MAXACALCITOL

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Search structure


Synonyms	1alpha,25-dihydroxy-22-oxavitamin d3 22-oxacalcitriol Maxacalcitol OCT Oxarol Prezios SCH 209579 SCH-209579
Status
Molecule Category	UNKNOWN
UNII	N2UJM5NBF6
EPA CompTox	DTXSID4048648


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

Structure


InChI Key	DTXXSJZBSTYZKE-ZDQKKZTESA-N
Smiles	C=C1/C(=C\C=C2/CCC[C@]3(C)[C@@H]([C@H](C)OCCC(C)(C)O)CC[C@@H]23)C[C@@H](O)C[C@@H]1O
InChI	InChI=1S/C26H42O4/c1-17-20(15-21(27)16-24(17)28)9-8-19-7-6-12-26(5)22(10-11-23(19)26)18(2)30-14-13-25(3,4)29/h8-9,18,21-24,27-29H,1,6-7,10-16H2,2-5H3/b19-8+,20-9-/t18-,21+,22+,23-,24-,26+/m0/s1

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C26H42O4
Molecular Weight	418.62
AlogP	4.69
Hydrogen Bond Acceptor	4.0
Hydrogen Bond Donor	3.0
Number of Rotational Bond	6.0
Polar Surface Area	69.92
Molecular species	NEUTRAL
Aromatic Rings	0.0
Heavy Atoms	30.0

Assay Description	Organism	Bioactivity	Reference
Antiproliferative activity against human keratinocyte assessed as inhibition of [3H]TdR uptake	Homo sapiens	22.6 nM
Transactivation of VDR in human HaCaT cells after 24 hrs by luciferase reporter gene assay	Homo sapiens	37.9 nM
Transactivation of VDR in human Caco2 cells after 24 hrs by luciferase reporter gene assay	Homo sapiens	40.8 nM
Activation of VDR in human HaCaT cells expressing lentiviral VDRE-luciferase vector assessed as VDRE-mediated transcriptional activity measured after 24 hrs by luciferase transcriptional reporter assay	Homo sapiens	159.7 nM
Activation of VDR in human Caco2 cells expressing lentiviral VDRE-luciferase vector assessed as VDRE-mediated transcriptional activity measured after 24 hrs by luciferase transcriptional reporter assay	Homo sapiens	144.5 nM
Activation of VDR in human Jurkat cells expressing lentiviral VDRE-luciferase vector assessed as VDRE-mediated transcriptional activity measured after 24 hrs by luciferase transcriptional reporter assay	Homo sapiens	0.855 nM

Related Entries

Cross References

Resources	Reference
ChEBI	31801
ChEMBL	CHEMBL333950
DrugCentral	1638
FDA SRS	N2UJM5NBF6
Guide to Pharmacology	2784
PDB	MCZ
PubChem	6398761
SureChEMBL	SCHEMBL17975926
ZINC	ZINC000004474617

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).