Calcifediol

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Calcifediol are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the Calcifediol?

The molecule Calcifediol presents a molecular formula of C27H44O2 and its IUPAC name is (1S,3Z)-3-[(2E)-2-[(1R,3aS,7aR)-1-[(2R)-6-hydroxy-6-methylheptan-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexan-1-ol.

Calcifediol, also known as 25-hydroxyvitamin D3, is a vitamin D metabolite that is produced in the liver. It is the most abundant circulating vitamin D metabolite in humans, and it is generally considered to be the most biologically active form of vitamin D. Calcifediol is converted to calcitriol (1,25-dihydroxyvitamin D3), the hormonally active form of vitamin D, in the kidney..

Calcifediol has a half-life in the circulation of about two weeks, and it is excreted in the urine. Calcifediol levels can be measured in the blood, and they are used to assess vitamin D status. Low calcifediol levels are associated with vitamin D deficiency, and high calcifediol levels can be seen in certain disorders of vitamin D metabolism..

Calcifediol has a number of potential health benefits. It has been shown to improve bone health, and it may also have a role in cancer prevention and treatment. Calcifediol is being investigated as a treatment for a variety of other conditions, including diabetes, obesity, and cardiovascular disease..

3D structure

Cartesian coordinates

Geometry of Calcifediol in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

Calcifediol JWUBBDSIWDLEOM-DTOXIADCSA-N chemical compound 2D structure molecule svg
Calcifediol

 

Molecule descriptors

 
IUPAC name(1S,3Z)-3-[(2E)-2-[(1R,3aS,7aR)-1-[(2R)-6-hydroxy-6-methylheptan-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexan-1-ol
InChI codeInChI=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
SMILESC=C1CC[C@H](O)C/C1=C/C=C1\CCC[C@@]2(C)[C@H]1CC[C@@H]2[C@H](C)CCCC(C)(C)O

