NP-MRD: Showing NP-Card for 25-Hydroxycholecalciferol (NP0049938)

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Record Information

Version

2.0

Created at

2022-03-17 21:20:33 UTC

Updated at

2022-03-17 21:20:33 UTC

NP-MRD ID

NP0049938

Secondary Accession Numbers

None

Natural Product Identification

Common Name

25-Hydroxycholecalciferol

Description

Calcidiol, also known as 25(OH)D3 or rayaldee, 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. Thus, calcidiol is considered to be a secosteroid lipid molecule. 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. Calcidiol is a drug which is used 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. Calcidiol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Calcidiol exists in all living organisms, ranging from bacteria to humans. Outside of the human body, Calcidiol is found, on average, in the highest concentration within a few different foods, such as milk (cow), other animal fats, and sausages and in a lower concentration in domestic pigs. Calcidiol has also been detected, but not quantified in, several different foods, such as wheats, syrups, lingonberries, bilberries, and other dish. This could make calcidiol a potential biomarker for the consumption of these foods. Calcidiol is a potentially toxic compound. 25-Hydroxycholecalciferol is found in Cucurbita pepo , Homo sapiens, Mus musculus and Solanum glaucophyllum. 25-Hydroxycholecalciferol was first documented in 1987 (PMID: 3040120). A hydroxycalciol that is calciol in which the hydrogen at position 25 has been replaced by a hydroxy group (PMID: 16886665) (PMID: 15585789) (PMID: 15384827) (PMID: 10469423) (PMID: 10089217) (PMID: 9543154).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 04191212102D          

 31 33  0  0  1  0            999 V2000
   -1.0890    1.2765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0890   -0.3735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4101   -0.2159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8950    0.4515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8035    0.8640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0890   -1.1985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8035    0.0390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8035   -1.6110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8035   -2.4360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0890   -2.8485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5179   -2.8485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0890   -3.6735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3745   -2.4360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5179   -3.6735    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8035   -4.0860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2324   -4.0860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3044    2.3565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4101    1.9440    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1246    2.3565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8390    1.9440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9825    2.3565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2680    1.1190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5535    2.3565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4101    1.1190    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1246    1.5315    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3745    0.0390    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3745   -0.7860    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3745    0.8640    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3745    1.6890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2680    1.9440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9825    1.5315    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 26 28  1  0  0  0  0
 28 24  1  0  0  0  0
 28  1  1  0  0  0  0
 26  2  1  0  0  0  0
 26  3  1  0  0  0  0
 24  4  1  0  0  0  0
  1  5  1  0  0  0  0
  2  6  2  0  0  0  0
  2  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  1  0  0  0  0
 10 13  2  0  0  0  0
 11 14  1  0  0  0  0
 12 15  1  0  0  0  0
 14 16  1  6  0  0  0
  3  4  1  0  0  0  0
  5  7  1  0  0  0  0
 14 15  1  0  0  0  0
 24 18  1  0  0  0  0
 18 17  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 23  1  0  0  0  0
 23 30  1  0  0  0  0
 30 21  1  0  0  0  0
 30 22  1  0  0  0  0
 24 25  1  6  0  0  0
 26 27  1  6  0  0  0
 28 29  1  1  0  0  0
 30 31  1  0  0  0  0
M  END


