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name Structure Reference Source Properties Activities Metabolism

Tetrahydroalstonine

AlkaPlorer ID: AK000646

Synonym: None

IUPAC Name: methyl (1S,15S,16S,20S)-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2(10),4,6,8,18-pentaene-19-carboxylate

Structure

SMILES: COC(=O)C1=CO[C@@H](C)[C@@H]2CN3CCC4=C(NC5=CC=CC=C45)[C@@H]3C[C@H]12

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InChI: InChI=1S/C21H24N2O3/c1-12-16-10-23-8-7-14-13-5-3-4-6-18(13)22-20(14)19(23)9-15(16)17(11-26-12)21(24)25-2/h3-6,11-12,15-16,19,22H,7-10H2,1-2H3/t12-,15-,16-,19-/m0/s1

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InChIKey: GRTOGORTSDXSFK-DLLGKBFGSA-N

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Source

Species Genus Family Order Class Phylum Kingdom Domain
Senecio halimifolius Senecio Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Cestrum parqui Cestrum Solanaceae Solanales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Klasea quinquefolia Klasea Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Prismatomeris sessiliflora Prismatomeris Rubiaceae Gentianales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Streptomyces albospinus Streptomyces Streptomycetaceae Kitasatosporales Actinomycetes Actinomycetota None Bacteria
Haplopappus paucidentatus Haplopappus Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Coleus xanthanthus Coleus Lamiaceae Lamiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Lethariella sernanderi Lethariella Parmeliaceae Lecanorales Lecanoromycetes Ascomycota Fungi Eukaryota
Uncaria rhynchophylla Uncaria Rubiaceae Gentianales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Lomatia ilicifolia Lomatia Proteaceae Proteales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Dictyostelium purpureum Dictyostelium Dictyosteliaceae Dictyosteliales Eumycetozoa Evosea None Eukaryota
Talaromyces funiculosus Talaromyces Trichocomaceae Eurotiales Eurotiomycetes Ascomycota Fungi Eukaryota
Solaster endeca Solaster Solasteridae Velatida Asteroidea Echinodermata Metazoa Eukaryota
Lomatia arborescens Lomatia Proteaceae Proteales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Monostroma nitidum Monostroma Monostromataceae Ulvales Ulvophyceae Chlorophyta Viridiplantae Eukaryota
Scutellaria glabrata Scutellaria Lamiaceae Lamiales Magnoliopsida Streptophyta Viridiplantae Eukaryota

Properties Information

Molecule Weight: 352.434

TPSA？: 54.56

MolLogP？: 3.1788000000000016

Number of H-Donors: 1

Number of H-Acceptors: 4

RingCount: 5

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Electrophorus electricus Acetylcholinesterase Inhibition 22.02 % 10.1016/j.bmc.2012.09.040
Equus caballus Cholinesterase Inhibition 89.06 % 10.1016/j.bmc.2012.09.040
Giardia intestinalis Putative fructose-1,6-bisphosphate aldolase Potency 5000.0 nM None
Homo sapiens Cytochrome P450 2D6 Ki 1100.0 nM 10.1021/jm00061a004
Homo sapiens DNA polymerase kappa Potency 16833.6 nM None
Homo sapiens Histone acetyltransferase GCN5 Potency 39810.7 nM None
Homo sapiens Menin/Histone-lysine N-methyltransferase MLL Potency 25118.9 nM None
Homo sapiens Serotonin 1a (5-HT1a) receptor EC50 100000.0 nM 10.1021/acs.jnatprod.9b00532
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 70794.6 nM None
Human immunodeficiency virus 1 Human immunodeficiency virus type 1 reverse transcriptase IC50 200.0 ug.mL-1 10.1021/np50073a012
None Unchecked Potency 25118.9 nM None

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT010991 COC(=O)C1=CO[C@@H](C)C2=CN3CCc4c([nH]c5ccccc45)[C@@H]3C[C@H]12>>COC(=O)C1=CO[C@@H](C)[C@@H]2CN3CCc4c([nH]c5ccccc45)[C@@H]3C[C@H]12 R05848
AKRT010993 COC(=O)C1=CO[C@@H](C)[C@@H]2CN3CCc4c([nH]c5ccccc45)[C@@H]3C[C@H]12>>COC(=O)C1=CO[C@@H](C)[C@@H]2C[N+]3=CCc4c([nH]c5ccccc45)[C@@H]3C[C@H]12 58204
AKRT010994 COC(=O)C1=CO[C@@H](C)[C@@H]2CN3CCc4c([nH]c5ccccc45)[C@@H]3C[C@H]12>>COC(=O)C1=CO[C@@H](C)[C@@H]2C[n+]3ccc4c([n-]c5ccccc54)c3C[C@H]12 R12282
AKRT010995 COC(=O)C1=CO[C@@H](C)[C@@H]2CN3CCc4c([nH]c5ccccc45)[C@@H]3C[C@H]12>>COC(=O)C1=CO[C@@H](C)[C@@H]2C[n+]3ccc4c([nH]c5ccccc54)c3C[C@H]12 58128