Psammaplin A
AlkaPlorer ID: AK325275
Synonym: None
IUPAC Name: (2Z)-3-(3-bromo-4-hydroxyphenyl)-N-[2-[2-[[(2Z)-3-(3-bromo-4-hydroxyphenyl)-2-hydroxyiminopropanoyl]amino]ethyldisulfanyl]ethyl]-2-hydroxyiminopropanamide
Structure
SMILES: O/N=C(\CC1=CC=C(O)C(Br)=C1)C(O)=NCCSSCCN=C(O)/C(CC1=CC=C(O)C(Br)=C1)=N/O
InChI: InChI=1S/C22H24Br2N4O6S2/c23-15-9-13(1-3-19(15)29)11-17(27-33)21(31)25-5-7-35-36-8-6-26-22(32)18(28-34)12-14-2-4-20(30)16(24)10-14/h1-4,9-10,29-30,33-34H,5-8,11-12H2,(H,25,31)(H,26,32)/b27-17+,28-18+
InChIKey: LMAFSGDNHVBIHU-XUIWWLCJSA-N
Reference
New Bromotyrosine Metabolites from the Sponge Aplysinella rhax
PubChem CID: 6400741
LOTUS: LTS0054517
SuperNatural Ⅲ: SN0209226-03
NPASS: NPC71888
Source
| Species | Genus | Family | Order | Class | Phylum | Kingdom | Domain |
|---|---|---|---|---|---|---|---|
| Humicola fuscoatra | Humicola | Chaetomiaceae | Sordariales | Sordariomycetes | Ascomycota | Fungi | Eukaryota |
| Aplysinella rhax | Aplysinella | Aplysinellidae | Verongiida | Demospongiae | Porifera | Metazoa | Eukaryota |
Properties Information
Molecule Weight: 664.3980000000004
TPSA？: 170.82000000000002
MolLogP？: 5.3628000000000045
Number of H-Donors: 6
Number of H-Acceptors: 10
RingCount: 2
Activities Information
| Organism | Target Name | Standard Type | Standard Value | Standard Units | doi |
|---|---|---|---|---|---|
| Artemia salina | Artemia salina | LC50 | 4.0 | ug.mL-1 | 10.1021/np50125a012 |
| Bacteria | Bacteria | MIC | 4.85 | ug m/L | 10.1021/jm050524f |
| Cricetulus griseus | CHO-K1 | EC50 | 900.0 | nM | 10.1016/j.bmcl.2006.08.091 |
| Homo sapiens | 786-0 | GI50 | 2065.38 | nM | None |
| Homo sapiens | A498 | GI50 | 2904.02 | nM | None |
| Homo sapiens | A549 | Activity | nan | None | 10.1016/j.ejmech.2015.04.001 |
| Homo sapiens | A549 | ED50 | 0.57 | ug ml-1 | 10.1021/np030162j |
| Homo sapiens | A549 | GI50 | 1435.49 | nM | None |
| Homo sapiens | A549 | GI50 | 4500.0 | nM | 10.1016/j.bmcl.2015.12.094 |
| Homo sapiens | A549 | GI50 | 7500.0 | nM | 10.1021/jm2016182 |
| Homo sapiens | A549 | IC50 | 1180.0 | nM | 10.1016/j.ejmech.2015.04.001 |
| Homo sapiens | A549 | IC50 | 1760.0 | nM | 10.1016/j.bmc.2021.116072 |
| Homo sapiens | A549 | IG50 | 2.9 | uM | 10.1021/acsmedchemlett.0c00369 |
| Homo sapiens | A549 | LC50 | 6.43 | ug.mL-1 | 10.1021/np50125a012 |
| Homo sapiens | ACHN | GI50 | 1621.81 | nM | None |
| Homo sapiens | BT-549 | GI50 | 6208.69 | nM | None |
| Homo sapiens | CAKI-1 | GI50 | 1465.55 | nM | None |
| Homo sapiens | CCRF-CEM | GI50 | 376.7 | nM | None |
| Homo sapiens | COLO 205 | GI50 | 1636.82 | nM | None |
