Identification

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Name
Aurodox
Accession Number
DB04124  (EXPT02115)
Type
Small Molecule
Groups
Experimental
Description

Aurodox is an antibiotic obtained from a streptomyces variant considered as possibly effective against streptococcus pyogenes infections. It may promote growth in poultry.

Structure
Thumb
Synonyms
  • 1-methylmocimycin
  • Goldinodox
  • Goldinomycin
External IDs
Antibiotic X-5108 / X-5108
Categories
UNII
PGP5RZH64G
CAS number
12704-90-4
Weight
Average: 810.9693
Monoisotopic: 810.430275458
Chemical Formula
C44H62N2O12
InChI Key
NTAHMPNXQOYXSX-WKSONYIQSA-N
InChI
InChI=1S/C44H62N2O12/c1-10-12-14-22-32-43(6,7)39(51)40(52)44(55,58-32)29(11-2)41(53)45-24-18-17-20-27(4)37(56-9)28(5)38-36(50)35(49)31(57-38)21-16-13-15-19-26(3)34(48)33-30(47)23-25-46(8)42(33)54/h10,12-23,25,28-29,31-32,35-40,47,49-52,55H,11,24H2,1-9H3,(H,45,53)/b12-10-,15-13+,18-17+,21-16+,22-14+,26-19+,27-20+/t28-,29-,31-,32+,35+,36+,37-,38+,39+,40-,44-/m1/s1
IUPAC Name
(2R)-N-[(2E,4E,6S,7R)-7-[(2S,3S,4R,5R)-3,4-dihydroxy-5-[(1E,3E,5E)-7-(4-hydroxy-1-methyl-2-oxo-1,2-dihydropyridin-3-yl)-6-methyl-7-oxohepta-1,3,5-trien-1-yl]oxolan-2-yl]-6-methoxy-5-methylocta-2,4-dien-1-yl]-2-[(2R,3R,4R,6S)-2,3,4-trihydroxy-5,5-dimethyl-6-[(1E,3Z)-penta-1,3-dien-1-yl]oxan-2-yl]butanimidic acid
SMILES
[H]\C(C)=C(/[H])\C(\[H])=C(/[H])[C@]1([H])O[C@](O)([C@]([H])(CC)C(O)=NC\C([H])=C(/[H])\C(\[H])=C(/C)[C@@]([H])(OC)[C@@]([H])(C)[C@]2([H])O[C@]([H])(C(\[H])=C(/[H])\C(\[H])=C(/[H])\C(\[H])=C(/C)C(=O)C3=C(O)C=CN(C)C3=O)[C@]([H])(O)[C@]2([H])O)[C@]([H])(O)[C@]([H])(O)C1(C)C

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UElongation factor Tu-BNot AvailableThermus thermophilus (strain HB8 / ATCC 27634 / DSM 579)
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 risk or severity of bleeding can be increased when Aurodox is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of bleeding can be increased when Aurodox is combined with (S)-Warfarin.
4-hydroxycoumarinThe risk or severity of bleeding can be increased when Aurodox is combined with 4-hydroxycoumarin.
AcenocoumarolThe risk or severity of bleeding can be increased when Aurodox is combined with Acenocoumarol.
Adenovirus type 7 vaccine liveThe therapeutic efficacy of Adenovirus type 7 vaccine live can be decreased when used in combination with Aurodox.
Anthrax immune globulin humanThe therapeutic efficacy of Anthrax immune globulin human can be decreased when used in combination with Aurodox.
Anthrax vaccineThe therapeutic efficacy of Anthrax vaccine can be decreased when used in combination with Aurodox.
Bacillus calmette-guerin substrain connaught live antigenThe therapeutic efficacy of Bacillus calmette-guerin substrain connaught live antigen can be decreased when used in combination with Aurodox.
Bacillus calmette-guerin substrain danish 1331 live antigenThe therapeutic efficacy of Bacillus calmette-guerin substrain danish 1331 live antigen can be decreased when used in combination with Aurodox.
Bacillus calmette-guerin substrain tice live antigenThe therapeutic efficacy of Bacillus calmette-guerin substrain tice live antigen can be decreased when used in combination with Aurodox.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
54688679
PubChem Substance
46506336
ChemSpider
16735686
ChEMBL
CHEMBL3221419
HET
MAU
PDB Entries
1ha3 / 4v68

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 Solubility0.00636 mg/mLALOGPS
logP4.29ALOGPS
logP4.32ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)6.37ChemAxon
pKa (Strongest Basic)3.92ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area219.04 Å2ChemAxon
Rotatable Bond Count17ChemAxon
Refractivity228.3 m3·mol-1ChemAxon
Polarizability89.59 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.5174
Blood Brain Barrier-0.9659
Caco-2 permeable-0.6678
P-glycoprotein substrateSubstrate0.7256
P-glycoprotein inhibitor INon-inhibitor0.5073
P-glycoprotein inhibitor IINon-inhibitor0.8819
Renal organic cation transporterNon-inhibitor0.8987
CYP450 2C9 substrateNon-substrate0.8498
CYP450 2D6 substrateNon-substrate0.832
CYP450 3A4 substrateSubstrate0.6324
CYP450 1A2 substrateNon-inhibitor0.7422
CYP450 2C9 inhibitorNon-inhibitor0.6948
CYP450 2D6 inhibitorNon-inhibitor0.8378
CYP450 2C19 inhibitorNon-inhibitor0.7
CYP450 3A4 inhibitorNon-inhibitor0.7413
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6225
Ames testNon AMES toxic0.6838
CarcinogenicityNon-carcinogens0.9026
BiodegradationNot ready biodegradable0.9663
Rat acute toxicity2.8423 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9922
hERG inhibition (predictor II)Non-inhibitor0.5697
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 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 c-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a C-glycosidic bond.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Carbohydrates and carbohydrate conjugates
Direct Parent
C-glycosyl compounds
Alternative Parents
Aryl ketones / Dihydropyridines / Hydroxypyridines / Pyridinones / Alpha-branched alpha,beta-unsaturated ketones / Monosaccharides / N-acyl amines / Oxanes / Acryloyl compounds / Vinylogous amides
show 16 more
Substituents
C-glycosyl compound / Aryl ketone / Pyridinone / Hydroxypyridine / Dihydropyridine / Monosaccharide / N-acyl-amine / Oxane / Hydropyridine / Pyridine
show 31 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Thermus thermophilus (strain HB8 / ATCC 27634 / DSM 579)
Pharmacological action
Unknown
General Function
Translation elongation factor activity
Specific Function
This protein promotes the GTP-dependent binding of aminoacyl-tRNA to the A-site of ribosomes during protein biosynthesis.
Gene Name
tufB
Uniprot ID
P60339
Uniprot Name
Elongation factor Tu-B
Molecular Weight
44782.015 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]

Drug created on June 13, 2005 07:24 / Updated on June 04, 2019 06:01