Calcidiol (CHEM002127)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (2)XML
Record Information
Version1.0
Creation Date2009-07-21 20:26:08 UTC
Update Date2026-05-14 16:24:16 UTC
Accession NumberCHEM002127
Identification
Common NameCalcidiol
ClassSmall Molecule
DescriptionThe major circulating metabolite of vitamin D3 (cholecalciferol). It is produced in the liver and is the best indicator of the body's vitamin D stores. It is effective in the treatment of rickets and osteomalacia, both in azotemic and non-azotemic patients. Calcifediol also has mineralizing properties.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Antihypocalcemic Agent
  • Antihypoparathyroid Agent
  • Antithyroid Agent
  • Bone Density Conservation Agent
  • Drug
  • Food Toxin
  • Metabolite
  • Natural Compound
  • Nutraceutical
  • Organic Compound
  • Vitamin
  • Vitamin D
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(3beta,5Z,7E)-9,10-Secocholesta-5,7,10(19)-triene-3,25-diolChEBI
(3S,5Z,7E)-9,10-Secocholesta-5,7,10-triene-3,25-diolChEBI
(5Z,7E)-(3S)-9,10-Secocholesta-5,7,10(19)-triene-3,25-diolChEBI
25(OH)D3ChEBI
25-HydroxycholecalciferolChEBI
25-Hydroxyvitamin D3ChEBI
3-{2-[1-(5-hydroxy-1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-4-ylidene]-ethylidene}-4-methylene-cyclohexanolChEBI
CalcifediolChEBI
Calcifediol anhydrousChEBI
CalcifediolumChEBI
RayaldeeChEBI
(3S,5Z,7E)-9,10-Seco-5,7,10(19)-cholestatriene-3,25-diolKegg
(3b,5Z,7E)-9,10-Secocholesta-5,7,10(19)-triene-3,25-diolGenerator
(3Β,5Z,7E)-9,10-secocholesta-5,7,10(19)-triene-3,25-diolGenerator
25-Hydroxy-cholecalciferolHMDB
5,6-cis-25-Hydroxyvitamin D3HMDB
9,10-Secocholesta-5,7,10(19)-triene-3b,25-diolHMDB
CalderolHMDB
DidrogylHMDB
HidroferolHMDB
25 Hydroxyvitamin D3HMDB
Calcifediol, (3 beta,5E,7E)-isomerHMDB
Monohydrate, 25-hydroxycholecalciferolHMDB
25-Hydroxycholecalciferol monohydrateHMDB
Anhydrous, calcifediolHMDB
Organon brand OF calcifediolHMDB
25 Hydroxyvitamin D 3HMDB
25-Hydroxyvitamin D 3HMDB
Aventis brand OF calcifediolHMDB
Calcifediol aventis brandHMDB
Calcifediol organon brandHMDB
DedrogylHMDB
25 HydroxycholecalciferolHMDB
25 Hydroxycholecalciferol monohydrateHMDB
Calcifediol faes brandHMDB
Calcifediol, (3 alpha,5Z,7E)-isomerHMDB
Faes brand OF calcifediolHMDB
CalcidiolMeSH
Chemical FormulaC27H44O2
Average Molecular Mass400.637 g/mol
Monoisotopic Mass400.334 g/mol
CAS Registry Number19356-17-3
IUPAC Name(1S,3Z)-3-{2-[(1R,3aS,4E,7aR)-1-[(2R)-6-hydroxy-6-methylheptan-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexan-1-ol
Traditional Name25-hydroxyvitamin D3
SMILESC[C@H](CCCC(C)(C)O)[C@@]1([H])CC[C@@]2([H])\C(CCC[C@]12C)=C\C=C1\C[C@@H](O)CCC1=C
InChI IdentifierInChI=1S/C27H44O2/c1-19-10-13-23(28)18-22(19)12-11-21-9-7-17-27(5)24(14-15-25(21)27)20(2)8-6-16-26(3,4)29/h11-12,20,23-25,28-29H,1,6-10,13-18H2,2-5H3/b21-11+,22-12-/t20-,23+,24-,25+,27-/m1/s1
InChI KeyJWUBBDSIWDLEOM-DTOXIADCSA-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
  • Tertiary alcohol
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginEndogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Mitochondria
Biofluid LocationsNot Available
Tissue Locations
  • Epidermis
  • Gonads
  • Kidney
  • Prostate
PathwaysNot Available
Applications
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityInsoluble
Predicted Properties
PropertyValueSource
Water Solubility0.0022 g/LALOGPS
logP6.71ALOGPS
logP5.65ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)18.38ChemAxon
pKa (Strongest Basic)-0.98ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity125.06 m³·mol⁻¹ChemAxon
Polarizability50.32 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-001i-2900000000-33a8e563016d6e2e358eSpectrum
