Hachimycin

Hachimycin, also known as trichomycin,[1] is a polyene macrolide antibiotic,[2] antiprotozoal,[3] and antifungal derived from streptomyces.[4] It was first described in 1950, and in most research cases have been used for gynecological infections.[3]

Hachimycin
Clinical data
ATC code
Identifiers
  • (4E,6E,8E,10E,12E,14E,16E)-3-[(2R,3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-19-[7-(4-aminophenyl)-5-hydroxy-7-oxoheptan-2-yl]-25,27,31,33,35,37-hexahydroxy-18-methyl-21,23-dioxo-20,39-dioxabicyclo[33.3.1]nonatriaconta-4,6,8,10,12,14,16-heptaene-38-carboxylic acid;(4E,6E,8E,10E,12E,14E,16E)-3-[(2R,3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-19-[7-(4-aminophenyl)-5-hydroxy-7-oxoheptan-2-yl]-27,29,31,33,35,37-hexahydroxy-18-methyl-21,23-dioxo-20,39-dioxabicyclo[33.3.1]nonatriaconta-4,6,8,10,12,14,16-heptaene-38-carboxylic acid
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC116H168N4O36
Molar mass2194.612 g·mol−1
3D model (JSmol)
  • CC1C=CC=CC=CC=CC=CC=CC=CC(CC2C(C(CC(O2)(CC(CC(CC(CC(CCCC(=O)CC(=O)OC1C(C)CCC(CC(=O)C3=CC=C(C=C3)N)O)O)O)O)O)O)O)C(=O)O)OC4C(C(C(C(O4)C)O)N)O.CC1C=CC=CC=CC=CC=CC=CC=CC(CC2C(C(CC(O2)(CC(CC(CCCC(CC(CC(=O)CC(=O)OC1C(C)CCC(CC(=O)C3=CC=C(C=C3)N)O)O)O)O)O)O)O)C(=O)O)OC4C(C(C(C(O4)C)O)N)O
  • InChI=1S/2C58H84N2O18/c1-35-17-14-12-10-8-6-4-5-7-9-11-13-15-20-46(76-57-54(71)52(60)53(70)37(3)75-57)32-49-51(56(72)73)48(68)34-58(74,78-49)33-45(66)29-44(65)28-43(64)27-40(61)18-16-19-41(62)31-50(69)77-55(35)36(2)21-26-42(63)30-47(67)38-22-24-39(59)25-23-38;1-35-17-14-12-10-8-6-4-5-7-9-11-13-15-20-46(76-57-54(71)52(60)53(70)37(3)75-57)32-49-51(56(72)73)48(68)34-58(74,78-49)33-45(66)28-41(62)19-16-18-40(61)27-43(64)29-44(65)31-50(69)77-55(35)36(2)21-26-42(63)30-47(67)38-22-24-39(59)25-23-38/h4-15,17,20,22-25,35-37,40,42-46,48-49,51-55,57,61,63-66,68,70-71,74H,16,18-19,21,26-34,59-60H2,1-3H3,(H,72,73);4-15,17,20,22-25,35-37,40-43,45-46,48-49,51-55,57,61-64,66,68,70-71,74H,16,18-19,21,26-34,59-60H2,1-3H3,(H,72,73)/b5-4-,8-6-,9-7-,12-10-,13-11-,17-14-,20-15-;5-4+,8-6+,9-7+,12-10+,13-11+,17-14-,20-15+/t35?,36?,37-,40?,42?,43?,44?,45?,46?,48?,49?,51?,52+,53-,54+,55?,57+,58?;35?,36?,37-,40?,41?,42?,43?,45?,46?,48?,49?,51?,52+,53-,54+,55?,57+,58?/m11/s1 checkY
  • Key:RZWQQZWPVPHLSY-UGMBPVHXSA-N checkY
  (verify)

References
  1. "Trichomycin - C116H168N4O36". PubChem. U.S. National Library of Medicine. Retrieved July 7, 2016.
  2. Mechlinski W, Schaffner CP (June 1980). "Characterization of aromatic heptaene macrolide antibiotics by high performance liquid chromatography". The Journal of Antibiotics. 33 (6): 591–599. doi:10.7164/antibiotics.33.591. PMID 6893446.
  3. Nakano H, Hattori K, Seki M, Hirata Y (1956). "Studies on Trichomycin. III". The Journal of Antibiotics, Series A. 9 (5): 172–175. doi:10.11554/antibioticsa.9.5_172.
  4. Komori T (July 1990). "Trichomycin B, a polyene macrolide from Streptomyces". The Journal of Antibiotics. 43 (7): 778–782. doi:10.7164/antibiotics.43.778. PMID 2387771.
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