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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2021-09-14 15:47:19 UTC
HMDB IDHMDB0015504
Secondary Accession Numbers
  • HMDB15504
Metabolite Identification
Common NameAlfacalcidol
DescriptionAlfacalcidol is an active metabolite of Vitamin D, which performs important functions in regulation of the calcium balance and the bone metabolism. Alfacalcidol is Vitamin D-hormone analog which is activated by the enzyme 25-hydroxylase in the liver for systemic and in osteoblasts for local D-hormone actions. It possesses a unique pattern of pleiotropic effects on, e.g. gut, bone, pararthyroids, muscle and brain. Alfacalcidol is superior to plain vitamin D (cholecalciferol) because the final kidney activation of the latter is regulated by a negative feedback mechanism. (PMID:17438884 ,17668216 ).
Structure
Data?1582753304
Synonyms
ValueSource
(5Z,7E)-9,10-Seco-5,7,10(19)-cholestatrien-1alpha,3beta-diolChEBI
1alpha-Hydroxy-vitamin D3ChEBI
1alpha-HydroxycholecalciferolChEBI
1alpha-Hydroxyvitamin D3ChEBI
9,10-Secocholesta-5,7,10(19)-triene-1alpha,3beta-diolChEBI
AlfacalcidolumChEBI
AlsiodolChEBI
(5Z,7E)-9,10-Seco-5,7,10(19)-cholestatrien-1a,3b-diolGenerator
(5Z,7E)-9,10-Seco-5,7,10(19)-cholestatrien-1α,3β-diolGenerator
1a-Hydroxy-vitamin D3Generator
1Α-hydroxy-vitamin D3Generator
1a-HydroxycholecalciferolGenerator
1Α-hydroxycholecalciferolGenerator
1a-Hydroxyvitamin D3Generator
1Α-hydroxyvitamin D3Generator
9,10-Secocholesta-5,7,10(19)-triene-1a,3b-diolGenerator
9,10-Secocholesta-5,7,10(19)-triene-1α,3β-diolGenerator
1-HydroxycholecalciferolHMDB
1 alpha-HydroxycholecalciferolHMDB
1-alpha-OxycholecalciferolHMDB
1-Hydroxycholecalciferol, (1alpha,3alpha-(5Z,7E))-isomerHMDB
1-Hydroxycholecalciferol, (1beta)-(5Z)-isomerHMDB
1alpha-OHD3HMDB
AlfaDHMDB
OksidevitHMDB
Un-alfaHMDB
1 alpha-Hydroxyvitamin D3HMDB
1-Hydroxycholecalciferol, (1beta,3beta-(5E,7E))-isomerHMDB
BondiolHMDB
Doss brand OF alfacalcidolHMDB
AlphacalcidolHMDB
1-Hydroxycholecalciferol, aluminum saltHMDB
EinsAlphaHMDB
EtalphaHMDB
EenalfadrieHMDB
One-AlphaHMDB
1a-Hydroxyvitamin D3 / 1a-hydroxycholecalciferolHMDB
1Α-hydroxyvitamin D3 / 1α-hydroxycholecalciferolHMDB
AlfacalcidolMeSH
Chemical FormulaC27H44O2
Average Molecular Weight400.6371
Monoisotopic Molecular Weight400.334130652
IUPAC Name(1R,3S,5Z)-5-{2-[(1R,3aS,4E,7aR)-7a-methyl-1-[(2R)-6-methylheptan-2-yl]-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexane-1,3-diol
Traditional Nameetα
CAS Registry Number41294-56-8
SMILES
CC(C)CCC[C@@H](C)[C@@]1([H])CC[C@@]2([H])\C(CCC[C@]12C)=C\C=C1\C[C@@H](O)C[C@H](O)C1=C
InChI Identifier
InChI=1S/C27H44O2/c1-18(2)8-6-9-19(3)24-13-14-25-21(10-7-15-27(24,25)5)11-12-22-16-23(28)17-26(29)20(22)4/h11-12,18-19,23-26,28-29H,4,6-10,13-17H2,1-3,5H3/b21-11+,22-12-/t19-,23-,24-,25+,26+,27-/m1/s1
InChI KeyOFHCOWSQAMBJIW-AVJTYSNKSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as vitamin d and derivatives. Vitamin D and derivatives are compounds containing a secosteroid backbone, usually secoergostane or secocholestane.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassVitamin D and derivatives
Direct ParentVitamin D and derivatives
Alternative Parents
Substituents
  • Triterpenoid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point136 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0016 g/LNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0016 g/LALOGPS
logP10(6.68) g/LALOGPS
logP10(5.82) g/LChemAxon
logS10(-5.4) g/LALOGPS
pKa (Strongest Acidic)14.39ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity124.7 m³·mol⁻¹ChemAxon
Polarizability50.55 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+199.45831661259
DarkChem[M-H]-197.49331661259

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Alfacalcidol,1TMS,#1C=C1/C(=C\C=C2/CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)CCCC(C)C)C[C@@H](O[Si](C)(C)C)C[C@@H]1O3242.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
Alfacalcidol,1TMS,#2C=C1/C(=C\C=C2/CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)CCCC(C)C)C[C@@H](O)C[C@@H]1O[Si](C)(C)C3233.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
Alfacalcidol,2TMS,#1C=C1/C(=C\C=C2/CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)CCCC(C)C)C[C@@H](O[Si](C)(C)C)C[C@@H]1O[Si](C)(C)C3181.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
Alfacalcidol,1TBDMS,#1C=C1/C(=C\C=C2/CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)CCCC(C)C)C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@H]1O3467.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
