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Cytochalasin B

AlkaPlorer ID: AK021225

Synonym: None

IUPAC Name: (1S,4E,6R,10R,12E,14S,15S,17S,18S,19S)-19-benzyl-6,15-dihydroxy-10,17-dimethyl-16-methylidene-2-oxa-20-azatricyclo[12.7.0.01,18]henicosa-4,12-diene-3,21-dione

Structure

SMILES: C=C1[C@@H](C)[C@H]2[C@H](CC3=CC=CC=C3)NC(=O)[C@]23OC(=O)/C=C/[C@H](O)CCC[C@@H](C)C/C=C/[C@H]3[C@@H]1O

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InChI: InChI=1S/C29H37NO5/c1-18-9-7-13-22(31)15-16-25(32)35-29-23(14-8-10-18)27(33)20(3)19(2)26(29)24(30-28(29)34)17-21-11-5-4-6-12-21/h4-6,8,11-12,14-16,18-19,22-24,26-27,31,33H,3,7,9-10,13,17H2,1-2H3,(H,30,34)/b14-8+,16-15+/t18-,19-,22-,23+,24+,26+,27-,29-/m1/s1

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InChIKey: GBOGMAARMMDZGR-TYHYBEHESA-N

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Source

Species Genus Family Order Class Phylum Kingdom Domain
Hypericum triquetrifolium Hypericum Hypericaceae Malpighiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Verpa digitaliformis Verpa Morchellaceae Pezizales Pezizomycetes Ascomycota Fungi Eukaryota
Scutellaria seleriana Scutellaria Lamiaceae Lamiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Crinum kirkii Crinum Amaryllidaceae Asparagales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Aconitum brevicalcaratum Aconitum Ranunculaceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Blumea densiflora Blumea Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Ophiarthrum elegans Ophiarthrum Ophiocomidae Amphilepidida Ophiuroidea Echinodermata Metazoa Eukaryota
Teucrium pestalozzae Teucrium Lamiaceae Lamiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Plantago lanceolata Plantago Plantaginaceae Lamiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Trifolium apertum Trifolium Fabaceae Fabales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Tripodanthus acutifolius Tripodanthus Loranthaceae Santalales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Veronica pectinata Veronica Plantaginaceae Lamiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Euonymus grandiflorus Euonymus Celastraceae Celastrales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Phoma sp. Phoma Didymellaceae Pleosporales Dothideomycetes Ascomycota Fungi Eukaryota
Ptilidium ciliare Ptilidium Ptilidiaceae Ptilidiales Jungermanniopsida Streptophyta Viridiplantae Eukaryota
Isodon japonicus Isodon Lamiaceae Lamiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Hymenocallis arenicola Hymenocallis Amaryllidaceae Asparagales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Streptomyces cyaneofuscatus Streptomyces Streptomycetaceae Kitasatosporales Actinomycetes Actinomycetota None Bacteria
Wardomyces inflatus Wardomyces Microascaceae Microascales Sordariomycetes Ascomycota Fungi Eukaryota
Cytisus scoparius Cytisus Fabaceae Fabales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Ammodendron conollyi Ammodendron Fabaceae Fabales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Nerium oleander Nerium Apocynaceae Gentianales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Malva sylvestris Malva Malvaceae Malvales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Fucus spiralis Fucus Fucaceae Fucales Phaeophyceae None None Eukaryota
Cratoxylum formosum Cratoxylum Hypericaceae Malpighiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Cirsium arvense Cirsium Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Streptomyces eurythermus Streptomyces Streptomycetaceae Kitasatosporales Actinomycetes Actinomycetota None Bacteria

