(4S,4aS,6S,12aS)-7-chloro-4-(dimethylamino)-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide hydrochloride

• ChemBase ID: 119323
• Molecular Formular: C22H24Cl2N2O8
• Molecular Mass: 515.34056
• Monoisotopic Mass: 514.0909711
• SMILES: [C@]12(C(=C3C(=O)c4c([C@](C3C[C@H]2[C@@H](C(=C(C1=O)C(=O)N)O)N(C)C)(O)C)c(ccc4O)Cl)O)O.Cl
• Canonical SMILES: CN([C@@H]1C(=C(C(=O)N)C(=O)[C@@]2([C@H]1CC1C(=C2O)C(=O)c2c([C@@]1(C)O)c(Cl)ccc2O)O)O)C.Cl
• InChI: InChI=1S/C22H23ClN2O8.ClH/c1-21(32)7-6-8-15(25(2)3)17(28)13(20(24)31)19(30)22(8,33)18(29)11(7)16(27)12-10(26)5-4-9(23)14(12)21;/h4-5,7-8,15,26,28-29,32-33H,6H2,1-3H3,(H2,24,31);1H/t7?,8-,15-,21-,22-;/m0./s1
• InChIKey: CBHYYLPALVVVEY-LYNLVHCPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S,4aS,6S,12aS)-7-chloro-4-(dimethylamino)-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide hydrochloride
• IUPAC Traditional name: aureomycin hydrochloride
• Synonyms: Chlortetracycline HCl; (4S,4aS,5aS,6S,12aS)-7-Chloro-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-2-naphthacenecarboxamide Hydrochloride; Aureociclina; Aureocycline; Aureomycin Hydrochloride; Aureomycin Monohydrochloride; Aureovit 12C80; Aurofac 100; Biomycin Hydrochloride; Chlortetracyclinium Chloride; Fermycin Soluble; Isphamycin; NSC 13252; Chlortetracycline Hydrochloride; (4S,4aS,6S,12aS)-7-chloro-4-(dimethylamino)-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide hydrochloride; Chlortetracycline hydrochloride; 7-Chlorotetracycline hydrochloride; 金霉素 盐酸盐; 氯四环素 盐酸盐

Database IDs

• CAS Number: 64-72-2
• EC Number: 200-591-7
• MDL Number: MFCD00082440
• Beilstein Number: 3858364
• PubChem SID: 24869844; 24892735; 162102869; 24856004
• PubChem CID: 54684459
• E Number: E702

CALCULATED PROPERTIES

• Acid pKa: 2.6491811
• H Acceptors: 9
• H Donor: 6
• LogD (pH = 5.5): -2.889993
• LogD (pH = 7.4): -3.3256438
• Log P: -2.8858275
• Molar Refractivity: 118.9931 cm^3
• Polarizability: 45.145546 Å^3
• Polar Surface Area: 181.62 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Water
• Apperance: Yellow Solid
• Melting Point: >200°C dec.; 210-215 °C (dec.)(lit.)
• Optical Rotation: [α]25/D -232°, c = 1 in H2O
• Fluorescence: λex 392 nm; λem 536 nm in 0.1 M Tris pH 8.0, 10 mM Ca2+

Safety Information

• Storage Condition: Refrigerator
• RTECS: QI7800000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 2
• Risk Statements: 36/37/38
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C; 2-8°C

Pharmacology Properties

• Target: Others

Product Information

• Purity: ≥75% (HPLC); ≥97.0% (AT); 80%
• Grade: VETRANAL™, analytical standard
• Salt Data: HCl
• Suitability: suitable for 1694 per US EPA; suitable for fluorescence
• Impurities: ≤3% water
• Biological Source: from Streptomyces aureofaciens
• Product Line: BioReagent
• Empirical Formula (Hill Notation): C22H23ClN2O8 · HCl

DETAILS

Sigma Aldrich - 26430

Application
Cell-permeable fluorescent probe for Ca2+ for measuring calcium flux in endoplasmic reticulum and other intracellular stores in situ.
Biochem/physiol Actions
Chlortetracycline is an antibiotic produced by some strains of Streptomyces aureofaciens.Mode of Action: Inhibits protein synthesis (elongation) by preventing binding of aminoacyl-tRNA to the 30S subunit. Antimicrobial spectrum: Gram-positive. Less active against Gram-negative bacteria than tetracycline.Mode of Resistance: Loss of cell wall permeability.
Quality
Recommended for fluorescent studies of calcium signaling in cells or tissues.

Sigma Aldrich - C4881

Application
Cell-permeable fluorescent probe for Ca2+ for measuring calcium flux in endoplasmic reticulum and other intracellular stores in situ.
Biochem/physiol Actions
Chlortetracycline is an antibiotic produced by some strains of Streptomyces aureofaciens.Mode of Action: Inhibits protein synthesis (elongation) by preventing binding of aminoacyl-tRNA to the 30S subunit. Antimicrobial spectrum: Gram-positive. Less active against Gram-negative bacterial than tetracycline.Mode of Resistance: Loss of cell wall permeability.
包装
5, 25, 100 g in glass bottle

Sigma Aldrich - 46133

Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - 271802

Other Notes
remainder mainly tetracycline hydrochloride

Toronto Research Chemicals - C426500

Chlortetracycline is an antibiotic substance isolated from the substrate of Streptomyces aureofaciens. Chlortetracycline is an antimicrobial and antibacterial.Chlortetracycline contains an undetermined amount of epi-chlortetracycline.

REFERENCES

• Skaletzki, B., et al.: Pharmazie, 29, 424 (1974)
• Martinez, M., et al.: Biochemistry, 40, 11965 (1974)
• Davidson, P., et al.: Food Technol., 55, 69 (1974)
• de la Fuente, R., et al.: Br. J. Pharmacol., 149, 551 (1974)