| Homo sapiens | CREB-binding protein/Histone acetyltransferase p300 | Inhibition | nan | % | 10.1016/j.bmc.2010.12.026 |
| Homo sapiens | DNA (cytosine-5)-methyltransferase 1 | IC50 | 18.6 | nM | 10.1021/jm2016182 |
| Homo sapiens | DNA (cytosine-5)-methyltransferase 1 | Inhibition | nan | % | 10.1021/jm2016182 |
| Homo sapiens | DU-145 | GI50 | 1892.34 | nM | None |
| Homo sapiens | EKVX | GI50 | 4487.45 | nM | None |
| Homo sapiens | HCC 2998 | GI50 | 2172.7 | nM | None |
| Homo sapiens | HCT-116 | GI50 | 1389.95 | nM | None |
| Homo sapiens | HCT-116 | IC50 | 610.0 | nM | 10.1016/j.bmc.2021.116072 |
| Homo sapiens | HCT-116 | IG50 | 2.3 | uM | 10.1021/acsmedchemlett.0c00369 |
| Homo sapiens | HCT-15 | ED50 | 0.68 | ug ml-1 | 10.1021/np030162j |
| Homo sapiens | HCT-15 | GI50 | 4886.52 | nM | None |
| Homo sapiens | Histone deacetylase | IC50 | 4.0 | nM | 10.1021/jm0303094 |
| Homo sapiens | Histone deacetylase | IC50 | 50.0 | nM | 10.1016/j.bmcl.2015.12.094 |
| Homo sapiens | Histone deacetylase | Inhibition | nan | % | 10.1016/j.bmcl.2015.12.094 |
| Homo sapiens | Histone deacetylase | Inhibition | nan | % | 10.1016/j.ejmech.2015.04.001 |
| Homo sapiens | Histone deacetylase 1 | IC50 | 8.0 | nM | 10.1021/acsmedchemlett.0c00369 |
| Homo sapiens | Histone deacetylase 1 | IC50 | 45.0 | nM | 10.1021/jm2016182 |
| Homo sapiens | Histone deacetylase 1 | Inhibition | nan | % | 10.1016/j.bmc.2010.12.026 |
| Homo sapiens | Histone deacetylase 1 | Inhibition | nan | % | 10.1021/acsmedchemlett.0c00369 |
| Homo sapiens | Histone deacetylase 1 | Inhibition | nan | % | 10.1021/jm2016182 |
| Homo sapiens | Histone deacetylase 2 | IC50 | 33.0 | nM | 10.1021/acsmedchemlett.0c00369 |
| Homo sapiens | Histone deacetylase 2 | Inhibition | nan | % | 10.1021/acsmedchemlett.0c00369 |
| Homo sapiens | Histone deacetylase 3 | Inhibition | nan | % | 10.1021/acsmedchemlett.0c00369 |
| Homo sapiens | Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2) | IC50 | 12.4 | nM | 10.1021/acsmedchemlett.0c00369 |
| Homo sapiens | Histone deacetylase 6 | IC50 | 311.0 | nM | 10.1021/acsmedchemlett.0c00369 |
| Homo sapiens | Histone deacetylase 6 | IC50 | 2800.0 | nM | 10.1021/jm2016182 |
| Homo sapiens | Histone deacetylase 6 | Inhibition | nan | % | 10.1021/acsmedchemlett.0c00369 |
| Homo sapiens | Histone deacetylase 6 | Inhibition | nan | % | 10.1021/jm2016182 |
| Homo sapiens | Histone deacetylase 6 | Inhibition | nan | % | 10.1021/jm300618u |
| Homo sapiens | Histone-lysine N-methyltransferase, H3 lysine-79 specific | Inhibition | nan | % | 10.1016/j.bmc.2021.116072 |
| Homo sapiens | HL-60 | Activity | 0.8 | % | 10.1021/acsmedchemlett.0c00369 |
