Boldine; (S)-form
AlkaPlorer ID: AK290850
Synonym: None
IUPAC Name: 1,10-dimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-2,9-diol
Structure
SMILES: COC1=C(O)C=C2CC3C4=C(C=C(O)C(OC)=C4C2=C1)CCN3C
InChI: InChI=1S/C19H21NO4/c1-20-5-4-10-7-15(22)19(24-3)18-12-9-16(23-2)14(21)8-11(12)6-13(20)17(10)18/h7-9,13,21-22H,4-6H2,1-3H3
InChIKey: LZJRNLRASBVRRX-UHFFFAOYSA-N
Reference
Phoebegrandines A and B, proaporphine-tryptamine dimers, from Phoebe grandis
PubChem CID: 248507
CAS: 476-70-0
LOTUS: LTS0198439
NPASS: NPC13504
COCONUT: CNP0354403.3
data_source: manually
Source
| Species | Genus | Family | Order | Class | Phylum | Kingdom | Domain |
|---|---|---|---|---|---|---|---|
| None | None | Atherospermataceae | Laurales | Magnoliopsida | Streptophyta | Viridiplantae | Eukaryota |
| Lindera aggregata | Lindera | Lauraceae | Laurales | Magnoliopsida | Streptophyta | Viridiplantae | Eukaryota |
Properties Information
Molecule Weight: 327.3800000000001
TPSA？: 62.16
MolLogP？: 2.8671000000000006
Number of H-Donors: 2
Number of H-Acceptors: 5
RingCount: 4
Activities Information
| Organism | Target Name | Standard Type | Standard Value | Standard Units | doi |
|---|---|---|---|---|---|
| Acinetobacter baumannii | Acinetobacter baumannii | Inhibition | -19.02 | % | 10.6019/CHEMBL4296182 |
| Bos taurus | Mitochondrial peptide methionine sulfoxide reductase | IC50 | 53925.0 | nM | None |
| Candida albicans | Candida albicans | Inhibition | -2.23 | % | 10.6019/CHEMBL4296182 |
| Cryptococcus neoformans | Cryptococcus neoformans | Inhibition | -8.59 | % | 10.6019/CHEMBL4296182 |
| Escherichia coli | Escherichia coli | Inhibition | 10.6 | % | 10.6019/CHEMBL4296182 |
| Giardia intestinalis | Putative fructose-1,6-bisphosphate aldolase | Potency | 6294.6 | nM | None |
| Giardia intestinalis | Putative fructose-1,6-bisphosphate aldolase | Potency | 15811.4 | nM | None |
| Homo sapiens | 15-hydroxyprostaglandin dehydrogenase [NAD+] | Potency | 28183.8 | nM | None |
| Homo sapiens | 15-hydroxyprostaglandin dehydrogenase [NAD+] | Potency | 31622.8 | nM | None |
| Homo sapiens | 786-0 | GI50 | 100000.0 | nM | None |
| 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 | 28183.8 | nM | None |
| Homo sapiens | Aldehyde dehydrogenase 1A1 | Potency | 31622.8 | nM | None |
| Homo sapiens | ATPase family AAA domain-containing protein 5 | Potency | 5802.4 | nM | None |
| Homo sapiens | Bromodomain adjacent to zinc finger domain protein 2B | Potency | 79432.8 | nM | None |
| Homo sapiens | BT-549 | GI50 | 100000.0 | nM | None |
| Homo sapiens | CAKI-1 | GI50 | 100000.0 | nM | None |
| Homo sapiens | CCRF-CEM | GI50 | 100000.0 | nM | None |
| Homo sapiens | COLO 205 | GI50 | 73451.39 | nM | None |
| Homo sapiens | Cytochrome P450 3A4 | Potency | 25118.9 | nM | None |
| Homo sapiens | DNA-(apurinic or apyrimidinic site) lyase | Potency | 44668.4 | nM | None |
| Homo sapiens | DNA polymerase eta | Potency | 28183.8 | nM | None |
| Homo sapiens | DNA polymerase iota | Potency | 5011.9 | nM | None |
| Homo sapiens | DNA polymerase kappa | Potency | 17782.8 | nM | None |
| Homo sapiens | DU-145 | GI50 | 100000.0 | nM | None |
| Homo sapiens | EKVX | GI50 | 100000.0 | nM | None |
| Homo sapiens | Endoplasmic reticulum-associated amyloid beta-peptide-binding protein | Potency | 31622.8 | nM | None |
| Homo sapiens | Flap endonuclease 1 | Potency | 25118.9 | nM | None |
| Homo sapiens | Glucagon-like peptide 1 receptor | Potency | 12589.3 | nM | None |
| Homo sapiens | HCC 2998 | GI50 | 100000.0 | nM | None |
| Homo sapiens | HCT-116 | GI50 | 77983.01 | nM | None |
| Homo sapiens | HCT-15 | GI50 | 100000.0 | nM | None |
| Homo sapiens | Histone acetyltransferase GCN5 | Potency | 794.3 | nM | None |
| Homo sapiens | HL-60 | GI50 | 91411.32 | nM | None |
| Homo sapiens | HOP-62 | GI50 | 100000.0 | nM | None |
