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Liriodenine

AlkaPlorer ID: AK000285

Synonym: None

IUPAC Name: 3,5-dioxa-11-azapentacyclo[10.7.1.02,6.08,20.014,19]icosa-1(20),2(6),7,9,11,14,16,18-octaen-13-one

Structure

SMILES: O=C1C2=CC=CC=C2C2=C3OCOC3=CC3=CC=NC1=C23

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InChI: InChI=1S/C17H9NO3/c19-16-11-4-2-1-3-10(11)14-13-9(5-6-18-15(13)16)7-12-17(14)21-8-20-12/h1-7H,8H2

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InChIKey: MUMCCPUVOAUBAN-UHFFFAOYSA-N

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Reference

Oxoaporphine Alkaloids from Rollinia papilionella

PubChem CID: 10144

CAS: 475-75-2

LOTUS: LTS0132761

SuperNatural Ⅲ: SN0235675

COCONUT: CNP0321376

data_source: manually

Source

Species Genus Family Order Class Phylum Kingdom Domain
Annona senegalensis Annona Annonaceae Magnoliales Magnoliopsida Streptophyta Viridiplantae Eukaryota

Properties Information

Molecule Weight: 275.263

TPSA？: 48.42

MolLogP？: 3.174900000000001

Number of H-Donors: 0

Number of H-Acceptors: 4

RingCount: 5

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Artemia Artemia LC50 1.1 ug.mL-1 10.1021/np50063a002
Aspergillus niger Aspergillus niger MIC 25.0 ug.mL-1 10.1021/np900572g
Bacillus subtilis Bacillus subtilis MIC 500.0 ug.mL-1 10.1021/np800788n
Candida albicans Candida albicans IC50 3.5 ug.mL-1 10.1021/np0200717
Candida albicans Candida albicans MIC 6.25 ug.mL-1 10.1021/np0200717
Candida albicans Candida albicans MIC 1000.0 ug.mL-1 10.1021/np800788n
Candida albicans Candida albicans MIC nan None 10.1021/np100013r
Candida dubliniensis Candida dubliniensis MIC 50.0 ug.mL-1 10.1021/np100013r
Candida dubliniensis Candida dubliniensis MIC 100.0 ug.mL-1 10.1021/np100013r
Candida parapsilosis Candida parapsilosis MIC nan None 10.1021/np100013r
Candida tropicalis Candida tropicalis MIC nan None 10.1021/np100013r
Chlorocebus sabaeus Vero CC50 48000.0 nM 10.1021/np970382v
Chlorocebus sabaeus Vero MTC 31.0 uM 10.1021/np970382v
Cryptococcus neoformans Cryptococcus neoformans IC50 2.0 ug.mL-1 10.1021/np0200717
Cryptococcus neoformans Cryptococcus neoformans MIC 12.5 ug.mL-1 10.1021/np0200717
Electrophorus electricus Acetylcholinesterase IC50 150000.0 nM 10.1021/np100247r
Enterococcus faecium Enterococcus faecium MIC 150.0 ug.mL-1 10.1021/np800788n
Enterococcus hirae Enterococcus hirae MIC 600.0 ug.mL-1 10.1021/np800788n
Escherichia coli Escherichia coli MIC 1000.0 ug.mL-1 10.1021/np800788n
Escherichia coli Escherichia coli MIC nan None 10.1021/np100013r
Homo sapiens 786-0 GI50 4246.2 nM None
Homo sapiens 786-0 GI50 7691.3 nM None
Homo sapiens A498 GI50 3483.37 nM None
Homo sapiens A549 ED50 0.72 ug ml-1 10.1021/np50071a028
Homo sapiens A549 GI50 3467.37 nM None
Homo sapiens A549 GI50 3475.36 nM None
Homo sapiens ACHN GI50 3935.5 nM None
Homo sapiens ACHN GI50 4315.19 nM None
Homo sapiens CAKI-1 GI50 3630.78 nM None
Homo sapiens CAKI-1 GI50 3767.04 nM None
Homo sapiens CCRF-CEM GI50 2697.74 nM None
Homo sapiens CCRF-CEM GI50 4102.04 nM None
Homo sapiens COLO 205 GI50 4236.43 nM None
Homo sapiens COLO 205 GI50 4786.3 nM None
Homo sapiens DLD-1 GI50 4045.76 nM None
