Isoboldine
AlkaPlorer ID: AK007402
Synonym: None
IUPAC Name: (6aS)-2,10-dimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-1,9-diol
Structure
SMILES: COC1=CC2=C(C=C1O)C[C@H]1C3=C(C=C(OC)C(O)=C23)CCN1C
InChI: InChI=1S/C19H21NO4/c1-20-5-4-10-8-16(24-3)19(22)18-12-9-15(23-2)14(21)7-11(12)6-13(20)17(10)18/h7-9,13,21-22H,4-6H2,1-3H3/t13-/m0/s1
InChIKey: LINHZVMHXABQLB-ZDUSSCGKSA-N
Reference
The alkaloids of Schefferomitra subaequalis (Anonaceae)
PubChem CID: 133323
CAS: 3019-51-0
LOTUS: LTS0035776
NPASS: NPC212794
data_source: manually
Source
Properties Information
Molecule Weight: 327.3800000000001
TPSA？: 62.16
MolLogP？: 2.867100000000001
Number of H-Donors: 2
Number of H-Acceptors: 5
RingCount: 4
Activities Information
| Organism | Target Name | Standard Type | Standard Value | Standard Units | doi |
|---|---|---|---|---|---|
| Giardia intestinalis | Putative fructose-1,6-bisphosphate aldolase | Potency | 3971.6 | nM | None |
| Homo sapiens | 15-hydroxyprostaglandin dehydrogenase [NAD+] | Potency | 35481.3 | nM | None |
| Homo sapiens | Aldehyde dehydrogenase 1A1 | Potency | 31622.8 | nM | None |
| Homo sapiens | ATP-dependent DNA helicase Q1 | Potency | 25118.9 | nM | None |
| Homo sapiens | Caspase-1 | Potency | 31622.8 | nM | None |
| Homo sapiens | Caspase-7 | Potency | 31622.8 | nM | None |
| Homo sapiens | Cellular tumor antigen p53 | Potency | 31622.8 | nM | None |
| Homo sapiens | Cytochrome P450 2C19 | Potency | 12589.3 | nM | None |
| Homo sapiens | Cytochrome P450 2C9 | Potency | 25118.9 | nM | None |
| Homo sapiens | Cytochrome P450 2D6 | Potency | 6309.6 | nM | None |
| Homo sapiens | Cytochrome P450 3A4 | Potency | 19952.6 | nM | None |
| Homo sapiens | DNA-(apurinic or apyrimidinic site) lyase | Potency | 31622.8 | nM | None |
| Homo sapiens | DNA polymerase kappa | Potency | 3162.3 | nM | None |
| Homo sapiens | Endoplasmic reticulum-associated amyloid beta-peptide-binding protein | Potency | 31622.8 | nM | None |
| Homo sapiens | Lysine-specific demethylase 4D-like | Potency | 28183.8 | nM | None |
| Homo sapiens | Menin/Histone-lysine N-methyltransferase MLL | Potency | 31622.8 | nM | None |
| Homo sapiens | Microtubule-associated protein tau | Potency | 11220.2 | nM | None |
| Homo sapiens | Microtubule-associated protein tau | Potency | 14125.4 | nM | None |
| Homo sapiens | Microtubule-associated protein tau | Potency | 25118.9 | nM | None |
| Homo sapiens | Neutrophil | IC50 | 5810.0 | nM | 10.1016/j.bmcl.2020.127224 |
| Homo sapiens | Neutrophil | Inhibition | 50.0 | % | 10.1016/j.bmcl.2020.127224 |
| Homo sapiens | Runt-related transcription factor 1/Core-binding factor subunit beta | Potency | 12589.3 | nM | None |
| Homo sapiens | Tyrosyl-DNA phosphodiesterase 1 | Potency | 29855.4 | nM | None |
| Homo sapiens | Tyrosyl-DNA phosphodiesterase 1 | Potency | 33498.3 | nM | None |
| Plasmodium falciparum | Plasmodium falciparum | IC50 | 0.668 | ug.mL-1 | 10.1021/np960195h |
| Plasmodium falciparum | Plasmodium falciparum | IC50 | 0.904 | ug.mL-1 | 10.1021/np960195h |
| Rattus norvegicus | Inositol monophosphatase 1 | Potency | 14125.4 | nM | None |
| Rattus norvegicus | Inositol monophosphatase 1 | Potency | 31622.8 | nM | None |
| None | ADMET | CC50 | 100000.0 | nM | 10.1016/j.bmc.2006.10.034 |
| None | B-cell | IC50 | 29600.0 | nM | 10.1016/j.bmc.2006.10.034 |
| None | T-cell | IC50 | 24000.0 | nM | 10.1016/j.bmc.2006.10.034 |
| None | T-cell | Ratio CC50/IC50 | 3.0 | None | 10.1016/j.bmc.2006.10.034 |
| None | Unchecked | Potency | 28183.8 | nM | None |
| None | Unchecked | Ratio CC50/IC50 | 4.0 | None | 10.1016/j.bmc.2006.10.034 |