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3,4,8-Trihydroxy-10-nitro-1-phenanthrenecarboxylic acid; 3,4-Methylene, 8-Me ether

AlkaPlorer ID: AK316597

Synonym: 8-Methoxy-6-nitrophenanthro[3,4-d]-1,3-dioxole-5-carboxylic acid, 8-Methoxy-3,4-methylenedioxy-10-nitro-1-phenanthrenecarboxylic acid, Aristolochic acid I, Aristolochic acid, Isoaristolochic acid, Aristolochin, Aristinic acid, Aristolochia yellow, Descresept, Tardolyt, TR 1736, Aristolochic acid A 

IUPAC Name: 8-methoxy-6-nitronaphtho[2,1-g][1,3]benzodioxole-5-carboxylate

Structure

SMILES: COC1=CC=CC2=C1C=C([N+](=O)[O-])C1=C(C(=O)[O-])C=C3OCOC3=C12

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InChI: InChI=1S/C17H11NO7/c1-23-12-4-2-3-8-9(12)5-11(18(21)22)14-10(17(19)20)6-13-16(15(8)14)25-7-24-13/h2-6H,7H2,1H3,(H,19,20)/p-1

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InChIKey: BBFQZRXNYIEMAW-UHFFFAOYSA-M

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Source

Species Genus Family Order Class Phylum Kingdom Domain
Papaver nudicaule Papaver Papaveraceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Couepia polyandra Couepia Chrysobalanaceae Malpighiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Asarum canadense Asarum Asaraceae Piperales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Akebia quinata Akebia Lardizabalaceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Dimerostemma asperatum Dimerostemma Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Aristolochia tuberosa Aristolochia Aristolochiaceae Piperales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Aristolochia indica Aristolochia Aristolochiaceae Piperales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Erysimum rhaeticum Erysimum Brassicaceae Brassicales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Aristolochia contorta Aristolochia Aristolochiaceae Piperales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Ficus cordata Ficus Moraceae Rosales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Dioscorea collettii Dioscorea Dioscoreaceae Dioscoreales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Manihot esculenta Manihot Euphorbiaceae Malpighiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
None Battus Papilionidae Lepidoptera Insecta Arthropoda Metazoa Eukaryota
Akebia trifoliata Akebia Lardizabalaceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Aristolochia heterophylla Aristolochia Aristolochiaceae Piperales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Aristolochia debilis Aristolochia Aristolochiaceae Piperales Magnoliopsida Streptophyta Viridiplantae Eukaryota
None Aristolochia Aristolochiaceae Piperales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Coffea canephora Coffea Rubiaceae Gentianales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Stephania tetrandra Stephania Menispermaceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Nerium oleander Nerium Apocynaceae Gentianales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Asarum heterotropoides Asarum Asaraceae Piperales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Aristolochia argentina Aristolochia Aristolochiaceae Piperales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Aristolochia kaempferi Aristolochia Aristolochiaceae Piperales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Asarum sieboldii Asarum Asaraceae Piperales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Aristolochia manshuriensis Aristolochia Aristolochiaceae Piperales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Mizuhopecten yessoensis Mizuhopecten Pectinidae Pectinida Bivalvia Mollusca Metazoa Eukaryota
Aristolochia fangchi Aristolochia Aristolochiaceae Piperales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Aristolochia rotunda Aristolochia Aristolochiaceae Piperales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Aristolochia moupinensis Aristolochia Aristolochiaceae Piperales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Rumex alpinus Rumex Polygonaceae Caryophyllales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Sinomenium acutum Sinomenium Menispermaceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Chondria atropurpurea Chondria Rhodomelaceae Ceramiales Florideophyceae Rhodophyta None Eukaryota
None Aristolochia Aristolochiaceae Piperales Magnoliopsida Streptophyta Viridiplantae Eukaryota

