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Castanospermine

AlkaPlorer ID: AK009525

Synonym: None

IUPAC Name: (1S,6S,7R,8R,8aR)-1,2,3,5,6,7,8,8a-octahydroindolizine-1,6,7,8-tetrol

Structure

SMILES: O[C@H]1[C@H](O)[C@@H](O)CN2CC[C@H](O)[C@H]12

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InChI: InChI=1S/C8H15NO4/c10-4-1-2-9-3-5(11)7(12)8(13)6(4)9/h4-8,10-13H,1-3H2/t4-,5-,6+,7+,8+/m0/s1

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InChIKey: JDVVGAQPNNXQDW-TVNFTVLESA-N

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Source

Species Genus Family Order Class Phylum Kingdom Domain
Gaillardia aestivalis Gaillardia Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Santolina pectinata Santolina Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Castanospermum australe Castanospermum Fabaceae Fabales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Helichrysum drakensbergense Helichrysum Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Cassine glauca Cassine Celastraceae Celastrales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Piper divaricatum Piper Piperaceae Piperales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Erythrina speciosa Erythrina Fabaceae Fabales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Prunus prostrata Prunus Rosaceae Rosales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Prosopis africana Prosopis Fabaceae Fabales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Paramignya monophylla Paramignya Rutaceae Sapindales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Richteria pyrethroides Richteria Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
None Aglaonema Araceae Alismatales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Xanthocercis zambesiaca Xanthocercis Fabaceae Fabales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Calystegia soldanella Calystegia Convolvulaceae Solanales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Commiphora sphaerocarpa Commiphora Burseraceae Sapindales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Plakortis angulospiculatus Plakortis Plakinidae Homosclerophorida Homoscleromorpha Porifera Metazoa Eukaryota
Morus bombycis Morus Moraceae Rosales Magnoliopsida Streptophyta Viridiplantae Eukaryota