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-00lr-2900000000-f6bedf68127696063061Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-001i-2900000000-33a8e563016d6e2e358eSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00lr-2900000000-f6bedf68127696063061Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ab9-3029000000-4c75b5cfbc422ba2a344Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-003r-1403290000-a8eb9294a6df1ce864d2Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00lr-0119100000-d3e0a5d2ecb614d781d4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0api-0369000000-146e7a23795c22f5b836Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kai-5296000000-412b0c2da61c93271acdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-ef5150b1dccaed2f9543Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000t-0009000000-4b22b5c88dc06c01fe89Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00si-2229000000-f4037186ef5a21a16859Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-21157f4aa99daf697271Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0009000000-cac0e3874faca9c17f03Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01ot-0339000000-37442d1a71c50883b377Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0549100000-68f99126c8d8b4ca7eb7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0g4i-5594100000-433f2a913eb577e9397aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ab9-1940000000-e03ff70cb44513aa8ae8Spectrum
Toxicity Profile
Route of ExposureOral, readily absorbed.
Mechanism of ToxicityCalcidiol is transformed in the kidney by 25-hydroxyvitamin D3-1-(alpha)-hydroxylase to calcitriol, the active form of vitamin D3. Calcitriol binds to intracellular receptors that then function as transcription factors to modulate gene expression. Like the receptors for other steroid hormones and thyroid hormones, the vitamin D receptor has hormone-binding and DNA-binding domains. The vitamin D receptor forms a complex with another intracellular receptor, the retinoid-X receptor, and that heterodimer is what binds to DNA. In most cases studied, the effect is to activate transcription, but situations are also known in which vitamin D suppresses transcription. Calcitriol increases the serum calcium concentrations by: increasing GI absorption of phosphorus and calcium, increasing osteoclastic resorption, and increasing distal renal tubular reabsorption of calcium. Calcitriol appears to promote intestinal absorption of calcium through binding to the vitamin D receptor in the mucosal cytoplasm of the intestine. Subsequently, calcium is absorbed through formation of a calcium-binding protein.
MetabolismCalcidiol undergoes hydroxylation in the mitochondria of kidney tissue, and this reaction is activated by the renal 25-hydroxyvitamin D3-1-(alpha)-hydroxylase to produce calcitriol (1,25- dihydroxycholecalciferol), the active form of vitamin D3. Half Life: 288 hours
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesUsed to treat vitamin D deficiency or insufficiency, refractory rickets (vitamin D resistant rickets), familial hypophosphatemia and hypoparathyroidism, and in the management of hypocalcemia and renal osteodystrophy in patients with chronic renal failure undergoing dialysis. Also used in conjunction with calcium in the management and prevention of primary or corticosteroid-induced osteoporosis.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsBone pain, constipation (especially in children or adolescents), diarrhea, drowsiness, dryness of mouth; headache (continuing), increased thirst, increase in frequency of urination, especially at night, or in amount of urine, irregular heartbeat, itching skin, loss of appetite, metallic taste, muscle pain, nausea or vomiting (especially in children or adolescents), unusual tiredness or weakness.
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB00146
HMDB IDHMDB0003550
FooDB IDFDB021782
Phenol Explorer IDNot Available
KNApSAcK IDC00040805
BiGG ID2289142
BioCyc IDNot Available
METLIN ID6949
PDB IDNot Available
Wikipedia LinkCalcifediol
Chemspider ID4446820
ChEBI ID17933
PubChem Compound ID5283731
Kegg Compound IDC01561
YMDB IDNot Available
ECMDB IDM2MDB005588
References
Synthesis Reference

Dae-Jung Kang, Jong-Hyuk Im, Hyun-Jung Jung, Jae-Hoon Kang, “BUFFER COMPOSITION FOR CATALYZING THE PREPARATION OF CALCITRIOL OR CALCIFEDIOL AND METHOD FOR PREPARING CALCITRIOL OR CALCIFEDIOL USING SAME.” U.S. Patent US20120064584, issued March 15, 2012.

