MiMeDB: Showing metabocard for 7-Dehydrocholesterol (MMDBc0049997)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-04-29 23:10:04 UTC

Update Date

2024-10-17 07:33:11 UTC

Metabolite ID

MMDBc0049997

Metabolite Identification

Common Name

7-Dehydrocholesterol

Description

7-Dehydrocholesterol (7-DHC), also known as provitamin D3 or 5,7-cholestadien-3-b-ol, belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Thus, 7-dehydrocholesterol is also classified as a sterol. 7-Dehydrocholesterol is known as a zoosterol, meaning that it is a sterol isolated from animals (to distinguish those sterols isolated from plants which are called phytosterols). 7-DHC functions in the serum as a cholesterol precursor and is photochemically converted to vitamin D3 in the skin. Therefore 7-DHC functions as provitamin-D3. The presence of 7-DHC in human skin enables humans and other mammals to manufacture vitamin D3 (cholecalciferol) from ultraviolet rays in the sun light, via an intermediate isomer pre-vitamin D3. 7-DHC absorbs UV light most effectively at wavelengths between 290 and 320 nm and, thus, the production of vitamin D3 will occur primarily at those wavelengths (PMID: 9625080 ). The two most important factors that govern the generation of pre-vitamin D3 are the quantity (intensity) and quality (appropriate wavelength) of the UVB irradiation reaching the 7-dehydrocholesterol deep in the stratum basale and stratum spinosum (PMID: 9625080 ). 7-DHC is also found in the milk of several mammalian species, including cows (PMID: 10999630 ; PMID: 225459 ). It was discovered by Nobel-laureate organic chemist Adolf Windaus. 7-DHC can be produced by animals and plants via different pathways (PMID: 23717318 ). It is not produced by fungi in significant amounts. 7-DHC is made by some algae and can also be produced by some bacteria.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(3beta)-Cholesta-5,7-dien-3-ol	ChEBI
5,7-Cholestadien-3-beta-ol	ChEBI
5,7-Cholestadien-3beta-ol	ChEBI
Provitamin D3	ChEBI
Cholesta-5,7-dien-3beta-ol	Kegg
(3b)-Cholesta-5,7-dien-3-ol	Generator
(3Β)-cholesta-5,7-dien-3-ol	Generator
5,7-Cholestadien-3-b-ol	Generator
5,7-Cholestadien-3-β-ol	Generator
5,7-Cholestadien-3b-ol	Generator
5,7-Cholestadien-3β-ol	Generator
Cholesta-5,7-dien-3b-ol	Generator
Cholesta-5,7-dien-3β-ol	Generator
(-)-7-Dehydrocholesterol	HMDB
10,13-Dimethyl-17-(6-methylheptan-2-yl)-2,3,4,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-ol	HMDB
17-(1,5-Dimethylhexyl)-10,13-dimethyl-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol	HMDB
5,7-Cholestandien-3-ol	HMDB
5,7-Cholestandien-3beta-ol	HMDB
7,8-Dehydro-cholesterol	HMDB
7,8-Didehydrocholesterol	HMDB
7-Dehydro-cholesterol	HMDB
7-Dehydrocholesterin	HMDB
7DHC	HMDB
Cholesta-5,7-dien-3 beta -ol	HMDB
Cholesta-5,7-dien-3-beta-ol	HMDB
Cholesta-5,7-dien-3-ol	HMDB
Dehydrocholesterin	HMDB
Dehydrocholesterol	HMDB
Delta5,7-Cholestadien-3beta-ol	HMDB
Delta5,7-Cholesterol	HMDB
Delta7-Cholesterol	HMDB
Provitamin-D3	HMDB
Provitamin D(3)	HMDB
Cholesta-5,7-dien-3 beta-ol	HMDB
7-Dehydrocholesterol, (3beta,10alpha)-isomer	HMDB
7-Dehydrocholesterol, (3beta,9beta,10alpha)-isomer	HMDB
7-DHC	HMDB
7-Dehydrocholesterol, (3alpha)-isomer	HMDB
7-Dehydrocholesterol, (3beta,9beta)-isomer	HMDB