  Mrv0541 04191212102D          

 31 33  0  0  1  0            999 V2000
   -1.0890    1.2765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0890   -0.3735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4101   -0.2159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8950    0.4515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8035    0.8640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0890   -1.1985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8035    0.0390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8035   -1.6110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8035   -2.4360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0890   -2.8485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5179   -2.8485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0890   -3.6735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3745   -2.4360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5179   -3.6735    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8035   -4.0860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2324   -4.0860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3044    2.3565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4101    1.9440    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1246    2.3565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8390    1.9440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9825    2.3565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2680    1.1190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5535    2.3565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4101    1.1190    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1246    1.5315    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3745    0.0390    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3745   -0.7860    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3745    0.8640    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3745    1.6890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2680    1.9440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9825    1.5315    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 26 28  1  0  0  0  0
 28 24  1  0  0  0  0
 28  1  1  0  0  0  0
 26  2  1  0  0  0  0
 26  3  1  0  0  0  0
 24  4  1  0  0  0  0
  1  5  1  0  0  0  0
  2  6  2  0  0  0  0
  2  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  1  0  0  0  0
 10 13  2  0  0  0  0
 11 14  1  0  0  0  0
 12 15  1  0  0  0  0
 14 16  1  6  0  0  0
  3  4  1  0  0  0  0
  5  7  1  0  0  0  0
 14 15  1  0  0  0  0
 24 18  1  0  0  0  0
 18 17  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 23  1  0  0  0  0
 23 30  1  0  0  0  0
 30 21  1  0  0  0  0
 30 22  1  0  0  0  0
 24 25  1  6  0  0  0
 26 27  1  6  0  0  0
 28 29  1  1  0  0  0
 30 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0049938

> <DATABASE_NAME>
NP-MRD

> <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

> <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

> <FORMULA>
C27H44O2

> <MOLECULAR_WEIGHT>
400.6371

> <EXACT_MASS>
400.334130652

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
50.319516931050124

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(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

> <ALOGPS_LOGP>
6.71

> <JCHEM_LOGP>
5.654346069666669

> <ALOGPS_LOGS>
-5.26

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.53076846661296

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.384341369959035

> <JCHEM_PKA_STRONGEST_BASIC>
-0.9842558878714639

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
125.06059999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.20e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
25-hydroxyvitamin D3

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-12         0                                  
HETATM    1  C   UNK     0      -2.033   2.383   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.033  -0.697   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.766  -0.403   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.671   0.843   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.367   1.613   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.033  -2.237   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.367   0.073   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.367  -3.007   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.367  -4.547   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.033  -5.317   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.700  -5.317   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.033  -6.857   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.699  -4.547   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.700  -6.857   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.367  -7.627   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -6.034  -7.627   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -0.568   4.399   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.766   3.629   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.099   4.399   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.433   3.629   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.434   4.399   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.100   2.089   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.767   4.399   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.766   2.089   0.000  0.00  0.00           C+0
HETATM   25  H   UNK     0       2.099   2.859   0.000  0.00  0.00           H+0
HETATM   26  C   UNK     0      -0.699   0.073   0.000  0.00  0.00           C+0
HETATM   27  H   UNK     0      -0.699  -1.467   0.000  0.00  0.00           H+0
HETATM   28  C   UNK     0      -0.699   1.613   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -0.699   3.153   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.100   3.629   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       7.434   2.859   0.000  0.00  0.00           O+0
CONECT    1   28    5                                                       
CONECT    2   26    6    7                                                  
CONECT    3   26    4                                                       
CONECT    4   24    3                                                       
CONECT    5    1    7                                                       
CONECT    6    2    8                                                       
CONECT    7    2    5                                                       
CONECT    8    6    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9   12   13                                                  
CONECT   11    9   14                                                       
CONECT   12   10   15                                                       
CONECT   13   10                                                            
CONECT   14   11   16   15                                                  
CONECT   15   12   14                                                       
CONECT   16   14                                                            
CONECT   17   18                                                            
CONECT   18   24   17   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   23                                                       
CONECT   21   30                                                            
CONECT   22   30                                                            
CONECT   23   20   30                                                       
CONECT   24   28    4   18   25                                             
CONECT   25   24                                                            
CONECT   26   28    2    3   27                                             
CONECT   27   26                                                            
CONECT   28   26   24    1   29                                             
CONECT   29   28                                                            
CONECT   30   23   21   22   31                                             
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   66    0
END

