CHEBI:66388 - microspinosamide

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ChEBI Name microspinosamide
ChEBI ID CHEBI:66388
Definition A cyclodepsipeptide isolated from the marine sponge Sidonops microspinosa and has been shown to exhibit anti-HIV-1 activity.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C75H109BrN18O22S
Net Charge 0
Average Mass 1726.74400
Monoisotopic Mass 1724.687
InChI InChI=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
InChIKey GUGALNGMVNRENE-DPOFQXJLSA-N
SMILES CCC(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](Cc1c[nH]c2ccccc12)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@H](CS(O)(=O)=O)C(=O)N[C@H]1[C@@H](C)OC(=O)[C@@H](CC(O)=O)NC(=O)[C@@H]2CCCN2C(=O)[C@H](NC(=O)[C@H](CCC(N)=O)N(C)C1=O)C(C)C
Metabolite of Species Details
Sidonops microspinosa (WORMS:170219) See: PubMed
Roles Classification
Biological Role(s): 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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 Number Type Source
8825233 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
11170684 PubMed citation Europe PMC
20411126 PubMed citation Europe PMC
Last Modified
10 April 2013