CALCIPOTRIENE

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Trade Names
Synonyms
Status
Molecule Category Free-form
UNII 143NQ3779B
EPA CompTox DTXSID0046648

Structure

InChI Key LWQQLNNNIPYSNX-UROSTWAQSA-N
Smiles C=C1/C(=C\C=C2/CCC[C@]3(C)[C@@H]([C@H](C)/C=C/[C@@H](O)C4CC4)CC[C@@H]23)C[C@@H](O)C[C@@H]1O
InChI
InChI=1S/C27H40O3/c1-17(6-13-25(29)20-8-9-20)23-11-12-24-19(5-4-14-27(23,24)3)7-10-21-15-22(28)16-26(30)18(21)2/h6-7,10,13,17,20,22-26,28-30H,2,4-5,8-9,11-12,14-16H2,1,3H3/b13-6+,19-7+,21-10-/t17-,22-,23-,24+,25-,26+,27-/m1/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C27H40O3
Molecular Weight 412.61
AlogP 5.09
Hydrogen Bond Acceptor 3.0
Hydrogen Bond Donor 3.0
Number of Rotational Bond 5.0
Polar Surface Area 60.69
Molecular species NEUTRAL
Aromatic Rings 0.0
Heavy Atoms 30.0

Bioactivity

Mechanism of Action Action Reference
Vitamin D receptor agonist AGONIST PubMed Wikipedia
Protein: Vitamin D receptor
Description: Vitamin D3 receptor
Organism : Homo sapiens
P11473 ENSG00000111424
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 1 Nuclear hormone receptor subfamily 1 group I Nuclear hormone receptor subfamily 1 group I member 1
- - 0 - 95
Assay Description Organism Bioactivity Reference
Inhibition of growth of human keratinocytes Homo sapiens 32.0 nM
Binding affinity to VDR receptor None 0.31 nM
Antifibrotic activity against TGFbeta1 stimulated rat LTC-14 cells assessed as inhibition of collagen 1 synthesis at 0.5 uM after 24 hrs by ELISA relative to calcipotriol Rattus norvegicus 100.0 %
Agonist activity at VDR in human LX2 cells assessed as inhibition of TGFbeta1-induced collagen-1 synthesis at 100 nM after 24 hrs by ELISA relative to calcipotriol Homo sapiens 95.0 %
Antibacterial activity against Staphylococcus aureus MRSA ATCC 43300 (CO-ADD:GP_020); MIC in CAMBH media, using NBS plates, by OD(600) Staphylococcus aureus subsp. aureus 9.78 %
Antibacterial activity against Escherichia coli ATCC 25922 (CO-ADD:GN_001); MIC in CAMBH media using NBS plates, by OD(600) Escherichia coli 4.8 %
Antibacterial activity against Klebsiella pneumoniae MDR ATCC 70063 (CO-ADD:GN_003); MIC in CAMBH media using NBS plates, by OD(600) Klebsiella pneumoniae 16.21 %
Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 (CO-ADD:GN_042); MIC in CAMBH media using NBS plates, by OD(600) Pseudomonas aeruginosa 13.54 %
Antibacterial activity against Acinetobacter baumannii ATCC 19606 (CO-ADD:GN_034); MIC in CAMBH media using NBS plates, by OD600 Acinetobacter baumannii 8.96 %
Antifungal activity against Candida albicans ATCC 90028 (CO-ADD:FG_001); MIC in YNB media using NBS plates, by OD630 Candida albicans 0.06 %
Antifungal activity against Cryptococcus neoformans H99 ATCC 208821 (CO-ADD:FG_002); MIC in YNB media using NBS plates, by Resazurin OD(600-570) Cryptococcus neoformans 0.21 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging Homo sapiens 10.28 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 5.208 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 0.12 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 0.12 %

Related Entries

Cross References

Resources Reference
ChEBI 50749
ChEMBL CHEMBL1200666
DrugBank DB02300
DrugCentral 465
FDA SRS 143NQ3779B
Human Metabolome Database HMDB0015567
Guide to Pharmacology 2778
KEGG D01125
PDB MC9
PubChem 5288783
SureChEMBL SCHEMBL2853
ZINC ZINC000003921872
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