Name: Lincomycin
SKU: 154-21-2

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Basic Information

Molecular Structure:
CAS No.:	154-21-2
Name:	Lincomycin

Formula:	C₁₈H₃₄N₂O₆S
Molecular Weight:	406.544
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;
EINECS:	205-824-6
Density:	1.3±0.1 g/cm³
Melting Point:	148-150 °C
Boiling Point:	646.8±55.0 °C at 760 mmHg
Flash Point:	345.0±31.5 °C
Appearance:	White crystalline solid
Hazard Symbols:	R36/37/38:;
Risk Codes:	Xi:; "> Xi:;
PSA:	147.79000
LogP:	0.27380

Synthetic route

: C34H61N3O9SSi3

: 154-21-2
lincomycin

Conditions

Conditions	Yield
With potassium carbonate In methanol at 130℃; for 20h;	98.4%

: C26H46N5O8S(1+)

: 154-21-2
lincomycin

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: Microbiological reaction 2: Microbiological reaction 3: aq. buffer / 30 °C / Microbiological reaction View Scheme

: C34H60N4O18S

: 154-21-2
lincomycin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: Microbiological reaction 2: aq. buffer / 30 °C / Microbiological reaction View Scheme

: C22H39N3O9S

: 154-21-2
lincomycin

Conditions

Conditions	Yield
In aq. buffer at 30℃; Microbiological reaction;

: C20H37N3O8S

: 154-21-2
lincomycin

Conditions

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;

: 859-18-7
lincomycin hydrochloride

: 154-21-2
lincomycin

Conditions

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

: C30H66N2O6SSi4

: 154-21-2
lincomycin

Conditions

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

: 25420-97-7
2,3,4-tris-O-(trimethylsilyl)lincomycin

: 154-21-2
lincomycin

Conditions

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

: 108-24-7
acetic anhydride

: 154-21-2
lincomycin

: 168399-17-5
(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

Conditions	Yield
With pyridine at 20℃; for 38h; Acetylation;	98.8%

: 75-77-4
chloro-trimethyl-silane

: 154-21-2
lincomycin

: C30H66N2O6SSi4

Conditions

Conditions	Yield
With pyridine; 1,1,1,3,3,3-hexamethyl-disilazane at 0 - 20℃; for 2h;	91%

Downstream Products

13380-36-4

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Consensus Reports

EPA Genetic Toxicology Program.

Specification

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.

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Consensus Reports

Specification