NAV

Tagetitoxin

Identification

Generic Name
Tagetitoxin
DrugBank Accession Number
DB04788
Background

Tagetitoxin is a bacterial phytotoxin. It preferentially inhibits eukaryotic RNA polymerase.

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 416.298
Monoisotopic: 416.029066598
Chemical Formula
C11H17N2O11PS
Synonyms
  • (1R,4R,5R,6R,7S,8R)-6-Acetoxy-7-amino-4-carbamoyl-4-hydroxy-8-(phosphonooxy)-9-oxa-3-thiabicyclo[3.3.1]nonane-1-carboxylic acid
Poor quality drug data slowing you down?
Unlock 38% more drug discovery time and eliminate decision-making doubts with this one-stop guide to quality drug data.
Download eBook
Poor quality drug data slowing you down?
Download eBook

Pharmacology

Indication

Not Available

Reduce drug development failure rates
Build, train, & validate machine-learning models
with evidence-based and structured datasets.
See how
Build, train, & validate predictive machine-learning models with structured datasets.
See how
Contraindications & Blackbox Warnings
Prevent Adverse Drug Events Today
Tap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.
Learn more
Avoid life-threatening adverse drug events with our Clinical API
Learn more
Pharmacodynamics

Not Available

Mechanism of action

Tagetitoxin inhibits all RNAP catalytic reactions. Tagetitoxin binding is mediated exclusively through polar interactions with the beta and beta' residues whose substitutions confer resistance to tagetitoxin in vitro.

TargetActionsOrganism
UDNA-directed RNA polymerase subunit betaNot AvailableThermus thermophilus (strain HB8 / ATCC 27634 / DSM 579)
UDNA-directed RNA polymerase subunit beta'Not 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

Adverse Effects
Improve decision support & research outcomes
With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!
See the data
Improve decision support & research outcomes with our structured adverse effects data.
See a data sample
Toxicity

Not Available

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.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as delta amino acids and derivatives. These are compounds containing a carboxylic acid group and an amino group at the C5 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
Delta amino acids and derivatives
Alternative Parents
Gamma amino acids and derivatives / Monoalkyl phosphates / Pyrans / Oxathianes / Oxanes / Dicarboxylic acids and derivatives / Monosaccharides / Primary carboxylic acid amides / Amino acids / Carboxylic acid esters
show 8 more
Substituents
1,4-oxathiane / Aliphatic heteropolycyclic compound / Alkyl phosphate / Amine / Amino acid / Carbonyl group / Carboxamide group / Carboxylic acid / Carboxylic acid ester / Delta amino acid or derivatives
show 22 more
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
87913-21-1
InChI Key
UVAAUIDYGIWLMB-HGNFPZBQSA-N
InChI
InChI=1S/C11H17N2O11PS/c1-3(14)22-5-4(12)6(24-25(19,20)21)10(9(16)17)2-26-11(18,8(13)15)7(5)23-10/h4-7,18H,2,12H2,1H3,(H2,13,15)(H,16,17)(H2,19,20,21)/t4-,5+,6+,7+,10+,11+/m0/s1
IUPAC Name
(1R,4R,5R,6R,7S,8R)-6-(acetyloxy)-7-amino-4-carbamoyl-4-hydroxy-8-(phosphonooxy)-9-oxa-3-thiabicyclo[3.3.1]nonane-1-carboxylic acid
SMILES
[H]N([H])[C@H]1[C@@H](OC(C)=O)[C@@]2([H])O[C@](CS[C@@]2(O)C(=O)N([H])[H])([C@@H]1OP(O)(O)=O)C(O)=O

References

General References
  1. Plet JR, Porter MJ: Synthesis of the bicyclic core of tagetitoxin. Chem Commun (Camb). 2006 Mar 21;(11):1197-9. Epub 2006 Feb 14. [Article]
  2. Vassylyev DG, Svetlov V, Vassylyeva MN, Perederina A, Igarashi N, Matsugaki N, Wakatsuki S, Artsimovitch I: Structural basis for transcription inhibition by tagetitoxin. Nat Struct Mol Biol. 2005 Dec;12(12):1086-93. Epub 2005 Nov 6. [Article]
  3. Mathews DE, Durbin RD: Mechanistic aspects of tagetitoxin inhibition of RNA polymerase from Escherichia coli. Biochemistry. 1994 Oct 4;33(39):11987-92. [Article]
  4. Steinberg TH, Mathews DE, Durbin RD, Burgess RR: Tagetitoxin: a new inhibitor of eukaryotic transcription by RNA polymerase III. J Biol Chem. 1990 Jan 5;265(1):499-505. [Article]
PubChem Compound
5327077
PubChem Substance
46506068
ChemSpider
4484333
ZINC
ZINC000012504512
PDBe Ligand
TGT
Wikipedia
Tagetitoxin
PDB Entries
2be5

