(20R)-1alpha,25-Dihydroxy-24,24-difluoro-2-methylene-19-norvitamin D3

ID: ALA3746759

Chembl Id: CHEMBL3746759

PubChem CID: 127038277

Max Phase: Preclinical

Molecular Formula: C27H42F2O3

Molecular Weight: 452.63

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Canonical SMILES:  C=C1[C@H](O)CC(=C/C=C2\CCC[C@]3(C)[C@@H]([C@H](C)CCC(F)(F)C(C)(C)O)CC[C@@H]23)C[C@H]1O

Standard InChI:  InChI=1S/C27H42F2O3/c1-17(12-14-27(28,29)25(3,4)32)21-10-11-22-20(7-6-13-26(21,22)5)9-8-19-15-23(30)18(2)24(31)16-19/h8-9,17,21-24,30-32H,2,6-7,10-16H2,1,3-5H3/b20-9+/t17-,21-,22+,23-,24-,26-/m1/s1

Standard InChI Key:  RFGCDSADQPSTSR-PXIOBPQKSA-N

Alternative Forms

  1. Parent:

    ALA3746759

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Associated Targets(Human)

HL-60 (67320 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Vdr Vitamin D receptor (379 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Rattus norvegicus (775804 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 452.63Molecular Weight (Monoisotopic): 452.3102AlogP: 5.95#Rotatable Bonds: 6
Polar Surface Area: 60.69Molecular Species: NEUTRALHBA: 3HBD: 3
#RO5 Violations: 1HBA (Lipinski): 3HBD (Lipinski): 3#RO5 Violations (Lipinski): 1
CX Acidic pKa: 12.76CX Basic pKa: CX LogP: 4.61CX LogD: 4.61
Aromatic Rings: Heavy Atoms: 32QED Weighted: 0.44Np Likeness Score: 1.90

References

1. Flores A, Massarelli I, Thoden JB, Plum LA, DeLuca HF..  (2015)  A Methylene Group on C-2 of 24,24-Difluoro-19-nor-1α,25-dihydroxyvitamin D3 Markedly Increases Bone Calcium Mobilization in Vivo.,  58  (24): [PMID:26630444] [10.1021/acs.jmedchem.5b01564]

Source