CHEBI:65556 - callipeltin A

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ChEBI Name callipeltin A
ChEBI ID CHEBI:65556
Definition A 10-membered cyclodepsipeptide containing four amino acids in the L- configuration, Ala, Leu, Thr (2 residues); one (Arg) in the D-configuration; two N-methyl amino acids, N-MeAla and N-MeGln; a methoxy tyrosine, a 3, 4-dimethyl-L-glutamine, and a 4-amino-7-guanidino-2,3 dihydroxypentanoic acid (AGDHE), formally derived from L-Arg. It is obtained from the shallow water sponge Callipelta and has been found to show activity against HIV virus.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C68H116N18O20
Net Charge 0
Average Mass 1505.75720
Monoisotopic Mass 1504.861
InChI InChI=1S/C68H116N18O20/c1-30(2)28-32(5)51(90)35(8)56(94)77-36(9)57(95)78-42(18-16-26-75-67(71)72)52(91)53(92)63(101)81-47(33(6)34(7)55(70)93)60(98)83-49-39(12)106-66(104)37(10)85(13)65(103)50(54(105-15)40-20-22-41(88)23-21-40)84-59(97)45(24-25-46(69)89)86(14)64(102)44(29-31(3)4)80-58(96)43(19-17-27-76-68(73)74)79-61(99)48(38(11)87)82-62(49)100/h20-23,30-39,42-45,47-54,87-88,90-92H,16-19,24-29H2,1-15H3,(H2,69,89)(H2,70,93)(H,77,94)(H,78,95)(H,79,99)(H,80,96)(H,81,101)(H,82,100)(H,83,98)(H,84,97)(H4,71,72,75)(H4,73,74,76)/t32-,33+,34-,35-,36-,37+,38-,39-,42+,43-,44+,45+,47+,48+,49+,50-,51-,52-,53-,54-/m1/s1
InChIKey UDTRUOCOOZKCCT-QVVVRIHHSA-N
SMILES [H][C@]1(NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](O)[C@H](O)[C@H](CCCNC(N)=N)NC(=O)[C@@H](C)NC(=O)[C@H](C)[C@H](O)[C@H](C)CC(C)C)[C@@H](C)[C@@H](C)C(N)=O)[C@@H](C)OC(=O)[C@H](C)N(C)C(=O)[C@]([H])(NC(=O)[C@H](CCC(N)=O)N(C)C(=O)[C@H](CC(C)C)NC(=O)[C@@H](CCCNC(N)=N)NC1=O)[C@H](OC)c1ccc(O)cc1)[C@@H](C)O
Metabolite of Species Details
Callipelta (WORMS:171128) See: DOI
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
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.
antifungal agent
An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing callipeltin A (CHEBI:65556) has role anti-HIV-1 agent (CHEBI:64947)
callipeltin A (CHEBI:65556) has role antifungal agent (CHEBI:35718)
callipeltin A (CHEBI:65556) has role metabolite (CHEBI:25212)
callipeltin A (CHEBI:65556) is a cyclodepsipeptide (CHEBI:35213)
callipeltin A (CHEBI:65556) is a guanidines (CHEBI:24436)
callipeltin A (CHEBI:65556) is a lactone (CHEBI:25000)
callipeltin A (CHEBI:65556) is a oligopeptide (CHEBI:25676)
callipeltin A (CHEBI:65556) is a phenols (CHEBI:33853)
IUPAC Name
(3S,4R)-N1-[(3S,6R,9S,12S,15R,18S,21S,22R)-9-(3-amino-3-oxopropyl)-15-(3-carbamimidamidopropyl)-18-[(1R)-1-hydroxyethyl]-6-[(R)-(4-hydroxyphenyl)(methoxy)methyl]-3,4,10,22-tetramethyl-12-(2-methylpropyl)-2,5,8,11,14,17,20-heptaoxo-1-oxa-4,7,10,13,16,19-hexaazacyclodocosan-21-yl]-N2-[(2R,3R,4S)-7-carbamimidamido-2,3-dihydroxy-4-({N-[(2R,3R,4R)-3-hydroxy-2,4,6-trimethylheptanoyl]-D-alanyl}amino)heptanoyl]-3,4-dimethyl-L-glutamamide
Citation Waiting for Citations Type Source
11112442 PubMed citation Europe PMC
Last Modified
05 March 2014