Responsive image

Common name


Oritavancin

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-(carbamoylmethyl)-5,15-dichloro-48-{[(2S,3R,4S,5S,6R)-3-{[(2S,4S,5R,6S)-4-({[4-(4-chlorophenyl)phenyl]methyl}amino)-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)pentanamido]-20,23,26,42,44-pentaoxo-7,13-dioxa-21,24,27,41,43-pentaazaoctacyclo[26.14.2.2³,

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)C4=CC(Cl)=C(OC5=C(O[C@@H]6O[C@H](CO)[C@@H](O)[C@H](O)[C@H]6O[C@H]6C[C@](C)(NCC7=CC=C(C=C7)C7=CC=C(Cl)C=C7)[C@@H](O)[C@H](C)O6)C(OC6=C(Cl)C=C(C=C6)[C@H]1O[C@H]1C[C@](C)(N)[C@@H](O)[C@H](C)O1)=CC3=C5)C=C4)C1=CC(=C(O)C=C1)C1=C(C=C(O)C=C1O)[C@H](NC2=O)C(O)=O

Compound class


Anti-Bacterial Agents; Antibacterials for Systemic Use; Antiinfectives for Systemic Use; Glycopeptide Antibacterials;

Therapeutic area


Investigated for use/treatment in bacterial infection and skin infections/disorders.

Common name


Oritavancin

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-(carbamoylmethyl)-5,15-dichloro-48-{[(2S,3R,4S,5S,6R)-3-{[(2S,4S,5R,6S)-4-({[4-(4-chlorophenyl)phenyl]methyl}amino)-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)pentanamido]-20,23,26,42,44-pentaoxo-7,13-dioxa-21,24,27,41,43-pentaazaoctacyclo[26.14.2.2³,

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)C4=CC(Cl)=C(OC5=C(O[C@@H]6O[C@H](CO)[C@@H](O)[C@H](O)[C@H]6O[C@H]6C[C@](C)(NCC7=CC=C(C=C7)C7=CC=C(Cl)C=C7)[C@@H](O)[C@H](C)O6)C(OC6=C(Cl)C=C(C=C6)[C@H]1O[C@H]1C[C@](C)(N)[C@@H](O)[C@H](C)O1)=CC3=C5)C=C4)C1=CC(=C(O)C=C1)C1=C(C=C(O)C=C1O)[C@H](NC2=O)C(O)=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

FORMULA


C86H97Cl3N10O26

Responsive image

Common name


Oritavancin

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-(carbamoylmethyl)-5,15-dichloro-48-{[(2S,3R,4S,5S,6R)-3-{[(2S,4S,5R,6S)-4-({[4-(4-chlorophenyl)phenyl]methyl}amino)-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)pentanamido]-20,23,26,42,44-pentaoxo-7,13-dioxa-21,24,27,41,43-pentaazaoctacyclo[26.14.2.2³,

Molecular weight


1793.101

clogP


1.784

clogS


-12.557

HBond Acceptor


26

HBond Donor


22

Total Polar
Surface Area


560.98

Number of Rings


13

Rotatable Bond


19

Drug ID Common name Structure CAS SMILE Frequency
FDBF00003 formamide Responsive image C(=O)N 0.1240
FDBF00007 propane Responsive image C(C)C 0.2412
FDBF00012 isobutane Responsive image C(C)(C)C 0.0611
FDBF00016 chlorobenzene Responsive image c1ccc(cc1)Cl 0.0718
FDBF00913 phenylmethanamine Responsive image NCc1ccccc1 0.0086
FDBF01164 N,3-dimethylbutan-1-amine Responsive image C(C(C)C)CNC 0.0007
FDBF03260 (2R,4R,5R,6R)-4,6-dimethyltetrahydropyran-2,5-diol Responsive image OC1OC(C(C(C1)C)O)C 0.0003
FDBF03262 (2R,3R,4S)-2,4-dimethyl-4-(methylamino)tetrahydropyran-3-ol Responsive image O1CCC(C(C1C)O)(C)NC 0.0003
20 , 3