(3R,5R,6S,7S,8S,9S,12S,13R,14R,15R)-6-[(2S,3R,4S,6S)-4-(dimethylamino)-3-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-14-hydroxy-8-[(2R,4S,5S,6S)-5-hydroxy-4-methoxy-6-methyl-tetrahydropyran-2-yl]oxy-5,7,9,12,13,15-hexamethyl-2,11-dioxaspiro[2.13]hexadecane-10,16-dione
Basic information
- CAS
3922-90-5- Standard SMILES
CO[C@H]1C[C@H](O[C@H]2[C@@H](C)[C@@H](O[C@@H]3O[C@@H](C)C[C@H](N(C)C)[C@H]3O)[C@H](C)C[C@@]3(CO3)C(=O)[C@H](C)[C@H](O)[C@@H](C)[C@H](C)OC(=O)[C@H]2C)O[C@@H](C)[C@@H]1O- InChIKey
RZPAKFUAFGMUPI-ZRLKJDMJSA-N- Molecular formula
- C35H61NO12
- Average molar mass
- 687.9 g/mol
- Monoisotopic mass
- 687.41937638
Names & identifiers
- Preferred name
- (3R,5R,6S,7S,8S,9S,12S,13R,14R,15R)-6-[(2S,3R,4S,6S)-4-(dimethylamino)-3-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-14-hydroxy-8-[(2R,4S,5S,6S)-5-hydroxy-4-methoxy-6-methyl-tetrahydropyran-2-yl]oxy-5,7,9,12,13,15-hexamethyl-2,11-dioxaspiro[2.13]hexadecane-10,16-dione
- IUPAC
- (3R,5R,6S,7S,8S,9S,12S,13R,14R,15R)-6-[(2S,3R,4S,6S)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-hydroxy-8-[(2R,4S,5S,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-5,7,9,12,13,15-hexamethyl-1,11-dioxaspiro[2.13]hexadecane-10,16-dione
- English name
- oleandomycin
- Molecular formula
- C35H61NO12
- Molecular weight
- 687.86
Names & synonyms
Matromycin (phosphate)SCHEMBL29684259PA-105(3R,5R,6S,7S,8S,9S,12S,13R,14R,15R)-6-[(2S,3R,4S,6S)-4-(dimethylamino)-3-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-14-hydroxy-8-[(2R,4S,5S,6S)-5-hydroxy-4-methoxy-6-methyl-tetrahydropyran-2-yl]oxy-5,7,9,12,13,15-hexamethyl-2,11-dioxaspiro[2.13]hexadecane-10,16-dione[3R-(3R*,5R*,6S*,7R*,8R*,11R*,12S*,13R*,14S*,15S*)]-12-[(2,6-Dideoxy-3-O-methyl-.alpha.-L-arabino-hexopyranosyl)oxy]-6-hydroxy-5,7,8,11,13,15-hexamethyl-14-[[3,4,6-trideoxy-3-(dimethylamino)-.beta.-D-xylo-hexopyranosyl]oxy]-1,9-dioxaspiro[2.13]hexadecane-4,10-dioneLandomycinPA 775C01946RomicilAmimycinoleandomycinOleandoMycin A
Show more names
Antibiotic PA-105AMiMycin, MatroMycin, PA 105
Properties
Computed structural properties
- XLogP
- 2.6
- Topological polar surface area
- 166 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 13
- Rotatable bonds
- 6
- Heavy atoms
- 48
- Formal charge
- 0
- Complexity
- 1,090
Physicochemical properties
- Melting point
- 110 °C · 110 °C (decomp)
- Boiling point
- 802.6 · 802.6±65.0 °C(Predicted)
- Density
- 1.21 · 1.21±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · -20°C Freezer
- solubility
- DMSO (Slightly), Methanol (Slightly)
- form
- Solid
- pka
- 8.84 · pKa 8.84(H2O,t =25,I=0.167) (Uncertain)
- color
- White to Off-White
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 8 ZQ646136 · P8ZQ646136
- ATC code
- 1 FA05 · J01FA05
- Hazardous Substances Data
- 3922 · 3922-90-5(Hazardous Substances Data)
- Toxicity
- 50 orl-rat: · LD50 orl-rat: 6700 mg/kg AMPMAR 39,259,1978
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- Toxicity
- LD50 orl-rat: 6700 mg/kg AMPMAR 39,259,1978
- Hazardous Substances Data
- 3922-90-5(Hazardous Substances Data)
Chemistry & industry
Applications
UsesOleandomycin is a 16-membered macrocyclic lactone, discovered in the 1950s, with broad spectrum antibacterial activity. Oleandomycin was developed as a human pharmaceutical but was regarded as less active than comparable products such as erythromycin and is today only available in combination with other antibiotics.
UsesAntibiotic substance produced by Streptomyces antibioticus no. ATCC 11891. Antibacterial.
Upstream & downstream products
Upstream raw materials
Additional notes
DefinitionChEBI: Oleandomycin is a member of oleandomycins. It is functionally related to an oleandolide. It is a conjugate base of an oleandomycin(1+).
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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