Homo sapiens DLD-1 GI50 4487.45 nM None
Homo sapiens DMS-114 GI50 4875.28 nM None
Homo sapiens DMS-114 GI50 10046.16 nM None
Homo sapiens DMS-273 GI50 3443.5 nM None
Homo sapiens DMS-273 GI50 5457.58 nM None
Homo sapiens EKVX GI50 3459.39 nM None
Homo sapiens EKVX GI50 5152.29 nM None
Homo sapiens HCC 2998 GI50 4508.17 nM None
Homo sapiens HCT-116 GI50 3169.57 nM None
Homo sapiens HCT-116 GI50 3288.52 nM None
Homo sapiens HCT-15 GI50 4415.7 nM None
Homo sapiens HCT-15 GI50 4897.79 nM None
Homo sapiens HCT-8 ED50 0.7 ug ml-1 10.1021/np50071a028
Homo sapiens HEK293 Activity nan None 10.1021/acs.jnatprod.6b00409
Homo sapiens HepG2 IC50 8300.0 nM 10.1021/acs.jnatprod.5b01037
Homo sapiens HL-60 GI50 2999.16 nM None
Homo sapiens HL-60 IC50 5500.0 nM 10.1021/acs.jnatprod.5b01037
Homo sapiens HOP-18 GI50 24888.57 nM None
Homo sapiens HOP-62 GI50 3890.45 nM None
Homo sapiens HOP-92 GI50 5610.48 nM None
Homo sapiens HOP-92 GI50 8689.6 nM None
Homo sapiens HT-29 GI50 4055.09 nM None
Homo sapiens HT-29 GI50 4954.5 nM None
Homo sapiens HT-29 IC50 10000.0 nM 10.1021/np3007414
Homo sapiens IGROV-1 GI50 3899.42 nM None
Homo sapiens IGROV-1 GI50 5970.35 nM None
Homo sapiens K562 GI50 3419.79 nM None
Homo sapiens K562 GI50 4285.49 nM None
Homo sapiens K562 IC50 5000.0 nM 10.1021/acs.jnatprod.5b01037
Homo sapiens KB ED50 1.0 ug ml-1 10.1021/np50071a028
Homo sapiens KB ED50 3.1 ug ml-1 10.1021/np50019a011
Homo sapiens KB IC50 5000.0 nM 10.1021/np900572g
Homo sapiens KM12 GI50 6441.69 nM None
Homo sapiens KM12 GI50 6501.3 nM None
Homo sapiens KM-20L2 GI50 5821.03 nM None
Homo sapiens KM-20L2 GI50 7144.96 nM None
Homo sapiens LOX IMVI GI50 3767.04 nM None
Homo sapiens LOX IMVI GI50 4216.97 nM None
Homo sapiens LXFL 529 GI50 5888.44 nM None
Homo sapiens LXFL 529 GI50 6516.28 nM None
Homo sapiens M14 GI50 6714.29 nM None
Homo sapiens M14 GI50 7533.56 nM None
Homo sapiens M19-MEL GI50 3749.73 nM None
Homo sapiens M19-MEL GI50 5861.38 nM None
Homo sapiens Malme-3M GI50 3026.91 nM None
Homo sapiens Malme-3M GI50 3589.22 nM None
Homo sapiens MCF7 IC50 5000.0 nM 10.1021/np900572g
Homo sapiens MOLT-4 GI50 3380.65 nM None
Homo sapiens MOLT-4 GI50 3672.82 nM None
Homo sapiens NCI-H226 GI50 4688.13 nM None
Homo sapiens NCI-H226 GI50 5272.3 nM None
Homo sapiens NCI-H23 GI50 4045.76 nM None
Homo sapiens NCI-H23 GI50 5395.11 nM None
Homo sapiens NCI-H322M GI50 6011.74 nM None
Homo sapiens NCI-H322M GI50 11220.18 nM None
Homo sapiens NCI-H460 GI50 3341.95 nM None
Homo sapiens NCI-H460 GI50 3589.22 nM None
Homo sapiens NCI-H460 IC50 5000.0 nM 10.1021/np900572g
Homo sapiens NCI-H522 GI50 885.12 nM None
Homo sapiens NCI-H522 GI50 4255.98 nM None
Homo sapiens Neuronal acetylcholine receptor; alpha3/beta4 Inhibition 19.3 % 10.1021/np3007414
Homo sapiens Neuronal acetylcholine receptor; alpha4/beta2 Inhibition 13.3 % 10.1021/np3007414
Homo sapiens OVCAR-3 GI50 9246.98 nM None
Homo sapiens OVCAR-3 GI50 10471.29 nM None
Homo sapiens OVCAR-4 GI50 5069.91 nM None
Homo sapiens OVCAR-4 GI50 8241.38 nM None
Homo sapiens OVCAR-5 GI50 11481.54 nM None
Homo sapiens OVCAR-5 GI50 16943.38 nM None
Homo sapiens OVCAR-8 GI50 4036.45 nM None
Homo sapiens OVCAR-8 GI50 5140.44 nM None
