calcidiol (CHEBI:17933)

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CHEBI:17933 - calcidiol

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ChEBI Name	calcidiol

ChEBI ID	CHEBI:17933

Definition	A hydroxycalciol that is calciol in which the hydrogen at position 25 has been replaced by a hydroxy group. A prehormone resulting from the oxidation of calciol in the liver, it is further hydroxylated in the kidney to give calcitriol, the active form of vitamin D₃.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:46387, CHEBI:13931, CHEBI:3304, CHEBI:19815

Supplier Information	No supplier information found for this compound.

Download	Molfile XML SDF

more structures >>

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20.1523 -22.1633 5.4464 C 0 0 0 0 0 0 0 0 0 0 0 0

18.7275 -22.6161 5.1006 C 0 0 0 0 0 0 0 0 0 0 0 0

17.7072 -21.7481 5.8566 C 0 0 1 0 0 0 0 0 0 0 0 0

17.7683 -20.2940 5.3551 C 0 0 0 0 0 0 0 0 0 0 0 0

19.1775 -19.7737 5.5378 C 0 0 0 0 0 0 0 0 0 0 0 0

19.3636 -18.5242 6.0074 C 0 0 0 0 0 0 0 0 0 0 0 0

20.7136 -17.9951 6.2469 C 0 0 0 0 0 0 0 0 0 0 0 0

21.0117 -16.6877 6.2632 C 0 0 0 0 0 0 0 0 0 0 0 0

19.9735 -15.5986 6.0041 C 0 0 0 0 0 0 0 0 0 0 0 0

20.3058 -20.6808 5.2007 C 0 0 0 0 0 0 0 0 0 0 0 0

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24.4096 -16.4487 7.8698 C 0 0 0 0 0 0 0 0 0 0 0 0

23.8685 -15.0082 7.7543 C 0 0 2 0 0 0 0 0 0 0 0 0

21.7977 -15.6684 8.9553 C 0 0 0 0 0 0 0 0 0 0 0 0

21.4532 -20.2210 4.6808 C 0 0 0 0 0 0 0 0 0 0 0 0

24.4310 -13.9765 8.7617 C 0 0 2 0 0 0 0 0 0 0 0 0

23.8496 -14.1174 10.1725 C 0 0 0 0 0 0 0 0 0 0 0 0

24.1915 -12.5633 8.2208 C 0 0 0 0 0 0 0 0 0 0 0 0

24.8742 -12.4548 6.8531 C 0 0 0 0 0 0 0 0 0 0 0 0

24.1627 -11.4254 5.9760 C 0 0 0 0 0 0 0 0 0 0 0 0

24.4225 -11.7791 4.4891 C 0 0 2 0 0 0 0 0 0 0 0 0

23.6006 -10.8766 3.5394 C 0 0 0 0 0 0 0 0 0 0 0 0

25.8489 -11.5325 4.1930 C 0 0 0 0 0 0 0 0 0 0 0 0

15.6892 -21.6791 5.2274 H 0 0 0 0 0 0 0 0 0 0 0 0

23.4981 -13.4355 3.5244 H 0 0 0 0 0 0 0 0 0 0 0 0

20.3606 -22.3743 6.5171 H 0 0 0 0 0 0 0 0 0 0 0 0

20.8815 -22.7111 4.8118 H 0 0 0 0 0 0 0 0 0 0 0 0

18.5978 -23.6795 5.3947 H 0 0 0 0 0 0 0 0 0 0 0 0

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19.7626 -14.5944 7.9304 H 0 0 0 0 0 0 0 0 0 0 0 0

19.6040 -13.5030 6.4893 H 0 0 0 0 0 0 0 0 0 0 0 0

21.7406 -13.0913 7.8076 H 0 0 0 0 0 0 0 0 0 0 0 0

22.0741 -13.6170 6.1032 H 0 0 0 0 0 0 0 0 0 0 0 0

22.7760 -15.9253 5.5247 H 0 0 0 0 0 0 0 0 0 0 0 0

23.8872 -17.8627 6.2538 H 0 0 0 0 0 0 0 0 0 0 0 0

22.8639 -18.0228 7.7438 H 0 0 0 0 0 0 0 0 0 0 0 0

25.4227 -16.5242 7.4199 H 0 0 0 0 0 0 0 0 0 0 0 0

24.4514 -16.7676 8.9332 H 0 0 0 0 0 0 0 0 0 0 0 0

24.2022 -14.4774 6.8371 H 0 0 0 0 0 0 0 0 0 0 0 0

22.5568 -15.5814 9.7621 H 0 0 0 0 0 0 0 0 0 0 0 0

21.4909 -16.7310 8.8485 H 0 0 0 0 0 0 0 0 0 0 0 0

20.9114 -15.0495 9.2125 H 0 0 0 0 0 0 0 0 0 0 0 0

21.5805 -19.1340 4.4906 H 0 0 0 0 0 0 0 0 0 0 0 0

22.2764 -20.9273 4.4404 H 0 0 0 0 0 0 0 0 0 0 0 0

25.5203 -14.1661 8.8701 H 0 0 0 0 0 0 0 0 0 0 0 0

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23.1008 -12.3816 8.1127 H 0 0 0 0 0 0 0 0 0 0 0 0

