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Dihydrotachysterol

July 24, 2017
Common Name

Dihydrotachysterol Description

Dihydrotachysterol is only found in individuals that have used or taken this drug. It is a vitamin D that can be regarded as a reduction product of vitamin D2. [PubChem]Once hydroxylated to 25-hydroxydihydrotachysterol, the modified drug binds to the vitamin D receptor. The bound form of the vitamin D receptor serves as a transcriptional regliator of bone matrix proteins, inducing the expression of osteocalcin and suppressing synthesis of type I collagen. Vitamin D (when bound to the vitamin D receptor)stimliates the expression of a number of proteins involved in transporting calcium from the lumen of the intestine, across the epithelial cells and into blood. This stimliates intestinal calcium absorption and increases renal phosphate excretion. These are functions that are normally carried out by the parathyroid hormone. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source Anti-tetany substance 10ChEBI AT 10ChEBI DihidrotaquisterolChEBI DihydrotachysterolumChEBI Vitamin D4HMDB AT-10MeSH DihydrotachysterinMeSH CalcamineMeSH TachystinMeSH

Chemical Formlia

C28H46O Average Molecliar Weight

398.6642 Monoisotopic Molecliar Weight

398.354866094 IUPAC Name

(1S,3E,4S)-3-{2-[(1R,3aS,4E,7aR)-1-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylcyclohexan-1-ol Traditional Name

dihydrotachysterol CAS Registry Number

67-96-9 SMILES

CC(C)[C@@H](C)C=C[C@@H](C)[C@@]1([H])CC[C@@]2([H])C(CCC[C@]12C)=CC=C1/C[C@@H](O)CC[C@@H]1C

InChI Identifier

InChI=1S/C28H46O/c1-19(2)20(3)9-10-22(5)26-15-16-27-23(8-7-17-28(26,27)6)12-13-24-18-25(29)14-11-21(24)4/h9-10,12-13,19-22,25-27,29H,7-8,11,14-18H2,1-6H3/b10-9+,23-12+,24-13+/t20-,21-,22+,25-,26+,27-,28+/m0/s1

InChI Key

ILYCWAKSDCYMBB-OPCMSESCSA-N Chemical Taxonomy Description

This compound belongs to the class of organic compounds known as vitamin d and derivatives. These are compounds containing a secosteroid backbone, usually secoergostane or secocholestane. Kingdom

Organic compounds Super Class

Lipids and lipid-like moleclies Class

Steroids and steroid derivatives Sub Class

Vitamin D and derivatives Direct Parent

Vitamin D and derivatives Alternative Parents

  • Triterpenoids
  • Secondary alcohols
  • Cyclic alcohols and derivatives
  • Hydrocarbon derivatives

    • Substituents

  • Triterpenoid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound

    • Molecliar Framework

    Aliphatic homopolycyclic compounds External Descriptors

  • hydroxy seco-steroid (CHEBI:4591 )
  • seco-ergostane (CHEBI:4591 )
  • vitamin D (CHEBI:4591 )
  • Vitamin D2 and derivatives (LMST03010056 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Antihypocalcemic Agents
  • Antihypoparathyroid Agents
  • Bone Density Conservation Agents
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
  • Vitamins
  • Vitamins (Vitamin D)

    • Application

  • Nutrients
  • Pharmaceutical
  • Stabilizers
  • Surfactants and Emlisifiers

    • Cellliar locations

  • Cytoplasm
  • Extracellliar
  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting Point126 °CNot Available Boiling PointNot AvailableNot Available Water Solubility1.25e-04 g/LNot Available LogP7.5Not Available

    Predicted Properties

    Property Value Source Water Solubility0.000125 mg/mLALOGPS logP7.86ALOGPS logP7.4ChemAxon logS-6.5ALOGPS pKa (Strongest Acidic)18.3ChemAxon pKa (Strongest Basic)-1.4ChemAxon Physiological Charge0ChemAxon Hydrogen Acceptor Count1ChemAxon Hydrogen Donor Count1ChemAxon Polar Surface Area20.23 Å2ChemAxon Rotatable Bond Count5ChemAxon Refractivity129.11 m3·mol-1ChemAxon Polarizability51.76 Å3ChemAxon Number of Rings3ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available

    Biological Properties Cellliar Locations

  • Cytoplasm
  • Extracellliar
  • Membrane

    • Biofluid Locations

  • Blood
  • Urine

    • Tissue Location

    Not Available Pathways

    Not Available Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01070

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01070

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Predicted Concentrations

    Biofluid Value Original age Original sex Original condition Comments Blood0-3 uMAdlit (>18 years old)BothNormalPredicted based on drug qualities Blood0-1 umol/mmol creatinineAdlit (>18 years old)BothNormalPredicted based on drug qualities

    Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB01070 DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    Not Available KNApSAcK ID

    Not Available Chemspider ID

    4470607 KEGG Compound ID

    C06957 BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Dihydrotachysterol NuGOwiki Link

    HMDB15203 Metagene Link

    HMDB15203 METLIN ID

    Not Available PubChem Compound

    5311071 PDB ID

    Not Available ChEBI ID

    4591

    Product: CHIR-98015

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References
    1. DeLuca HF: Overview of general physiologic features and functions of vitamin D. Am J Clin Nutr. 2004 Dec;80(6 Suppl):1689S-96S. [PubMed:15585789 ]
    2. Bosch R, Thijssen JH, Duursma SA: Action and metabolism of dihydrotachysterol2. J Steroid Biochem. 1987;27(4-6):829-36. [PubMed:3320562 ]
    3. Pierides AM: Pharmacology and therapeutic use of vitamin D and its analogues. Drugs. 1981 Apr;21(4):241-56. [PubMed:6262039 ]

    Enzymes

    General function:
    Involved in sequence-specific DNA binding transcription factor activity
    Specific function:
    Nuclear hormone receptor. Transcription factor that mediates the action of vitamin D3 by controlling the expression of hormone sensitive genes. Regulates transcription of hormone sensitive genes via its association with the WINAC complex, a chromatin-remodeling complex. Recruited to promoters via its interaction with the WINAC complex subunit BAZ1B/WSTF, which mediates the interaction with acetylated histones, an essential step for VDR-promoter association. Plays a central role in calcium homeostasis
    Gene Name:
    VDR
    Uniprot ID:
    P11473
    Molecular weight:
    48288.6
    References
    1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
    2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
    3. Qaw F, Calverley MJ, Schroeder NJ, Trafford DJ, Makin HL, Jones G: In vivo metabolism of the vitamin D analog, dihydrotachysterol. Evidence for formation of 1 alpha,25- and 1 beta,25-dihydroxy-dihydrotachysterol metabolites and studies of their biological activity. J Biol Chem. 1993 Jan 5;268(1):282-92. [PubMed:8380156 ]
    4. Qaw FS, Makin HL, Jones G: Metabolism of 25-hydroxydihydrotachysterol3 in bone cells in vitro. Steroids. 1992 May;57(5):236-43. [PubMed:1336906 ]
    5. Gallagher JC, Sai AJ: Vitamin D insufficiency, deficiency, and bone health. J Clin Endocrinol Metab. 2010 Jun;95(6):2630-3. doi: 10.1210/jc.2010-0918. [PubMed:20525913 ]
    6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

    PMID: 11095202

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