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name Structure Reference Source Properties Activities Metabolism

Dihydrochelerythrine

AlkaPlorer ID: AK000766

Synonym: 12,13-Dihydro-1,2-dimethoxy-12-methyl[1,3]benzodioxolo[5,6-c]phenanthridine, Toddalinine, Dihydrotoddaline 

IUPAC Name: 1,2-dimethoxy-12-methyl-13H-[1,3]benzodioxolo[5,6-c]phenanthridine

Structure

SMILES: COC1=C(OC)C2=C(C=C1)C1=C(C3=C(C=C1)C=C1OCOC1=C3)N(C)C2

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InChI: InChI=1S/C21H19NO4/c1-22-10-16-13(6-7-17(23-2)21(16)24-3)14-5-4-12-8-18-19(26-11-25-18)9-15(12)20(14)22/h4-9H,10-11H2,1-3H3

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InChIKey: ALZAZMCIBRHMFF-UHFFFAOYSA-N

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Source

Species Genus Family Order Class Phylum Kingdom Domain
Garcinia xanthochymus Garcinia Clusiaceae Malpighiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Alchornea cordifolia Alchornea Euphorbiaceae Malpighiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Rauvolfia salicifolia Rauvolfia Apocynaceae Gentianales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Plectosphaerella cucumerina Plectosphaerella Plectosphaerellaceae Glomerellales Sordariomycetes Ascomycota Fungi Eukaryota
Coptis chinensis Coptis Ranunculaceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Rehmannia glutinosa Rehmannia Orobanchaceae Lamiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Alexandrium excavatum Alexandrium Pyrocystaceae Gonyaulacales Dinophyceae None None Eukaryota
Tetradium glabrifolium Tetradium Rutaceae Sapindales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Balanophora japonica Balanophora Balanophoraceae Santalales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Strychnos spinosa Strychnos Loganiaceae Gentianales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Zanthoxylum bungeanum Zanthoxylum Rutaceae Sapindales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Hygrophorus eburneus Hygrophorus Hygrophoraceae Agaricales Agaricomycetes Basidiomycota Fungi Eukaryota
Myoporum acuminatum Myoporum Scrophulariaceae Lamiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Crambe fruticosa Crambe Brassicaceae Brassicales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Inula grantioides Inula Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Coptis japonica Coptis Ranunculaceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Coptis deltoidea Coptis Ranunculaceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Juniperus horizontalis Juniperus Cupressaceae Cupressales Pinopsida Streptophyta Viridiplantae Eukaryota
Plectranthus caninus Plectranthus Lamiaceae Lamiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Vitex divaricata Vitex Lamiaceae Lamiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Pueraria tuberosa Pueraria Fabaceae Fabales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Coptis teeta Coptis Ranunculaceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Zanthoxylum nitidum Zanthoxylum Rutaceae Sapindales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Diabelia spathulata Diabelia Caprifoliaceae Dipsacales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Garcinia lucida Garcinia Clusiaceae Malpighiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Salmonella enterica Salmonella Enterobacteriaceae Enterobacterales Gammaproteobacteria Pseudomonadota None Bacteria
Glycosmis pseudoracemosa Glycosmis Rutaceae Sapindales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Cynoglossum amabile Cynoglossum Boraginaceae Boraginales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Liatris aspera Liatris Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Cota tinctoria Cota Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Lathyrus tingitanus Lathyrus Fabaceae Fabales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Canarina canariensis Canarina Campanulaceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Nicotiana plumbaginifolia Nicotiana Solanaceae Solanales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Heterodermia obscurata Heterodermia Physciaceae Caliciales Lecanoromycetes Ascomycota Fungi Eukaryota
Fusarium incarnatum Fusarium Nectriaceae Hypocreales Sordariomycetes Ascomycota Fungi Eukaryota
Corynanthe pachyceras Corynanthe Rubiaceae Gentianales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Streptomyces pulveraceus Streptomyces Streptomycetaceae Kitasatosporales Actinomycetes Actinomycetota None Bacteria
Chelidonium majus Chelidonium Papaveraceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota

Properties Information

Molecule Weight: 349.38600000000014

TPSA？: 40.16

MolLogP？: 4.202500000000004

Number of H-Donors: 0

Number of H-Acceptors: 5

RingCount: 5

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Bacillus subtilis Bacillus subtilis Activity nan None 10.1021/np50074a026
Chlorocebus sabaeus Vero IC50 35400.0 nM 10.1021/np0702281
Escherichia coli Escherichia coli Activity nan None 10.1021/np50074a026
Hepatitis B virus Hepatitis B virus IC50 50.0 nM 10.1016/j.ejmech.2014.01.046
Homo sapiens A-431 Inhibition 30.39 % 10.1016/j.bmc.2016.04.059
Homo sapiens A549 Activity nan None 10.1016/j.bmc.2016.04.059
Homo sapiens Dipeptidyl peptidase IV IC50 56230.0 nM 10.1039/C0MD00245C
Homo sapiens HCT-116 IC50 10000.0 nM 10.1016/j.bmcl.2015.05.031
Homo sapiens HCT-15 GI 56.5 % 10.1016/j.ejmech.2017.06.021
Homo sapiens HeLa Activity nan None 10.1016/j.bmc.2016.04.059
Homo sapiens HL-60 IC50 10000.0 nM 10.1016/j.bmcl.2015.05.031
Homo sapiens MCF7 GI nan None 10.1016/j.ejmech.2017.06.021
Homo sapiens MDA-MB-231 Inhibition 8.65 % 10.1016/j.bmc.2016.04.059
Homo sapiens PC-3 GI 26.6 % 10.1016/j.ejmech.2017.06.021
Leishmania donovani Leishmania donovani Activity 70.9 % 10.1021/np0702281
Leishmania donovani Leishmania donovani IC50 2000.0 nM 10.1021/np0702281
Leishmania donovani Leishmania donovani Inhibition 36.0 % 10.1021/np0702281
Leishmania donovani Leishmania donovani Inhibition 89.0 % 10.1021/np0702281
Leishmania donovani Leishmania donovani Inhibition 100.0 % 10.1021/np0702281
Micrococcus luteus Micrococcus luteus Activity nan None 10.1021/np50074a026
Penicillium oxalicum Penicillium oxalicum Activity nan None 10.1021/np50074a026
Trypanosoma brucei brucei Trypanosoma brucei brucei IC50 800.0 nM 10.1021/np0702281
None NON-PROTEIN TARGET Activity nan None 10.1016/j.bmc.2016.04.059
None NON-PROTEIN TARGET Inhibition nan % 10.1016/j.bmc.2016.04.059
None Unchecked Activity nan None 10.1016/j.bmc.2016.04.059
None Unchecked Delta Tm -1.0 degrees C 10.1016/j.bmc.2016.04.059
None Unchecked Delta Tm 17.6 degrees C 10.1016/j.bmc.2016.04.059
None Unchecked Delta Tm 24.0 degrees C 10.1016/j.bmc.2016.04.059
None Unchecked GI 16.0 % 10.1016/j.ejmech.2017.06.021
None Unchecked IC50 5800.0 nM 10.1016/j.bmc.2016.04.059
None Unchecked K 5.5 10'5/M 10.1016/j.bmc.2016.04.059

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT011888 COc1ccc2c(c1OC)CN(C)C(O)Cc1cc3c(cc1C(=O)C2)OCO3>>COc1ccc2c(c1OC)CN(C)c1c-2ccc2cc3c(cc12)OCO3 RXN-15541
AKRT011891 COc1ccc2c(c1OC)CN(C)c1c-2ccc2cc3c(cc12)OCO3>>COc1ccc2c(c[n+](C)c3c4cc5c(cc4ccc23)OCO5)c1OC RXN-15542
AKRT011899 COc1ccc2c(c[n+](C)c3c4cc5c(cc4ccc23)OCO5)c1OC>>COc1ccc2c(c1OC)CN(C)c1c-2ccc2cc3c(cc12)OCO3 RXN-15543