Homo sapiens Protein tyrosine phosphatase receptor type C-associated protein IC50 182000.0 nM 10.1016/0960-894X(95)00250-W
Homo sapiens RPMI-8226 GI50 3198.9 nM None
Homo sapiens RPMI-8226 GI50 3483.37 nM None
Homo sapiens RXF 393 GI50 5058.25 nM None
Homo sapiens RXF 393 GI50 5546.26 nM None
Homo sapiens RXF 631 GI50 4226.69 nM None
Homo sapiens RXF 631 GI50 4539.42 nM None
Homo sapiens SF-268 GI50 6025.6 nM None
Homo sapiens SF-268 GI50 6137.62 nM None
Homo sapiens SF-268 IC50 5000.0 nM 10.1021/np900572g
Homo sapiens SF-295 GI50 4864.07 nM None
Homo sapiens SF-295 GI50 6123.5 nM None
Homo sapiens SF-539 GI50 3531.83 nM None
Homo sapiens SF-539 GI50 7979.95 nM None
Homo sapiens SK-MEL-2 GI50 4187.94 nM None
Homo sapiens SK-MEL-2 GI50 5997.91 nM None
Homo sapiens SK-MEL-28 GI50 5272.3 nM None
Homo sapiens SK-MEL-28 GI50 5584.7 nM None
Homo sapiens SK-MEL-5 GI50 2837.92 nM None
Homo sapiens SK-OV-3 GI50 17864.88 nM None
Homo sapiens SK-OV-3 GI50 22233.1 nM None
Homo sapiens SN12C GI50 4977.37 nM None
Homo sapiens SN12C GI50 5821.03 nM None
Homo sapiens SNB-19 GI50 5675.45 nM None
Homo sapiens SNB-19 GI50 7998.34 nM None
Homo sapiens SNB-75 GI50 4178.3 nM None
Homo sapiens SNB-75 GI50 5997.91 nM None
Homo sapiens SNB-78 GI50 6039.49 nM None
Homo sapiens SNB-78 GI50 14927.94 nM None
Homo sapiens SW-620 GI50 3819.44 nM None
Homo sapiens SW-620 GI50 4920.4 nM None
Homo sapiens TK-10 GI50 3019.95 nM None
Homo sapiens TK-10 GI50 10185.91 nM None
Homo sapiens U-251 GI50 5445.03 nM None
Homo sapiens U-251 GI50 6324.12 nM None
Homo sapiens UACC-257 GI50 2588.21 nM None
Homo sapiens UACC-257 GI50 5236.0 nM None
Homo sapiens UACC-62 GI50 2766.94 nM None
Homo sapiens UACC-62 GI50 4570.88 nM None
Homo sapiens UO-31 GI50 3419.79 nM None
Homo sapiens UO-31 GI50 4943.11 nM None
Homo sapiens XF498 GI50 4688.13 nM None
Homo sapiens XF498 GI50 5754.4 nM None
Kocuria rhizophila Kocuria rhizophila MIC nan None 10.1021/np100013r
Leishmania amazonensis Leishmania amazonensis Activity 90.0 % 10.1021/np960223w
Leishmania amazonensis Leishmania amazonensis Activity 100.0 ug ml-1 10.1021/np960223w
Leishmania braziliensis Leishmania braziliensis Activity 90.0 % 10.1021/np960223w
Leishmania braziliensis Leishmania braziliensis IC50 58500.0 nM 10.1021/np050422s
Leishmania donovani Leishmania donovani Activity 90.0 % 10.1021/np960223w
Leishmania donovani Leishmania donovani Activity 100.0 ug ml-1 10.1021/np960223w
Leishmania guyanensis Leishmania guyanensis IC50 21500.0 nM 10.1021/np050422s
Micrococcus luteus Micrococcus luteus MIC 6.3 ug.mL-1 10.1021/np900572g
Micrococcus luteus Micrococcus luteus MIC 150.0 ug.mL-1 10.1021/np800788n
Mus musculus 3T3-L1 Activity nan None 10.1016/j.bmcl.2013.04.013
Mus musculus B16-F10 IC50 10000.0 nM 10.1021/acs.jnatprod.5b01037
Mus musculus BV-2 Activity nan None 10.1021/acs.jnatprod.1c00055
Mus musculus BV-2 IC50 5000.0 nM 10.1021/acs.jnatprod.1c00055
Mus musculus L1210 ED50 2.33 ug ml-1 10.1021/np50071a028
Mus musculus P388 ED50 0.57 ug ml-1 10.1021/np50071a028
Mus musculus RAW264.7 Activity nan None 10.1021/acs.jnatprod.1c00146
Mus musculus RAW264.7 IC50 1390.0 nM 10.1016/j.ejmech.2021.113165
Mus musculus RAW264.7 IC50 10500.0 nM 10.1021/acs.jnatprod.1c00146
