(4R,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: 157753
• 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-MOMXNFOMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R,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: (4R,4aS,12aS)-4-(dimethylamino)-3,10,11,12a-tetrahydroxy-6-methyl-1,12-dioxo-4a,5-dihydro-4H-tetracene-2-carboxamide hydrochloride
• Synonyms: (4R,4aS,12aS)-4-(Dimethylamino)-1,4,4a,5,12,12a-hexahydro-3,10,11,12a-tetrahydroxy-6-methyl-1,12-dioxo-2-naphthacenecarboxamide monohydrochloride; 4-Epianhydrotetracycline hydrochloride; (4R,4aS,12aS)-4-(Dimethylamino)-1,4,4a,5,12,12a-hexahydro-3,10,11,12a-tetrahydroxy-6-methyl-1,12-dioxo-2-naphthacenecarboxamide Hydrochloride; 4-Epianhydrotetracycline Hydrochloride; (4R,4aS,12aS)-4-(二甲氨基)-1,4,4a,5,12,12a-六氢-3,10,11,12a-四羟基-6-甲基-1,12-二氧代-2-并四苯甲酰胺 单盐酸盐; 4-差向脱水四环素 盐酸盐

Database IDs

• CAS Number: 4465-65-0
• MDL Number: MFCD00151455
• Beilstein Number: 3840711
• PubChem SID: 24863225; 162251890
• PubChem CID: 54682545

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: Methanol
• Apperance: Orange Solid
• Melting Point: 195-201°C

Safety Information

• Storage Condition: -20°C Freezer
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Grade: VETRANAL™, analytical standard
• Suitability: suitable for 1694 per US EPA
• Empirical Formula (Hill Notation): C22H22N2O7 · HCl

DETAILS

Sigma Aldrich - 37921

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

Toronto Research Chemicals - E578070

An antibiotic derived from Tetracycline. Studies have shown that this derivative can have a 250-fold higher toxicity depending on the system under study.

REFERENCES

• Simmons, D., et al.: J. Pharm. Sci., 55, 1313 (1966)
• Paemen, L., et al.: Biochem. Pharmacol., 52, 105 (1966)