RETINOL

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Search structure


Synonyms	Aquasol a Arovit NSC-122759 Nepalm Oleovitamin a Retinol Retinol (vit a) Retinol acetate Retinol palmitate Ro-a-vit Vitamin A Vitamin A 1 Vitamin A Solubilized Vitamin a Vitamin a oil
Status
Molecule Category	UNKNOWN
ATC	D10AD02 R01AX02 S01XA02
UNII	G2SH0XKK91
EPA CompTox	DTXSID3023556


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

Structure


InChI Key	FPIPGXGPPPQFEQ-OVSJKPMPSA-N
Smiles	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/CO)C(C)(C)CCC1
InChI	InChI=1S/C20H30O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,21H,7,10,14-15H2,1-5H3/b9-6+,12-11+,16-8+,17-13+

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C20H30O
Molecular Weight	286.46
AlogP	5.51
Hydrogen Bond Acceptor	1.0
Hydrogen Bond Donor	1.0
Number of Rotational Bond	5.0
Polar Surface Area	20.23
Molecular species	NEUTRAL
Aromatic Rings	0.0
Heavy Atoms	21.0

Assay Description	Organism	Bioactivity	Reference
Dissociation constant with retinol binding protein was determined	None	70.0 nM
Decrease in collagenase expression in Coll-CAT gene transfected human HaCaT cells co-transfected with c-Jun relative to control	Homo sapiens	7.3 %
Decrease in collagenase expression in Coll-CAT gene transfected human HaCaT cells co-transfected with c-Jun and retinoic acid receptor relative to control	Homo sapiens	33.0 %
Binding affinity to bovine beta-lactoglobulins by fluorescence spectroscopy	Bos taurus	36.0 nM
Binding affinity to reindeer beta-lactoglobulin by fluorescence spectroscopy	Rangifer tarandus	200.0 nM
Binding affinity to His-tagged recombinant human sRBP expressed in Escherichia coli BL21(DE3) assessed as apparent dissociation constant after 5 mins by fluorescence spectrophotometric analysis	Homo sapiens	182.0 nM
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	18.99 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	31.96 %
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	2.81 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	8.51 %
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	-0.05 %		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	-0.05 %
Inhibition of alpha-synuclein fibril formation (unknown origin) incubated for 24 hrs to 7 days by thioflavin S based fluorescence assay	Homo sapiens	190.0 nM
Inhibition of amyloid beta (1 to 40) (unknown origin) incubated for 24 hrs to 7 days by thioflavin S based fluorescence assay	Homo sapiens	180.0 nM

Related Entries

Cross References

Resources	Reference
ChEBI	17336
ChEMBL	CHEMBL986
DrugBank	DB00162
DrugCentral	2831
FDA SRS	G2SH0XKK91
Guide to Pharmacology	4053
KEGG	C17276
PDB	RTL
PharmGKB	PA451884
PubChem	445354
SureChEMBL	SCHEMBL3112
ZINC	ZINC000003831417

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).