Properties Information

Molecule Weight: 340.2670000000001

TPSA？: 110.96

MolLogP？: 2.002

Number of H-Donors: 0

Number of H-Acceptors: 7

RingCount: 4

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Acinetobacter baumannii Acinetobacter baumannii Inhibition -2.12 % 10.6019/CHEMBL4296183
Bacillus anthracis Anthrax lethal factor Potency 10000.0 nM None
Candida albicans Candida albicans Inhibition 8.48 % 10.6019/CHEMBL4296183
Cavia porcellus Ileum Inhibition 64.0 % 10.1021/np800041t
Cavia porcellus Ileum Inhibition 100.0 % 10.1021/np800041t
Cryptococcus neoformans Cryptococcus neoformans Inhibition -6.51 % 10.6019/CHEMBL4296183
Electrophorus electricus Acetylcholinesterase Inhibition -16.99 % 10.1016/j.bmc.2012.09.040
Equus caballus Cholinesterase Inhibition 22.66 % 10.1016/j.bmc.2012.09.040
Escherichia coli Escherichia coli Inhibition 5.35 % 10.6019/CHEMBL4296183
Giardia intestinalis Putative fructose-1,6-bisphosphate aldolase Potency 22334.2 nM None
Homo sapiens 786-0 GI50 37153.52 nM None
Homo sapiens A498 GI50 29376.5 nM None
Homo sapiens A549 GI50 45919.8 nM None
Homo sapiens ACHN GI50 41591.06 nM None
Homo sapiens Aldehyde dehydrogenase 1A1 Potency 19952.6 nM None
Homo sapiens Aldehyde dehydrogenase 1A1 Potency 39810.7 nM None
Homo sapiens Aldehyde dehydrogenase 1A1 Potency 44668.4 nM None
Homo sapiens BT-549 GI50 39445.73 nM None
Homo sapiens CAKI-1 GI50 27227.01 nM None
Homo sapiens CCRF-CEM GI50 20044.72 nM None
Homo sapiens COLO 205 GI50 1306.17 nM None
Homo sapiens Cyclin-dependent kinase 2 Activity nan None 10.1016/j.bmcl.2010.01.007
Homo sapiens Cyclin-dependent kinase 2 IC50 20000.0 nM 10.1016/j.bmcl.2010.01.007
Homo sapiens Cytochrome P450 3A4 Potency 63.1 nM None
Homo sapiens Cytochrome P450 3A4 Potency 10000.0 nM None
Homo sapiens DNA dC->dU-editing enzyme APOBEC-3F Potency 7943.3 nM None
Homo sapiens DU-145 GI50 30130.06 nM None
Homo sapiens EKVX GI50 43351.09 nM None
Homo sapiens Geminin Potency 4109.5 nM None
Homo sapiens Glucagon-like peptide 1 receptor Potency 28183.8 nM None
Homo sapiens Glutaminase kidney isoform, mitochondrial Potency 12589.3 nM None
Homo sapiens HCC 2998 GI50 2798.98 nM None
Homo sapiens HCT-116 GI50 29853.83 nM None
Homo sapiens HCT-15 GI50 18155.16 nM None
Homo sapiens HEK293 EC50 118340.0 nM 10.1039/C6MD00496B
Homo sapiens HL-60 GI50 23067.47 nM None
Homo sapiens HOP-62 GI50 23659.2 nM None
Homo sapiens HOP-92 GI50 77983.01 nM None
Homo sapiens Hs-578T GI50 52844.53 nM None
Homo sapiens HT-29 GI50 889.2 nM None
Homo sapiens IGROV-1 GI50 29376.5 nM None
Homo sapiens K562 GI50 33884.42 nM None
Homo sapiens KM12 GI50 27289.78 nM None
Homo sapiens LOX IMVI GI50 35481.34 nM None
Homo sapiens M14 GI50 43853.07 nM None
Homo sapiens Malme-3M GI50 46773.51 nM None
Homo sapiens MCF7 GI50 49431.07 nM None
Homo sapiens MDA-MB-231 GI50 39084.09 nM None
Homo sapiens MDA-MB-435 GI50 54827.7 nM None
Homo sapiens MDA-N GI50 100000.0 nM None
Homo sapiens Menin/Histone-lysine N-methyltransferase MLL Potency 4466.8 nM None
Homo sapiens Menin/Histone-lysine N-methyltransferase MLL Potency 35481.3 nM None
Homo sapiens Microtubule-associated protein tau Potency 12589.3 nM None
Homo sapiens Microtubule-associated protein tau Potency 14125.4 nM None
Homo sapiens Microtubule-associated protein tau Potency 17782.8 nM None
Homo sapiens Microtubule-associated protein tau Potency 39810.7 nM None