View in JSmol

Synonyms

Value	Source
(3beta,5Z,7E)-9,10-Secocholesta-5,7,10(19)-triene-3,25-diol	ChEBI
(3S,5Z,7E)-9,10-Secocholesta-5,7,10-triene-3,25-diol	ChEBI
(5Z,7E)-(3S)-9,10-Secocholesta-5,7,10(19)-triene-3,25-diol	ChEBI
25(OH)D3	ChEBI
25-Hydroxycholecalciferol	ChEBI
25-Hydroxyvitamin D3	ChEBI
3-{2-[1-(5-hydroxy-1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-4-ylidene]-ethylidene}-4-methylene-cyclohexanol	ChEBI
Calcifediol	ChEBI
Calcifediol anhydrous	ChEBI
Calcifediolum	ChEBI
Rayaldee	ChEBI
(3S,5Z,7E)-9,10-Seco-5,7,10(19)-cholestatriene-3,25-diol	Kegg
(3b,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
25-Hydroxy-cholecalciferol	HMDB
5,6-cis-25-Hydroxyvitamin D3	HMDB
9,10-Secocholesta-5,7,10(19)-triene-3b,25-diol	HMDB
Calderol	HMDB
Didrogyl	HMDB
Hidroferol	HMDB
25 Hydroxyvitamin D3	HMDB
Calcifediol, (3 beta,5E,7E)-isomer	HMDB
Monohydrate, 25-hydroxycholecalciferol	HMDB
25-Hydroxycholecalciferol monohydrate	HMDB
Anhydrous, calcifediol	HMDB
Organon brand OF calcifediol	HMDB
25 Hydroxyvitamin D 3	HMDB
25-Hydroxyvitamin D 3	HMDB
Aventis brand OF calcifediol	HMDB
Calcifediol aventis brand	HMDB
Calcifediol organon brand	HMDB
Dedrogyl	HMDB
25 Hydroxycholecalciferol	HMDB
25 Hydroxycholecalciferol monohydrate	HMDB
Calcifediol faes brand	HMDB
Calcifediol, (3 alpha,5Z,7E)-isomer	HMDB
Faes brand OF calcifediol	HMDB
Calcidiol	MeSH