| Homo sapiens | HOP-92 | GI50 | 78342.96 | nM | None |
| Homo sapiens | Hs-578T | GI50 | 100000.0 | nM | None |
| Homo sapiens | HT-29 | GI50 | 62230.03 | nM | None |
| Homo sapiens | IGROV-1 | GI50 | 100000.0 | nM | None |
| Homo sapiens | K562 | GI50 | 100000.0 | nM | None |
| Homo sapiens | KM12 | GI50 | 100000.0 | nM | None |
| Homo sapiens | LOX IMVI | GI50 | 100000.0 | nM | None |
| Homo sapiens | Lysine-specific demethylase 4D-like | Potency | 22387.2 | nM | None |
| Homo sapiens | Lysine-specific demethylase 4D-like | Potency | 28183.8 | nM | None |
| Homo sapiens | Lysine-specific demethylase 4D-like | Potency | 31622.8 | nM | None |
| Homo sapiens | Lysosomal alpha-glucosidase | Potency | 35481.3 | nM | None |
| Homo sapiens | M14 | GI50 | 100000.0 | nM | None |
| Homo sapiens | Malme-3M | GI50 | 100000.0 | nM | None |
| 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 | 11220.2 | nM | None |
| Homo sapiens | Menin/Histone-lysine N-methyltransferase MLL | Potency | 31622.8 | nM | None |
| Homo sapiens | Microtubule-associated protein tau | Potency | 707.9 | nM | None |
| Homo sapiens | Microtubule-associated protein tau | Potency | 11220.2 | nM | None |
| Homo sapiens | Microtubule-associated protein tau | Potency | 35481.3 | nM | None |
| Homo sapiens | MOLT-4 | GI50 | 58344.51 | nM | None |
| Homo sapiens | Muscleblind-like protein 1 | Potency | 15848.9 | nM | None |
| Homo sapiens | Muscleblind-like protein 1 | Potency | 19952.6 | nM | None |
| Homo sapiens | NCI/ADR-RES | GI50 | 100000.0 | nM | None |
| Homo sapiens | NCI-H226 | GI50 | 69662.65 | 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 | NCI-H522 | GI50 | 56363.77 | nM | None |
| Homo sapiens | OVCAR-3 | GI50 | 98855.31 | 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 | 96605.09 | nM | None |
| Homo sapiens | Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 | Potency | 56234.1 | nM | None |
| Homo sapiens | RPMI-8226 | GI50 | 100000.0 | nM | None |
| Homo sapiens | Runt-related transcription factor 1/Core-binding factor subunit beta | Potency | 25118.9 | nM | None |
| Homo sapiens | Runt-related transcription factor 1/Core-binding factor subunit beta | Potency | 28183.8 | nM | None |
| Homo sapiens | RXF 393 | GI50 | 100000.0 | nM | None |
| Homo sapiens | SF-268 | GI50 | 100000.0 | nM | None |
| Homo sapiens | SF-295 | GI50 | 100000.0 | nM | None |
| Homo sapiens | SF-539 | GI50 | 39902.49 | 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 | 89742.88 | 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 | 81096.11 | nM | None |
| Homo sapiens | SR | GI50 | 59703.53 | 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 | U-251 | GI50 | 86099.38 | 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 |
| Klebsiella pneumoniae | Klebsiella pneumoniae | Inhibition | 7.6 | % | 10.6019/CHEMBL4296182 |
| Mus musculus | Nuclear receptor ROR-gamma | Potency | 28183.8 | nM | None |
| Plasmodium falciparum | Plasmodium falciparum | Potency | 13115.4 | nM | None |
| Plasmodium falciparum | Plasmodium falciparum | Potency | 16511.3 | nM | None |
| Pseudomonas aeruginosa | Pseudomonas aeruginosa | Inhibition | 17.23 | % | 10.6019/CHEMBL4296182 |
| Rattus norvegicus | Dual specificity tyrosine-phosphorylation-regulated kinase 1A | AC50 | 3826.0 | nM | None |
| Rattus norvegicus | Thioredoxin reductase 1, cytoplasmic | Potency | 28183.8 | nM | None |
| Severe acute respiratory syndrome coronavirus 2 | SARS-CoV-2 | IC50 | 19952.62 | nM | 10.6019/CHEMBL4651402 |
| Severe acute respiratory syndrome coronavirus 2 | SARS-CoV-2 | IC50 | 20000.0 | nM | 10.6019/CHEMBL4651402 |
| Staphylococcus aureus | Staphylococcus aureus | Inhibition | 8.78 | % | 10.6019/CHEMBL4296182 |
| Trypanosoma cruzi | Cruzipain | Potency | 31622.8 | nM | None |
| None | Unchecked | Potency | 15848.9 | nM | None |