CHOLECALCIFEROL

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Search structure


Synonyms	7-dehydrocholesterol, activated AK R215 COMPONENT COLECALCIFEROL AK-R215 COMPONENT COLECALCIFEROL Accrete d3 Aciferol d3 Adcal-d3 Aviticol Bio-vitamin d3 Biolife vitamin d3 Cacit d3 Calceos Calci-d Calcichew d3 Calcichew d3 fte Calcichew d3 once daily Caldrink d3 Calfovit d3 Cholecalciferol Colecal d3 Colecalciferol Colecalciferolum Colekal-d3 Colevit d3 Cubicole d3 D-max D-tracetten D-vit3 D3 lemon melts D3-50 Dekristol Delsterol Delta-d Deparal Desunin Dihydrocholesterol Dlux 400 E-d3 Ebivit Evacal d3 Fultium daily d3 Fultium-d3 Hux d3 Invita d3 Iso d3 Kora liquid NSC-375571 Natecal d3 Nature's remedy vitamin d3 Neo-d Nphd3 Osteocaps d3 Plenachol Pro d3 Pro d3 folic Pro d3 forte Provitina Ricketon Royalvit d3 Stexerol-d3 Stivit-d3 Sunvit-d3 1,000 Sunvit-d3 10,000 Sunvit-d3 2,000 Sunvit-d3 20,000 Sunvit-d3 3,000 Sunvit-d3 400 Sunvit-d3 5,000 Sunvit-d3 50,000 Sunvit-d3 800 Synervit-d3 Theical d-3 Thorens Vigantol Vigantoletten Vigantoletten 500 Vit d3 streuli Vita-d3 Vitamin D 3 Vitamin d Vitamin d (cholecalciferol) Vitamin d assay system suitability Vitamin d-3 Vitamin d3 Vitamin d3 (as cholecalciferol) Zymad
Status
Molecule Category	Free-form
UNII	1C6V77QF41
EPA CompTox	DTXSID6026294


Active Pharmaceutical Ingredients Bioactive chemicals	Exact Similarity SubStructure	Threshold (%) >= 70

Structure


InChI Key	QYSXJUFSXHHAJI-YRZJJWOYSA-N
Smiles	C=C1CC[C@H](O)C/C1=C/C=C1\CCC[C@]2(C)[C@@H]([C@H](C)CCCC(C)C)CC[C@@H]12
InChI	InChI=1S/C27H44O/c1-19(2)8-6-9-21(4)25-15-16-26-22(10-7-17-27(25,26)5)12-13-23-18-24(28)14-11-20(23)3/h12-13,19,21,24-26,28H,3,6-11,14-18H2,1-2,4-5H3/b22-12+,23-13-/t21-,24+,25-,26+,27-/m1/s1

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C27H44O
Molecular Weight	384.65
AlogP	7.62
Hydrogen Bond Acceptor	1.0
Hydrogen Bond Donor	1.0
Number of Rotational Bond	6.0
Polar Surface Area	20.23
Molecular species	NEUTRAL
Aromatic Rings	0.0
Heavy Atoms	28.0

Bioactivity

Mechanism of Action	Action	Reference
Vitamin D receptor agonist	AGONIST	PubMed PubMed


Protein: Vitamin D receptor Description: Vitamin D3 receptor Organism : Homo sapiens P11473 ENSG00000111424

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Ion channel Ligand-gated ion channel Glycine receptor	400	-	-	-	-
Other cytosolic protein	-	11000	-	-	-
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	-	-	-	8336
Unclassified protein	-	22000-31000	-	-	74-80

