Paromomycin
(2S,3S,4R,5R,6R)-5-amino-2-(aminomethyl)-6-[(2R,3S,4R,5S)-5-[(1R,2R,3S,5R,6S)-3,5-diamino-2-[(2S,3R,4R,5S,6R)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-hydroxycyclohexyl]oxy-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxyoxane-3,4-diol
Molecular Identity
Paromomycin
(2S,3S,4R,5R,6R)-5-amino-2-(aminomethyl)-6-[(2R,3S,4R,5S)-5-[(1R,2R,3S,5R,6S)-3,5-diamino-2-[(2S,3R,4R,5S,6R)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-hydroxycyclohexyl]oxy-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxyoxane-3,4-diol
PubChem CID: 165580
Paromomycin is an amino cyclitol glycoside that is the 1-O-(2-amino-2-deoxy-alpha-D-glucopyranoside) and the 3-O-(2,6-diamino-2,6-dideoxy-beta-L-idopyranosyl)-beta-D-ribofuranoside of 4,6-diamino-2,3-dihydroxycyclohexane (the 1R,2R,3S,4R,6S diastereoisomer). It is obtained from various Streptomyces species. A broad-spectrum antibiotic, it is used (generally as the sulfate salt) for the treatment of acute and chronic intestinal protozoal infections, but is not effective for extraintestinal protozoal infections. It is also used as a therapeutic against visceral leishmaniasis. It has a role as an antiparasitic agent, an anthelminthic drug, an antiprotozoal drug and an antibacterial drug. It is an amino cyclitol glycoside and an aminoglycoside antibiotic. It is functionally related to a streptamine. It is a conjugate base of a paromomycin(5+).
2D Structure
Properties
C23H45N5O14
Molecular Formula
615.60
Molecular Weight
g/mol
615.2963
Exact Mass
Da
-8.7
XLogP
Drug-like (Lipinski: < 5)
347
TPSA
May have limited oral absorption
13
H-Bond Donors
19
H-Bond Acceptors
870
Complexity
SMILES
Canonical SMILES
SMILES: C1C(C(C(C(C1N)OC2C(C(C(C(O2)CO)O)O)N)OC3C(C(C(O3)CO)OC4C(C(C(C(O4)CN)O)O)N)O)O)NIsomeric SMILES
SMILES: C1[C@H]([C@@H]([C@H]([C@@H]([C@H]1N)O[C@@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)N)O[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O[C@@H]4[C@@H]([C@H]([C@@H]([C@@H](O4)CN)O)O)N)O)O)NSynonyms(20)
paromomycinAminosidincatenulinMonomycin A7542-37-2Neomycin EHydroxymycinCrestomycinPaucimycinAMINOSIDINEParomomycineEstomycinQuintomycin CParomomycin IZygomycin A1
Data from PubChem (NCBI)
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Drug Network
Trials and conditions connected to Paromomycin
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