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Mupirocin(CAS No. 12650-69-0)

Mupirocin C26H44O9 (cas 12650-69-0) Molecular Structure

12650-69-0 Structure

Identification and Related Records

【Name】
Mupirocin
【Iupac name】
9-[(E)-4-[(2S,3R,4R,5S)-3,4-dihydroxy-5-[[(2S,3S)-3-[(2S,
3S)-3-hydroxybutan-2-yl]oxiran-2-yl]methyl]oxan-2-yl]-3-methylbut-2-
enoyl]oxynonanoic acid
【CAS Registry number】
12650-69-0
【Synonyms】
5,9-Anhydro-2,3,4,8-tetradeoxy-8-[[3-(2-hydroxy-1-methylpropyl)oxiranyl]methyl]-3-methyl-[2E,8[2S,3S(1S,2S)]]-L-talonon-2-enonic acid 8-carboxyoctyl ester
Mupirocinum
Pseudomonic acid
Pseudomonic acid A
UNII-D0GX863OA5
【Molecular Formula】
C26H44O9 (Products with the same molecular formula)
【Molecular Weight】
500.62216
【Inchi】
InChI=1S/C26H44O9/c1-16(13-23(30)33-11-9-7-5-4-6-8-10-22(28)29)12-20-25(32)24(31)19(15-34-20)14-21-26(35-21)17(2)18(3)27/h13,17-21,24-27,31-32H,4-12,14-15H2,1-3H3,(H,28,29)/b16-13+/t17-,18-,19-,20-,21-,24+,25-,26-/m0/s1
【InChIKey】
MINDHVHHQZYEEK-HBBNESRFSA-N
【Canonical SMILES】
CC(C1C(O1)CC2COC(C(C2O)O)CC(=CC(=O)OCCCCCCCCC(=O)O)C)C(C)O
【Isomers smiles】
C[C@H]([C@H]1[C@@H](O1)C[C@H]2CO[C@H]([C@@H]([C@@H]2O)O)C/C(=C/C(=O)
OCCCCCCCCC(=O)O)/C)[C@H](C)O

Chemical and Physical Properties

【Appearance】
solid
【Density】
1.183 g/cm3
【Melting Point】
77-780C
【Boiling Point】
672.3 ºC at 760 mmHg
【Vapour】
5.91E-21mmHg at 25°C
【Refractive Index】
1.524
【Flash Point】
216.5 ºC
【Water】
12 mg/mL in water
【Solubilities】
H2O: 12 mg/mL, soluble
【Storage temp】
Store cool, dark and dry.
【Computed Properties】
Molecular Weight:500.62216 [g/mol]
Molecular Formula:C26H44O9
XLogP3-AA:3
H-Bond Donor:4
H-Bond Acceptor:9
Rotatable Bond Count:17
Exact Mass:500.298533
MonoIsotopic Mass:500.298533
Topological Polar Surface Area:146
Heavy Atom Count:35
Formal Charge:0
Complexity:694
Isotope Atom Count:0
Defined Atom Stereocenter Count:8
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:1
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1

Safety and Handling

【Safety Statements 】
S2
【Specification】

The?IUPAC name of?Mupirocin is?9-[(E)-4-[(2S,3R,4R,5S)-3,4-dihydroxy-5-[[(2S,3S)-3-[(2S,3S)-3-hydroxybutan-2-yl]oxiran-2-yl]methyl]oxan-2-yl]-3-methylbut-2-enoyl]oxynonanoic acid. With the?CAS registry number 12650-69-0,?it is also named as Pseudomonic acid.?The product's categories are?active pharmaceutical ingredients; intermediates & fine chemicals; pharmaceuticals.?It is white crystalline solid?which is an antibiotic originally isolated from Pseudomonas fluorescens NCIMB 10586, developed by Beecham.

The other characteristics of this product can be summarized as:?(1)ACD/LogP: 3.44; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 2.64; (4)ACD/LogD (pH 7.4): 0.85; (5)ACD/BCF (pH 5.5): 38.7; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 282.5; (8)ACD/KOC (pH 7.4): 4.53; (9)#H bond acceptors: 9; (10)#H bond donors: 4; (11)#Freely Rotating Bonds: 20; (12)Index of Refraction: 1.524; (13)Molar Refractivity: 129.51 cm3; (14)Molar Volume: 423 cm3; (15)Polarizability: 51.34×10-24 cm3; (16)Surface Tension: 49 dyne/cm; (17)Enthalpy of Vaporization: 113.01 kJ/mol; (18)Vapour Pressure: 5.91E-21 mmHg at 25°C; (19)Rotatable Bond Count: 17; (20)Exact Mass: 500.298533; (21)MonoIsotopic Mass: 500.298533; (22)Topological Polar Surface Area: 146; (23)Heavy Atom Count: 35.

Preparation of Mupirocin: It is?obtained by the Pseudomonas fluorescens which produces a class of substances, including Pseudomonas acid A, B, C, D. Mupirocin is one of the major metabolites Pseudomonas acid A.

Uses of Mupirocin:?is bacteriostatic at low concentrations and bactericidal at high concentrations. It is used topically and is effective against Gram-positive bacteria, including MRSA.?treatment for bacterial skin infections

People can use the following data to convert to the molecule structure.
1. SMILES:O=C(O)CCCCCCCCOC(=O)\C=C(/C)C[C@@H]2OC[C@H](C[C@@H]1O[C@H]1[C@@H](C)[C@@H](O)C)[C@@H](O)[C@H]2O
2.?InChI:InChI=1/C26H44O9/c1-16(13-23(30)33-11-9-7-5-4-6-8-10-22(28)29)12-20-25(32)24(31)19(15-34-20)14-21-26(35-21)17(2)18(3)27/h13,17-21,24-27,31-32H,4-12,14-15H2,1-3H3,(H,28,29)/b16-13+/t17-,18-,19-,20-,21-,24+,25-,26-/m0/s1

The following are the toxicity data which has been tested.

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intravenous 1638mg/kg (1638mg/kg) ? United States Patent Document. Vol. #4206224,
mouse LD50 oral 5gm/kg (5000mg/kg) ? United States Patent Document. Vol. #4206224,
mouse LD50 subcutaneous 4gm/kg (4000mg/kg) ? United States Patent Document. Vol. #4206224,
rat LD50 intravenous 1310mg/kg (1310mg/kg) ? United States Patent Document. Vol. #4206224,
rat LD50 oral 5gm/kg (5000mg/kg) ? United States Patent Document. Vol. #4206224,
rat LD50 subcutaneous 5gm/kg (5000mg/kg) ? United States Patent Document. Vol. #4206224,

Use and Manufacturing

【Usage】

Major component of the pseudomonic acid, an antibiotic complex produced by Pseudomonas fluorescens NCIB 10586. Topical antibacterial

Biomedical Effects and Toxicity

【Pharmacological Action】
- Substances that reduce the growth or reproduction of BACTERIA.
- Compounds which inhibit the synthesis of proteins. They are usually ANTI-BACTERIAL AGENTS or toxins. Mechanism of the action of inhibition includes the interruption of peptide-chain elongation, the blocking the A site of ribosomes, the misreading of the genetic code or the prevention of the attachment of oligosaccharide side chains to glycoproteins.

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Raw materials

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