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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 Solubility37.5 mg/mLALOGPS
logP-1.5ALOGPS
logP-3.8Chemaxon
logS-1ALOGPS
pKa (Strongest Acidic)0.85Chemaxon
pKa (Strongest Basic)8.72Chemaxon
Physiological Charge-2Chemaxon
Hydrogen Acceptor Count10Chemaxon
Hydrogen Donor Count6Chemaxon
Polar Surface Area228.93 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity80.58 m3·mol-1Chemaxon
Polarizability34.21 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.9526
Blood Brain Barrier-0.8728
Caco-2 permeable-0.678
P-glycoprotein substrateNon-substrate0.5244
P-glycoprotein inhibitor INon-inhibitor0.755
P-glycoprotein inhibitor IINon-inhibitor1.0
Renal organic cation transporterNon-inhibitor0.9637
CYP450 2C9 substrateNon-substrate0.6653
CYP450 2D6 substrateNon-substrate0.8187
CYP450 3A4 substrateNon-substrate0.5
CYP450 1A2 substrateNon-inhibitor0.7787
CYP450 2C9 inhibitorNon-inhibitor0.8173
CYP450 2D6 inhibitorNon-inhibitor0.9095
CYP450 2C19 inhibitorNon-inhibitor0.793
CYP450 3A4 inhibitorNon-inhibitor0.892
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9468
Ames testNon AMES toxic0.5863
CarcinogenicityNon-carcinogens0.9072
BiodegradationNot ready biodegradable0.9783
Rat acute toxicity2.5607 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9967
hERG inhibition (predictor II)Non-inhibitor0.8383
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-MSsplash10-0005-9302000000-a6f854df9ca6b9d05d7f
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-0001900000-a882debbf55a3e8e98a8
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-3001900000-315a9c68a5a0c7207e85
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0uy0-0209300000-7fc101c6d6e66cbbcb3c
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0fb9-3009000000-e0140bbf5306e6bf0ccb
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0l2o-0495000000-8b587a8c5736341dd983
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9000100000-3a0eaf62c3ae11090404
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-163.1676
predicted
DeepCCS 1.0 (2019)
[M+H]+165.56317
predicted
DeepCCS 1.0 (2019)
[M+Na]+171.55873
predicted
DeepCCS 1.0 (2019)

Targets

Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.
Learn more
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
Learn more
Details1. DNA-directed RNA polymerase subunit beta
Kind
Protein
Organism
Thermus thermophilus (strain HB8 / ATCC 27634 / DSM 579)
Pharmacological action
Unknown
General Function
Ribonucleoside binding
Specific Function
DNA-dependent RNA polymerase catalyzes the transcription of DNA into RNA using the four ribonucleoside triphosphates as substrates.
Gene Name
rpoB
Uniprot ID
Q8RQE9
Uniprot Name
DNA-directed RNA polymerase subunit beta
Molecular Weight
125263.41 Da
References
  1. Vassylyev DG, Svetlov V, Vassylyeva MN, Perederina A, Igarashi N, Matsugaki N, Wakatsuki S, Artsimovitch I: Structural basis for transcription inhibition by tagetitoxin. Nat Struct Mol Biol. 2005 Dec;12(12):1086-93. Epub 2005 Nov 6. [Article]
Details2. DNA-directed RNA polymerase subunit beta'
Kind
Protein
Organism
Thermus thermophilus (strain HB8 / ATCC 27634 / DSM 579)
Pharmacological action
Unknown
General Function
Dna-directed rna polymerase activity
Specific Function
DNA-dependent RNA polymerase catalyzes the transcription of DNA into RNA using the four ribonucleoside triphosphates as substrates.
Gene Name
rpoC
Uniprot ID
Q8RQE8
Uniprot Name
DNA-directed RNA polymerase subunit beta'
Molecular Weight
170755.075 Da
References
  1. Vassylyev DG, Svetlov V, Vassylyeva MN, Perederina A, Igarashi N, Matsugaki N, Wakatsuki S, Artsimovitch I: Structural basis for transcription inhibition by tagetitoxin. Nat Struct Mol Biol. 2005 Dec;12(12):1086-93. Epub 2005 Nov 6. [Article]

Drug created at September 11, 2007 17:49 / Updated at June 12, 2020 16:52