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Oritavancin (LY-333328)

CAT: 0931-T37881-01Size: 2 mgDry Ice: NoHazardous: No
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CAT#:0931-T37881-01Size:2 mg
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CAS Number
171099-57-3
Target
Antibiotic, Antibacterial, Others
Related Pathways
Others, Microbiology/Virology
Bioactivity
Oritavancin is a novel semisynthetic glycopeptide antibiotics. On August 6, 2014, the FDA approved oritavancin for treatment of skin infections. Oritavancin possesses potent and rapid bactericidal activity in vitro against a broad spectrum of both resistant and susceptible Gram-positive bacteria, including Staphylococcus aureus, MRSA, enterococci, and streptococci.
Smiles
[H][C@]12NC(=O)[C@]([H])(NC(=O)[C@]3([H])NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](NC(=O)[C@@H](CC(C)C)NC)[C@H](O)c4ccc(Oc5cc3cc(Oc3ccc(cc3Cl)[C@H]1O[C@H]1C[C@](C)(N)[C@@H](O)[C@H](C)O1)c5O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O[C@H]1C[C@](C)(NCc3ccc(cc3)-c3ccc(Cl)cc3)[C@@H](O)[C@H](C)O1)c(Cl)c4)c1ccc(O)c(c1)-c1c(O)cc(O)cc1[C@H](NC2=O)C(O)=O
Molecular Formula
C86H97Cl3N10O26
Molecular Weight
1793.12
Shipping Conditions
Ice Packs
Storage Temperature
-20°C

Chemical Information

Oritavancin

Oritavancin is a semisynthetic glycopeptide used (as its bisphosphate salt) for the treatment of acute bacterial skin and skin structure infections caused or suspected to be caused by susceptible isolates of designated Gram-positive microorganisms including MRSA. It has a role as an antimicrobial agent and an antibacterial drug. It is a glycopeptide, a disaccharide derivative and a semisynthetic derivative. It is functionally related to a vancomycin aglycone.

CAS Number171099-57-3
PubChem CID16136912
IUPAC Name(1S,2R,18R,19R,22S,25R,28R,40S)-2-[(2R,4S,5R,6S)-4-amino-5-hydroxy-4,6-dimethyloxan-2-yl]oxy-22-(2-amino-2-oxoethyl)-5,15-dichloro-48-[(2S,3R,4S,5S,6R)-3-[(2S,4S,5R,6S)-4-[[4-(4-chlorophenyl)phenyl]methylamino]-5-hydroxy-4,6-dimethyloxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-18,32,35,37-tetrahydroxy-19-[[(2R)-4-methyl-2-(methylamino)pentanoyl]amino]-20,23,26,42,44-pentaoxo-7,13-dioxa-21,24,27,41,43-pentazaoctacyclo[26.14.2.23,6.214,17.18,12.129,33.010,25.034,39]pentaconta-3,5,8,10,12(48),14,16,29(45),30,32,34(39),35,37,46,49-pentadecaene-40-carboxylic acid
Molecular FormulaC86H97Cl3N10O26
Molecular Weight1793.1
XLogP1.5
Topological Polar Surface Area561
Hydrogen Bond Donor Count20
Hydrogen Bond Acceptor Count29
Rotatable Bond Count19
Heavy Atom Count125
Formal Charge0
Complexity3700
SMILES
C[C@H]1[C@@H]([C@@](C[C@@H](O1)O[C@H]2[C@H]3C(=O)N[C@@H](C4=C(C(=CC(=C4)O)O)C5=C(C=CC(=C5)[C@H](C(=O)N3)NC(=O)[C@H]6C7=CC(=C(C(=C7)OC8=C(C=C2C=C8)Cl)O[C@H]9[C@@H]([C@H]([C@@H]([C@H](O9)CO)O)O)O[C@H]1C[C@]([C@H]([C@@H](O1)C)O)(C)NCC1=CC=C(C=C1)C1=CC=C(C=C1)Cl)OC1=C(C=C(C=C1)[C@H]([C@H](C(=O)N[C@H](C(=O)N6)CC(=O)N)NC(=O)[C@@H](CC(C)C)NC)O)Cl)O)C(=O)O)(C)N)O
InChI
InChI=1S/C86H97Cl3N10O26/c1-35(2)22-51(92-7)77(110)98-67-69(105)42-15-20-55(49(88)24-42)120-57-26-44-27-58(73(57)125-84-74(71(107)70(106)59(34-100)122-84)124-62-32-86(6,76(109)37(4)119-62)93-33-38-8-10-39(11-9-38)40-12-17-45(87)18-13-40)121-56-21-16-43(25-50(56)89)72(123-61-31-85(5,91)75(108)36(3)118-61)68-82(115)97-66(83(116)117)48-28-46(101)29-54(103)63(48)47-23-41(14-19-53(47)102)64(79(112)99-68)96-80(113)65(44)95-78(111)52(30-60(90)104)94-81(67)114/h8-21,23-29,35-37,51-52,59,61-62,64-72,74-76,84,92-93,100-103,105-109H,22,30-34,91H2,1-7H3,(H2,90,104)(H,94,114)(H,95,111)(H,96,113)(H,97,115)(H,98,110)(H,99,112)(H,116,117)/t36-,37-,51+,52-,59+,61-,62-,64+,65+,66-,67+,68-,69+,70+,71-,72+,74+,75-,76-,84-,85-,86-/m0/s1
InChIKey
VHFGEBVPHAGQPI-LXKZPTCJSA-N
Chemical Structure
2D Structure
2D structure of Oritavancin
CAS: 171099-57-3
CID: 16136912
Formula: C86H97Cl3N10O26
MW: 1793.1
Interactive 3D Structure
Loading 3D structure...
Computed Properties
PropertyValue
Molecular Weight1793.1
XLogP31.5
Hydrogen Bond Donor Count20
Hydrogen Bond Acceptor Count29
Rotatable Bond Count19
Exact Mass1790.564106
Monoisotopic Mass1790.564106
Topological Polar Surface Area561 Ų
Heavy Atom Count125
Formal Charge0
Complexity3700
Isotope Atom Count0
Defined Atom Stereocenter Count22
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes