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Surotomycin

CAT: 0013-GTR19242017-02Size: 50 mgDry Ice: NoHazardous: No
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CAT#:0013-GTR19242017-02Size:50 mg
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Description
Surotomycin is a cyclic lipopeptide antibiotic derived from phenylbutyrate, effective against Gram-positive bacteria. It is utilized in research to study Clostridioides difficile infections, demonstrating bactericidal activity in both in vitro assays and in vivo animal models.
CAS Number
1233389-51-9
Smiles
C ([C@@H] (C (N[C@@H] (C (N[C@H] (C (N[C@H]1[C@@H] (C) OC (=O) [C@H] (CC (=O) C2=C (N) C=CC=C2) NC (=O) [C@] ([C@@H] (CC (O) =O) C) (NC (=O) [C@@H] (CO) NC (=O) CNC (=O) [C@H] (CC (O) =O) NC (=O) [C@@H] (C) NC (=O) [C@H] (CC (O) =O) NC (=O) [C@H] (CCCN) NC (=O) CNC1=O) [H]) =O) CC (O) =O) =O) CC (N) =O) =O) NC (/C=C (\C) /C3=CC=C (CCCCC) C=C3) =O) C=4C=5C (NC4) =CC=CC5
Molecular Formula
C77H101N17O26
Molecular Weight
1680.72
Storage Conditions
-20°C
Notes
For research use only.

Chemical Information

Surotomycin

Surotomycin has been used in trials studying the treatment of Diarrhea and Clostridium Difficile Infection. It is a benzenebutanoic acid derivative patented by Cubist Pharmaceuticals, Inc. as antibacterial agents for the treatment of Gram-positive infections. Surotomycin has a fourfold greater in vitro potency than vancomycin against C. Difficile and other Gram-positive bacteria with minimal impact on the Gram-negative organisms of the intestinal microbiota. Surotomycin, given orally, has been shown to be highly effective against both initial and relapsing hamster Clostridium difficile-associated diarrhea, with a potency similar to vancomycin. Surotomycin is non-inferior to vancomycin and offers a promising alternative for the treatment and prevention of C. diff infection.

CAS Number1233389-51-9
PubChem CID46700778
IUPAC Name(3S)-3-[[(2R)-4-amino-2-[[(2S)-3-(1H-indol-3-yl)-2-[[(E)-3-(4-pentylphenyl)but-2-enoyl]amino]propanoyl]amino]-4-oxobutanoyl]amino]-4-[[(3S,6S,9R,15S,18R,21S,24S,30S,31R)-3-[2-(2-aminophenyl)-2-oxoethyl]-24-(3-aminopropyl)-15,21-bis(carboxymethyl)-6-[(2R)-1-carboxypropan-2-yl]-9-(hydroxymethyl)-18,31-dimethyl-2,5,8,11,14,17,20,23,26,29-decaoxo-1-oxa-4,7,10,13,16,19,22,25,28-nonazacyclohentriacont-30-yl]amino]-4-oxobutanoic acid
Molecular FormulaC77H101N17O26
Molecular Weight1680.7
XLogP-4
Topological Polar Surface Area702
Hydrogen Bond Donor Count22
Hydrogen Bond Acceptor Count28
Rotatable Bond Count33
Heavy Atom Count120
Formal Charge0
Complexity3730
SMILES
CCCCCC1=CC=C(C=C1)/C(=C/C(=O)N[C@@H](CC2=CNC3=CC=CC=C32)C(=O)N[C@H](CC(=O)N)C(=O)N[C@@H](CC(=O)O)C(=O)N[C@H]4[C@H](OC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](NC(=O)CNC(=O)[C@@H](NC(=O)[C@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)CNC4=O)CCCN)CC(=O)O)C)CC(=O)O)CO)[C@H](C)CC(=O)O)CC(=O)C5=CC=CC=C5N)C)/C
InChI
InChI=1S/C77H101N17O26/c1-6-7-8-14-41-20-22-42(23-21-41)37(2)25-58(98)86-49(27-43-33-81-47-18-12-10-15-44(43)47)71(113)89-50(29-57(80)97)72(114)91-53(32-64(107)108)73(115)94-66-40(5)120-77(119)54(28-56(96)45-16-9-11-17-46(45)79)92-76(118)65(38(3)26-61(101)102)93-74(116)55(36-95)87-60(100)34-82-68(110)51(30-62(103)104)88-67(109)39(4)84-70(112)52(31-63(105)106)90-69(111)48(19-13-24-78)85-59(99)35-83-75(66)117/h9-12,15-18,20-23,25,33,38-40,48-55,65-66,81,95H,6-8,13-14,19,24,26-32,34-36,78-79H2,1-5H3,(H2,80,97)(H,82,110)(H,83,117)(H,84,112)(H,85,99)(H,86,98)(H,87,100)(H,88,109)(H,89,113)(H,90,111)(H,91,114)(H,92,118)(H,93,116)(H,94,115)(H,101,102)(H,103,104)(H,105,106)(H,107,108)/b37-25+/t38-,39-,40-,48+,49+,50-,51+,52+,53+,54+,55-,65+,66+/m1/s1
InChIKey
DYNMYYRPPFVAKR-CWXHRMTKSA-N
Chemical Structure
2D Structure
2D structure of Surotomycin
CAS: 1233389-51-9
CID: 46700778
Formula: C77H101N17O26
MW: 1680.7
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight1680.7
XLogP3-4
Hydrogen Bond Donor Count22
Hydrogen Bond Acceptor Count28
Rotatable Bond Count33
Exact Mass1679.71036639
Monoisotopic Mass1679.71036639
Topological Polar Surface Area702 Ų
Heavy Atom Count120
Formal Charge0
Complexity3730
Isotope Atom Count0
Defined Atom Stereocenter Count13
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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CatalogName
T202524-01Surotomycin

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