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Name |
Lincomycin A |
EINECS | 205-824-6 |
CAS No. | 154-21-2 | Density | 1.3±0.1 g/cm3 |
PSA | 147.79000 | LogP | 0.27380 |
Solubility | N/A | Melting Point |
148-150 °C |
Formula | C18H34N2O6S | Boiling Point | 646.8±55.0 °C at 760 mmHg |
Molecular Weight | 406.544 | Flash Point | 345.0±31.5 °C |
Transport Information | N/A | Appearance | White crystalline solid |
Safety | Risk Codes |
Xi:; |
|
Molecular Structure | Hazard Symbols | R36/37/38:; | |
Synonyms |
D-erythro-D-galacto-Octopyranoside,methyl 6,8-dideoxy-6-(1-methyl-4-propyl-L-2-pyrrolidinecarboxamido)-1-thio-,trans-a- (8CI);D-erythro-a-D-galacto-Octopyranoside, methyl6,8-dideoxy-6-[[(1-methyl-4-propyl-2-pyrrolidinyl)carbonyl]amino]-1-thio-,(2S-trans)-;Lincomycin (7CI);Cillimycin;Jiemycin;Lincolcina;Lincolnensin;Lincomix;Lincomycin A;Medoglycine;U 10,149A;U 10149;Lincomycin; |
Article Data | 9 |
lincomycin
Conditions | Yield |
---|---|
With potassium carbonate In methanol at 130℃; for 20h; | 98.4% |
lincomycin
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: Microbiological reaction 2: Microbiological reaction 3: aq. buffer / 30 °C / Microbiological reaction View Scheme |
lincomycin
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: Microbiological reaction 2: aq. buffer / 30 °C / Microbiological reaction View Scheme |
lincomycin
Conditions | Yield |
---|---|
In aq. buffer at 30℃; Microbiological reaction; |
lincomycin
Conditions | Yield |
---|---|
With pyridoxal 5'-phosphate; LmbF enzyme; S-methyltransferase LmbG; S-adenosyl-L-methionine In aq. phosphate buffer at 30℃; for 2h; pH=7.5; Enzymatic reaction; |
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: pyridine / 8 h / 2 - 20 °C 2: acetic acid / methanol / 18 h / 30 °C 3: triphenylphosphine; di-isopropyl azodicarboxylate / toluene / 20 h / 30 °C 4: potassium carbonate / methanol / 20 h / 130 °C View Scheme |
lincomycin
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: acetic acid / methanol / 18 h / 30 °C 2: triphenylphosphine; di-isopropyl azodicarboxylate / toluene / 20 h / 30 °C 3: potassium carbonate / methanol / 20 h / 130 °C View Scheme |
2,3,4-tris-O-(trimethylsilyl)lincomycin
lincomycin
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: triphenylphosphine; di-isopropyl azodicarboxylate / toluene / 20 h / 30 °C 2: potassium carbonate / methanol / 20 h / 130 °C View Scheme |
acetic anhydride
lincomycin
(2R,3S,4S,5R,6R)-2-((1R,2R)-2-acetoxy-1-((2S,4R)-1-methyl-4-propylpyrrolidine-2-carboxamido)propyl)-6-(methylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate
Conditions | Yield |
---|---|
With pyridine at 20℃; for 38h; Acetylation; | 98.8% |
Conditions | Yield |
---|---|
With pyridine; 1,1,1,3,3,3-hexamethyl-disilazane at 0 - 20℃; for 2h; | 91% |
The Lincomycin A, with the CAS registry number 154-21-2, is also known as Methyl 6,8-dideoxy-6-[[[(2S,4R)-1-methyl-4-propyl-2-pyrrolidinyl]carbonyl]amino]-1-thio-D-erythro-alpha-D-gluco-octopyranoside. It belongs to the product categories of 13C & 2H Sugars; Carbohydrates & Derivatives; Intermediates & Fine Chemicals; Pharmaceuticals. Its EINECS number is 205-824-6. This chemical's molecular formula is C18H34N2O6S and molecular weight is 406.54. What's more, its systematic name is Methyl (5R)-5-[(1R,2R)-2-hydroxy-1-{[(4R)-1-methyl-4-propyl-L-prolyl]amino}propyl]-1-thio-β-L-arabinopyranoside. Its classification codes are: (1)Anti-Bacterial Agents; (2)Anti-Infective Agents; (3)Antibacterial; (4)Drug / Therapeutic Agent; (5)Enzyme Inhibitors; (6)Mutation data; (7)Natural Product; (8)Protein Synthesis Inhibitors. This chemical is an antibiotic produced by Streptomyces lincolnensis var. lincolnensis. It has been used in the treatment of staphylococcal, streptococcal, and Bacteroides fragilis infections.
