Lavendustin A
AlkaPlorer ID: AK002887
Synonym: None
IUPAC Name: 5-[(2,5-dihydroxyphenyl)methyl-[(2-hydroxyphenyl)methyl]amino]-2-hydroxybenzoic acid
Structure
SMILES: O=C(O)C1=CC(N(CC2=CC=CC=C2O)CC2=CC(O)=CC=C2O)=CC=C1O
InChI: InChI=1S/C21H19NO6/c23-16-6-8-19(25)14(9-16)12-22(11-13-3-1-2-4-18(13)24)15-5-7-20(26)17(10-15)21(27)28/h1-10,23-26H,11-12H2,(H,27,28)
InChIKey: ULTTYPMRMMDONC-UHFFFAOYSA-N
Reference
Isolation of a Novel Tyrosine Kinase Inhibitor, Lavendustin A, from Streptomyces griseolavendus
PubChem CID: 3894
CAS: 125697-92-9
LOTUS: LTS0107462
SuperNatural Ⅲ: SN0373809
NPASS: NPC112336
COCONUT: CNP0269688
{NPAtlas: NPA013242
Source
| Species | Genus | Family | Order | Class | Phylum | Kingdom | Domain |
|---|---|---|---|---|---|---|---|
| None | Streptomyces | Streptomycetaceae | Kitasatosporales | Actinomycetes | Actinomycetota | None | Bacteria |
Properties Information
Molecule Weight: 381.38400000000007
TPSA？: 121.46
MolLogP？: 3.414000000000002
Number of H-Donors: 5
Number of H-Acceptors: 6
RingCount: 3
Activities Information
| Organism | Target Name | Standard Type | Standard Value | Standard Units | doi |
|---|---|---|---|---|---|
| Bacillus subtilis | 4'-phosphopantetheinyl transferase ffp | Potency | 15848.9 | nM | None |
| Bacillus subtilis | 4'-phosphopantetheinyl transferase ffp | Potency | 17782.8 | nM | None |
| Bacillus subtilis | 4'-phosphopantetheinyl transferase ffp | Potency | 31622.8 | nM | None |
| Dengue virus | Dengue virus | Activity | nan | None | 10.1073/pnas.0611681104 |
| Electrophorus electricus | Acetylcholinesterase | Inhibition | 2.35 | % | 10.1016/j.bmc.2012.09.040 |
| Equus caballus | Cholinesterase | Inhibition | 17.66 | % | 10.1016/j.bmc.2012.09.040 |
| Equus caballus | Ferritin light chain | Potency | 50118.7 | nM | None |
| Homo sapiens | 15-hydroxyprostaglandin dehydrogenase [NAD+] | Potency | 10000.0 | nM | None |
| Homo sapiens | 3-phosphoinositide dependent protein kinase-1 | Thermal melting change | 0.6 | degrees C | 10.1073/pnas.0708800104 |
| Homo sapiens | 786-0 | GI50 | 100000.0 | nM | None |
| Homo sapiens | A-431 | IC50 | 26.0 | ug.mL-1 | 10.1021/np50066a009 |
| Homo sapiens | A498 | GI50 | 100000.0 | nM | None |
| Homo sapiens | A549 | GI50 | 100000.0 | nM | None |
| Homo sapiens | ACHN | GI50 | 100000.0 | nM | None |
| Homo sapiens | Aldehyde dehydrogenase 1A1 | Potency | 22387.2 | nM | None |
| Homo sapiens | Aldehyde dehydrogenase 1A1 | Potency | 25118.9 | nM | None |
| Homo sapiens | AMP-activated protein kinase, alpha-2 subunit | Thermal melting change | -1.1 | degrees C | 10.1073/pnas.0708800104 |
| Homo sapiens | BT-549 | GI50 | 6208.69 | nM | None |
| Homo sapiens | CaM kinase I delta | Thermal melting change | 0.1 | degrees C | 10.1073/pnas.0708800104 |
| Homo sapiens | CaM kinase I gamma | Thermal melting change | 0.2 | degrees C | 10.1073/pnas.0708800104 |
| Homo sapiens | CaM kinase II alpha | Thermal melting change | 1.3 | degrees C | 10.1073/pnas.0708800104 |
| Homo sapiens | CaM kinase II beta | Thermal melting change | -0.1 | degrees C | 10.1073/pnas.0708800104 |
| Homo sapiens | CaM kinase II delta | Thermal melting change | 0.3 | degrees C | 10.1073/pnas.0708800104 |