Molecular Formula

C₂₇H₄₄O

Average Mass

384.6377

Monoisotopic Mass

384.33921603

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

434-16-2

SMILES

Not Available

InChI Identifier

InChI=1S/C27H44O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h9-10,18-19,21,23-25,28H,6-8,11-17H2,1-5H3/t19-,21+,23-,24+,25+,26+,27-/m1/s1

InChI Key

UCTLRSWJYQTBFZ-DDPQNLDTSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Cholestane steroids

Direct Parent

Cholesterols and derivatives

Alternative Parents

Substituents

Cholesterol
Cholesterol-skeleton
3-hydroxy-delta-5-steroid
3-hydroxy-delta-7-steroid
3-beta-hydroxysteroid
3-beta-hydroxy-delta-5-steroid
3-hydroxysteroid
Hydroxysteroid
Delta-7-steroid
Delta-5-steroid
Cyclic alcohol
Secondary alcohol
Alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

cholestanoid (CHEBI:17759 )
3beta-sterol (CHEBI:17759 )
Vitamin D3 and derivatives (C01164 )
Cholestane and derivatives (C01164 )
Cholesterol and derivatives (LMST01010069 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Not Available

Spectra

Not Available

Biological Properties

Cellular Locations

Cytoplasm
Endoplasmic reticulum
Extracellular
Membrane

Biospecimen Locations

Adrenal Gland
Blood
Brain
Cerebrospinal Fluid (CSF)
Epidermis
Feces
Fibroblasts
Liver
Testis
Urine

Tissue Locations

Adrenal Gland
Brain
Epidermis
Fibroblasts
Liver
Testis

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191714	Hydroxymethylglutaryl-CoA synthase, mitochondrial	Enzyme	P54868	Homo sapiens
MMDBp0191806	Lathosterol oxidase	Unknown	O75845	Homo sapiens
MMDBp0192106	Non-specific lipid-transfer protein	Enzyme	P22307	Homo sapiens
MMDBp0192195	7-dehydrocholesterol reductase	Enzyme	Q9UBM7	Homo sapiens
MMDBp0192362	Cholesterol side-chain cleavage enzyme, mitochondrial	Unknown	P05108	Homo sapiens
MMDBp0193337	Delta(24)-sterol reductase	Unknown	Q15392	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank
Kandutsch-Russell Pathway (Cholesterol Biosynthesis)

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0000670	7-Dehydrocholesterol	Cholesterol	7-dehydrocholesterol reductase	VMH	15670717
MMDBr0001592	Lathosterol	7-Dehydrocholesterol	cytochrome P450, family 7, subfamily A, polypeptide 1	VMH	10344195
MMDBr0002036	7-Dehydrocholesterol	Previtamin D3	Not Available	VMH	6281884
MMDBr0004198	7-Dehydrocholesterol	27Alpha-Hydroxy-7-Dehydrocholesterol	Not Available	VMH	11254748 12581873
MMDBr0009545	Lathosterol	7-Dehydrocholesterol	sterol-C5-desaturase	VMH; KEGG	30371894
MMDBr0009546	Lathosterol	7-Dehydrocholesterol	sterol-C5-desaturase	VMH; KEGG	30371894
MMDBr0009547	7-Dehydrocholesterol	Cholesterol	7-dehydrocholesterol reductase	VMH; KEGG	30371894
MMDBr0009660	7-Dehydrocholesterol	Vitamin D3	Not Available	VMH	30371894

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Smith-lemli-opitz syndrome		Association	Human Cerebrospinal Fluid (CSF)	HMDB	9266395
Smith-lemli-opitz syndrome	Increased	Association	Human Blood	HMDB	11590227

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites
Viruses/Bamfordvirae	Nucleocytoviricota	1
Eukaryota/Fungi	Basidiomycota	11	Human feces
Eukaryota/Fungi	Ascomycota	3

