(4R,4aS,5aS,6S,12aS)-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: 157752
• Molecular Formular: C22H25ClN2O8
• Molecular Mass: 480.8955
• Monoisotopic Mass: 480.12994345
• SMILES: C[C@]1(c2cccc(c2C(=O)C2=C([C@]3([C@@H](C[C@H]12)[C@H](C(=C(C3=O)C(=O)N)O)N(C)C)O)O)O)O.Cl
• Canonical SMILES: CN([C@H]1C(=C(C(=O)N)C(=O)[C@@]2([C@H]1C[C@H]1C(=C2O)C(=O)c2c([C@@]1(C)O)cccc2O)O)O)C.Cl
• InChI: InChI=1S/C22H24N2O8.ClH/c1-21(31)8-5-4-6-11(25)12(8)16(26)13-9(21)7-10-15(24(2)3)17(27)14(20(23)30)19(29)22(10,32)18(13)28;/h4-6,9-10,15,25,27-28,31-32H,7H2,1-3H3,(H2,23,30);1H/t9-,10-,15+,21+,22-;/m0./s1
• InChIKey: XMEVHPAGJVLHIG-DXDJYCPMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R,4aS,5aS,6S,12aS)-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: (4R,4aS,5aS,6S,12aS)-4-(dimethylamino)-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide hydrochloride
• Synonyms: 4-epi-Tetracycline hydrochloride; 4-Epitetracycline hydrochloride; (4R,4aS,5aS,6S,12aS)-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; Quatrimycin Hydrochloride; [4R-(4α,4aβ,5aβ,6α,12aβ)]-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; 4-Epitetracycline Hydrochloride; 4-epi-Tetracycline Hydrochloride; 4-差向-四环素 盐酸盐; 4-差向四环素 盐酸盐

Database IDs

• CAS Number: 23313-80-6
• MDL Number: MFCD00865028
• PubChem SID: 24863624; 162251889
• PubChem CID: 54686189

CALCULATED PROPERTIES

• Acid pKa: -2.2437224
• H Acceptors: 9
• H Donor: 6
• LogD (pH = 5.5): -4.3970165
• LogD (pH = 7.4): -6.222226
• Log P: -3.5476153
• Molar Refractivity: 114.1883 cm^3
• Polarizability: 43.205765 Å^3
• Polar Surface Area: 181.62 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Pale Yellow Solid
• Melting Point: 218-223°C (dec.)

Safety Information

• Storage Condition: Amber Vial, -20°C Freezer, Under Inert Atmosphere
• RTECS: QJ1898250
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 63-36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335-H361
• GHS Precautionary statements: P261-P281-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges

Product Information

• Grade: VETRANAL™, analytical standard
• Empirical Formula (Hill Notation): C22H24N2O8 · HCl

DETAILS

Sigma Aldrich - 37918

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

Toronto Research Chemicals - T291405

Metabolite of Tetracycline (T291400).

REFERENCES

• Diana, J., et al.: J. Pharm. Biomed. Anal., 39, 523 (2005)
• Fritz, J., et al.: Food Chem., 105, 1297 (2005)
• Gratacos-Cubarsi, M., et al.: J. Agric. Food Chem., 55, 4610 (2005)