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(-)-demecolcine

AlkaPlorer ID: AK001986

Synonym: 'N-methyl-N-desacetylcolchicine', 'Colchamine', 'Demecolcine', 'Colcemid', 'N-desacetyl-N-methylcolchicine', "Reichstein's F", '(-)-colchamine', "Santavy's substance F", 'N-methyl-N-deacetylcolchicine', 'N-deacetyl-N-methylcolchicine'

IUPAC Name: (7S)-1,2,3,10-tetramethoxy-7-(methylamino)-6,7-dihydro-5H-benzo[a]heptalen-9-one

Structure

SMILES: CN[C@H]1CCC2=CC(OC)=C(OC)C(OC)=C2C2=CC=C(OC)C(=O)C=C21

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InChI: InChI=1S/C21H25NO5/c1-22-15-8-6-12-10-18(25-3)20(26-4)21(27-5)19(12)13-7-9-17(24-2)16(23)11-14(13)15/h7,9-11,15,22H,6,8H2,1-5H3/t15-/m0/s1

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InChIKey: NNJPGOLRFBJNIW-HNNXBMFYSA-N

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Properties Information

Molecule Weight: 371.4330000000001

TPSA？: 66.02000000000001

MolLogP？: 2.954900000000001

Number of H-Donors: 1

Number of H-Acceptors: 6

RingCount: 3

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Artemia Artemia LC50 61.0 ug.mL-1 10.1021/np0496587
Aspergillus niger Aspergillus niger MIC 500.0 ug.mL-1 10.1021/np0496587
Bos taurus Monoamine oxidase A Activity nan None 10.1021/jm800656v
Bos taurus Monoamine oxidase B Activity nan None 10.1021/jm800656v
Bos taurus Tubulin beta chain IC50 2400.0 nM 10.1021/jm00164a015
Cricetulus griseus CHO Log CR 1.2 None 10.1021/jm00169a014
Homo sapiens A2780S Activity nan None 10.1021/acs.jmedchem.1c01451
Homo sapiens A2780S Ratio 100.0 None 10.1021/acs.jmedchem.1c01451
Homo sapiens Geminin Potency 32.6 nM None
Homo sapiens Geminin Potency 75.0 nM None
Homo sapiens Geminin Potency 112.2 nM None
Homo sapiens Geminin Potency 118.9 nM None
Homo sapiens HeLa Activity 64.7 % 10.1021/jm00195a017
Homo sapiens HT-29 Activity 25.0 nM 10.1016/j.bmcl.2009.04.010
Homo sapiens K562 Activity 16.0 nM 10.1016/j.bmcl.2009.04.010
Homo sapiens KB ED50 0.25 ug ml-1 10.1021/np50022a010
Homo sapiens MCF7 Activity 7.8 nM 10.1016/j.bmcl.2009.04.010
Homo sapiens MCF7 Activity 40.73 % 10.1021/jm800203e
Homo sapiens MCF7 Activity 75.27 % 10.1021/jm800203e
Homo sapiens MCF7 EC50 600.0 nM 10.1021/np0496587
Homo sapiens NCI-H460 EC50 690.0 nM 10.1021/np0496587
Homo sapiens Nuclear factor erythroid 2-related factor 2 Potency 103.2 nM None
Homo sapiens Nuclear receptor subfamily 0 group B member 1 IC50 834.47 nM None
Homo sapiens Paired box protein Pax-8 AC50 260.0 nM None
Homo sapiens PC-3 Activity 31.0 nM 10.1016/j.bmcl.2009.04.010
Homo sapiens Pregnane X receptor Activity nan None 10.1124/dmd.110.035105
Homo sapiens Pregnane X receptor EC50 12600.0 nM 10.1124/dmd.110.035105
Homo sapiens Pregnane X receptor EC50 14100.0 nM 10.1124/dmd.110.035105
Homo sapiens Pregnane X receptor Efficacy 51.1 % 10.1124/dmd.110.035105
Homo sapiens Pregnane X receptor Efficacy 103.0 % 10.1124/dmd.110.035105
Homo sapiens SF-268 EC50 6200.0 nM 10.1021/np0496587
Homo sapiens SW-620 Activity 31.0 nM 10.1016/j.bmcl.2009.04.010
Homo sapiens Tubulin Activity 32.82 % 10.1021/acs.jmedchem.1c01451
Homo sapiens Tubulin Activity 63.04 % 10.1021/acs.jmedchem.1c01451
