A lipopeptide antibiotic
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Enramycin A

Item No. 40847

Technical Information
Formal Name
(2S)-N-[(2Z,4E)-10-methyl-1-oxo-2,4-undecadien-1-yl]-L-α-aspartyl-L-threonyl-(2R)-2-(4-hydroxyphenyl)glycyl-D-ornithyl-D-allothreonyl-(2S)-2-(4-hydroxyphenyl)glycyl-(2R)-2-(4-hydroxyphenyl)glycyl-L-allothreonyl-N5-(aminocarbonyl)-L-ornithyl-3-[(5R)-2-amino-4,5-dihydro-1H-imidazol-5-yl]-D-alanyl-(2S)-2-(4-hydroxyphenyl)glycyl-D-seryl-(2S)-2-(3,5-dichloro-4-hydroxyphenyl)glycylglycyl-3-[(5R)-2-amino-4,5-dihydro-1H-imidazol-5-yl]-L-alanyl-D-alanyl-2-(4-hydroxyphenyl)-glycine (17→2)-lactone
CAS Number
34438-27-2
Synonyms
  • Enduramycin A
Molecular Formula
C107H138Cl2N26O31
Formula Weight
Purity
≥95%
A solid
Methanol: Slightly Soluble: 0.1-1 mg/mlWater: Slightly Soluble: 0.1-1 mg/ml
SMILES
O=C(/C=C\C=C\CCCCC(C)C)N[C@H](C(N[C@H](C(N[C@@H](C(N[C@@H](C(N[C@@](C(N[C@H]1C2=CC=C(O)C=C2)=O)([C@H](O)C)[H])=O)CCCN)=O)C3=CC=C(O)C=C3)=O)[C@@H](C)OC([C@@H](NC([C@@H](C)NC([C@H](C[C@@]4([H])NC(N)=NC4)NC(CNC([C@@H](NC([C@@H](CO)NC([C@@H](NC([C@@H](C[C@H]5NC(N)=NC5)NC([C@H](CCCNC(N)=O)NC([C@@](NC([C@H](NC1=O)C6=CC=C(O)C=C6)=O)([C@H](C)O)[H])=O)=O)=O)C7=CC=C(O)C=C7)=O)=O)C8=CC(Cl)=C(O)C(Cl)=C8)=O)=O)=O)=O)C9=CC=C(O)C=C9)=O)=O)CC(O)=O
InChi Code
InChI=1S/C107H138Cl2N26O31/c1-50(2)15-11-9-7-8-10-12-18-76(144)121-74(45-78(146)147)94(154)129-81-54(6)166-104(164)87(59-27-37-67(143)38-28-59)135-89(149)51(3)118-92(152)72(43-61-46-116-105(111)119-61)122-77(145)48-115-96(156)86(60-41-68(108)88(148)69(109)42-60)131-95(155)75(49-136)126-101(161)82(55-19-29-63(139)30-20-55)130-93(153)73(44-62-47-117-106(112)120-62)125-90(150)71(17-14-40-114-107(113)165)123-97(157)79(52(4)137)128-102(162)84(57-23-33-65(141)34-24-57)134-103(163)85(58-25-35-66(142)36-26-58)132-98(158)80(53(5)138)127-91(151)70(16-13-39-110)124-100(160)83(133-99(81)159)56-21-31-64(140)32-22-56/h8,10,12,18-38,41-42,50-54,61-62,70-75,79-87,136-143,148H,7,9,11,13-17,39-40,43-49,110H2,1-6H3,(H,115,156)(H,118,152)(H,121,144)(H,122,145)(H,123,157)(H,124,160)(H,125,150)(H,126,161)(H,127,151)(H,128,162)(H,129,154)(H,130,153)(H,131,155)(H,132,158)(H,133,159)(H,134,163)(H,135,149)(H,146,147)(H3,111,116,119)(H3,112,117,120)(H3,113,114,165)/b10-8+,18-12-/t51-,52+,53-,54-,61-,62-,70-,71+,72+,73-,74+,75-,79+,80-,81+,82+,83-,84-,85+,86+,87+/m1/s1
InChi Key
IPZGNBNNEDCXBK-SWEPSTQMSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    Product Description

    Enramycin A is a lipopeptide antibiotic that has been found in S. fungicidicus.1 It also inhibits avian myeloblastosis virus reverse transcriptase by 50% when used at a concentration of 10 µg/ml in a cell-free assay.2 Formulations containing enramycin A have been used as feed additives to prevent bacterial necrotic enteritis in livestock.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Iwasaki, H., Horii, S., Asai, M., et alEnduracidin, a new antibiotic. VIII. Structures of enduracidins A and B. Chem. Pharm. Bull. 21(6), 1184-1191 (1973).

    2. Inouye, Y., Take, Y., Nakamura, S., et alScreening for inhibitors of avian myeloblastosis virus reverse transcriptase and effect on the replication of AIDS-virus. J. Antibiot. (Tokyo) 40(1), 100-104 (1987).