Chemical Formula

C₂₇H₄₄O₂

Average Mass

400.6371 Da

Monoisotopic Mass

400.33413 Da

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 Name

25-hydroxyvitamin D3

CAS Registry Number

19356-17-3

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

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

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Abelmoschus esculentus	FooDB	DTU Food
Abramis brama	FooDB	DTU Food
Acipenseridae	FooDB	DTU Food
Actinidia chinensis	FooDB	DTU Food
Agaricus bisporus	FooDB	DTU Food
Allium cepa L.	FooDB	DTU Food
Allium sativum	FooDB	DTU Food
Allium schoenoprasum	FooDB	DTU Food
Anacardium occidentale	FooDB	DTU Food
Ananas comosus	FooDB	DTU Food
Anarhichas lupus	FooDB	DTU Food
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	DTU Food
Anethum graveolens	FooDB	DTU Food
Anguilliformes	FooDB	DTU Food
Annona cherimola	FooDB	DTU Food
Anser anser	FooDB	FooDB
Anthriscus cerefolium	FooDB	DTU Food
Apium graveolens	FooDB	DTU Food
Apium graveolens var. rapaceum	FooDB	DTU Food
Apium graveolens var. secalinum	FooDB	DTU Food
Arachis hypogaea	FooDB	DTU Food
Armoracia rusticana	FooDB	DTU Food
Asparagus officinalis	FooDB	DTU Food
Astacidea	FooDB	DTU Food
Avena sativa L.	FooDB	DTU Food
Averrhoa carambola	FooDB	DTU Food
Belone belone	FooDB	DTU Food
Bertholletia excelsa	FooDB	DTU Food
Beta vulgaris ssp. cicla	FooDB	DTU Food
Bison bison	FooDB	FooDB
Bos taurus	FooDB	DTU Food
Bos taurus X Bison bison	FooDB	FooDB
Brachyura	FooDB	DTU Food
Brassica napus	FooDB	DTU Food
Brassica napus var. napus	FooDB	DTU Food
Brassica oleracea	FooDB	DTU Food
Brassica oleracea var. botrytis	FooDB	DTU Food
Brassica oleracea var. gemmifera	FooDB	DTU Food
Brassica oleracea var. gongylodes	FooDB	DTU Food
Brassica oleracea var. italica	FooDB	DTU Food
Brassica oleracea var. sabauda	FooDB	DTU Food
Brassica rapa	FooDB	DTU Food
Brassica rapa ssp. chinensis	FooDB	DTU Food
Brassica rapa var. rapa	FooDB	DTU Food
Bubalus bubalis	FooDB	FooDB
Cantharellus cibarius	FooDB	DTU Food
Capra aegagrus hircus	FooDB	FooDB
Capsicum annuum	FooDB	DTU Food
Carica papaya L.	FooDB	DTU Food
Caridea	FooDB	DTU Food
Carthamus tinctorius	FooDB	DTU Food
Carya illinoinensis	FooDB	DTU Food
Castanea	FooDB	DTU Food
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Cicer arietinum	FooDB	DTU Food
Cichorium endivia	FooDB	DTU Food
Cichorium intybus	FooDB	DTU Food
Cinnamomum	FooDB	DTU Food
Cirsium	FooDB	DTU Food
Citrullus lanatus	FooDB	DTU Food
Citrus ×limon (L.) Burm. f. (pro sp.)	FooDB	DTU Food
Citrus aurantiifolia	FooDB	DTU Food
Citrus limon	FooDB	DTU Food
Citrus paradisi	FooDB	DTU Food
Citrus reticulata	FooDB	DTU Food
Citrus X sinensis (L.) Osbeck (pro. sp.)	FooDB	DTU Food
Clupeinae	FooDB	DTU Food
Cocos nucifera	FooDB	DTU Food
Coffea arabica L.	FooDB	DTU Food
Coffea canephora	FooDB	DTU Food
Columba	FooDB	FooDB
Columbidae	FooDB	DTU Food
Coregonus	FooDB	DTU Food
Coriandrum sativum L.	FooDB	DTU Food
Corylus	FooDB	DTU Food
Cucumis melo	FooDB	DTU Food
Cucumis sativus L.	FooDB	DTU Food
Cucurbita	FooDB	DTU Food
Cucurbita pepo	Plant	KNApSAcK
Cyclopteridae	FooDB	DTU Food
Cydonia oblonga	FooDB	DTU Food
Cynara scolymus	FooDB	DTU Food
Daucus carota ssp. sativus	FooDB	DTU Food
Dioscorea	FooDB	DTU Food
Diospyros	FooDB	DTU Food
Dromaius novaehollandiae	FooDB	FooDB
Elaeis	FooDB	DTU Food
Engraulidae	FooDB	DTU Food
Equus caballus	FooDB	FooDB
Eriobotrya japonica	FooDB	DTU Food
Esox lucius	FooDB	DTU Food
Eucheuma	FooDB	DTU Food
Fagopyrum esculentum	FooDB	DTU Food
Ficus carica	FooDB	DTU Food
Foeniculum vulgare	FooDB	DTU Food
Fragaria x ananassa	FooDB	DTU Food
Gadiformes	FooDB	DTU Food
Gadus	FooDB	DTU Food
Gallus gallus	FooDB	DTU Food
Gastropoda	FooDB	DTU Food
Glycine max	FooDB	DTU Food
Gossypium	FooDB	DTU Food
Helianthus annuus L.	FooDB	DTU Food