Physical properties of Lincomycin A are: (1)ACD/LogP: 0.91±0.66; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): -1.80; (4)ACD/LogD (pH 7.4): -0.17; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 1.00; (8)ACD/KOC (pH 7.4): 6.26; (9)#H bond acceptors: 8; (10)#H bond donors: 5; (11)#Freely Rotating Bonds: 11; (12)Polar Surface Area: 147.79 Å2; (13)Index of Refraction: 1.583; (14)Molar Refractivity: 104.7±0.4 cm3; (15)Molar Volume: 313.3±5.0 cm3; (16)Polarizability: 41.5±0.5×10-24cm3; (17)Surface Tension: 60.7±5.0 dyne/cm; (18)Density: 1.3±0.1 g/cm3; (19)Flash Point: 345.0±31.5 °C; (20)Enthalpy of Vaporization: 109.2±6.0 kJ/mol; (21)Boiling Point: 646.8±55.0 °C at 760 mmHg; (22)Vapour Pressure: 0.0±4.4 mmHg at 25°C.
You can still convert the following datas into molecular structure:
(1)SMILES: CCC[C@@H]1C[C@H](N(C1)C)C(=O)N[C@@H]([C@@H]2[C@@H]([C@@H]([C@H]([C@H](O2)SC)O)O)O)[C@@H](C)O
(2)Std. InChI: InChI=1S/C18H34N2O6S/c1-5-6-10-7-11(20(3)8-10)17(25)19-12(9(2)21)16-14(23)13(22)15(24)18(26-16)27-4/h9-16,18,21-24H,5-8H2,1-4H3,(H,19,25)/t9-,10-,11+,12-,13+,14-,15-,16-,18-/m1/s1
(3)Std. InChIKey: OJMMVQQUTAEWLP-KIDUDLJLSA-N
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
guinea pig | LD50 | intraperitoneal | 1800mg/kg (1800mg/kg) | BRAIN AND COVERINGS: RECORDINGS FROM SPECIFIC AREAS OF CNS BLOOD: OTHER CHANGES | Antibiotiki i Khimioterapiya. Antibiotics and Chemotherapy. Vol. 35(2), Pg. 40, 1990. |
mouse | LD50 | intraperitoneal | 1gm/kg (1000mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Antimicrobial Agents and Chemotherapy Vol. -, |
mouse | LD50 | intravenous | 214mg/kg (214mg/kg) | Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 7, Pg. 913, 1965. | |
mouse | LD50 | oral | 13900mg/kg (13900mg/kg) | BRAIN AND COVERINGS: RECORDINGS FROM SPECIFIC AREAS OF CNS BLOOD: OTHER CHANGES | Antibiotiki i Khimioterapiya. Antibiotics and Chemotherapy. Vol. 35(2), Pg. 40, 1990. |
rabbit | LDLo | intramuscular | 200ug/kg (.2mg/kg) | Recueil de Medecine Veterinaire. Vol. 156, Pg. 915, 1980. | |
rat | LD50 | intraperitoneal | 1900mg/kg (1900mg/kg) | BLOOD: OTHER CHANGES BRAIN AND COVERINGS: RECORDINGS FROM SPECIFIC AREAS OF CNS | Antibiotiki i Khimioterapiya. Antibiotics and Chemotherapy. Vol. 35(2), Pg. 40, 1990. |
rat | LD50 | oral | 1gm/kg (1000mg/kg) | "Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978Vol. 1, Pg. 186, 1978. | |
rat | LD50 | subcutaneous | 9778mg/kg (9778mg/kg) | Toxicology and Applied Pharmacology. Vol. 18, Pg. 185, 1971. |