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CHEBI:66388 - microspinosamide

Default Structure
ChEBI IDCHEBI:66388
ChEBI Namemicrospinosamide
Stars
DefinitionA cyclodepsipeptide isolated from the marine sponge Sidonops microspinosa and has been shown to exhibit anti-HIV-1 activity.
Last Modified10 April 2013
DownloadsMolfile
FormulaC75H109BrN18O22S
Net Charge0
Average Mass1726.772
Monoisotopic Mass1724.68679
SMILESCCC(C)(C)[C@H](NC(=O)[C@H](NC(=O)[C@@H]1CCCN1C(=O)C(NC(=O)[C@@H](C)NC=O)C(O)c1ccc(Br)cc1)C(C)(C)C)C(=O)N[C@H](Cc1cnc2ccccc12)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@H](CS(=O)(=O)O)C(=O)N[C@@H]1C(=O)N(C)[C@@H](CCC(N)=O)C(=O)N[C@H](C(C)C)C(=O)N2CCC[C@H]2C(=O)N[C@H](CC(=O)O)C(=O)O[C@@H]1C
InChIInChI=1S/C75H109BrN18O22S/c1-12-75(9,10)59(91-67(107)58(74(6,7)8)90-66(106)51-22-17-31-94(51)71(111)56(89-60(100)38(4)82-36-95)57(99)40-23-25-42(76)26-24-40)68(108)84-46(32-41-34-81-44-19-14-13-18-43(41)44)62(102)83-45(20-15-29-80-73(78)79)61(101)86-48(35-117(113,114)115)63(103)88-55-39(5)116-72(112)47(33-53(97)98)85-65(105)50-21-16-30-93(50)70(110)54(37(2)3)87-64(104)49(27-28-52(77)96)92(11)69(55)109/h13-14,18-19,23-26,34,36-39,45-51,54-59,81,99H,12,15-17,20-22,27-33,35H2,1-11H3,(H2,77,96)(H,82,95)(H,83,102)(H,84,108)(H,85,105)(H,86,101)(H,87,104)(H,88,103)(H,89,100)(H,90,106)(H,91,107)(H,97,98)(H4,78,79,80)(H,113,114,115)/t38-,39-,45+,46-,47-,48-,49+,50+,51+,54-,55+,56?,57?,58+,59-/m1/s1
InChIKeyGUGALNGMVNRENE-DPOFQXJLSA-N
Species of MetaboliteComponentSourceComments
Sidonops microspinosa (WORMS:170219) - PubMed (11170684)
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
anti-HIV-1 agent  An anti-HIV agent that destroys or inhibits the replication of HIV-1, the more infective and more virulent of the two types of HIV virus.
ChEBI Ontology
Outgoing Relation(s)
microspinosamide (CHEBI:66388) has role anti-HIV-1 agent (CHEBI:64947)
microspinosamide (CHEBI:66388) has role metabolite (CHEBI:25212)
microspinosamide (CHEBI:66388) is a cyclodepsipeptide (CHEBI:35213)
microspinosamide (CHEBI:66388) is a organosulfonic acid (CHEBI:33551)
IUPAC Name 
N-formyl-D-alanyl-4-bromo-β-hydroxyphenylalanyl-L-prolyl-3-methyl-D-valyl-3-methyl-L-isoleucyl-D-tryptophyl-L-arginyl-N-[(3R,6R,7S,10S,13R,18aS)-10-(3-amino-3-oxopropyl)-3-(carboxymethyl)-6,9-dimethyl-1,4,8,11,14-pentaoxo-13-(propan-2-yl)hexadecahydro-6H-pyrrolo[2,1-f][1,4,7,10,13]oxatetraazacyclohexadecin-7-yl]-3-sulfo-D-alaninamide
Registry NumbersSources
Reaxys:8825233Reaxys
Citations