| Homo sapiens | HL-60 | Activity | 2.6 | % | 10.1021/acsmedchemlett.0c00369 |
| Homo sapiens | HL-60 | Activity | 3.4 | % | 10.1021/acsmedchemlett.0c00369 |
| Homo sapiens | HL-60 | Activity | 3.7 | % | 10.1021/acsmedchemlett.0c00369 |
| Homo sapiens | HL-60 | Activity | 3.9 | % | 10.1021/acsmedchemlett.0c00369 |
| Homo sapiens | HL-60 | Activity | 4.1 | % | 10.1021/acsmedchemlett.0c00369 |
| Homo sapiens | HL-60 | Activity | 7.8 | % | 10.1021/acsmedchemlett.0c00369 |
| Homo sapiens | HL-60 | Activity | 24.9 | % | 10.1021/acsmedchemlett.0c00369 |
| Homo sapiens | HL-60 | Activity | 26.7 | % | 10.1021/acsmedchemlett.0c00369 |
| Homo sapiens | HL-60 | Activity | 66.2 | % | 10.1021/acsmedchemlett.0c00369 |
| Homo sapiens | HL-60 | Activity | 67.1 | % | 10.1021/acsmedchemlett.0c00369 |
| Homo sapiens | HL-60 | Activity | 88.8 | % | 10.1021/acsmedchemlett.0c00369 |
| Homo sapiens | HL-60 | Activity | nan | None | 10.1021/acsmedchemlett.0c00369 |
| Homo sapiens | HL-60 | GI50 | 290.0 | nM | 10.1016/j.bmcl.2015.12.094 |
| Homo sapiens | HL-60 | GI50 | 370.0 | nM | 10.1021/acsmedchemlett.0c00369 |
| Homo sapiens | HL-60 | GI50 | 425.6 | nM | None |
| Homo sapiens | HOP-62 | GI50 | 885.12 | nM | None |
| Homo sapiens | HOP-92 | GI50 | 4008.67 | nM | None |
| Homo sapiens | Hs-578T | GI50 | 1766.04 | nM | None |
| Homo sapiens | HT-29 | GI50 | 1348.96 | nM | None |
| Homo sapiens | IGROV-1 | GI50 | 1172.2 | nM | None |
| Homo sapiens | K562 | GI50 | 1807.17 | nM | None |
| Homo sapiens | KM12 | GI50 | 1472.31 | nM | None |
| Homo sapiens | LOX IMVI | GI50 | 1297.18 | nM | None |
| Homo sapiens | M14 | GI50 | 1318.26 | nM | None |
| Homo sapiens | Malme-3M | GI50 | 597.04 | nM | None |
| Homo sapiens | MCF7 | Activity | 36.0 | % | 10.1021/np050397q |
| Homo sapiens | MCF7 | Activity | 62.0 | % | 10.1021/np050397q |
| Homo sapiens | MCF7 | Activity | nan | None | 10.1021/np050397q |
| Homo sapiens | MCF7 | GI50 | 1270.0 | nM | 10.1021/jm2016182 |
| Homo sapiens | MCF7 | GI50 | 2023.02 | nM | None |
| Homo sapiens | MCF7 | GI50 | 2260.0 | nM | 10.1016/j.bmcl.2015.12.094 |
| Homo sapiens | MCF7 | IC50 | 5000.0 | nM | 10.1021/np050397q |
| Homo sapiens | MCF7 | IG50 | 4.14 | uM | 10.1021/acsmedchemlett.0c00369 |
| Homo sapiens | MDA-MB-231 | Activity | nan | None | 10.1016/j.bmc.2021.116072 |
| Homo sapiens | MDA-MB-231 | GI50 | 1778.28 | nM | None |
| Homo sapiens | MDA-MB-231 | IC50 | 1310.0 | nM | 10.1016/j.bmc.2021.116072 |
| Homo sapiens | MDA-MB-435 | GI50 | 1510.08 | nM | None |
| Homo sapiens | MDA-N | GI50 | 1603.25 | nM | None |
| Homo sapiens | MOLT-4 | GI50 | 401.79 | nM | None |