Homo sapiens MOLT-4 GI50 26668.59 nM None
Homo sapiens NCI/ADR-RES GI50 38106.58 nM None
Homo sapiens NCI-H226 GI50 33728.73 nM None
Homo sapiens NCI-H23 GI50 39445.73 nM None
Homo sapiens NCI-H322M GI50 55335.01 nM None
Homo sapiens NCI-H460 GI50 27733.2 nM None
Homo sapiens NCI-H522 GI50 28054.34 nM None
Homo sapiens Nuclear factor erythroid 2-related factor 2 Potency 11582.1 nM None
Homo sapiens OVCAR-3 GI50 33884.42 nM None
Homo sapiens OVCAR-4 GI50 31988.95 nM None
Homo sapiens OVCAR-5 GI50 25351.29 nM None
Homo sapiens OVCAR-8 GI50 28707.81 nM None
Homo sapiens Panel NCI-60 (60 carcinoma cell lines) GI50 883.0 nM 10.1021/jm049838d
Homo sapiens Parathyroid hormone receptor Potency 31622.8 nM None
Homo sapiens PC-3 GI50 46451.53 nM None
Homo sapiens Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 Potency 14125.4 nM None
Homo sapiens RPMI-8226 GI50 24660.39 nM None
Homo sapiens RXF 393 GI50 23442.29 nM None
Homo sapiens SF-268 GI50 33806.48 nM None
Homo sapiens SF-295 GI50 32433.96 nM None
Homo sapiens SF-539 GI50 24888.57 nM None
Homo sapiens SK-MEL-2 GI50 57809.6 nM None
Homo sapiens SK-MEL-28 GI50 41879.36 nM None
Homo sapiens SK-MEL-5 GI50 43954.16 nM None
Homo sapiens SK-OV-3 GI50 49545.02 nM None
Homo sapiens SN12C GI50 74301.91 nM None
Homo sapiens SNB-19 GI50 37497.3 nM None
Homo sapiens SNB-75 GI50 30902.95 nM None
Homo sapiens Solute carrier organic anion transporter family member 1B1 Inhibition 76.91 % 10.1124/mol.112.084152
Homo sapiens Solute carrier organic anion transporter family member 1B3 Inhibition 107.62 % 10.1124/mol.112.084152
Homo sapiens SR GI50 21727.01 nM None
Homo sapiens Survival motor neuron protein Potency 10000.0 nM None
Homo sapiens SW-620 GI50 31988.95 nM None
Homo sapiens T47D GI50 50118.72 nM None
Homo sapiens TK-10 GI50 46881.34 nM None
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 8176.7 nM None
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 11550.0 nM None
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 18356.4 nM None
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 29855.4 nM None
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 33498.3 nM None
Homo sapiens U-251 GI50 36897.76 nM None
Homo sapiens UACC-257 GI50 97723.72 nM None
Homo sapiens UACC-62 GI50 31405.09 nM None
Homo sapiens UO-31 GI50 40550.85 nM None
Klebsiella pneumoniae Klebsiella pneumoniae Inhibition -1.07 % 10.6019/CHEMBL4296183
Mesocricetus auratus Syrian golden hamster Activity nan None 10.1021/np50032a017
Mus musculus Nuclear receptor ROR-gamma Potency 1258.9 nM None
Mus musculus Nuclear receptor ROR-gamma Potency 28183.8 nM None
Pseudomonas aeruginosa Pseudomonas aeruginosa Inhibition 7.59 % 10.6019/CHEMBL4296183
Rattus norvegicus Rattus norvegicus Activity nan None 10.1021/np50032a017
Salmonella enterica subsp. enterica serovar Typhimurium Salmonella typhimurium Activity nan None 10.1021/np300137f
Staphylococcus aureus Staphylococcus aureus Inhibition -13.97 % 10.6019/CHEMBL4296183
None NON-PROTEIN TARGET Anticonvulsant activity nan None 10.1016/s0960-894x(03)00535-3
None NON-PROTEIN TARGET IC50 10.0 ug.mL-1 10.1016/j.bmcl.2011.01.067
None No relevant target Drug metabolism nan None 10.1021/np300137f
None Unchecked Potency 891.3 nM None
None Unchecked Potency 3162.3 nM None
None Unchecked Potency 14125.4 nM None
None Unchecked Potency 32642.7 nM None
None Unchecked Potency 35481.3 nM None

Metabolism Information