ContaminantDB: 8-Dehydrocholesterol

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (25)XML

Record Information

Version

1.0

Creation Date

2014-08-29 06:18:25 UTC

Update Date

2026-04-06 13:28:12 UTC

Accession Number

CHEM003269

Identification

Common Name

8-Dehydrocholesterol

Class

Small Molecule

Description

8-Dehydrocholesterol belongs to the cholestane steroids, a subclass of steroids and steroid derivatives within the organic compounds. This endogenous solid has the formula C27H44O and an average molecular weight of 384.64 g/mol. It is further classified under the superclass of lipids and lipid-like molecules.

Contaminant Sources

FooDB Chemicals
T3DB toxins

Contaminant Type

Animal Toxin
Food Toxin
Metabolite
Natural Compound
Organic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3b-Cholesta-5,8-dien-3-ol	HMDB
Cholesta-5,8-dien-3 beta-ol	MeSH, HMDB

Chemical Formula

C₂₇H₄₄O

Average Molecular Mass

384.638 g/mol

Monoisotopic Mass

384.339 g/mol

CAS Registry Number

70741-38-7

IUPAC Name

Not Available

Traditional Name

8-dehydrocholesterol

SMILES

[H][C@@]1(CC[C@@]2([H])C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)CC1=CC3)[C@H](C)CCCC(C)C

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/h9,18-19,21,23-24,28H,6-8,10-17H2,1-5H3/t19-,21+,23-,24+,26+,27-/m1/s1

InChI Key

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

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Cholesterol and derivatives (LMST01010242 )

Biological Properties

Status

Detected and Not Quantified

Origin

Endogenous

Cellular Locations

Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB Link	KEGG Link
Steroid Biosynthesis	SMP00023	map00100
CHILD Syndrome	SMP00387	Not Available
Chondrodysplasia Punctata II, X Linked Dominant (CDPX2)	SMP00388	Not Available
Smith-Lemli-Opitz Syndrome (SLOS)	SMP00389	Not Available
Steroid Biosynthesis	SMP0000023	Not Available
Smith-Lemli-Opitz Syndrome (SLOS)	SMP0000389	Not Available
CHILD Syndrome	SMP0000387	Not Available
Desmosterolosis	SMP0000386	Not Available
Chondrodysplasia Punctata II, X-Linked Dominant (CDPX2)	SMP0000388	Not Available
Lysosomal Acid Lipase Deficiency (Wolman Disease)	SMP0000319	Not Available
Ibandronate Action Pathway	SMP0000079	Not Available
Simvastatin Action Pathway	SMP0000082	Not Available
Pravastatin Action Pathway	SMP0000089	Not Available
Rosuvastatin Action Pathway	SMP0000092	Not Available
Alendronate Action Pathway	SMP0000095	Not Available
Hypercholesterolemia	SMP0000209	Not Available
Lovastatin Action Pathway	SMP0000099	Not Available
Zoledronate Action Pathway	SMP0000107	Not Available
Cerivastatin Action Pathway	SMP0000111	Not Available
Risedronate Action Pathway	SMP0000112	Not Available
Pamidronate Action Pathway	SMP0000117	Not Available
Fluvastatin Action Pathway	SMP0000119	Not Available
Cholesteryl Ester Storage Disease	SMP0000508	Not Available
Hyper-IgD Syndrome	SMP0000509	Not Available
Mevalonic Aciduria	SMP0000510	Not Available
Wolman Disease	SMP0000511	Not Available
Smith-Lemli-Opitz Syndrome (SLOS)	SMP0125635	Not Available
CHILD Syndrome	SMP0125637	Not Available
Desmosterolosis	SMP0125638	Not Available
Chondrodysplasia Punctata II, X-Linked Dominant (CDPX2)	SMP0125639	Not Available
Lysosomal Acid Lipase Deficiency (Wolman Disease)	SMP0125640	Not Available
Hypercholesterolemia	SMP0125641	Not Available
Hyper-IgD Syndrome	SMP0125642	Not Available
Mevalonic Aciduria	SMP0125643	Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.00091 g/L	ALOGPS
logP	6.91	ALOGPS
logP	6.66	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	18.27	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	121.2 m³·mol⁻¹	ChemAxon
Polarizability	50.14 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ar0-1019000000-8455a6c27493f97ebe56	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-002f-3104900000-efe703ec411e4c08c1ab	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014r-0009000000-8f5b8c3c66952dc51dc0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05p9-3239000000-83a847e9f50d75c56b64	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-5249000000-d434b4187b0bc28431c4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0009000000-e7c8524cf153f94d3913	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0009000000-484d145862cff531746a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0gb9-1009000000-9618317ed2447b79a252	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0009000000-4d7a5f3b63c0fb62f1d7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0009000000-4d7a5f3b63c0fb62f1d7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-0009000000-5f56c8ce69939caba813	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00kr-0009000000-76127d016864d5ef3d22	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05g0-8469000000-301b48e0bb654ed1e226	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4l-9860000000-09ecca53ca89272c952c	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

This is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0002027

FooDB ID

FDB022805

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

114943

ChEBI ID

89982

PubChem Compound ID

129846

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. 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.

2. Haas D, Armbrust S, Haas JP, Zschocke J, Muhlmann K, Fusch C, Neumann LM: Smith-Lemli-Opitz syndrome with a classical phenotype, oesophageal achalasia and borderline plasma sterol concentrations. J Inherit Metab Dis. 2005;28(6):1191-6.

3. Sikora DM, Pettit-Kekel K, Penfield J, Merkens LS, Steiner RD: The near universal presence of autism spectrum disorders in children with Smith-Lemli-Opitz syndrome. Am J Med Genet A. 2006 Jul 15;140(14):1511-8.

4. Chevy F, Humbert L, Wolf C: Sterol profiling of amniotic fluid: a routine method for the detection of distal cholesterol synthesis deficit. Prenat Diagn. 2005 Nov;25(11):1000-6.

8-Dehydrocholesterol (CHEM003269)

Structure for CHEM003269: 8-Dehydrocholesterol