| Homo sapiens | NAD-dependent deacetylase sirtuin 1 | Inhibition | nan | % | 10.1016/j.bmc.2010.12.026 |
| Homo sapiens | NCI/ADR-RES | GI50 | 1291.22 | nM | None |
| Homo sapiens | NCI-H1299 | AC50 | 7500.0 | nM | 10.1021/np050397q |
| Homo sapiens | NCI-H226 | GI50 | 9817.48 | nM | None |
| Homo sapiens | NCI-H23 | GI50 | 3198.9 | nM | None |
| Homo sapiens | NCI-H322M | GI50 | 1588.55 | nM | None |
| Homo sapiens | NCI-H460 | GI50 | 901.57 | nM | None |
| Homo sapiens | NCI-H522 | GI50 | 682.34 | nM | None |
| Homo sapiens | OVCAR-3 | GI50 | 1870.68 | nM | None |
| Homo sapiens | OVCAR-4 | GI50 | 3104.56 | nM | None |
| Homo sapiens | OVCAR-5 | GI50 | 2213.09 | nM | None |
| Homo sapiens | OVCAR-8 | GI50 | 1517.05 | nM | None |
| Homo sapiens | PC-3 | GI50 | 1606.94 | nM | None |
| Homo sapiens | PC-3 | GI50 | 3520.0 | nM | 10.1016/j.bmcl.2015.12.094 |
| Homo sapiens | Peroxisome proliferator-activated receptor gamma | Activity | nan | None | 10.1021/np050397q |
| Homo sapiens | Peroxisome proliferator-activated receptor gamma | EC50 | 5700.0 | nM | 10.1021/np050397q |
| Homo sapiens | RPMI-8226 | GI50 | 1355.19 | nM | None |
| Homo sapiens | RXF 393 | GI50 | 796.16 | nM | None |
| Homo sapiens | SF-268 | GI50 | 1618.08 | nM | None |
| Homo sapiens | SF-295 | GI50 | 1342.76 | nM | None |
| Homo sapiens | SF-539 | GI50 | 1717.91 | nM | None |
| Homo sapiens | SK-HEP1 | IC50 | 1290.0 | nM | 10.1016/j.bmc.2021.116072 |
| Homo sapiens | SK-MEL-2 | ED50 | 0.13 | ug ml-1 | 10.1021/np030162j |
| Homo sapiens | SK-MEL-2 | GI50 | 1099.01 | nM | None |
| Homo sapiens | SK-MEL-28 | GI50 | 3162.28 | nM | None |
| Homo sapiens | SK-MEL-5 | GI50 | 926.83 | nM | None |
| Homo sapiens | SK-OV-3 | ED50 | 0.14 | ug ml-1 | 10.1021/np030162j |
| Homo sapiens | SK-OV-3 | GI50 | 933.25 | nM | None |
| Homo sapiens | SN12C | GI50 | 1425.61 | nM | None |
| Homo sapiens | SNB-19 | GI50 | 2079.7 | nM | None |
| Homo sapiens | SNB-75 | GI50 | 889.2 | nM | None |
| Homo sapiens | SNU-638 | IC50 | 560.0 | nM | 10.1016/j.bmc.2021.116072 |
| Homo sapiens | SR | GI50 | 380.19 | nM | None |
| Homo sapiens | SW-620 | GI50 | 1636.82 | nM | None |
| Homo sapiens | T47D | Activity | nan | None | 10.1021/np050397q |
| Homo sapiens | T47D | GI50 | 3706.81 | nM | None |
| Homo sapiens | TK-10 | GI50 | 2924.15 | nM | None |
| Homo sapiens | U-251 | GI50 | 1096.48 | nM | None |
| Homo sapiens | U-937 | Activity | 60.0 | % | 10.1016/j.bmc.2010.12.026 |
| Homo sapiens | U-937 | Activity | nan | None | 10.1016/j.bmc.2010.12.026 |
| Homo sapiens | U-937 | Activity | nan | None | 10.1021/jm300618u |
| Homo sapiens | UACC-257 | GI50 | 1599.56 | nM | None |
| Homo sapiens | UACC-62 | GI50 | 1717.91 | nM | None |