Exposure Sources

Source Type	Activity	Data Source	Reference
Cosmetics	Not Available	U.S. Environmental Protection Agency	CompTox
Domestics	Not Available	U.S. Environmental Protection Agency	CompTox
Domestics	Not Available	U.S. Environmental Protection Agency	CompTox
Cosmetics	Not Available	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB
Human Blood	Detected and Quantified	0.21				uM	Children (1-13 years old)	Male	Lathosterolosis	HMDB	24142275
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.3 +/- 0.2		0.1	0.6	uM	Infant (0-1 year old)	Both	Smith-Lemli-Opitz syndrome	HMDB	9266395
Human Blood	Detected and Quantified	369.0		46.0	1220.0	uM	Adult (>18 years old)	Both	Smith-Lemli-Opitz syndrome	HMDB	11590227
Human Blood	Detected and Quantified	<0.65				uM	Children (1-13 years old)	Male	Normal	HMDB	24142275
Human Cerebrospinal fluid (csf)	Detected and Quantified			0	0.02	uM	Adult (>18 years old)	Both	Normal	HMDB	10946022
Human Urine	Detected and Quantified	0.029		0.0068	0.051	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	16451140
Human Blood	Detected and Quantified	5.0	2.2			uM	Adult (>18 years old)	Both	Normal	HMDB	11590227
Human Adrenal gland	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Brain	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Epidermis	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Fibroblasts	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Liver	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Testis	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0000032