Mus musculus RAW264.7 IC50 34700.0 nM 10.1016/j.bmc.2020.115462
Mycobacterium tuberculosis Mycobacterium tuberculosis MIC 12.5 ug.mL-1 10.1016/j.ejmech.2011.12.029
Mycobacterium tuberculosis Mycobacterium tuberculosis MIC 12.5 ug.mL-1 10.1016/j.ejmech.2017.06.005
Mycobacterium tuberculosis Mycobacterium tuberculosis MIC 12.5 ug.mL-1 10.1016/j.ejmech.2022.114173
Mycolicibacterium smegmatis Mycolicibacterium smegmatis MIC 12.0 ug.mL-1 10.1021/np900572g
Nakaseomyces glabratus Nakaseomyces glabratus MIC nan None 10.1021/np100013r
Poliovirus 2 Poliovirus 2 Activity nan None 10.1021/np970382v
Prescottella equi Prescottella equi MIC 10.0 ug.mL-1 10.1021/np800788n
Pseudomonas aeruginosa Pseudomonas aeruginosa MIC 1000.0 ug.mL-1 10.1021/np800788n
Pseudomonas aeruginosa Pseudomonas aeruginosa MIC nan None 10.1021/np100013r
Rattus norvegicus Dopamine D1 receptor IC50 75000.0 nM 10.1021/jm060959i
Rattus norvegicus Dopamine D2 receptor IC50 59000.0 nM 10.1021/jm060959i
Rattus norvegicus Dopamine transporter IC50 31000.0 nM 10.1021/jm060959i
Rattus norvegicus Dopamine transporter IC50 31200.0 nM 10.1021/np50124a001
Rattus norvegicus Voltage-gated L-type calcium channel alpha-1C subunit IC50 2500.0 nM None
Saccharomyces cerevisiae Saccharomyces cerevisiae Activity 16.7 ug ml-1 10.1021/np50103a009
Saccharomyces cerevisiae Saccharomyces cerevisiae Activity 500.0 ug ml-1 10.1021/np50103a009
Saccharomyces cerevisiae Saccharomyces cerevisiae Activity nan None 10.1021/np50103a009
Saccharomyces cerevisiae Saccharomyces cerevisiae IZ 15.0 mm 10.1021/np50103a009
Saccharomyces cerevisiae Saccharomyces cerevisiae MIC 12.0 ug.mL-1 10.1021/np900572g
Salmonella enterica Salmonella enterica MIC 1000.0 ug.mL-1 10.1021/np800788n
Staphylococcus aureus Staphylococcus aureus IC50 2.0 ug.mL-1 10.1021/np0200717
Staphylococcus aureus Staphylococcus aureus MIC 3.13 ug.mL-1 10.1021/np0200717
Staphylococcus aureus Staphylococcus aureus MIC 1000.0 ug.mL-1 10.1021/np800788n
Staphylococcus aureus Staphylococcus aureus MIC nan None 10.1021/np100013r
Staphylococcus epidermidis Staphylococcus epidermidis MIC 50.0 ug.mL-1 10.1021/np100013r
Sus scrofa Pancreatic triacylglycerol lipase Inhibition nan % 10.1016/j.bmcl.2013.04.013
Trypanosoma cruzi Trypanosoma cruzi Activity 50.0 % 10.1021/np960223w
None Molecular identity unknown IC50 600.0 nM 10.1021/acs.jnatprod.6b00409
None Molecular identity unknown Inhibition nan % 10.1021/acs.jnatprod.6b00409
None NON-PROTEIN TARGET Activity 0.3 None 10.1021/np100013r
None NON-PROTEIN TARGET Activity 5.3 % 10.1021/np9700735
None NON-PROTEIN TARGET Activity 5.4 % 10.1021/np9700735
None NON-PROTEIN TARGET Activity 40.5 % 10.1021/np9700735
None NON-PROTEIN TARGET Activity 84.1 % 10.1021/np9700735
None NON-PROTEIN TARGET Activity nan None 10.1021/acs.jnatprod.6b00409
None NON-PROTEIN TARGET Activity nan None 10.1021/np50063a002
None NON-PROTEIN TARGET ED50 1.6 ug ml-1 10.1021/np50053a020
None Unchecked IC50 34800.0 nM 10.1021/acs.jnatprod.5b01037
None Unchecked IC50 56800.0 nM 10.1016/j.bmc.2020.115462
None Unchecked Ratio IC50 1.9 None 10.1021/np50124a001
None Unchecked Ratio IC50 2.4 None 10.1021/np50124a001

Metabolism Information