| Homo sapiens | CaM kinase II gamma | Thermal melting change | -0.1 | degrees C | 10.1073/pnas.0708800104 |
| Homo sapiens | CaM kinase IV | Thermal melting change | 0.5 | degrees C | 10.1073/pnas.0708800104 |
| Homo sapiens | CaM-kinase kinase beta | Thermal melting change | 0.5 | degrees C | 10.1073/pnas.0708800104 |
| Homo sapiens | cAMP-dependent protein kinase alpha-catalytic subunit | Thermal melting change | 1.2 | degrees C | 10.1073/pnas.0708800104 |
| Homo sapiens | Casein kinase I gamma 1 | Thermal melting change | 1.4 | degrees C | 10.1073/pnas.0708800104 |
| Homo sapiens | Casein kinase I gamma 2 | Thermal melting change | 0.6 | degrees C | 10.1073/pnas.0708800104 |
| Homo sapiens | Casein kinase I isoform gamma-3 | Thermal melting change | 0.8 | degrees C | 10.1073/pnas.0708800104 |
| Homo sapiens | CCRF-CEM | GI50 | 45394.16 | nM | None |
| Homo sapiens | COLO 205 | GI50 | 100000.0 | nM | None |
| Homo sapiens | Cyclin-dependent kinase 2 | Thermal melting change | 1.3 | degrees C | 10.1073/pnas.0708800104 |
| Homo sapiens | Cyclin-dependent kinase 6 | Thermal melting change | 0.4 | degrees C | 10.1073/pnas.0708800104 |
| Homo sapiens | Cyclin-dependent kinase-like 1 | Thermal melting change | -0.3 | degrees C | 10.1073/pnas.0708800104 |
| Homo sapiens | Death-associated protein kinase 3 | Thermal melting change | 0.8 | degrees C | 10.1073/pnas.0708800104 |
| Homo sapiens | DNA-(apurinic or apyrimidinic site) lyase | Potency | 11220.2 | nM | None |
| Homo sapiens | DNA-(apurinic or apyrimidinic site) lyase | Potency | 39810.7 | nM | None |
| Homo sapiens | DNA polymerase kappa | Potency | 11220.2 | nM | None |
| Homo sapiens | DNA polymerase kappa | Potency | 26679.5 | nM | None |
| Homo sapiens | DNA polymerase kappa | Potency | 28183.8 | nM | None |
| Homo sapiens | DU-145 | GI50 | 100000.0 | nM | None |
| Homo sapiens | Dual specificity mitogen-activated protein kinase kinase 2 | Thermal melting change | 0.5 | degrees C | 10.1073/pnas.0708800104 |
| Homo sapiens | Dual specificity mitogen-activated protein kinase kinase 6 | Thermal melting change | -1.1 | degrees C | 10.1073/pnas.0708800104 |
| Homo sapiens | Dual specificity protein kinase CLK2 | Thermal melting change | 0.5 | degrees C | 10.1073/pnas.0708800104 |
| Homo sapiens | Dual specificity protein kinase CLK3 | Thermal melting change | 0.3 | degrees C | 10.1073/pnas.0708800104 |
| Homo sapiens | Dual specificty protein kinase CLK1 | Thermal melting change | 0.5 | degrees C | 10.1073/pnas.0708800104 |
| Homo sapiens | EKVX | GI50 | 100000.0 | nM | None |
| Homo sapiens | Epidermal growth factor receptor erbB1 | IC50 | 0.004 | ug.mL-1 | 10.1021/np50089a001 |
| Homo sapiens | Epidermal growth factor receptor erbB1 | IC50 | 4100.0 | nM | 10.1021/jm00050a005 |
| Homo sapiens | Glycogen synthase kinase-3 beta | Thermal melting change | -0.1 | degrees C | 10.1073/pnas.0708800104 |
| Homo sapiens | HaCaT | IC50 | 100000.0 | nM | 10.1021/jm00050a005 |
| Homo sapiens | HCC 2998 | GI50 | 100000.0 | nM | None |
| Homo sapiens | HCT-116 | GI50 | 100000.0 | nM | None |