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • (1S,3Z)-3-[(2E)-2-[(1R,3aS,7aR)-1-[(1R)-5-hydroxy-1,5-dimethyl-hexyl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylene-cyclohexanol
  • (1S,3Z)-3-[(2E)-2-[(1R,3aS,7aR)-1-[(2R)-6-hydroxy-6-methylheptan-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexan-1-ol
  • (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
  • (3S,5Z,14beta,17alpha)-9,10-secocholesta-5,7,10-triene-3,25-diol
  • (3S,5Z,7E)-9,10-seco-5,7,10(19)-cholestatriene-3,25-diol
  • (3S,5Z,7E)-9,10-secocholesta-5,7,10(19)-triene-3,25-diol
  • (3S,5Z,7E)-9,10-secocholesta-5,7,10-triene-3,25-diol
  • (3b,5Z,7E)- 9,10-Secocholesta-5,7,10(19)-triene-3,25-diol
  • (3beta,5Z,7E)-9,10-secocholesta-5,7,10(19)-triene-3,25-diol
  • (5E,7E)-9,10-Secocholesta-5,7,10(19)-triene-3beta,25-diol
  • (5Z,7E)-(3S)-9,10-seco-5,7,10(19)-cholestatriene-3,25-diol
  • (5Z,7E)-(3S)-9,10-secocholesta-5,7,10(19)-triene-3,25-diol
  • (5Z,7E)-9,10-Seco-5,7,10(19)-cholestatrien-3beta,25-diol
  • (5Z,7E)-9,10-Secocholesta-5,7,10(19)-triene-3b,25-diol monohydrate
  • (?R,1R,3aS,4E,7aR)-4-[(2Z)-2-[(5S)-5-hydroxy-2-methylenecyclohexylidene]ethylidene]octahydro-?,?,?,7a-tetramethyl-1H-indene-1-pentanol
  • (S,Z)-3-((E)-2-((1R,3aS,7aR)-1-((R)-6-hydroxy-6-methylheptan-2-yl)-7a-methylhexahydro-1H-inden-4(2H)-ylidene)ethylidene)-4-methylenecyclohexanol
  • 19356-17-3
  • 1H-Indene-1-pentanol, octahydro-4-[(2Z)-2-[(5S)-5-hydroxy-2-methylenecyclohexylidene]ethylidene]-.alpha.,.alpha.,.epsilon.,7a-tetramethyl-, (.epsilon.R,1R,3aS,4E,7aR)-
  • 25(OH)D3
  • 25-(OH)Vitamin D3
  • 25-Hydroxy vitamin D3
  • 25-Hydroxycholecalciferol
  • 25-Hydroxycholescalciferol
  • 25-Hydroxyvitamin D
  • 25-hydroxy-cholecalciferol
  • 25-hydroxyvitamin D3
  • 25-hydroxyvitamin D3 / 25-hydroxycholecalciferol / calcidiol
  • 3-{2-[1-(5-HYDROXY-1,5-DIMETHYL-HEXYL)-7A-METHYL-OCTAHYDRO-INDEN-4-YLIDENE]-ETHYLIDENE}-4-METHYLENE-CYCLOHEXANOL
  • 356C173
  • 36149-00-5
  • 5,6-cis-25-Hydroxyvitamin D3
  • 5,6-trans-25-Hydroxycholescalciferol
  • 5,6-trans-9,10-Seco-5,7,10(19)-cholestatrien-3beta,25-diol
  • 64719-49-9
  • 9,10-Secocholesta-5,7,10(19)-triene-1,25-diol, (3.beta,.5Z,7E)-
  • 9,10-Secocholesta-5,7,10(19)-triene-3,25-diol, (3beta,5Z,7E)-
  • 9,10-Secocholesta-5,7,10(19)-triene-3b,25-diol
  • A923587
  • AB01275461-01
  • AB01275461_02
  • AC-31367
  • ACT06833
  • AMY2863
  • B91135EC-8937-4D8B-A533-CCD82F33C1B0
  • BCP9000472
  • BCPP000306
  • BDBM50521013
  • BML2-E02
  • BSPBio_001411
  • C01561
  • CALCIFEDIOL, ANHYDROUS
  • CALCIFEDIOL,ANHYDROUS
  • CCG-268657
  • CS-0800
  • Calcidiol
  • Calcifediol
  • Calcifediol anhydrous
  • Calcifediolum
  • Calcifidiol
  • Calderol
  • Cholecalciferol, 25-hydroxy-
  • DB00146
  • DM100
  • DSSTox_CID_2721
  • DSSTox_GSID_22721
  • DSSTox_RID_76699
  • Delakmin
  • Didrogyl
  • GTPL6921
  • HMS1361G13
  • HMS1791G13
  • HMS1989G13
  • HMS2089L21
  • HMS3402G13
  • HY-32351
  • Hidroferol
  • Hy-D
  • IDI1_033881
  • LMST03020246
  • MFCD00867077
  • NCGC00161326-01
  • NCGC00161326-04
  • Q139307
  • Rayaldee
  • Ro 8-8892
  • Rovimix Hy-D
  • Ryaldee
  • SR-05000001468
  • SR-05000001468-1
  • T0WXW8F54E
  • U 32070 E
  • U 32070E
  • U-32070E
  • Vitamin D, 25-hydroxy-
  • W-201718
  • s1469

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC4474414
  • CAS-19356-17-3
  • UNII-T0WXW8F54E
  • AKOS015965097
  • BRD-K77175907-001-01-5
  • DTXSID0022721
  • CHEMBL1040
  • CHEBI:17933
  • CHEBI:94743
  • Tox21_111987
  • EINECS 242-990-9
  • SCHEMBL3296
  • Spectrum5_001931

Physico-Chemical properties

IUPAC name(1S,3Z)-3-[(2E)-2-[(1R,3aS,7aR)-1-[(2R)-6-hydroxy-6-methylheptan-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexan-1-ol
Molecular formulaC27H44O2
Molecular weight400.637
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity126.24
LogP6.7
Topological polar surface area40.5

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.