(4S,4aS,12aS)-4-(dimethylamino)-3,10,11,12a-tetrahydroxy-6-methyl-1,12-dioxo-1,4,4a,5,12,12a-hexahydrotetracene-2-carboxamide hydrochloride

• ChemBase ID: 156478
• Molecular Formular: C22H23ClN2O7
• Molecular Mass: 462.88022
• Monoisotopic Mass: 462.11937877
• SMILES: Cc1c2cccc(c2c(c2c1C[C@H]1[C@@H](C(=C(C(=O)[C@]1(C2=O)O)C(=O)N)O)N(C)C)O)O.Cl
• Canonical SMILES: CN([C@@H]1C(=C(C(=O)N)C(=O)[C@@]2([C@H]1Cc1c(C2=O)c(O)c2c(c1C)cccc2O)O)O)C.Cl
• InChI: InChI=1S/C22H22N2O7.ClH/c1-8-9-5-4-6-12(25)13(9)17(26)14-10(8)7-11-16(24(2)3)18(27)15(21(23)30)20(29)22(11,31)19(14)28;/h4-6,11,16,25-27,31H,7H2,1-3H3,(H2,23,30);1H/t11-,16-,22-;/m0./s1
• InChIKey: XBSQEFHDCDFNJU-WPJNXPDPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S,4aS,12aS)-4-(dimethylamino)-3,10,11,12a-tetrahydroxy-6-methyl-1,12-dioxo-1,4,4a,5,12,12a-hexahydrotetracene-2-carboxamide hydrochloride
• IUPAC Traditional name: anhydrotetracycline hydrochloride
• Synonyms: (4S,4aS,12aS)-4-(Dimethylamino)-1,4,4a,5,12,12a-hexahydro-3,10,11,12a-tetrahydroxy-6-methyl-1,12-dioxo-2-naphthacenecarboxamide monohydrochloride; Anhydrotetracycline hydrochloride; (4S,4aS,12aS)-4-(Dimethylamino)-1,4,4a,5,12,12a-hexahydro-3,10,11,12a-tetrahydroxy-6-methyl-1,12-dioxo-2-naphthacenecarboxamide Hydrochloride; Anhydrotetracycline Hydrochloride; (4S,4aS,12aS)-4-(Dimethylamino)-1,4,4a,5,12,12a-hexahydro-3,10,11,12a-tetrahydroxy-6-methyl-1,12-dioxo-2-naphthacenecarboxamide 单盐酸盐; 脱水四环素 盐酸盐

Database IDs

• CAS Number: 13803-65-1
• MDL Number: MFCD00151453
• Beilstein Number: 4228856
• PubChem SID: 162250616; 24863223
• PubChem CID: 54710409

CALCULATED PROPERTIES

• Acid pKa: -2.1894276
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): -1.359568
• LogD (pH = 7.4): -1.4408685
• Log P: -1.3589157
• Molar Refractivity: 112.3446 cm^3
• Polarizability: 43.505196 Å^3
• Polar Surface Area: 161.39 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Mehanol
• Apperance: Yellow Solid
• Melting Point: 239-243°C (dec.)

Safety Information

• Storage Condition: Refrigerator
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Grade: certified reference material; TraceCERT®; VETRANAL™, analytical standard
• Suitability: suitable for 1694 per US EPA
• Shelf Life: (limited shelf life, expiry date on the label)
• Empirical Formula (Hill Notation): C22H22N2O7 · HCl

DETAILS

Sigma Aldrich - 37919

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Sigma Aldrich - 94664

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General description
Certified content by quantitative NMR incl. uncertainty and expiry are given in the certificate.Download your certificate at: http://www.sigma-aldrich.com.
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Toronto Research Chemicals - A656050

A Tetracycline derivative exhibiting no antibiotic activity, a useful effector of tetracycline-dependent gene expression in bacterial expression systems.

REFERENCES

• Sokoloski, T., et al.: J. Pharm. Sci., 66, 1159 (1977)
• Paemen, L., et al.: Biochem. Pharmacol., 5, 105 (1977)