Properties Information

Molecule Weight: 189.211

TPSA？: 84.16

MolLogP？: -2.482099999999999

Number of H-Donors: 4

Number of H-Acceptors: 5

RingCount: 2

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Dengue virus Dengue virus IC50 1000.0 nM 10.1021/jm900652e
dengue virus type 2 dengue virus type 2 EC50 28000.0 nM 10.1021/acs.jmedchem.5b01653
Electrophorus electricus Acetylcholinesterase Inhibition -10.55 % 10.1016/j.bmc.2012.09.040
Equus caballus Cholinesterase Inhibition 0.79 % 10.1016/j.bmc.2012.09.040
Homo sapiens A498 GI50 100000.0 nM None
Homo sapiens A549 GI50 100000.0 nM None
Homo sapiens Beta-glucocerebrosidase Potency 3548.1 nM None
Homo sapiens Beta-glucocerebrosidase Potency 14125.4 nM None
Homo sapiens Beta-glucosidase IC50 19000.0 nM 10.1021/jm301557k
Homo sapiens CAKI-1 GI50 100000.0 nM None
Homo sapiens CCRF-CEM GI50 100000.0 nM None
Homo sapiens Chromobox protein homolog 1 Potency 89125.1 nM None
Homo sapiens COLO 205 GI50 100000.0 nM None
Homo sapiens DLD-1 GI50 100000.0 nM None
Homo sapiens DMS-114 GI50 100000.0 nM None
Homo sapiens DMS-273 GI50 100000.0 nM None
Homo sapiens DNA polymerase kappa Potency 39810.7 nM None
Homo sapiens EKVX GI50 100000.0 nM None
Homo sapiens Geminin Potency 23109.3 nM None
Homo sapiens H4 Activity 36.45 % 10.1073/pnas.0709695104
Homo sapiens H4 Activity 37.35 % 10.1073/pnas.0709695104
Homo sapiens H4 Activity 40.02 % 10.1073/pnas.0709695104
Homo sapiens H4 Activity 83.53 % 10.1073/pnas.0709695104
Homo sapiens H4 Activity 84.26 % 10.1073/pnas.0709695104
Homo sapiens H4 Activity 85.6 % 10.1073/pnas.0709695104
Homo sapiens H4 Activity 88.75 % 10.1073/pnas.0709695104
Homo sapiens H4 Activity 156.81 % 10.1073/pnas.0709695104
Homo sapiens H4 Activity 157.35 % 10.1073/pnas.0709695104
Homo sapiens H4 Activity 171.2 % 10.1073/pnas.0709695104
Homo sapiens H4 Activity 174.29 % 10.1073/pnas.0709695104
Homo sapiens HCC 2998 GI50 95499.26 nM None
Homo sapiens HCT-116 GI50 100000.0 nM None
Homo sapiens HCT-15 GI50 100000.0 nM None
Homo sapiens Histone deacetylase 6 Inhibition 1.62 % 10.6019/CHEMBL4808148
Homo sapiens Histone deacetylase 6 Inhibition 14.78 % 10.6019/CHEMBL4808148
Homo sapiens HL-60 GI50 39810.72 nM None
Homo sapiens HOP-18 GI50 100000.0 nM None
Homo sapiens HOP-62 GI50 100000.0 nM None
Homo sapiens HOP-92 GI50 100000.0 nM None
Homo sapiens HT-29 GI50 100000.0 nM None
Homo sapiens IGROV-1 GI50 100000.0 nM None
Homo sapiens JM1 Cytotoxicity 0.0 % 10.1016/S0960-894X(01)80958-6
Homo sapiens JM1 Cytotoxicity 4.0 % 10.1016/S0960-894X(01)80958-6
Homo sapiens JM1 IC50 7300.0 nM 10.1016/S0960-894X(01)80958-6
Homo sapiens JM1 IC50 8800.0 nM 10.1016/S0960-894X(01)80958-6
Homo sapiens JM1 IC90 24500.0 nM 10.1016/S0960-894X(01)80958-6
Homo sapiens JM1 IC90 28200.0 nM 10.1016/S0960-894X(01)80958-6
Homo sapiens K562 GI50 100000.0 nM None
Homo sapiens KM12 GI50 100000.0 nM None
Homo sapiens KM-20L2 GI50 100000.0 nM None
Homo sapiens LOX IMVI GI50 100000.0 nM None
Homo sapiens Lysosomal alpha-glucosidase Potency 562.3 nM None
Homo sapiens Lysosomal alpha-glucosidase Potency 1258.9 nM None
Homo sapiens Lysosomal alpha-glucosidase Potency 1980.0 nM None
Homo sapiens Lysosomal alpha-glucosidase Potency 3548.1 nM None
Homo sapiens Lysosomal alpha-glucosidase Potency 5011.9 nM None
Homo sapiens Lysosomal alpha-glucosidase Potency 11220.2 nM None
Homo sapiens M19-MEL GI50 32809.53 nM None
Homo sapiens Malme-3M GI50 90573.26 nM None
Homo sapiens MCF7 GI50 100000.0 nM None
Homo sapiens MOLT-4 GI50 100000.0 nM None
Homo sapiens NCI/ADR-RES GI50 100000.0 nM None
Homo sapiens NCI-H226 GI50 100000.0 nM None
Homo sapiens NCI-H23 GI50 100000.0 nM None
Homo sapiens NCI-H322M GI50 100000.0 nM None
Homo sapiens NCI-H460 GI50 100000.0 nM None
Homo sapiens NCI-H522 GI50 100000.0 nM None
Homo sapiens OVCAR-3 GI50 100000.0 nM None
Homo sapiens OVCAR-4 GI50 86696.19 nM None
Homo sapiens OVCAR-5 GI50 100000.0 nM None
Homo sapiens OVCAR-8 GI50 100000.0 nM None
Homo sapiens Parathyroid hormone receptor Potency 44668.4 nM None
Homo sapiens Peptide-N(4)-(N-acetyl-beta-glucosaminyl)asparagine amidase Delta Tm 2.84 degrees C 10.1016/j.bmc.2016.08.019
Homo sapiens Peptide-N(4)-(N-acetyl-beta-glucosaminyl)asparagine amidase Kd 94300.0 nM 10.1016/j.bmc.2016.08.019
Homo sapiens RPMI-8226 GI50 100000.0 nM None
Homo sapiens RXF 393 GI50 100000.0 nM None
Homo sapiens SF-268 GI50 100000.0 nM None
Homo sapiens SF-295 GI50 100000.0 nM None
Homo sapiens SF-539 GI50 100000.0 nM None
Homo sapiens SK-MEL-2 GI50 99311.6 nM None
Homo sapiens SK-MEL-28 GI50 100000.0 nM None
Homo sapiens SK-MEL-5 GI50 100000.0 nM None
Homo sapiens SK-OV-3 GI50 100000.0 nM None
Homo sapiens SN12C GI50 100000.0 nM None
Homo sapiens SN12K1 GI50 100000.0 nM None
Homo sapiens SNB-19 GI50 100000.0 nM None
Homo sapiens SNB-75 GI50 100000.0 nM None
Homo sapiens SNB-78 GI50 100000.0 nM None
Homo sapiens SW-620 GI50 100000.0 nM None
Homo sapiens TAR DNA-binding protein 43 Potency 354.8 nM None
Homo sapiens U-251 GI50 100000.0 nM None
Homo sapiens UACC-257 GI50 100000.0 nM None
Homo sapiens UACC-62 GI50 100000.0 nM None
Homo sapiens UO-31 GI50 94406.09 nM None
Homo sapiens XF498 GI50 100000.0 nM None
Mus musculus Mus musculus Activity nan None 10.1021/np970277l
Mus musculus P388 GI50 100000.0 nM None
Mus musculus P388/ADR GI50 90991.33 nM None
Plasmodium falciparum Plasmodium falciparum Potency 9285.0 nM None
Severe acute respiratory syndrome coronavirus 2 Replicase polyprotein 1ab Inhibition 9.653 % 10.6019/CHEMBL4495564
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition -8.5 % 10.21203/rs.3.rs-23951/v1
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition 0.09 % 10.6019/CHEMBL4495565
None Unchecked Activity nan None 10.1021/np50069a011
None Unchecked IC50 1100.0 nM 10.1016/j.bmcl.2009.05.125
None Unchecked IC50 1300.0 nM 10.1016/j.bmcl.2009.05.125
None Unchecked IC50 8000.0 nM 10.1016/j.bmc.2013.03.004
None Unchecked Inhibition 50.0 % 10.1021/np50069a011
None Unchecked Inhibition 96.0 % 10.1016/j.bmc.2011.07.019
None Unchecked Inhibition 100.0 % 10.1016/j.bmc.2011.07.019
None Unchecked Ki 15.0 nM 10.1021/acs.jmedchem.5b00951
None Unchecked Ki 100.0 nM 10.1016/j.bmc.2011.07.019
None Unchecked Ki 1500.0 nM 10.1021/acs.jmedchem.5b00951
None Unchecked Ki 23000000.0 nM 10.1038/nchembio.81

Metabolism Information