| Homo sapiens | HCT-15 | GI50 | 100000.0 | nM | None |
| Homo sapiens | Histone acetyltransferase GCN5 | Potency | 22387.2 | nM | None |
| Homo sapiens | Histone acetyltransferase GCN5 | Potency | 39810.7 | nM | None |
| Homo sapiens | Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 | Potency | 2238.7 | nM | None |
| Homo sapiens | HL-60 | GI50 | 100000.0 | nM | None |
| Homo sapiens | HOP-62 | GI50 | 100000.0 | nM | None |
| Homo sapiens | HOP-92 | GI50 | 100000.0 | nM | None |
| Homo sapiens | Hs-578T | GI50 | 19769.7 | nM | None |
| Homo sapiens | HT-29 | GI50 | 100000.0 | nM | None |
| Homo sapiens | IGROV-1 | GI50 | 100000.0 | nM | None |
| Homo sapiens | Inactive serine/threonine-protein kinase VRK3 | Thermal melting change | 0.7 | degrees C | 10.1073/pnas.0708800104 |
| Homo sapiens | K562 | GI50 | 100000.0 | nM | None |
| Homo sapiens | KM12 | GI50 | 100000.0 | nM | None |
| Homo sapiens | LOX IMVI | GI50 | 34914.03 | nM | None |
| Homo sapiens | M14 | GI50 | 100000.0 | nM | None |
| Homo sapiens | Malme-3M | GI50 | 100000.0 | nM | None |
| Homo sapiens | MAP kinase ERK1 | Thermal melting change | 0.3 | degrees C | 10.1073/pnas.0708800104 |
| Homo sapiens | MAP kinase p38 beta | Thermal melting change | 0.3 | degrees C | 10.1073/pnas.0708800104 |
| Homo sapiens | MCF7 | GI50 | 100000.0 | nM | None |
| Homo sapiens | MDA-MB-231 | GI50 | 100000.0 | nM | None |
| Homo sapiens | MDA-MB-435 | GI50 | 100000.0 | nM | None |
| Homo sapiens | MDA-N | GI50 | 100000.0 | nM | None |
| Homo sapiens | Menin/Histone-lysine N-methyltransferase MLL | Potency | 31622.8 | nM | None |
| Homo sapiens | Menin/Histone-lysine N-methyltransferase MLL | Potency | 39810.7 | nM | None |
| Homo sapiens | Microtubule-associated protein tau | Potency | 14125.4 | nM | None |
| Homo sapiens | Microtubule-associated protein tau | Potency | 17782.8 | nM | None |
| Homo sapiens | Microtubule-associated protein tau | Potency | 22387.2 | nM | None |
| Homo sapiens | Mitogen-activated protein kinase 6 | Thermal melting change | 0.8 | degrees C | 10.1073/pnas.0708800104 |
| Homo sapiens | Mitogen-activated protein kinase kinase kinase 5 | Thermal melting change | 0.2 | degrees C | 10.1073/pnas.0708800104 |
| Homo sapiens | MOLT-4 | GI50 | 100000.0 | nM | None |
| Homo sapiens | Myotonin-protein kinase | Thermal melting change | 0.9 | degrees C | 10.1073/pnas.0708800104 |
| Homo sapiens | NCI/ADR-RES | GI50 | 100000.0 | nM | None |
| Homo sapiens | NCI-H226 | GI50 | 100000.0 | nM | None |
| Homo sapiens | NCI-H23 | GI50 | 100000.0 | nM | None |
| Homo sapiens | NCI-H322M | GI50 | 100000.0 | nM | None |
| Homo sapiens | NCI-H460 | GI50 | 100000.0 | nM | None |
| Homo sapiens | OVCAR-3 | GI50 | 100000.0 | nM | None |
| Homo sapiens | OVCAR-4 | GI50 | 100000.0 | nM | None |
| Homo sapiens | OVCAR-5 | GI50 | 100000.0 | nM | None |
| Homo sapiens | OVCAR-8 | GI50 | 100000.0 | nM | None |
| Homo sapiens | PC-3 | GI50 | 42266.86 | nM | None |
| Homo sapiens | PDZ-binding kinase | Thermal melting change | 0.0 | degrees C | 10.1073/pnas.0708800104 |
| Homo sapiens | Regulator of G-protein signaling 4 | Potency | 75.2 | nM | None |
