Theonellamide A
AlkaPlorer ID: AK327108
Synonym: None
IUPAC Name: (1S,5R,7S,10S,14S,17S,20S,23R,26S,30S,33S,36S,39S)-33-benzyl-14-[(1S)-1-(4-bromophenyl)ethyl]-17-[(1R)-1,2-dihydroxy-2-iminoethyl]-3,5,9,10,13,16,19,22,25,28,32,35,38,41-tetradecahydroxy-39-[(1S)-1-hydroxyethyl]-20-(2-hydroxy-2-iminoethyl)-26,36-bis(hydroxymethyl)-30-[(1S,2E,4E)-1-hydroxy-3-methyl-5-phenylpenta-2,4-dienyl]-44-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-2,8,12,15,18,21,24,27,31,34,37,40,44-tridecaza-46-azoniatricyclo[21.18.6.143,46]octatetraconta-2,8,12,15,18,21,24,27,31,34,37,40,43(48),45-tetradecaene-7-carboxylate
Structure
SMILES: CC(/C=C/C1=CC=CC=C1)=C\[C@H](O)[C@@H]1CC(O)=N[C@@H](CO)C(O)=N[C@@H]2C[N+]3=CN([C@@H]4O[C@H](CO)[C@H](O)[C@H](O)[C@H]4O)C(=C3)C[C@H](N=C(O)C[C@H](O)C[C@@H](C(=O)[O-])N=C(O)[C@@H](O)CN=C(O)[C@H]([C@@H](C)C3=CC=C(Br)C=C3)N=C(O)[C@H]([C@@H](O)C(=N)O)N=C(O)[C@H](CC(=N)O)N=C2O)C(O)=N[C@@H]([C@H](C)O)C(O)=N[C@@H](CO)C(O)=N[C@@H](CC2=CC=CC=C2)C(O)=N1
InChI: InChI=1S/C76H99BrN16O28/c1-34(14-15-37-10-6-4-7-11-37)20-51(99)43-26-56(103)82-49(30-94)69(113)87-48-29-92-28-41(93(33-92)75-63(107)62(106)60(104)53(32-96)121-75)22-45(66(110)90-58(36(3)97)73(117)88-50(31-95)70(114)84-44(65(109)83-43)21-38-12-8-5-9-13-38)81-55(102)24-42(98)23-47(76(119)120)86-71(115)52(100)27-80-72(116)57(35(2)39-16-18-40(77)19-17-39)89-74(118)59(61(105)64(79)108)91-67(111)46(25-54(78)101)85-68(48)112/h4-20,28,33,35-36,42-53,57-63,75,94-100,104-107H,21-27,29-32H2,1-3H3,(H16-,78,79,80,81,82,83,84,85,86,87,88,89,90,91,101,102,103,108,109,110,111,112,113,114,115,116,117,118,119,120)/b15-14+,34-20+/t35-,36-,42+,43-,44-,45-,46-,47-,48+,49-,50-,51-,52-,53+,57-,58-,59-,60-,61+,62-,63+,75+/m0/s1
InChIKey: WVJFAKMMDQFEDM-UZGFQBTNSA-N
Reference
Theonellamides A-E, cytotoxic bicyclic peptides, from a marine sponge Theonella sp.
PubChem CID: 45382315
LOTUS: LTS0152424
SuperNatural Ⅲ: SN0421029-02
{NPAtlas: NPA028458
Source
| Species | Genus | Family | Order | Class | Phylum | Kingdom | Domain |
|---|---|---|---|---|---|---|---|
| None | Entotheonella | None | None | None | Candidatus Tectomicrobia | None | Bacteria |
Properties Information
Molecule Weight: 1764.6160000000011
TPSA？: 759.9400000000004
MolLogP？: -0.4912600000000129
Number of H-Donors: 27
Number of H-Acceptors: 29
RingCount: 7
Activities Information
| Organism | Target Name | Standard Type | Standard Value | Standard Units | doi |
|---|---|---|---|---|---|
| None | Lipid bilayer | Kd | 420000.0 | nM | 10.1016/j.bmc.2016.08.043 |
| None | Molecular identity unknown | IC50 | 2000.0 | nM | 10.1016/j.bmc.2016.08.043 |
| None | NON-PROTEIN TARGET | IC50 | 500.0 | nM | 10.1016/j.bmc.2016.08.043 |
| None | NON-PROTEIN TARGET | IC50 | 2000.0 | nM | 10.1016/j.bmc.2016.08.043 |
| None | No relevant target | Activity | nan | None | 10.1016/j.bmc.2016.08.043 |
| None | No relevant target | D | 0.47 | 10'-10m2/s | 10.1016/j.bmc.2016.08.043 |
| None | No relevant target | D | 0.55 | 10'-10m2/s | 10.1016/j.bmc.2016.08.043 |
| None | No relevant target | D | 0.91 | 10'-10m2/s | 10.1016/j.bmc.2016.08.043 |
| None | No relevant target | D | 1.82 | 10'-10m2/s | 10.1016/j.bmc.2016.08.043 |
| None | Unchecked | Activity | nan | None | 10.1016/j.bmc.2016.08.043 |
| None | Unchecked | Kd | 9200.0 | nM | 10.1016/j.bmc.2016.08.043 |
| None | Unchecked | Ratio | 0.36 | None | 10.1016/j.bmc.2016.08.043 |
| None | Unchecked | Ratio | 0.54 | None | 10.1016/j.bmc.2016.08.043 |
| None | Unchecked | Ratio | 0.85 | None | 10.1016/j.bmc.2016.08.043 |