Properties Information

Molecule Weight: 479.61700000000025

TPSA？: 95.86

MolLogP？: 3.492100000000003

Number of H-Donors: 3

Number of H-Acceptors: 5

RingCount: 4

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Chlorocebus sabaeus Vero Activity nan None 10.1038/nchembio.144
Cirsium arvense Cirsium arvense Activity nan None 10.1021/jf8004178
Cricetulus griseus CHO IC50 0.26 ug.mL-1 10.1021/np030524n
Cricetulus griseus CHO Log CR 1.04 None 10.1021/jm00169a014
Electrophorus electricus Acetylcholinesterase Inhibition -2.03 % 10.1016/j.bmc.2012.09.040
Equus caballus Cholinesterase Inhibition 8.94 % 10.1016/j.bmc.2012.09.040
Homo sapiens A498 Activity nan None 10.1016/j.bmc.2008.05.019
Homo sapiens A549 IC50 2130.0 nM 10.1016/j.bmcl.2012.03.058
Homo sapiens Bromodomain adjacent to zinc finger domain protein 2B Potency 100000.0 nM None
Homo sapiens Glucose transporter IC50 4100.0 nM 10.5281/zenodo.7360676
Homo sapiens H4 Activity 30.58 % 10.1073/pnas.0709695104
Homo sapiens H4 Activity 208.73 % 10.1073/pnas.0709695104
Homo sapiens H4 Activity 247.77 % 10.1073/pnas.0709695104
Homo sapiens H4 Activity 286.43 % 10.1073/pnas.0709695104
Homo sapiens HCT-116 IC50 12000.0 nM 10.1021/acs.jnatprod.1c00907
Homo sapiens HCT-15 IC50 1940.0 nM 10.1016/j.bmcl.2012.03.058
Homo sapiens HeLa Activity nan None 10.1016/j.bmcl.2012.03.058
Homo sapiens HeLa IC50 7900.0 nM 10.1016/j.bmcl.2012.03.058
Homo sapiens HeLa Inhibition nan % 10.1016/j.bmcl.2012.03.058
Homo sapiens HepG2 IC50 9500.0 nM 10.1021/acs.jnatprod.1c00907
Homo sapiens Histone deacetylase 6 Inhibition -24.86 % 10.6019/CHEMBL4808148
Homo sapiens Histone deacetylase 6 Inhibition -2.92 % 10.6019/CHEMBL4808148
Homo sapiens HL-60 IC50 30.0 ug.mL-1 10.1021/np000436s
Homo sapiens HL-60 IC50 30.0 ug.mL-1 10.1021/np030086k
Homo sapiens HL-60 IC50 40.0 ug.mL-1 10.1021/np030524n
Homo sapiens Intercellular adhesion molecule (ICAM-1), Integrin alpha-L/beta-2 IC50 0.25 ug.mL-1 10.1021/np000436s
Homo sapiens Intercellular adhesion molecule (ICAM-1), Integrin alpha-L/beta-2 IC50 7.1 ug.mL-1 10.1021/np030524n
Homo sapiens Intercellular adhesion molecule (ICAM-1), Integrin alpha-L/beta-2 MIC 0.39 ug.mL-1 10.1021/np000436s
Homo sapiens Intercellular adhesion molecule (ICAM-1), Integrin alpha-L/beta-2 MIC 2.3 ug.mL-1 10.1021/np030524n
Homo sapiens Leukocyte adhesion glycoprotein LFA-1 alpha IC50 5.5 ug.mL-1 10.1021/np030086k
Homo sapiens Leukocyte adhesion glycoprotein LFA-1 alpha MIC 2.5 ug.mL-1 10.1021/np030086k
Homo sapiens MAP kinase ERK2 Potency 8912.5 nM None
Homo sapiens MCF7 IC50 5200.0 nM 10.1021/acs.jnatprod.1c00907
Homo sapiens MDA-MB-231 Activity 8.2 % 10.1016/j.bmc.2020.115928
Homo sapiens MDA-MB-231 Activity nan None 10.1016/j.bmc.2020.115928
Homo sapiens MDA-MB-231 LED nan None 10.1016/j.bmc.2020.115928
Homo sapiens Monoamine oxidase A Activity nan None 10.1021/jm800656v
Homo sapiens Monoamine oxidase B Activity nan None 10.1021/jm800656v
Homo sapiens Niemann-Pick C1 protein Potency 1122.0 nM None
Homo sapiens Prelamin-A/C Potency 631.0 nM None
Homo sapiens Ras-related protein Rab-9A Potency 6309.6 nM None
Homo sapiens SK-MEL-2 IC50 670.0 nM 10.1016/j.bmcl.2012.03.058
Homo sapiens SK-OV-3 IC50 460.0 nM 10.1016/j.bmcl.2012.03.058
Homo sapiens Solute carrier family 2, facilitated glucose transporter member 2 IC50 10000.0 nM 10.5281/zenodo.7360664
Homo sapiens Solute carrier family 2, facilitated glucose transporter member 3 IC50 3900.0 nM 10.5281/zenodo.7360656
Homo sapiens Solute carrier family 2, facilitated glucose transporter member 4 IC50 3900.0 nM 10.5281/zenodo.7360638
Homo sapiens XF498 IC50 2360.0 nM 10.1016/j.bmcl.2012.03.058
Mus musculus RAW264.7 IC50 5.6 ug.mL-1 10.1021/np030524n
Mus musculus RAW264.7 IC50 6.5 ug.mL-1 10.1021/np030524n
Rattus norvegicus C6 Activity nan None 10.1021/np960144k
Schistosoma mansoni Thioredoxin glutathione reductase Potency 63095.7 nM None
Sonchus arvensis Sonchus arvensis Activity nan None 10.1021/jf8004178
Vibrio parahaemolyticus Vibrio parahaemolyticus MIC 4.0 ug.mL-1 10.1021/acs.jnatprod.1c00907
None ADMET Activity nan None 10.1016/j.bmc.2020.115928
None No relevant target LogD 3.37 None 10.1021/jm00169a014
None Unchecked Activity 43.5 % 10.1016/j.bmc.2020.115928
None Unchecked Activity nan None 10.1021/np960144k
None Unchecked IC50 423.96 nM None
None Unchecked Inhibition 4.2 % 10.1021/np50113a004
None Unchecked Inhibition 45.5 % 10.1021/np50113a004
None Unchecked Inhibition nan % 10.1016/j.bmc.2020.115889
None Unchecked Inhibition nan % 10.1016/j.bmc.2020.115928
None Unchecked Inhibition nan % 10.1021/acs.jmedchem.6b01134
None Unchecked Potency 12589.3 nM None
None Unchecked Ratio 0.04 None 10.1021/np030524n
None Unchecked Ratio 1.1 None 10.1021/np030524n
None Unchecked Ratio 5.5 None 10.1021/np030086k
None Unchecked Ratio 13.0 None 10.1021/np030086k
None Unchecked Ratio 17.2 None 10.1021/np030524n
None Unchecked Ratio 76.9 None 10.1021/np000436s
None Unchecked Ratio IC50 120.0 None 10.1021/np000436s

Metabolism Information