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β-Apooxytetracycline

CAT: 0931-T35425-01Size: 500 µgDry Ice: NoHazardous: No
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CAT#:0931-T35425-01Size:500 µg
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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CAS Number
18751-99-0
Target
Others, Drug Metabolite
Related Pathways
Others, Metabolism
Bioactivity
β-Apooxytetracycline is a potential impurity found in commercial preparations of oxytetracycline. β-Apooxytetracycline is a degradation product formed from oxytetracycline via acid hydrolysis. It has a relative potency of 0.1 compared with oxytetracycline for inhibiting the growth of aerobic sludge bacteria, an MIC50 value of 32 mg/L for tetracycline-sensitive strains of Pseudomonas, and MIC50 values of greater than 32 mg/L for tetracycline-sensitive strains of Agrobacterium, Moraxella, and Bacillus, as well as tetracycline-resistant strains of E. coli. β-Apooxytetracycline (10 mg/kg) is toxic to rats, decreasing body weight, disrupting blood cell counts, and inducing hepatocyte necrosis.
Smiles
[H][C@@]1(OC(=O)c2c1c(C)c1cccc(O)c1c2O)[C@@]1([H])[C@@H](O)C(=O)C(C(N)=O)=C(O)[C@H]1N(C)C
Molecular Formula
C22H22N2O8
Molecular Weight
442.424
Shipping Conditions
Ice Packs
Storage Temperature
-20°C

Chemical Information

4-(4,5-dihydroxy-9-methyl-3-oxo-1H-benzo[f][2]benzofuran-1-yl)-3-(dimethylamino)-2,5-dihydroxy-6-oxocyclohexene-1-carboxamide

Beta-Apooxytetracycline is a naphthofuran.

CAS Number18751-99-0
PubChem CID54710410
IUPAC Name4-(4,5-dihydroxy-9-methyl-3-oxo-1H-benzo[f][2]benzofuran-1-yl)-3-(dimethylamino)-2,5-dihydroxy-6-oxocyclohexene-1-carboxamide
Molecular FormulaC22H22N2O8
Molecular Weight442.4
XLogP2
Topological Polar Surface Area171
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count9
Rotatable Bond Count3
Heavy Atom Count32
Formal Charge0
Complexity857
SMILES
CC1=C2C=CC=C(C2=C(C3=C1C(OC3=O)C4C(C(=C(C(=O)C4O)C(=O)N)O)N(C)C)O)O
InChI
InChI=1S/C22H22N2O8/c1-7-8-5-4-6-9(25)11(8)16(26)12-10(7)20(32-22(12)31)13-15(24(2)3)17(27)14(21(23)30)19(29)18(13)28/h4-6,13,15,18,20,25-28H,1-3H3,(H2,23,30)
InChIKey
DRKMHDAKULCOKQ-UHFFFAOYSA-N
Chemical Structure
2D Structure
2D structure of 4-(4,5-dihydroxy-9-methyl-3-oxo-1H-benzo[f][2]benzofuran-1-yl)-3-(dimethylamino)-2,5-dihydroxy-6-oxocyclohexene-1-carboxamide
CAS: 18751-99-0
CID: 54710410
Formula: C22H22N2O8
MW: 442.4
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight442.4
XLogP32
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count9
Rotatable Bond Count3
Exact Mass442.13761566
Monoisotopic Mass442.13761566
Topological Polar Surface Area171 Ų
Heavy Atom Count32
Formal Charge0
Complexity857
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count4
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

Alternative Products

CatalogName
BA7367-5β-Apooxytetracycline
HY-137324-01α-Apooxytetracycline
HY-135577Rβ-Apooxytetracycline (Standard)
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