micafungin (CHEBI:600520)

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CHEBI:600520 - micafungin

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ChEBI ID	CHEBI:600520
ChEBI Name	micafungin
Stars
Definition	A cyclic hexapeptide echinocandin antibiotic which exerts its effect by inhibiting the synthesis of 1,3-β-D-glucan, an integral component of the fungal cell wall. It is used as the sodium salt for the treatment of invasive candidiasis, and of aspergillosis in patients who are intolerant of other therapy.
Secondary ChEBI IDs	CHEBI:473847, CHEBI:530001, CHEBI:533643, CHEBI:533785
Last Modified	22 February 2017
Downloads	Molfile

Formula	C56H71N9O23S
Net Charge	0
Average Mass	1270.291
Monoisotopic Mass	1269.43835
SMILES	CCCCCOc1ccc(-c2cc(-c3ccc(C(=O)N[C@H]4C[C@@H](O)[C@@H](O)NC(=O)[C@@H]5[C@@H](O)[C@@H](C)CN5C(=O)[C@H]([C@H](O)CC(N)=O)NC(=O)[C@H]([C@H](O)[C@@H](O)c5ccc(O)c(OS(=O)(=O)O)c5)NC(=O)[C@@H]5C[C@@H](O)CN5C(=O)[C@H]([C@@H](C)O)NC4=O)cc3)no2)cc1
InChI	InChI=1S/C56H71N9O23S/c1-4-5-6-17-86-32-14-11-28(12-15-32)39-21-33(63-87-39)27-7-9-29(10-8-27)49(75)58-34-20-38(70)52(78)62-54(80)45-46(72)25(2)23-65(45)56(82)43(37(69)22-41(57)71)60-53(79)44(48(74)47(73)30-13-16-36(68)40(18-30)88-89(83,84)85)61-51(77)35-19-31(67)24-64(35)55(81)42(26(3)66)59-50(34)76/h7-16,18,21,25-26,31,34-35,37-38,42-48,52,66-70,72-74,78H,4-6,17,19-20,22-24H2,1-3H3,(H2,57,71)(H,58,75)(H,59,76)(H,60,79)(H,61,77)(H,62,80)(H,83,84,85)/t25-,26+,31+,34-,35-,37+,38+,42-,43-,44-,45-,46-,47-,48-,52+/m0/s1
InChIKey	PIEUQSKUWLMALL-YABMTYFHSA-N

Roles Classification

Chemical Roles:	Bronsted base A molecular entity capable of accepting a hydron from a donor (Brønsted acid). Bronsted base A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:	EC 2.4.1.34 (1,3-beta-glucan synthase) inhibitor A EC 2.4.1.* (hexosyltransferase) inhibitor that inhibits the action of 1,3-β-glucan synthase (EC 2.4.1.34). antifungal agent An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce. antifungal drug Any antifungal agent used to prevent or treat fungal infections in humans or animals. antifungal agent An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce. antifungal agent An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
Applications:	antiinfective agent A substance used in the prophylaxis or therapy of infectious diseases. antifungal drug Any antifungal agent used to prevent or treat fungal infections in humans or animals.

ChEBI Ontology

Outgoing Relation(s)
	micafungin (CHEBI:600520) has role antiinfective agent (CHEBI:35441)
	micafungin (CHEBI:600520) is a antibiotic antifungal drug (CHEBI:87113)
	micafungin (CHEBI:600520) is a echinocandin (CHEBI:57248)

IUPAC Names
5-[(1S,2S)-2-{(2R,6S,9S,11R,12R,14aS,15S,16S,20S,23S,25aS)-20-[(1R)-3-amino-1-hydroxy-3-oxopropyl]-2,11,12,15-tetrahydroxy-6-[(1R)-1-hydroxyethyl]-16-methyl-5,8,14,19,22,25-hexaoxo-9-[(4-{5-[4-(pentyloxy)phenyl]isoxazol-3-yl}benzoyl)amino]tetracosahydro-1H-dipyrrolo[2,1-c:2',1'-l][1,4,7,10,13,16]hexaazacyclohenicosin-23-yl}-1,2-dihydroxyethyl]-2-hydroxyphenyl hydrogen sulfate
5.1:6-anhydro{(4R,5R)-4,5-dihydroxy-N²-(4-{5-[4-(pentyloxy)phenyl]isoxazol-3-yl}benzoyl)-L-ornithyl-L-threonyl-(4R)-4-hydroxy-L-prolyl-(4S)-4-hydroxy-4-[4-hydroxy-3-(sulfooxy)phenyl]-L-threonyl-(3R)-3-hydroxy-L-glutaminyl-(3S,4S)-3-hydroxy-4-methyl-L-proline}

INNs	Source
micafungin	KEGG DRUG
micafungin	ChemIDplus

Synonym	Source
Mycamine	ChemIDplus

Manual Xrefs	Databases
D08218	KEGG DRUG
DB01141	DrugBank

Registry Numbers	Sources
Beilstein:9610508	Beilstein
CAS:235114-32-6	KEGG DRUG
CAS:235114-32-6	ChemIDplus

Citations