(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

• ChemBase ID: 4334
• Molecular Formular: C11H17N2O11PS
• Molecular Mass: 416.298241
• Monoisotopic Mass: 416.029067
• SMILES: CC(=O)O[C@@H]1[C@H](N)[C@H](OP(=O)(O)O)[C@]2(CS[C@](O)([C@@H]1O2)C(=O)N)C(=O)O
• Canonical SMILES: CC(=O)O[C@@H]1[C@H](N)[C@H](OP(=O)(O)O)[C@@]2(O[C@H]1[C@@](O)(SC2)C(=O)N)C(=O)O
• 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
• InChIKey: UVAAUIDYGIWLMB-HGNFPZBQSA-N

NAMES AND DATABASE IDS

Names

• 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
• IUPAC Traditional name: tagetitoxin
• Synonyms: TGT; (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; Tagetitoxin

Database IDs

• CAS Number: 87913-21-1
• PubChem SID: 160967766; 46506068
• PubChem CID: 5327077

CALCULATED PROPERTIES

JChem

• Acid pKa: 0.85314023
• H Acceptors: 10
• H Donor: 6
• LogD (pH = 5.5): -6.371804
• LogD (pH = 7.4): -8.75602
• Log P: -3.8289819
• Molar Refractivity: 80.5767 cm^3
• Polarizability: 33.565437 Å^3
• Polar Surface Area: 228.93 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -1.5
• LOG S: -1.05
• Solubility (Water): 3.75e+01 g/l

DETAILS

DrugBank - DB04788

• Drug Groups: experimental
• Description: Tagetitoxin is a bacterial phytotoxin. It preferentially inhibits eukaryotic RNA polymerase.
• References: Plet JR, Porter MJ: Synthesis of the bicyclic core of tagetitoxin. Chem Commun (Camb). 2006 Mar 21;(11):1197-9. Epub 2006 Feb 14. [Pubmed] ; 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. [Pubmed] ; Mathews DE, Durbin RD: Mechanistic aspects of tagetitoxin inhibition of RNA polymerase from Escherichia coli. Biochemistry. 1994 Oct 4;33(39):11987-92. [Pubmed] ; 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. [Pubmed]

REFERENCES

• Plet JR, Porter MJ: Synthesis of the bicyclic core of tagetitoxin. Chem Commun (Camb). 2006 Mar 21;(11):1197-9. Epub 2006 Feb 14. Pubmed
• 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. Pubmed
• Mathews DE, Durbin RD: Mechanistic aspects of tagetitoxin inhibition of RNA polymerase from Escherichia coli. Biochemistry. 1994 Oct 4;33(39):11987-92. Pubmed
• 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. Pubmed