Homo sapiens Tubulin Activity 147.7 pmol 10.1021/acs.jmedchem.1c01451
Homo sapiens Tubulin Activity 283.66 pmol 10.1021/acs.jmedchem.1c01451
Homo sapiens Tubulin Activity nan None 10.1016/j.ejmech.2021.113897
Homo sapiens Tubulin Tubulin binding 93.0 % 10.1021/jm00135a005
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 20.6 nM None
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 130.0 nM None
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 167.9 nM None
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 237.1 nM None
Homo sapiens U-251 Activity nan None 10.1021/jm501997q
Micrococcus luteus Micrococcus luteus MIC 500.0 ug.mL-1 10.1021/np0496587
Mus musculus Mus musculus Log 1/LD50 3.63 None 10.1021/jm00137a031
Mus musculus Mus musculus Toxicity 21.6 uM kg-1 10.1021/jm00135a005
Mus musculus Mus musculus Toxicity 236.7 uM kg-1 10.1021/jm00135a005
Mus musculus Mus musculus Toxicity 237.0 mg kg-1 10.1021/jm00164a015
Mus musculus P388 Log 1/C 4.66 None 10.1021/jm00135a004
Mus musculus P388 Potency 10.8 uM kg-1 10.1021/jm00135a005
Mycolicibacterium smegmatis Mycolicibacterium smegmatis MIC 500.0 ug.mL-1 10.1021/np0496587
Rattus norvegicus Nuclear receptor subfamily 1 group I member 2 EC50 90.0 nM 10.1124/dmd.110.035105
Rattus norvegicus Nuclear receptor subfamily 1 group I member 2 Efficacy 103.0 % 10.1124/dmd.110.035105
Rattus norvegicus Peripheral myelin protein 22 Potency 80.9 nM None
Rattus norvegicus Peripheral myelin protein 22 Potency 177.7 nM None
Saccharomyces cerevisiae Saccharomyces cerevisiae MIC 500.0 ug.mL-1 10.1021/np0496587
None NON-PROTEIN TARGET Potency 10583.9 nM None
None NON-PROTEIN TARGET Potency 11875.4 nM None
None NON-PROTEIN TARGET Potency 14950.2 nM None
None No relevant target IC50 67595.0 nM None
None No relevant target LogD 1.37 None 10.1021/jm00169a014
None No relevant target LogP 1.37 None 10.1021/jm070524a
None No relevant target LogP 1.53 None 10.1021/jm00135a004
None No relevant target LogP 1.53 None 10.1021/jm00137a031
None Unchecked AC50 48.8 nM None
None Unchecked AC50 61.5 nM None
None Unchecked AC50 96.6 nM None
None Unchecked AC50 96.7 nM None
None Unchecked AC50 113.0 nM None
None Unchecked AC50 217.0 nM None
None Unchecked AC50 234.0 nM None
None Unchecked AC50 318.0 nM None
None Unchecked AC50 6350.0 nM None
None Unchecked AC50 100000.0 nM None
None Unchecked Activity nan None 10.1016/j.bmcl.2009.04.010
None Unchecked EC50 78.0 nM None
None Unchecked EC50 80.0 nM None
None Unchecked EC50 85.0 nM None
None Unchecked EC50 100.0 nM None
None Unchecked IC50 160.0 nM None
None Unchecked IC50 2400.0 nM 10.1021/np50070a044
None Unchecked IC50 3580.0 nM 10.1016/j.bmcl.2009.04.010
None Unchecked IC50 80000.0 nM None
None Unchecked Potency 631.0 nM None
None Unchecked Potency 10000.0 nM None

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT010927 CN[C@H]1CCc2cc(OC)c(OC)c(OC)c2-c2ccc(OC)c(=O)cc21>>C=O RXN-9209
AKRT010928 CN[C@H]1CCc2cc(OC)c(OC)c(OC)c2-c2ccc(OC)c(=O)cc21>>COc1cc2c(c(OC)c1OC)-c1ccc(OC)c(=O)cc1[C@@H](N)CC2 RXN-9209
AKRT011624 COc1cc2c(c(OC)c1OC)-c1ccc(OC)c(=O)cc1[C@@H](N(C)C=O)CC2>>CN[C@H]1CCc2cc(OC)c(OC)c(OC)c2-c2ccc(OC)c(=O)cc21 RXN-13557