MSDSLink
General References
1. A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)
2. Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W. Physico-chemical characteristics of goat and sheep milk. Small Ruminant Res.(2007) 68:88-113 doi: 10.1016/j.smallrumres.2006.09.013
3. Pirjo H. Mattila, Vieno I. Piironen, Esko J. Uusi-Rauva, and Pekka E. Koivistoinen. 1995. Contents of Cholecalciferol, Ergocalciferol, and Their 25-Hydroxylated Metabolites in Milk Products and Raw Meat and Liver As Determined by HPLC. J. Agric. Food Chem. 43 (9), pp 2394–2399
4. Mascarenas, J. L.; Mourino, A.; Castedo, L. Studies on the synthesis of side-chain hydroxylated metabolites of vitamin D. 3. Synthesis of 25-ketovitamin D3 and 25-hydroxyvitamin D3. Journal of Organic Chemistry (1986), 51(8), 1269-72.
5. Shepard RM, Horst RL, Hamstra AJ, DeLuca HF: Determination of vitamin D and its metabolites in plasma from normal and anephric man. Biochem J. 1979 Jul 15;182(1):55-69.
6. Passadakis P, Ersoy F, Tam P, Memmos D, Siamopoulos K, Ozener C, Akcicek F, Camsari T, Ates K, Ataman R, Vlachojannis J, Dombros N, Utas C, Akpolat T, Bozfakioglu S, Wu GG, Karayaylali I, Arinsoy T, Stathakis C, Yavuz M, Tsakiris D, Dimitriades A, Yilmaz ME, Gultekin M, Karayalcin B, Challa A, Polat N, Oreopoulos DG: Serum levels of prostate-specific antigen and vitamin D in peritoneal dialysis patients. Adv Perit Dial. 2004;20:203-8.
7. Park SB, Suh DH, Youn JI: A pilot study to assess the safety and efficacy of topical calcipotriol treatment in childhood psoriasis. Pediatr Dermatol. 1999 Jul-Aug;16(4):321-5.
8. Haden ST, Fuleihan GE, Angell JE, Cotran NM, LeBoff MS: Calcidiol and PTH levels in women attending an osteoporosis program. Calcif Tissue Int. 1999 Apr;64(4):275-9.
9. Flanagan JN, Young MV, Persons KS, Wang L, Mathieu JS, Whitlatch LW, Holick MF, Chen TC: Vitamin D metabolism in human prostate cells: implications for prostate cancer chemoprevention by vitamin D. Anticancer Res. 2006 Jul-Aug;26(4A):2567-72.
10. Gacad MA, Adams JS: Proteins in the heat shock-70 family specifically bind 25-hydroxyvitamin D3 and 17beta-estradiol. J Clin Endocrinol Metab. 1998 Apr;83(4):1264-7.
11. Feingold KR, Williams ML, Pillai S, Menon GK, Halloran BP, Bikle DD, Elias PM: The effect of vitamin D status on cutaneous sterologenesis in vivo and in vitro. Biochim Biophys Acta. 1987 Sep 14;930(2):193-200.
12. DeLuca HF: Overview of general physiologic features and functions of vitamin D. Am J Clin Nutr. 2004 Dec;80(6 Suppl):1689S-96S.
13. Brunk E, Sahoo S, Zielinski DC, Altunkaya A, Drager A, Mih N, Gatto F, Nilsson A, Preciat Gonzalez GA, Aurich MK, Prlic A, Sastry A, Danielsdottir AD, Heinken A, Noronha A, Rose PW, Burley SK, Fleming RMT, Nielsen J, Thiele I, Palsson BO: Recon3D enables a three-dimensional view of gene variation in human metabolism. Nat Biotechnol. 2018 Mar;36(3):272-281. doi: 10.1038/nbt.4072. Epub 2018 Feb 19.
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15. https://www.ncbi.nlm.nih.gov/pubmed/?term=18689406
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17. https://www.ncbi.nlm.nih.gov/pubmed/?term=22536761
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=23090338
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=23566108
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=9080330