| Homo sapiens | UDP-glucose 4-epimerase | IC50 | 3600.0 | nM | 10.1016/j.bmcl.2006.08.091 |
| Homo sapiens | UO-31 | GI50 | 1741.81 | nM | None |
| Homo sapiens | WI-38 | GI50 | 3440.0 | nM | 10.1021/jm2016182 |
| Homo sapiens | XF498 | ED50 | 0.57 | ug ml-1 | 10.1021/np030162j |
| Human immunodeficiency virus 1 | Human immunodeficiency virus 1 | Activity | 100.0 | % | 10.1021/np400889x |
| Human immunodeficiency virus 1 | Human immunodeficiency virus 1 | EC50 | 200.0 | nM | 10.1021/np400889x |
| Mus musculus | P388 | IC50 | 0.3 | ug.mL-1 | 10.1016/j.bmc.2021.116510 |
| Mus musculus | P388 | LC50 | 0.64 | ug.mL-1 | 10.1021/np50125a012 |
| Mus musculus | Protein Wnt-3a | Activity | nan | None | 10.1016/j.bmc.2008.10.077 |
| Mycobacterium tuberculosis | Mycothiol S-conjugate amidase | IC50 | 2800.0 | nM | 10.1016/s0960-894x(02)00385-2 |
| Mycobacterium tuberculosis | Mycothiol S-conjugate amidase | IC50 | 2800.0 | nM | 10.1021/jm050524f |
| Rattus norvegicus | Adenosine A1 receptor | IC50 | 20000.0 | nM | 10.1021/np990335y |
| Staphylococcus aureus | Sortase A | IC50 | 47400.0 | nM | 10.1021/acs.jmedchem.1c00386 |
| Staphylococcus aureus | Staphylococcus aureus | MIC | 200.0 | ug.mL-1 | 10.1021/acs.jmedchem.1c00386 |
| Trypanosoma brucei | Trypanosoma brucei | EC50 | 2600.0 | nM | 10.1016/j.bmcl.2006.08.091 |
| Trypanosoma brucei | Trypanosoma brucei | EC50 | 2600.0 | nM | 10.1021/np800711a |
| None | ADMET | Activity | 18.2 | g | 10.1021/acsmedchemlett.0c00369 |
| None | ADMET | Activity | 18.4 | g | 10.1021/acsmedchemlett.0c00369 |
| None | Molecular identity unknown | Activity | nan | None | 10.1021/jm300618u |
| None | NON-PROTEIN TARGET | IC50 | 1620.0 | nM | 10.1016/j.ejmech.2015.04.001 |
| None | Unchecked | Activity | 0.34 | g | 10.1021/acsmedchemlett.0c00369 |
| None | Unchecked | Activity | 66.04 | % | 10.1021/acsmedchemlett.0c00369 |
| None | Unchecked | Activity | nan | None | 10.1016/j.bmc.2008.10.077 |
| None | Unchecked | Activity | nan | None | 10.1021/jm300618u |
| None | Unchecked | IC50 | 4.2 | nM | 10.1016/j.bmc.2010.12.026 |
| None | Unchecked | IC50 | 4.2 | nM | 10.1021/jm2016182 |
| None | Unchecked | IC50 | 18.6 | nM | 10.1016/j.bmc.2010.12.026 |
| None | Unchecked | IC50 | 4200.0 | nM | 10.1021/np050397q |
| None | Unchecked | IC50 | 15000.0 | nM | 10.1016/j.bmcl.2006.08.091 |
| None | Unchecked | IG50 | 2.64 | uM | 10.1021/acsmedchemlett.0c00369 |
| None | Unchecked | Inhibition | 75.0 | % | 10.1016/j.bmcl.2006.08.091 |
| None | Unchecked | Inhibition | nan | % | 10.1021/jm2016182 |
| None | Unchecked | Ratio IC50 | 62.0 | None | 10.1021/jm2016182 |