| Homo sapiens | Ribosomal protein S6 kinase alpha 3 | Thermal melting change | -0.2 | degrees C | 10.1073/pnas.0708800104 |
| Homo sapiens | Ribosomal protein S6 kinase alpha 3 | Thermal melting change | 1.7 | degrees C | 10.1073/pnas.0708800104 |
| Homo sapiens | RPMI-8226 | GI50 | 100000.0 | nM | None |
| Homo sapiens | Runt-related transcription factor 1/Core-binding factor subunit beta | Potency | 31622.8 | nM | None |
| Homo sapiens | RXF 393 | GI50 | 100000.0 | nM | None |
| Homo sapiens | Serine/threonine-protein kinase 10 | Thermal melting change | 0.1 | degrees C | 10.1073/pnas.0708800104 |
| Homo sapiens | Serine/threonine-protein kinase 16 | Thermal melting change | 2.6 | degrees C | 10.1073/pnas.0708800104 |
| Homo sapiens | Serine/threonine-protein kinase 17A | Thermal melting change | 0.1 | degrees C | 10.1073/pnas.0708800104 |
| Homo sapiens | Serine/threonine-protein kinase 2 | Thermal melting change | -0.7 | degrees C | 10.1073/pnas.0708800104 |
| Homo sapiens | Serine/threonine-protein kinase 25 | Thermal melting change | nan | None | 10.1073/pnas.0708800104 |
| Homo sapiens | Serine/threonine-protein kinase 38 | Thermal melting change | 0.2 | degrees C | 10.1073/pnas.0708800104 |
| Homo sapiens | Serine/threonine-protein kinase Chk2 | Thermal melting change | 0.8 | degrees C | 10.1073/pnas.0708800104 |
| Homo sapiens | Serine/threonine-protein kinase MST1 | Thermal melting change | 0.5 | degrees C | 10.1073/pnas.0708800104 |
| Homo sapiens | Serine/threonine-protein kinase MST4 | Thermal melting change | 0.4 | degrees C | 10.1073/pnas.0708800104 |
| Homo sapiens | Serine/threonine-protein kinase MST4 | Thermal melting change | 2.1 | degrees C | 10.1073/pnas.0708800104 |
| Homo sapiens | Serine/threonine-protein kinase NEK2 | Thermal melting change | 1.3 | degrees C | 10.1073/pnas.0708800104 |
| Homo sapiens | Serine/threonine-protein kinase NEK6 | Thermal melting change | 0.4 | degrees C | 10.1073/pnas.0708800104 |
| Homo sapiens | Serine/threonine-protein kinase OSR1 | Thermal melting change | -0.1 | degrees C | 10.1073/pnas.0708800104 |
| Homo sapiens | Serine/threonine-protein kinase PAK 4 | Thermal melting change | 0.1 | degrees C | 10.1073/pnas.0708800104 |
| Homo sapiens | Serine/threonine-protein kinase PAK6 | Thermal melting change | -0.3 | degrees C | 10.1073/pnas.0708800104 |
| Homo sapiens | Serine/threonine-protein kinase PAK7 | Thermal melting change | -0.5 | degrees C | 10.1073/pnas.0708800104 |
| Homo sapiens | Serine/threonine-protein kinase PCTAIRE-1 | Thermal melting change | 0.0 | degrees C | 10.1073/pnas.0708800104 |
| Homo sapiens | Serine/threonine-protein kinase PIM1 | Thermal melting change | 1.1 | degrees C | 10.1073/pnas.0708800104 |
| Homo sapiens | Serine/threonine-protein kinase PIM2 | Thermal melting change | 1.1 | degrees C | 10.1073/pnas.0708800104 |
| Homo sapiens | Serine/threonine-protein kinase PIM3 | Thermal melting change | 0.4 | degrees C | 10.1073/pnas.0708800104 |
| Homo sapiens | Serine/threonine-protein kinase PLK1 | Thermal melting change | 0.9 | degrees C | 10.1073/pnas.0708800104 |
| Homo sapiens | Serine/threonine-protein kinase PLK4 | Thermal melting change | 1.1 | degrees C | 10.1073/pnas.0708800104 |
