2-[(1S,2R,3R,7R,8S,9S,10R,12R,16S)-9-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-3-ethyl-7-hydroxy-2,8,12,16-tetramethyl-5,13-dioxo-4,17-dioxabicyclo[14.1.0]heptadec-14-en-10-yl]acetaldehyde

• ChemBase ID: 156262
• Molecular Formular: C31H51NO9
• Molecular Mass: 581.73794
• Monoisotopic Mass: 581.35638222
• SMILES: CC[C@H]1[C@H]([C@H]2[C@@](O2)(/C=C/C(=O)[C@@H](C[C@@H]([C@H]([C@H]([C@@H](CC(=O)O1)O)C)O[C@H]1[C@@H]([C@H](C[C@H](O1)C)N(C)C)O)CC=O)C)C)C
• Canonical SMILES: O=CC[C@H]1C[C@@H](C)C(=O)/C=C/[C@]2(C)O[C@H]2[C@@H]([C@@H](OC(=O)C[C@H]([C@@H]([C@@H]1O[C@@H]1O[C@H](C)C[C@@H]([C@H]1O)N(C)C)C)O)CC)C
• InChI: InChI=1S/C31H51NO9/c1-9-25-20(5)29-31(6,41-29)12-10-23(34)17(2)14-21(11-13-33)28(19(4)24(35)16-26(36)39-25)40-30-27(37)22(32(7)8)15-18(3)38-30/h10,12-13,17-22,24-25,27-30,35,37H,9,11,14-16H2,1-8H3/t17-,18-,19+,20-,21+,22+,24-,25-,27-,28-,29+,30+,31+/m1/s1
• InChIKey: IUPCWCLVECYZRV-KKFOQTHKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(1S,2R,3R,7R,8S,9S,10R,12R,16S)-9-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-3-ethyl-7-hydroxy-2,8,12,16-tetramethyl-5,13-dioxo-4,17-dioxabicyclo[14.1.0]heptadec-14-en-10-yl]acetaldehyde
• IUPAC Traditional name: 2-[(1S,2R,3R,7R,8S,9S,10R,12R,16S)-9-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-3-ethyl-7-hydroxy-2,8,12,16-tetramethyl-5,13-dioxo-4,17-dioxabicyclo[14.1.0]heptadec-14-en-10-yl]acetaldehyde
• Synonyms: Rosaramicin; Rosamicin from Micromonospora rosaria

Database IDs

• CAS Number: 35834-26-5
• EC Number: 252-742-1
• MDL Number: MFCD00133803
• Beilstein Number: 1633003
• PubChem SID: 162250400
• PubChem CID: 6537204

CALCULATED PROPERTIES

• Acid pKa: 12.79468
• H Acceptors: 9
• H Donor: 2
• LogD (pH = 5.5): 0.51455915
• LogD (pH = 7.4): 2.2145782
• Log P: 2.6783903
• Molar Refractivity: 153.4187 cm^3
• Polarizability: 61.214565 Å^3
• Polar Surface Area: 135.13 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: methanol: soluble10 mg/mL, clear, light yellow

Safety Information

• RTECS: JG6800000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20/21/22
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H312-H332
• GHS Precautionary statements: P280
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0% (TLC)
• Empirical Formula (Hill Notation): C31H51NO9

DETAILS

Sigma Aldrich - 83904

Biochem/physiol Actions
Macrolide antibiotic similar to erythromycin, and with a similar spectrum of bactericidal activity.1 Against a wide variety of anaerobes, rosamicin is at least as potent as, and in some cases more potent than, erythromycin.2