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021882

KNApSAcK ID

C00023747

Chemspider ID

Not Available

KEGG Compound ID

C01164

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

7-Dehydrocholesterol

METLIN ID

Not Available

PubChem Compound

439423

PDB ID

Not Available

ChEBI ID

17759

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Adachi A, Kobayashi T: Identification of vitamin D3 and 7-dehydrocholesterol in cow's milk by gas chromatography-mass spectrometry and their quantitation by high-performance liquid chromatography. J Nutr Sci Vitaminol (Tokyo). 1979;25(2):67-78. doi: 10.3177/jnsv.25.67. [PubMed:225459 ]
Moody JP, Humphries CA, Allan SM, Paterson CR: Determination of 7-dehydrocholesterol in human skin by high-performance liquid chromatography. J Chromatogr. 1990 Aug 24;530(1):19-27. doi: 10.1016/s0378-4347(00)82298-7. [PubMed:2277111 ]
van Rooij A, Nijenhuis AA, Wijburg FA, Schutgens RB: Highly increased CSF concentrations of cholesterol precursors in Smith-Lemli-Opitz syndrome. J Inherit Metab Dis. 1997 Aug;20(4):578-80. doi: 10.1023/a:1005355026186. [PubMed:9266395 ]
Paterson CR, Moody JP, Pennington CR: Skin content of 7-dehydrocholesterol in patients with malabsorption. Nutrition. 1997 Sep;13(9):771-3. doi: 10.1016/s0899-9007(97)00186-x. [PubMed:9290088 ]
Norman AW: Sunlight, season, skin pigmentation, vitamin D, and 25-hydroxyvitamin D: integral components of the vitamin D endocrine system. Am J Clin Nutr. 1998 Jun;67(6):1108-10. doi: 10.1093/ajcn/67.6.1108. [PubMed:9625080 ]
Andersson HC, Frentz J, Martinez JE, Tuck-Muller CM, Bellizaire J: Adrenal insufficiency in Smith-Lemli-Opitz syndrome. Am J Med Genet. 1999 Feb 19;82(5):382-4. [PubMed:10069708 ]
Jira PE, Wevers RA, de Jong J, Rubio-Gozalbo E, Janssen-Zijlstra FS, van Heyst AF, Sengers RC, Smeitink JA: Simvastatin. A new therapeutic approach for Smith-Lemli-Opitz syndrome. J Lipid Res. 2000 Aug;41(8):1339-46. [PubMed:10946022 ]
Gomis DB, Fernandez MP, Gutierrez Alvarez MD: Simultaneous determination of fat-soluble vitamins and provitamins in milk by microcolumn liquid chromatography. J Chromatogr A. 2000 Sep 1;891(1):109-14. doi: 10.1016/s0021-9673(00)00623-3. [PubMed:10999630 ]
GarciaFuentes E, icioso Recio MV, del Castillo Acedo Del Olmo E, atas Jurado MM, Arana Aguera M, Lopez Lopez J: [Biochemical diagnosis of Smith-Lemli-Opitz syndrome in a patient with congenital adrenal hyperplasia]. An Esp Pediatr. 2000 Nov;53(5):482-7. [PubMed:11141372 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. doi: 10.1038/35036052. [PubMed:11413487 ]
Johnson DW, ten Brink HJ, Jakobs C: A rapid screening procedure for cholesterol and dehydrocholesterol by electrospray ionization tandem mass spectrometry. J Lipid Res. 2001 Oct;42(10):1699-705. [PubMed:11590227 ]
Lehmann B, Genehr T, Knuschke P, Pietzsch J, Meurer M: UVB-induced conversion of 7-dehydrocholesterol to 1alpha,25-dihydroxyvitamin D3 in an in vitro human skin equivalent model. J Invest Dermatol. 2001 Nov;117(5):1179-85. doi: 10.1046/j.0022-202x.2001.01538.x. [PubMed:11710930 ]
Muzzin KB, Harper LF: Smith-Lemli-Opitz syndrome: a review, case report and dental implications. Spec Care Dentist. 2003;23(1):22-7. doi: 10.1111/j.1754-4505.2003.tb00285.x. [PubMed:12887150 ]
Dietschy JM, Turley SD: Thematic review series: brain Lipids. Cholesterol metabolism in the central nervous system during early development and in the mature animal. J Lipid Res. 2004 Aug;45(8):1375-97. doi: 10.1194/jlr.R400004-JLR200. [PubMed:15254070 ]
Jezela-Stanek A, Malunowicz EM, Ciara E, Popowska E, Goryluk-Kozakiewicz B, Spodar K, Czerwiecka M, Jezuita J, Nowaczyk MJ, Krajewska-Walasek M: Maternal urinary steroid profiles in prenatal diagnosis of Smith-Lemli-Opitz syndrome: first patient series comparing biochemical and molecular studies. Clin Genet. 2006 Jan;69(1):77-85. doi: 10.1111/j.1399-0004.2006.00551.x. [PubMed:16451140 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. doi: 10.1194/jlr.R600022-JLR200. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. doi: 10.1194/jlr.R700005-JLR200. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
O'Byrne SM, Blaner WS: Retinol and retinyl esters: biochemistry and physiology. J Lipid Res. 2013 Jul;54(7):1731-43. doi: 10.1194/jlr.R037648. Epub 2013 Apr 26. [PubMed:23625372 ]
Japelt RB, Jakobsen J: Vitamin D in plants: a review of occurrence, analysis, and biosynthesis. Front Plant Sci. 2013 May 13;4:136. doi: 10.3389/fpls.2013.00136. eCollection 2013. [PubMed:23717318 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
Linda T. Welson (2006). Triglycerides and Cholesterol Research. Nova Science Publishers Inc..

Showing metabocard for 7-Dehydrocholesterol (MMDBc0049997)

MOL for #<Metabolite:0x00007fdb4c45b9b8>

3D MOL for #<Metabolite:0x00007fdb4c45b9b8>

3D SDF for #<Metabolite:0x00007fdb4c45b9b8>

3D-SDF for #<Metabolite:0x00007fdb4c45b9b8>

PDB for #<Metabolite:0x00007fdb4c45b9b8>

3D PDB for #<Metabolite:0x00007fdb4c45b9b8>

SMILES for #<Metabolite:0x00007fdb4c45b9b8>

INCHI for #<Metabolite:0x00007fdb4c45b9b8>

Structure for #<Metabolite:0x00007fdb4c45b9b8>

3D Structure for #<Metabolite:0x00007fdb4c45b9b8>