| Homo sapiens | Serine/threonine-protein kinase RIO2 | Thermal melting change | 0.0 | degrees C | 10.1073/pnas.0708800104 |
| Homo sapiens | Serine/threonine-protein kinase VRK1 | Thermal melting change | 0.3 | degrees C | 10.1073/pnas.0708800104 |
| Homo sapiens | Serine/threonine-protein kinase VRK2 | Thermal melting change | -0.6 | degrees C | 10.1073/pnas.0708800104 |
| Homo sapiens | SF-268 | GI50 | 100000.0 | nM | None |
| Homo sapiens | SF-295 | GI50 | 100000.0 | nM | None |
| Homo sapiens | SF-539 | GI50 | 100000.0 | nM | None |
| Homo sapiens | SK-MEL-2 | GI50 | 100000.0 | nM | None |
| Homo sapiens | SK-MEL-28 | GI50 | 100000.0 | nM | None |
| Homo sapiens | SK-MEL-5 | GI50 | 100000.0 | nM | None |
| Homo sapiens | SK-OV-3 | GI50 | 100000.0 | nM | None |
| Homo sapiens | SN12C | GI50 | 100000.0 | nM | None |
| Homo sapiens | SNB-19 | GI50 | 100000.0 | nM | None |
| Homo sapiens | SNB-75 | GI50 | 10000.0 | nM | None |
| Homo sapiens | SR | GI50 | 82794.22 | nM | None |
| Homo sapiens | SW-620 | GI50 | 100000.0 | nM | None |
| Homo sapiens | T47D | GI50 | 100000.0 | nM | None |
| Homo sapiens | TK-10 | GI50 | 100000.0 | nM | None |
| Homo sapiens | TRAF2- and NCK-interacting kinase | Thermal melting change | 0.0 | degrees C | 10.1073/pnas.0708800104 |
| Homo sapiens | Tyrosine-protein kinase JAK1 | Thermal melting change | 0.4 | degrees C | 10.1073/pnas.0708800104 |
| Homo sapiens | Tyrosine-protein kinase LCK | IC50 | 8000.0 | nM | 10.1021/jm00072a022 |
| Homo sapiens | Tyrosyl-DNA phosphodiesterase 1 | Potency | 100.0 | nM | None |
| Homo sapiens | Tyrosyl-DNA phosphodiesterase 1 | Potency | 20596.2 | nM | None |
| Homo sapiens | Tyrosyl-DNA phosphodiesterase 1 | Potency | 29092.9 | nM | None |
| Homo sapiens | U-251 | GI50 | 100000.0 | nM | None |
| Homo sapiens | UACC-257 | GI50 | 100000.0 | nM | None |
| Homo sapiens | UACC-62 | GI50 | 100000.0 | nM | None |
| Homo sapiens | UO-31 | GI50 | 100000.0 | nM | None |
| Homo sapiens | Vitamin D receptor | Potency | 50118.7 | nM | None |
| Homo sapiens | Vitamin D receptor | Potency | 89125.1 | nM | None |
| Mus musculus | Epidermal growth factor receptor erbB1 | Activity | nan | None | 10.1021/np50066a009 |
| Mus musculus | Epidermal growth factor receptor erbB1 | IC50 | 0.0044 | ug.mL-1 | 10.1021/np50066a009 |
| Mus musculus | L1210 | IC50 | 28.0 | ug.mL-1 | 10.1021/np50066a009 |
| Mus musculus | NIH3T3 | IC50 | 19.5 | ug.mL-1 | 10.1021/np50066a009 |
| Mus musculus | P388 | IC50 | 21.5 | ug.mL-1 | 10.1021/np50066a009 |
| None | ADMET | IC50 | 22.0 | ug.mL-1 | 10.1021/np50066a009 |
| None | Unchecked | IC50 | 6.4 | ug.mL-1 | 10.1021/np50066a009 |
| None | Unchecked | IC50 | 100.0 | ug.mL-1 | 10.1021/np50066a009 |
| None | Unchecked | IC50 | 500.0 | nM | 10.1073/pnas.0708800104 |
| None | Unchecked | IC50 | 7000.0 | nM | 10.1021/jm00072a022 |
| None | Unchecked | IC50 | 9000.0 | nM | 10.1021/jm00072a022 |
| None | Unchecked | IC50 | 200000.0 | nM | 10.1073/pnas.0708800104 |
| None | Unchecked | Potency | 19952.6 | nM | None |
| None | Unchecked | Potency | 22387.2 | nM | None |