythronolide B hydroxylase
Molecular Weight
45098.685 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. 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
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. [PubMed:11020135]

Drug created on June 13, 2005 07:24 / Updated on November 02, 2018 05:49