(9R,10S)-10-(acetyloxy)-8,8-dimethyl-2-oxo-2H,8H,9H,10H-pyrano[2,3-h]chromen-9-yl 3-methylbut-2-enoate

• ChemBase ID: 177687
• Molecular Formular: C21H22O7
• Molecular Mass: 386.39518
• Monoisotopic Mass: 386.13655304
• SMILES: c1(=O)ccc2c(o1)c1c(cc2)OC([C@@H]([C@H]1OC(=O)C)OC(=O)C=C(C)C)(C)C
• Canonical SMILES: CC(=O)O[C@H]1c2c(ccc3c2oc(=O)cc3)OC([C@@H]1OC(=O)C=C(C)C)(C)C
• InChI: InChI=1S/C21H22O7/c1-11(2)10-16(24)27-20-19(25-12(3)22)17-14(28-21(20,4)5)8-6-13-7-9-15(23)26-18(13)17/h6-10,19-20H,1-5H3/t19-,20+/m0/s1
• InChIKey: FNVCLGWRMXTDSM-VQTJNVASSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (9R,10S)-10-(acetyloxy)-8,8-dimethyl-2-oxo-2H,8H,9H,10H-pyrano[2,3-h]chromen-9-yl 3-methylbut-2-enoate
• IUPAC Traditional name: (9R,10S)-10-(acetyloxy)-8,8-dimethyl-2-oxo-9H,10H-pyrano[2,3-h]chromen-9-yl 3-methylbut-2-enoate
• Synonyms: (4S,4aS,5aR,12aS)-4-(Dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1-11-dioxo-2-naphthacenecarboxamide Hydrochloride; Bonomycin; Norcycline; 6-Demethyl-6-deoxytetracycline Hydrochloride; GS 2147; Sancycline Hydrochloride

Database IDs

• CAS Number: 6625-20-3
• PubChem SID: 164233597
• PubChem CID: 71752152

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 3.315271
• LogD (pH = 7.4): 3.315271
• Log P: 3.315271
• Molar Refractivity: 100.4546 cm^3
• Polarizability: 39.082222 Å^3
• Polar Surface Area: 88.13 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Yellow Solid
• Melting Point: >200°C (dec.)

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under inert atmosphere

DETAILS

Toronto Research Chemicals - S111500

A semi-synthetic antibiotic related to Tetracycline.

REFERENCES

• Gozalbes, R., et al.: J. Pharm. Pharmacol., 51, 111 (1999)
• Estrada, E., et al.: J. Med. Chem., 43, 1975 (1999)
• Gonzalez, H., et al.: J. Mol. Mod., 8, 237 (1999)