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26.4072 -11.4021 5.1449 H 0 0 0 0 0 0 0 0 0 0 0 0

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27 29 1 0 0 0 0

27 28 1 0 0 0 0

26 27 1 0 0 0 0

25 26 1 0 0 0 0

24 25 1 0 0 0 0

22 24 1 0 0 0 0

22 23 1 0 0 0 0

19 22 1 0 0 0 0

18 19 1 0 0 0 0

17 18 1 0 0 0 0

16 17 1 0 0 0 0

15 20 1 0 0 0 0

15 19 1 0 0 0 0

15 16 1 0 0 0 0

14 15 1 0 0 0 0

13 14 1 0 0 0 0

12 21 2 0 0 0 0

11 13 1 0 0 0 0

10 16 1 0 0 0 0

10 11 1 0 0 0 0

9 10 2 0 0 0 0

8 9 1 0 0 0 0

7 12 1 0 0 0 0

7 8 2 0 0 0 0

6 7 1 0 0 0 0

5 6 1 0 0 0 0

4 5 1 0 0 0 0

3 12 1 0 0 0 0

3 4 1 0 0 0 0

2 27 1 0 0 0 0

1 5 1 0 0 0 0

30 1 1 0 0 0 0

31 2 1 0 0 0 0

32 3 1 0 0 0 0

33 3 1 0 0 0 0

34 4 1 0 0 0 0

35 4 1 0 0 0 0

36 5 1 0 0 0 0

37 6 1 0 0 0 0

38 6 1 0 0 0 0

39 8 1 0 0 0 0

40 9 1 0 0 0 0

41 11 1 0 0 0 0

42 11 1 0 0 0 0

43 13 1 0 0 0 0

44 13 1 0 0 0 0

45 14 1 0 0 0 0

46 14 1 0 0 0 0

47 16 1 0 0 0 0

48 17 1 0 0 0 0

49 17 1 0 0 0 0

50 18 1 0 0 0 0

51 18 1 0 0 0 0

52 19 1 0 0 0 0

53 20 1 0 0 0 0

54 20 1 0 0 0 0

55 20 1 0 0 0 0

56 21 1 0 0 0 0

57 21 1 0 0 0 0

58 22 1 0 0 0 0

59 23 1 0 0 0 0

60 23 1 0 0 0 0

61 23 1 0 0 0 0

62 24 1 0 0 0 0

63 24 1 0 0 0 0

64 25 1 0 0 0 0

65 25 1 0 0 0 0

66 26 1 0 0 0 0

67 26 1 0 0 0 0

68 28 1 0 0 0 0

69 28 1 0 0 0 0

70 28 1 0 0 0 0

71 29 1 0 0 0 0

72 29 1 0 0 0 0

73 29 1 0 0 0 0

M END): 20 ms

reading 73 atoms

ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false

1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them.

Default Van der Waals type for model set to Babel

73 atoms created

ModelSet: not autobonding; use forceAutobond=true to force automatic bond creation

Script completed

Jmol script terminated

Molfile expand

Wikipedia	License
Calcifediol, also known as calcidiol, 25-hydroxycholecalciferol, or 25-hydroxyvitamin D3 (abbreviated 25(OH)D3), is a form of vitamin D produced in the liver by hydroxylation of vitamin D3 (cholecalciferol) by the enzyme vitamin D 25-hydroxylase. Calcifediol can be further hydroxylated by the enzyme 25(OH)D-1α-hydroxylase, primarily in the kidney, to form calcitriol (1,25-(OH)2D3), which is the active hormonal form of vitamin D. Calcifediol is strongly bound in blood by the vitamin D-binding protein. Measurement of serum calcifediol is the usual test performed to determine a person's vitamin D status, to show vitamin D deficiency or sufficiency. Calcifediol is available as an oral medication in some countries to supplement vitamin D status.
Read full article at Wikipedia