Alfacalcidol,1TBDMS,#2C=C1/C(=C\C=C2/CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)CCCC(C)C)C[C@@H](O)C[C@@H]1O[Si](C)(C)C(C)(C)C3446.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
Alfacalcidol,2TBDMS,#1C=C1/C(=C\C=C2/CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)CCCC(C)C)C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@H]1O[Si](C)(C)C(C)(C)C3613.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Alfacalcidol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a5l-1019000000-4bbe28a5b3bcf0e3f2862017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Alfacalcidol GC-MS (2 TMS) - 70eV, Positivesplash10-004i-7101590000-c90de60556296aeee67c2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Alfacalcidol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alfacalcidol 10V, Positive-QTOFsplash10-0f89-0129200000-ce55736fb60be5e0024f2017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alfacalcidol 20V, Positive-QTOFsplash10-00e9-2496000000-6be131b12013c8feea5c2017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alfacalcidol 40V, Positive-QTOFsplash10-074j-6395000000-2c39ba62f7c36fc0a44a2017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alfacalcidol 10V, Negative-QTOFsplash10-0002-0009000000-cdef64e29d5e6355c8fe2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alfacalcidol 20V, Negative-QTOFsplash10-000t-0009000000-a22d1c4bcbcd6fbeaf2c2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alfacalcidol 40V, Negative-QTOFsplash10-001i-1129000000-91782a773e5f99cf32702017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alfacalcidol 10V, Positive-QTOFsplash10-0ue9-0379600000-d676c4ba59a242f280622021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alfacalcidol 20V, Positive-QTOFsplash10-00rm-4298100000-c624703a1882c35b89752021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alfacalcidol 40V, Positive-QTOFsplash10-03ka-5931000000-5fa16451ff2ca2eab28c2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alfacalcidol 10V, Negative-QTOFsplash10-0002-0009000000-dc23ba87137530d83f682021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alfacalcidol 20V, Negative-QTOFsplash10-0002-0309000000-c5c00960affa6353a8102021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alfacalcidol 40V, Negative-QTOFsplash10-002b-0629000000-2b1b864f66e3930d49a02021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01436 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01436 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01436
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4445376
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAlfacalcidol
METLIN IDNot Available
PubChem Compound5282181
PDB IDNot Available
ChEBI ID31186
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Galesanu C, Ciubotariu C, Melnic G, Galesanu MR: [Postmenopausal osteoporosis. Digital Rx radiogrammetry in the diagnosis and follow-up of treatment with alfacalcidol]. Rev Med Chir Soc Med Nat Iasi. 2006 Oct-Dec;110(4):833-41. [PubMed:17438884 ]
  2. Ringe JD, Schacht E: Improving the outcome of established therapies for osteoporosis by adding the active D-hormone analog alfacalcidol. Rheumatol Int. 2007 Dec;28(2):103-11. Epub 2007 Aug 1. [PubMed:17668216 ]
  3. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  4. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  5. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  6. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  7. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Catalyzes the conversion of 25-hydroxyvitamin D3 (25(OH)D) to 1-alpha,25-dihydroxyvitamin D3 (1,25(OH)2D) plays an important role in normal bone growth, calcium metabolism, and tissue differentiation.
Gene Name:
CYP27B1
Uniprot ID:
O15528
Molecular weight:
56503.475
References
  1. Uchida E, Kagawa N, Sakaki T, Urushino N, Sawada N, Kamakura M, Ohta M, Kato S, Inouye K: Purification and characterization of mouse CYP27B1 overproduced by an Escherichia coli system coexpressing molecular chaperonins GroEL/ES. Biochem Biophys Res Commun. 2004 Oct 15;323(2):505-11. [PubMed:15369780 ]
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. Reinhart GA: Vitamin D analogs: novel therapeutic agents for cardiovascular disease? Curr Opin Investig Drugs. 2004 Sep;5(9):947-51. [PubMed:15503649 ]
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  3. Fujishima T, Tsuji G, Tanaka C, Harayama H: Novel vitamin D receptor ligands having a carboxyl group as an anchor to arginine 274 in the ligand-binding domain. J Steroid Biochem Mol Biol. 2010 Jul;121(1-2):60-2. doi: 10.1016/j.jsbmb.2010.04.020. Epub 2010 May 6. [PubMed:20435140 ]