Helianthus tuberosus	FooDB	DTU Food
Hippoglossus hippoglossus	FooDB	DTU Food
Homo sapiens	LOTUS Database	35616633
Hordeum vulgare	FooDB	DTU Food
Ipomoea batatas	FooDB	DTU Food
Juglans	FooDB	DTU Food
Juglans nigra L.	FooDB	DTU Food
Lactuca sativa	FooDB	DTU Food
Lagopus muta	FooDB	DTU Food
Lens culinaris	FooDB	DTU Food
Lepidium sativum	FooDB	DTU Food
Leporidae	FooDB	DTU Food
Lepus timidus	FooDB	DTU Food
Limanda limanda	FooDB	DTU Food
Linum usitatissimum	FooDB	DTU Food
Litchi chinensis	FooDB	DTU Food
Lota lota	FooDB	DTU Food
Malus	FooDB	DTU Food
Malus pumila	FooDB	DTU Food
Mangifera indica	FooDB	DTU Food
Manihot esculenta	FooDB	DTU Food
Medicago sativa	FooDB	DTU Food
Melanitta fusca	FooDB	FooDB
Melanogrammus aeglefinus	FooDB	DTU Food
Meleagris gallopavo	FooDB	DTU Food
Merlangius merlangus	FooDB	DTU Food
Micromesistius poutassou	FooDB	DTU Food
Microstomus kitt	FooDB	DTU Food
Molva molva	FooDB	DTU Food
Mus musculus	LOTUS Database	35616633
Musa x paradisiaca	FooDB	DTU Food
Myristica fragrans	FooDB	DTU Food
Mytilidae	FooDB	DTU Food
Nephropidae	FooDB	DTU Food
Nephrops norvegicus	FooDB	DTU Food
Numida meleagris	FooDB	FooDB
Octopus vulgaris	FooDB	DTU Food
Odocoileus	FooDB	FooDB
Olea europaea	FooDB	DTU Food
Oncorhynchus mykiss	FooDB	DTU Food
Opuntia	FooDB	DTU Food
Oryctolagus	FooDB	FooDB
Oryza sativa	FooDB	DTU Food
Ovis aries	FooDB	DTU Food
Panicum miliaceum	FooDB	DTU Food
Papaver	FooDB	DTU Food
Passiflora edulis	FooDB	DTU Food
Pastinaca sativa	FooDB	DTU Food
Perciformes	FooDB	DTU Food
Persea americana	FooDB	DTU Food
Petroselinum crispum	FooDB	DTU Food
Phaseolus vulgaris	FooDB	DTU Food
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Phoenix dactylifera	FooDB	DTU Food
Phyllostachys edulis	FooDB	DTU Food
Physalis	FooDB	DTU Food
Pinus	FooDB	DTU Food
Piper nigrum L.	FooDB	DTU Food
Pistacia vera	FooDB	DTU Food
Pisum sativum	FooDB	DTU Food
Pleuronectidae	FooDB	DTU Food
Pleuronectiformes	FooDB	DTU Food
Pleurotus ostreatus	FooDB	DTU Food
Pollachius	FooDB	DTU Food
Prunus armeniaca	FooDB	DTU Food
Prunus avium L.	FooDB	DTU Food
Prunus domestica	FooDB	DTU Food
Prunus dulcis	FooDB	DTU Food
Prunus persica	FooDB	DTU Food
Prunus persica var. nucipersica	FooDB	DTU Food
Psidium guajava	FooDB	DTU Food
Punica granatum	FooDB	DTU Food
Pyrus communis	FooDB	DTU Food
Ranidae	FooDB	DTU Food
Raphanus sativus var. longipinnatus	FooDB	DTU Food
Reinhardtius hippoglossoides	FooDB	DTU Food
Rheum rhabarbarum	FooDB	DTU Food
Ribes nigrum	FooDB	DTU Food
Ribes rubrum	FooDB	DTU Food
Ribes uva-crispa	FooDB	DTU Food
Rosa	FooDB	DTU Food
Rumex acetosa	FooDB	DTU Food
Saccharina japonica	FooDB	DTU Food
Salmonidae	FooDB	DTU Food
Salvelinus	FooDB	DTU Food
Salvelinus namaycush	FooDB	DTU Food
Sambucus nigra L.	FooDB	DTU Food
Sander lucioperca	FooDB	DTU Food
Scombridae	FooDB	DTU Food
Scophthalmus maximus	FooDB	DTU Food
Scorzonera hispanica	FooDB	DTU Food
Sebastes alutus	FooDB	DTU Food
Sebastes viviparus	FooDB	DTU Food
Secale cereale	FooDB	DTU Food
Sechium edule	FooDB	DTU Food
Sesamum indicum	FooDB	DTU Food
Siluriformes	FooDB	DTU Food
Solanum glaucophyllum	LOTUS Database	35616633
Solanum lycopersicum	FooDB	DTU Food
Solanum melongena	FooDB	DTU Food
Solanum tuberosum	FooDB	DTU Food
Spinacia oleracea	FooDB	DTU Food
Squalus acanthias	FooDB	DTU Food
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	DTU Food
Tamarindus indica	FooDB	DTU Food
Taraxacum officinale	FooDB	DTU Food
Thunnus	FooDB	DTU Food
Trisopterus esmarkii	FooDB	DTU Food
Triticum	FooDB	DTU Food
Triticum durum	FooDB	DTU Food
Vaccinium	FooDB	DTU Food
Vaccinium myrtillus	FooDB	DTU Food
Vaccinium vitis-idaea	FooDB	DTU Food
Vigna angularis	FooDB	DTU Food
Vigna radiata	FooDB	DTU Food
Vitis	FooDB	DTU Food
Zea mays L.	FooDB	DTU Food
Zingiber officinale	FooDB	DTU Food

