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154-21-2

Basic Information
CAS No.: 154-21-2
Name: D-erythro-α-D-galacto-Octopyranoside, methyl 6,8-dideoxy-6-[[[(2S,4R)-1-methyl-4-propyl-2-pyrrolidinyl]carbonyl]amino]-1-thio-
Molecular Structure:
Molecular Structure of 154-21-2 (D-erythro-α-D-galacto-Octopyranoside, methyl 6,8-dideoxy-6-[[[(2S,4R)-1-methyl-4-propyl-2-pyrrolidinyl]carbonyl]amino]-1-thio-)
Formula: C18H34N2O6S
Molecular Weight: 406.54
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
Solubility:
Appearance: White crystalline solid
Hazard Symbols: R36/37/38:;
Risk Codes:  Xi:;
">  Xi:;
Safety:
Transport Information:
PSA: 147.79000
LogP: 0.27380
Downstream Products
13380-36-4
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  • Lincomycin

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  • Lincomycin

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    Lincomycin

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  • Lincomycin;

  • Casno:

    154-21-2

    Lincomycin;

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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.