Amantamide
AlkaPlorer ID: AK118368
Synonym: None
IUPAC Name: methyl (2S)-1-[(2R)-2-[[2-[[(2S,3S)-2-[[(2R)-2-[[(2S)-1-[(2S)-2-[[(2S)-2-[[(2S)-2-(butanoylamino)-3-methylbutanoyl]-methylamino]-4-methylpentanoyl]amino]-4-methylpentanoyl]pyrrolidine-2-carbonyl]-methylamino]-3-methylbutanoyl]amino]-3-methylpentanoyl]amino]acetyl]-methylamino]-3-phenylpropanoyl]pyrrolidine-2-carboxylate
Structure
SMILES: CCCC(=O)N[C@H](C(=O)N(C)[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N1CCC[C@H]1C(=O)N(C)[C@@H](C(=O)N[C@H](C(=O)NCC(=O)N(C)[C@H](CC1=CC=CC=C1)C(=O)N1CCC[C@H]1C(=O)OC)[C@@H](C)CC)C(C)C)C(C)C
InChI: InChI=1S/C57H93N9O11/c1-16-23-45(67)60-47(36(7)8)56(75)63(13)43(31-35(5)6)50(69)59-40(30-34(3)4)53(72)65-28-21-26-41(65)54(73)64(14)49(37(9)10)52(71)61-48(38(11)17-2)51(70)58-33-46(68)62(12)44(32-39-24-19-18-20-25-39)55(74)66-29-22-27-42(66)57(76)77-15/h18-20,24-25,34-38,40-44,47-49H,16-17,21-23,26-33H2,1-15H3,(H,58,70)(H,59,69)(H,60,67)(H,61,71)/t38-,40-,41-,42-,43-,44+,47-,48-,49+/m0/s1
InChIKey: ZPZNPEATKLIUKY-SFHKMCQHSA-N
Reference
Discovery of Amantamide, a Selective CXCR7 Agonist from Marine Cyanobacteria
PubChem CID: 146683173
{NPAtlas: NPA026754
Source
| Species | Genus | Family | Order | Class | Phylum | Kingdom | Domain |
|---|
Properties Information
Molecule Weight: 1080.422999999999
TPSA？: 244.25
MolLogP？: 3.6861000000000113
Number of H-Donors: 4
Number of H-Acceptors: 11
RingCount: 3
Activities Information
| Organism | Target Name | Standard Type | Standard Value | Standard Units | doi |
|---|---|---|---|---|---|
| Escherichia coli | Escherichia coli | Activity | nan | None | 10.1021/acs.jnatprod.1c00983 |
| Homo sapiens | CCRF-CEM | IC50 | 8300.0 | nM | 10.1021/acs.jnatprod.1c00983 |
| Homo sapiens | C-X-C chemokine receptor type 7 | EC50 | 2500.0 | nM | 10.1021/acs.jmedchem.2c01198 |
| Homo sapiens | K562 | IC50 | 25000.0 | nM | 10.1021/acs.jnatprod.1c00983 |
| Homo sapiens | U-937 | IC50 | 6100.0 | nM | 10.1021/acs.jnatprod.1c00983 |
| Pseudomonas aeruginosa | Pseudomonas aeruginosa | Activity | nan | None | 10.1021/acs.jnatprod.1c00983 |
| Salmonella enterica subsp. enterica serovar Gallinarum | Salmonella enterica subsp. enterica serovar Gallinarum | Activity | nan | None | 10.1021/acs.jnatprod.1c00983 |
| Staphylococcus aureus | Staphylococcus aureus | Activity | nan | None | 10.1021/acs.jnatprod.1c00983 |
| None | Unchecked | Activity | nan | None | 10.1021/acs.jnatprod.1c00983 |