ANDROGRAPHOLIDE

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Synonyms
Status
Molecule Category UNKNOWN
UNII 410105JHGR
EPA CompTox DTXSID3045980

Structure

InChI Key BOJKULTULYSRAS-OTESTREVSA-N
Smiles C=C1CC[C@@H]2[C@](C)(CO)[C@H](O)CC[C@@]2(C)[C@@H]1C/C=C1/C(=O)OC[C@H]1O
InChI
InChI=1S/C20H30O5/c1-12-4-7-16-19(2,9-8-17(23)20(16,3)11-21)14(12)6-5-13-15(22)10-25-18(13)24/h5,14-17,21-23H,1,4,6-11H2,2-3H3/b13-5+/t14-,15-,16+,17-,19+,20+/m1/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C20H30O5
Molecular Weight 350.46
AlogP 1.96
Hydrogen Bond Acceptor 5.0
Hydrogen Bond Donor 3.0
Number of Rotational Bond 3.0
Polar Surface Area 86.99
Molecular species NEUTRAL
Aromatic Rings 0.0
Heavy Atoms 25.0
Assay Description Organism Bioactivity Reference
Inhibition of TNFalpha secretion in mouse J774A.1 cells at 20 uM after 24 hrs by ELISA Mus musculus 63.94 %
Inhibition of LPS-induced TNFalpha secretion in mouse J774A.1 cells at 20 uM after 24 hrs by ELISA Mus musculus 62.54 %
Inhibition of IL6 secretion in mouse J774A.1 cells at 20 uM after 24 hrs by ELISA Mus musculus 49.21 %
Inhibition of LPS-induced IL6 secretion in mouse J774A.1 cells at 20 uM after 24 hrs by ELISA Mus musculus 56.0 %
Antiviral activity against HIV1 in human TZM-bl cells assessed as viral infectivity by luciferase assay Human immunodeficiency virus 1 590.0 nM Antiviral activity against HIV1 in human TZM-bl cells assessed as viral infectivity by luciferase assay Human immunodeficiency virus 1 588.84 nM
Inhibition of TNFalpha-stimulated HUVEC adhesion to BCECF-AM-labeled human HL60 cells at 20 uM pretreated for 16 hrs before TNFalpha challenge measured after 6 hrs by fluorescence assay Homo sapiens 73.0 %
Inhibition of electric eel AChE at 2 mg/ml by Ellman's method Electrophorus electricus 25.09 %
Inhibition of horse BChE at 2 mg/ml by Ellman's method Equus caballus 8.56 %
Antiinvasive activity against human SGC7901 cells at 10 uM after 24 hrs by matrigel invasion assay relative to control Homo sapiens 17.7 %
Antimigratory activity against human A549 cells at 5 uM after 12 to 48 hrs by wound-healing assay relative to control Homo sapiens 28.6 %
Antimigratory activity against human SGC7901 cells at 10 uM after 12 to 48 hrs by wound-healing assay relative to control Homo sapiens 20.8 %
Antimigratory activity against human 5637 cells at 5 uM after 12 to 48 hrs by wound-healing assay relative to control Homo sapiens 34.5 %
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 80.16 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 84.72 %
Cytotoxicity against human HeLa cells by MTT assay Homo sapiens 10.42 ug.mL-1
Cytotoxicity against rat IEC-6 cells by MTT assay Rattus norvegicus 8.26 ug.mL-1
Cytotoxicity against human ACHN cells by MTT assay Homo sapiens 3.03 ug.mL-1
Cytotoxicity against mouse B16 cells by MTT assay Mus musculus 7.54 ug.mL-1
Cytotoxicity against human A549 cells by MTT assay Homo sapiens 9.71 ug.mL-1
Inhibition of cell proliferation in HUVEC at 10 uM after 48 hrs by MTT assay relative to control Homo sapiens 10.4 %
Inhibition of cell proliferation in HUVEC at 40 uM after 48 hrs by MTT assay relative to control Homo sapiens 38.7 %
Inhibition of cell proliferation in HUVEC at 80 uM after 48 hrs by MTT assay relative to control Homo sapiens 26.4 %
Antiinflammatory activity in mouse BV2 cells assessed as reduction in LPS-induced NO production at 20 uM incubated for 24 hrs by Griess method Mus musculus 76.7 %
Antiinflammatory activity in 2 hrs NAC-pretreated mouse RAW264.7 cells assessed as inhibition of LPS-induced TNFalpha release at 10 uM preincubated for 1 hr followed by LPS stimulation and measured after 4 hrs by ELISA relative to control Mus musculus 17.0 %
Antiinflammatory activity in 4 hrs NAC-pretreated mouse RAW264.7 cells assessed as inhibition of LPS-induced TNFalpha release at 10 uM preincubated for 1 hr followed by LPS stimulation and measured after 4 hrs by ELISA relative to control Mus musculus 30.0 %
Antiinflammatory activity in 24 hrs NAC-pretreated mouse RAW264.7 cells assessed as inhibition of LPS-induced TNFalpha release at 10 uM preincubated for 1 hr followed by LPS stimulation and measured after 4 hrs by ELISA relative to control Mus musculus 62.0 %
Inhibition of GST-tagged recombinant RANKL/M-CSF-induced osteoclastogenesis in C57BL/6 mouse bone marrow derived macrophages assessed as TRAcP enzymatic activity incubated for 5 days with subsequent replenishment of media for 2 days and measured by leucocyte acid phosphatase staining method Mus musculus 550.0 nM

Cross References

Resources Reference
ChEBI 65408
ChEMBL CHEMBL186141
DrugBank DB05767
FDA SRS 410105JHGR
Guide to Pharmacology 9675
PubChem 5318517
SureChEMBL SCHEMBL12056309
ZINC ZINC000003881797
CONTENTS