MiMeDB: Showing metabocard for 7,8-Didehydrodesmosterol (MMDBc0033507)

Microbial

Human

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:51:28 UTC

Update Date

2025-01-15 20:21:36 UTC

Metabolite ID

MMDBc0033507

Metabolite Identification

Common Name

7,8-Didehydrodesmosterol

Description

7-Dehydrodesmosterol is a sterol intermediate in the biosynthesis of steroids. 7-Dehydrodesmosterol is a substrate of the enzyme 24-dehydrocholesterol reductase (EC:1.3.1.72), an important enzyme in the biosynthesis of Cholesterol. Cholesterol is synthesized from either Lathosterol, 7-Dehydrocholesterol, Desmosterol or Cholestenol by the enzyme 3beta-hydroxysterol delta7 reductase (EC 1.3.1.21, Dhcr7). The Smith-Lemli-Opitz syndrome (SLOS, OMIM 270400 ) is caused by a genetic defect in cholesterol biosynthesis; mutations in the enzyme 3beta-hydroxysterol delta7 reductase lead to a failure of cholesterol synthesis, with an accumulation of precursor sterols, such as 7-Dehydrodesmosterol. SLOS results in craniofacial, limb as well as major organ defects, including the brain. In individuals with this syndrome, mental retardation, as well as other CNS dysfunction, is almost 100% prevalent. (PMID: 15862627 , 17197219 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Molecular Formula

C₂₇H₄₂O

Average Mass

382.6218

Monoisotopic Mass

382.323566

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

1715-86-2

SMILES

Not Available

InChI Identifier

InChI=1S/C27H42O/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/h7,9-10,19,21,23-25,28H,6,8,11-17H2,1-5H3

InChI Key

RUSSPKPUXDSHNC-UHFFFAOYSA-N

Chemical Taxonomy

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Not Available

Spectra

Not Available

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (eluted)	2025-10-24	316.2
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-24	37.1
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-24	696.7
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-24	1029.2
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-24	1026.0
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (eluted)	2025-10-24	757.1
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	3632.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (void)	2025-10-24	93.3
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-24	380.3
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	1034.0
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	724.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	319.0
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	303.5
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (void)	2025-10-24	8.7
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	297.1
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	580.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	564.2
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-24	1863.4
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-24	2068.1

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	7,8-Didehydrodesmosterol_TMS_1	CC(C)=CCCC(C)C1CCC2C3=CC=C4CC(O[Si](C)(C)C)CCC4(C)C3CCC21C	standard non polar	2025-10-24	1325.46
Gas Chromatography	7,8-Didehydrodesmosterol_TMS_1	CC(C)=CCCC(C)C1CCC2C3=CC=C4CC(O[Si](C)(C)C)CCC4(C)C3CCC21C	standard polar	2025-10-24	2920.83

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0020065	5a-Cholesta-7,24-dien-3b-ol	7,8-Didehydrodesmosterol	Delta(7)-sterol 5(6)-desaturase ERG3	Desaturation	PathBank	31602464

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

Not Available

General References

Yu H, Wessels A, Tint GS, Patel SB: Partial rescue of neonatal lethality of Dhcr7 null mice by a nestin promoter-driven DHCR7 transgene expression. Brain Res Dev Brain Res. 2005 Apr 21;156(1):46-60. doi: 10.1016/j.devbrainres.2005.01.012. [PubMed:15862627 ]
Solca C, Pandit B, Yu H, Tint GS, Patel SB: Loss of apolipoprotein E exacerbates the neonatal lethality of the Smith-Lemli-Opitz syndrome mouse. Mol Genet Metab. 2007 May;91(1):7-14. doi: 10.1016/j.ymgme.2006.11.009. Epub 2007 Jan 2. [PubMed:17197219 ]

Showing metabocard for 7,8-Didehydrodesmosterol (MMDBc0033507)

MOL for #<Metabolite:0x00005624ca127e98>

3D MOL for #<Metabolite:0x00005624ca127e98>

3D SDF for #<Metabolite:0x00005624ca127e98>

3D-SDF for #<Metabolite:0x00005624ca127e98>

PDB for #<Metabolite:0x00005624ca127e98>

3D PDB for #<Metabolite:0x00005624ca127e98>

SMILES for #<Metabolite:0x00005624ca127e98>

INCHI for #<Metabolite:0x00005624ca127e98>

Structure for #<Metabolite:0x00005624ca127e98>

3D Structure for #<Metabolite:0x00005624ca127e98>