Assay Description	Organism	Bioactivity	Reference
Inhibition of Hedgehog signaling pathway in oxysterols-induced mouse C3H10T1/2 cells assessed as down-regulation of endogenous Gli1 mRNA level at 5 uM by RT-PCR analysis relative to oxysterol	Mus musculus	31.7 %
Estrogen antagonistic activity in immature Rattus norvegicus Sprague-Dawley (rat) assessed as inhibition of ethynylestradiol-induced increase in uterine weight at 10 mg/kg, po qd for 3 days	Rattus norvegicus	39.0 %
Inhibition of Hedgehog signaling in mouse M210B4 cells assessed as downregulation of Gli1 mRNA expression at 10 uM after 24 hrs by RT-PCR analysis relative to 20(S)-hydroxycholesterol and 22(S)-hydroxycholesterol	Mus musculus	53.0 %
Inhibition of Hedgehog signaling in mouse C3H10T1/2 cells assessed as downregulation of Gli1 mRNA expression at 5 uM after 24 hrs by RT-PCR analysis relative to 20(S)-hydroxycholesterol and 22(S)-hydroxycholesterol	Mus musculus	35.7 %
Agonist activity at human VDR expressed in HEK293 cells by luciferase reporter gene assay	Homo sapiens	0.21 nM
Inhibition of hedgehog signaling in mouse C3H10T1/2 cells assessed as reduction in Gli1 mRNA level at 5 uM after 24 hrs by quantitative PCR analysis relative to control	Mus musculus	35.7 %
Inhibition of hedgehog signaling in mouse ASZ cells assessed as reduction in Gli1 mRNA level after 24 hrs by quantitative PCR analysis	Mus musculus	2.1 %
Potentiation of human GlyR-alpha1 expressed in Xenopus laevis oocytes assessed as induction of glycine-activated currents after 1 to 4 days by two-electrode voltage clamp assay	Homo sapiens	400.0 nM
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	-32.61 %
Activation of VDR in mouse ASZ001 cells assessed as change in Cyp24A1 mRNA expression after 48 hrs by q-PCR analysis	Mus musculus	900.0 nM
Inhibition of Escherichia coli GroEL expressed in Escherichia coliDH5alpha/Escherichia coli GroES expressed in Escherichia coli BL21 (DE3) assessed as reduction in GroEL/GroES-mediated denatured soluble pig heart MDH refolding by measuring MDH enzyme activity using sodium mesoxalate as substrate after 20 to 40 mins by malachite green dye based spectrometric analysis relative to untreated control	Escherichia coli	80.0 %
Inhibition of Escherichia coli GroEL expressed in Escherichia coli DH5alpha/Escherichia coli GroES expressed in Escherichia coli BL21 (DE3) assessed as reduction in GroEL/GroES-mediated denatured rhodanese refolding by measuring rhodanese enzyme activity after 45 mins by Fe(SCN)3 dye based spectrometric analysis relative to untreated control	Escherichia coli	74.0 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	14.36 %
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	-0.14 %		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	-0.14 %

Related Entries

Cross References

Resources	Reference
ChEBI	28940
ChEMBL	CHEMBL1042
DrugBank	DB00169
DrugCentral	2840
FDA SRS	1C6V77QF41
Human Metabolome Database	HMDB0000876
KEGG	C05443
PubChem	5283710
SureChEMBL	SCHEMBL3126
ZINC	ZINC000004474460

CONTENTS

PREMIER has received funding from the Innovative Medicines Initiative 2 Joint Undertaking (JU) under grant agreement No 875508. The JU receives support from the EU’s Horizon 2020 research and innovation programme and the European Federation of Pharmaceutical Industries and Associations (EFPIA). The views reflect only the authors’ perspective and the JU is not responsible for any use that may be made of the information this manuscript contains.

Elements of the website have been developed under projects PREMIER and the Biocenter Finland Drug Discovery and Chemical Biology network. CSC-IT is thanked for providing computational resources. Content of the website is provided without guarantee for correctness. Data has been collected and integrated from multiple public sources, for the largest: FDA, HUGO Gene Nomenclature Committee, ChEMBL, IUPHAR/BPS guide to pharmacology, Reactome, UniProt, and Ensembl. Credit is given to Ensembl for collecting species images (provided under public domain licences such as Wikimedia and NHGRI).