Showing Compound 25-Hydroxycholecalciferol (FDB021782)

Record Information

Version

1.0

Creation date

2011-04-06 18:26:21 UTC

Update date

2019-11-26 03:20:52 UTC

Primary ID

FDB021782

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

25-Hydroxycholecalciferol

Description

Calfcifediol is a prehormone that is produced in the liver by hydroxylation of vitamin D3 (cholecalciferol) by the enzyme cholecalciferol 25-hydroxylase. Calcifediol is then converted in the kidneys into calcitriol (1,25-(OH)2D3), a secosteroid hormone that is the active form of vitamin D. It can also be converted into 24-hydroxycalcidiol in the kidneys via 24-hydroxylation. [Wikipedia]. 25-Hydroxycholecalciferol is found in many foods, some of which are green zucchini, green bell pepper, red bell pepper, and other animal fat.

CAS Number

19356-17-3

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Show entries

Search:

Synonym	Source
(3b,5Z,7E)-9,10-Secocholesta-5,7,10(19)-triene-3,25-diol	Generator
(3b,5Z,7e)-9,10-Secocholesta-5,7,10(19)-triene-3,25-diol	Generator
(3beta,5Z,7E)-9,10-Secocholesta-5,7,10(19)-triene-3,25-diol	ChEBI
(3beta,5Z,7e)-9,10-Secocholesta-5,7,10(19)-triene-3,25-diol	ChEBI
(3S,5Z,7E)-9,10-Seco-5,7,10(19)-cholestatriene-3,25-diol	Kegg
(3S,5Z,7E)-9,10-Secocholesta-5,7,10-triene-3,25-diol	ChEBI
(3S,5Z,7e)-9,10-Secocholesta-5,7,10-triene-3,25-diol	ChEBI
(3Β,5Z,7E)-9,10-secocholesta-5,7,10(19)-triene-3,25-diol	Generator
(3β,5Z,7e)-9,10-secocholesta-5,7,10(19)-triene-3,25-diol	Generator
(5Z,7E)-(3S)-9,10-Secocholesta-5,7,10(19)-triene-3,25-diol	ChEBI

Showing 1 to 10 of 48 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.0022 g/L	ALOGPS
logP	6.71	ALOGPS
logP	5.65	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	18.38	ChemAxon
pKa (Strongest Basic)	-0.98	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	125.06 m³·mol⁻¹	ChemAxon
Polarizability	50.32 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Chemical Formula

C27H44O2

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

InChI Identifier

InChI=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 Key

JWUBBDSIWDLEOM-DTOXIADCSA-N

Isomeric SMILES

C[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

Average Molecular Weight

400.6371

Monoisotopic Molecular Weight

400.334130652

Classification

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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Vitamin D and derivatives

Direct Parent

Vitamin 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 Framework

Aliphatic homopolycyclic compounds

External Descriptors

diol (CHEBI:17933 )
D3 vitamins (CHEBI:17933 )
hydroxycalciol (CHEBI:17933 )
Vitamin D3 and derivatives (C01561 )
Vitamin D3 and derivatives (LMST03020246 )

Ontology

Physiological effect

Health effect:

Observation:

Drowsiness

Health condition:

Chronic renal failure

General disorders and administration site conditions:

Pain

Nervous system disorders:

Headache

Gastrointestinal disorders:

Renal and urinary disorders:

Nephrotic syndrome

Disposition

Route of exposure:

Enteral:

Ingestion

Extracellular

Tissue and substructures:

Organ and components:

Subcellular:

Biofluid and excreta:

Process

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

System process:

Reproduction

Cellular process:

Cell signaling

Role

Biological role:

Molecular messenger:

Signaling molecule

Industrial application:

Food and nutrition:

Nutritional supplement

Pharmaceutical industry:

Pharmaceutical

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Show entries

Search:

Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	25-Hydroxycholecalciferol, 2 TMS, GC-MS Spectrum	splash10-001i-2900000000-33a8e563016d6e2e358e	Spectrum
GC-MS	25-Hydroxycholecalciferol, 2 TMS, GC-MS Spectrum	splash10-00lr-2900000000-f6bedf68127696063061	Spectrum
GC-MS	25-Hydroxycholecalciferol, non-derivatized, GC-MS Spectrum	splash10-001i-2900000000-33a8e563016d6e2e358e	Spectrum
GC-MS	25-Hydroxycholecalciferol, non-derivatized, GC-MS Spectrum	splash10-00lr-2900000000-f6bedf68127696063061	Spectrum
Predicted GC-MS	25-Hydroxycholecalciferol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0ab9-3029000000-4c75b5cfbc422ba2a344	Spectrum
Predicted GC-MS	25-Hydroxycholecalciferol, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-003r-1403290000-a8eb9294a6df1ce864d2	Spectrum
Predicted GC-MS	25-Hydroxycholecalciferol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	25-Hydroxycholecalciferol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00lr-0119100000-d3e0a5d2ecb614d781d4	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0api-0369000000-146e7a23795c22f5b836	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0kai-5296000000-412b0c2da61c93271acd	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0009000000-ef5150b1dccaed2f9543	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000t-0009000000-4b22b5c88dc06c01fe89	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00si-2229000000-f4037186ef5a21a16859	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0009000000-21157f4aa99daf697271	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-0009000000-cac0e3874faca9c17f03	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01ot-0339000000-37442d1a71c50883b377	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0549100000-68f99126c8d8b4ca7eb7	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0g4i-5594100000-433f2a913eb577e9397a	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ab9-1940000000-e03ff70cb44513aa8ae8	2021-09-22	View Spectrum