Formula

C27H44O2

Net Charge

Average Mass

400.63706

Monoisotopic Mass

400.33413

InChI

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

InChIKey

JWUBBDSIWDLEOM-DTOXIADCSA-N

SMILES

[H][C@@]1(CC[C@]2([H])[C@]1(C)CCC\C2=C/C=C1/C[C@@H](O)CCC1=C)[C@H](C)CCCC(C)(C)O

Metabolite of Species	Details
Mus musculus (NCBI:txid10090)	Source: BioModels - MODEL1507180067 See: PubMed
Homo sapiens (NCBI:txid9606)	See: DOI

Roles Classification
Biological Role(s):	human metabolite Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens). metabolite Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites. mouse metabolite Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus). fat-soluble vitamin (role) Any vitamin that dissolves in fats and are stored in body tissues. Unlike the water-soluble vitamins, they are stored in the body for long periods of time and generally pose a greater risk for toxicity when consumed in excess. (via vitamin D )

Application(s):	bone density conservation agent An agent that inhibits bone resorption and/or favor bone mineralization and bone regeneration. Used to heal bone fractures and to treat bone diseases such as osteopenia and osteoporosis. nutraceutical A product in capsule, tablet or liquid form that provide essential nutrients, such as a vitamin, an essential mineral, a protein, an herb, or similar nutritional substance.

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	calcidiol (CHEBI:17933) has role bone density conservation agent (CHEBI:50646) calcidiol (CHEBI:17933) has role human metabolite (CHEBI:77746) calcidiol (CHEBI:17933) has role metabolite (CHEBI:25212) calcidiol (CHEBI:17933) has role mouse metabolite (CHEBI:75771) calcidiol (CHEBI:17933) has role nutraceutical (CHEBI:50733) calcidiol (CHEBI:17933) is a D₃ vitamins (CHEBI:73558) calcidiol (CHEBI:17933) is a diol (CHEBI:23824) calcidiol (CHEBI:17933) is a hydroxycalciol (CHEBI:47042)

Incoming	calcidiol 25-O-(β-D-glucuronate) (CHEBI:139277) has functional parent calcidiol (CHEBI:17933) calcidiol 25-O-(β-D-glucuronide) (CHEBI:139610) has functional parent calcidiol (CHEBI:17933) calcidiol 3-O-(β-D-glucuronate) (CHEBI:139278) has functional parent calcidiol (CHEBI:17933) calcidiol 3-O-(β-D-glucuronide) (CHEBI:139613) has functional parent calcidiol (CHEBI:17933)

IUPAC Name

(3S,5Z,7E)-9,10-secocholesta-5,7,10(19)-triene-3,25-diol

INNs	Sources
calcifediol	ChEBI
calcifédiol	ChEBI
calcifediol	WHO MedNet
calcifediolum	ChEBI

Synonyms	Sources
(3β,5Z,7E)-9,10-secocholesta-5,7,10(19)-triene-3,25-diol	ChemIDplus
(3S,5Z,7E)-9,10-secocholesta-5,7,10-triene-3,25-diol	PDBeChem
(5Z,7E)-(3S)-9,10-secocholesta-5,7,10(19)-triene-3,25-diol	JCBN
25(OH)D₃	ChEBI
25-hydroxycholecalciferol	JCBN
25-Hydroxyvitamin D3	KEGG COMPOUND
25-hydroxyvitamin D₃	ChEBI
3-{2-[1-(5-HYDROXY-1,5-DIMETHYL-HEXYL)-7A-METHYL-OCTAHYDRO-INDEN-4-YLIDENE]-ETHYLIDENE}-4-METHYLENE-CYCLOHEXANOL	PDBeChem
Calcidiol	KEGG COMPOUND
calcidiol	UniProt
Calcifediol	KEGG COMPOUND
Calcifediol anhydrous	KEGG COMPOUND

Brand Name	Source
Rayaldee	ChEBI

Manual Xrefs	Databases
464	DrugCentral
C01561	KEGG COMPOUND
Calcifediol	Wikipedia
DB00146	DrugBank
LMST03020246	LIPID MAPS
VDY	PDBeChem
View more database links

Registry Numbers	Types	Sources
19356-17-3	CAS Registry Number	KEGG COMPOUND
19356-17-3	CAS Registry Number	ChemIDplus
4270041	Reaxys Registry Number	Reaxys

Citations	Types	Sources
16549446	PubMed citation	Europe PMC
18689406	PubMed citation	Europe PMC
22487892	PubMed citation	Europe PMC
22536761	PubMed citation	Europe PMC
23090338	PubMed citation	Europe PMC
23566108	PubMed citation	Europe PMC
9080330	PubMed citation	Europe PMC

Last Modified

04 August 2021

CHEBI:17933 - calcidiol

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