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.

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 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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

External Links

HMDB ID

HMDB0003550

DrugBank ID

DB00146

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

17933

Good Scents ID

Not Available

References

General References

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. [PubMed:16886665 ]
DeLuca HF: Overview of general physiologic features and functions of vitamin D. Am J Clin Nutr. 2004 Dec;80(6 Suppl):1689S-96S. [PubMed:15585789 ]
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. [PubMed:15384827 ]
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. doi: 10.1046/j.1525-1470.1999.00084.x. [PubMed:10469423 ]
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. doi: 10.1007/s002239900618. [PubMed:10089217 ]
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. doi: 10.1210/jcem.83.4.4725. [PubMed:9543154 ]
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. doi: 10.1016/0167-4889(87)90031-0. [PubMed:3040120 ]
Kemmis CM, Salvador SM, Smith KM, Welsh J: Human mammary epithelial cells express CYP27B1 and are growth inhibited by 25-hydroxyvitamin D-3, the major circulating form of vitamin D-3. J Nutr. 2006 Apr;136(4):887-92. doi: 10.1093/jn/136.4.887. [PubMed:16549446 ]
Matsumura T, Kato T, Sugiyama N, Tasaka-Fujita M, Murayama A, Masaki T, Wakita T, Imawari M: 25-Hydroxyvitamin D3 suppresses hepatitis C virus production. Hepatology. 2012 Oct;56(4):1231-9. doi: 10.1002/hep.25763. [PubMed:22487892 ]
Thienpont LM, Stepman HC, Vesper HW: Standardization of measurements of 25-hydroxyvitamin D3 and D2. Scand J Clin Lab Invest Suppl. 2012;243:41-9. doi: 10.3109/00365513.2012.681950. [PubMed:22536761 ]
Jones AP, Palmer D, Zhang G, Prescott SL: Cord blood 25-hydroxyvitamin D3 and allergic disease during infancy. Pediatrics. 2012 Nov;130(5):e1128-35. doi: 10.1542/peds.2012-1172. Epub 2012 Oct 22. [PubMed:23090338 ]
de Brito Galvao JF, Nagode LA, Schenck PA, Chew DJ: Calcitriol, calcidiol, parathyroid hormone, and fibroblast growth factor-23 interactions in chronic kidney disease. J Vet Emerg Crit Care (San Antonio). 2013 Mar-Apr;23(2):134-62. doi: 10.1111/vec.12036. [PubMed:23566108 ]

Showing NP-Card for 25-Hydroxycholecalciferol (NP0049938)

MOL for NP0049938 (25-Hydroxycholecalciferol)

3D MOL for NP0049938 (25-Hydroxycholecalciferol)

3D SDF for NP0049938 (25-Hydroxycholecalciferol)

3D-SDF for NP0049938 (25-Hydroxycholecalciferol)

PDB for NP0049938 (25-Hydroxycholecalciferol)

3D PDB for NP0049938 (25-Hydroxycholecalciferol)

SMILES for NP0049938 (25-Hydroxycholecalciferol)

INCHI for NP0049938 (25-Hydroxycholecalciferol)

Structure for NP0049938 (25-Hydroxycholecalciferol)

3D Structure for NP0049938 (25-Hydroxycholecalciferol)