Streptolydigin

Identification

Logo pink
Are you a
new drug developer?
Contact us to learn more about our customized products and solutions.
Logo pink
Stay in the know!
As part of our commitment to providing the most up-to-date drug information, we will be releasing #DrugBankUpdates with our newly added curated drug pages.
#DrugBankUpdates
Name
Streptolydigin
Accession Number
DB04785
Type
Small Molecule
Groups
Experimental
Description

Streptolydigin is an antibiotic isolated from culture filtrates of Streptomyces lydicus. It is active against gram-postive bacteria except micrococci.

Structure
Thumb
Synonyms
  • Afragilimycin A
  • Portamycin
External IDs
Antibiotic D-45 / NSC-3360
International/Other Brands
Portamycin
Categories
UNII
6MON4029Q8
CAS number
7229-50-7
Weight
Average: 600.6998
Monoisotopic: 600.304681016
Chemical Formula
C32H44N2O9
InChI Key
KVTPRMVXYZKLIG-NCAOFHFGSA-N
InChI
InChI=1S/C32H44N2O9/c1-16(14-17(2)28-18(3)23-12-13-32(15-40-32)31(6,42-23)43-28)8-9-22(36)25-27(37)26(19(4)29(38)33-7)34(30(25)39)24-11-10-21(35)20(5)41-24/h8-9,12-14,17-21,23-24,26,28,35-36H,10-11,15H2,1-7H3,(H,33,38)/b9-8+,16-14+,25-22+/t17-,18+,19+,20+,21+,23-,24+,26+,28-,31-,32-/m1/s1
IUPAC Name
(2S)-2-[(2S,4E)-4-[(2E,4E,6R)-6-[(1R,2R,5R,6S,7R)-1,6-dimethyl-8,9-dioxaspiro[bicyclo[3.3.1]nonane-2,2'-oxiran]-3-en-7-yl]-1-hydroxy-4-methylhepta-2,4-dien-1-ylidene]-1-[(2S,5S,6S)-5-hydroxy-6-methyloxan-2-yl]-3,5-dioxopyrrolidin-2-yl]-N-methylpropanamide
SMILES
[H][C@@]1([C@H](C)C(=O)NC)N([C@@H]2CC[C@H](O)[C@H](C)O2)C(=O)\C(=C(\O)/C=C/C(/C)=C/[C@@H](C)[C@@]2([H])O[C@@]3(C)O[C@H](C=C[C@@]33CO3)[C@@H]2C)C1=O

Pharmacology

Indication
Not Available
Pharmacodynamics

Streptolydigin is an antibiotic which works by blocking nucleic acid chain elongation by binding to the polymerase, thus stopping RNA polymerase activity inside a cell. Specifically, it inhibits the assembly of the RNA polymerase II transcription complex and DNA polymerase III transcription. It is active against a number of gram positive bacteria.

Mechanism of action
Not Available
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
  • Enteric bacteria and other eubacteria
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
(R)-warfarinThe risk or severity of bleeding can be increased when Streptolydigin is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of bleeding can be increased when Streptolydigin is combined with (S)-Warfarin.
4-hydroxycoumarinThe risk or severity of bleeding can be increased when Streptolydigin is combined with 4-hydroxycoumarin.
AcenocoumarolThe risk or severity of bleeding can be increased when Streptolydigin is combined with Acenocoumarol.
BCG vaccineThe therapeutic efficacy of BCG vaccine can be decreased when used in combination with Streptolydigin.
ClorindioneThe risk or severity of bleeding can be increased when Streptolydigin is combined with Clorindione.
CoumarinThe risk or severity of bleeding can be increased when Streptolydigin is combined with Coumarin.
DicoumarolThe risk or severity of bleeding can be increased when Streptolydigin is combined with Dicoumarol.
DiphenadioneThe risk or severity of bleeding can be increased when Streptolydigin is combined with Diphenadione.
Ethyl biscoumacetateThe risk or severity of bleeding can be increased when Streptolydigin is combined with Ethyl biscoumacetate.
Additional Data Available
  • Extended Description
    Extended Description

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

    Learn more
  • Severity
    Severity

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

    Learn more
  • Evidence Level
    Evidence Level

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

    Learn more
  • Action
    Action

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

    Learn more
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
54708748
PubChem Substance
46505558
ChemSpider
21270076
ChEBI
45773
ChEMBL
CHEMBL1236068
HET
STD
Wikipedia
Streptolydigin
PDB Entries
1zyr / 2a6h / 2ppb

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 Solubility0.0386 mg/mLALOGPS
logP1.78ALOGPS
logP2.09ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)5.29ChemAxon
pKa (Strongest Basic)-0.48ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area147.16 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity160.29 m3·mol-1ChemAxon
Polarizability63.96 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.8435
Blood Brain Barrier-0.9824
Caco-2 permeable-0.632
P-glycoprotein substrateSubstrate0.7381
P-glycoprotein inhibitor INon-inhibitor0.5781
P-glycoprotein inhibitor IINon-inhibitor0.6987
Renal organic cation transporterNon-inhibitor0.8953
CYP450 2C9 substrateNon-substrate0.7662
CYP450 2D6 substrateNon-substrate0.85
CYP450 3A4 substrateSubstrate0.7436
CYP450 1A2 substrateNon-inhibitor0.8165
CYP450 2C9 inhibitorNon-inhibitor0.7315
CYP450 2D6 inhibitorNon-inhibitor0.9006
CYP450 2C19 inhibitorNon-inhibitor0.7712
CYP450 3A4 inhibitorNon-inhibitor0.7387
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9076
Ames testAMES toxic0.5386
CarcinogenicityNon-carcinogens0.9381
BiodegradationNot ready biodegradable0.9488
Rat acute toxicity2.8753 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9972
hERG inhibition (predictor II)Non-inhibitor0.8705
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 beta amino acids and derivatives. These are amino acids having a (-NH2) group attached to the beta carbon atom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Beta amino acids and derivatives
Alternative Parents
Ketals / Pyrrolidine-3-ones / Pyrrolidine-2-ones / Pyrans / Oxanes / 1,3-dioxanes / N-alkylpyrrolidines / Vinylogous acids / Tertiary carboxylic acid amides / Secondary carboxylic acid amides
show 12 more
Substituents
Beta amino acid or derivatives / Ketal / Meta-dioxane / Pyrrolidone / 2-pyrrolidone / 3-pyrrolidone / Oxane / Pyran / N-alkylpyrrolidine / Pyrrolidine
show 26 more
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
pyrrolidinone, monocarboxylic acid amide, organic heterotricyclic compound, epoxide, N-glycosyl compound, bridged compound, enol, cyclic ketal, oxaspiro compound (CHEBI:45773)

Drug created on September 11, 2007 11:49 / Updated on January 02, 2020 05:32