7-DEHYDROCHOLESTEROL

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C27H44O
Molecular Weight	384.6377
Optical Activity	UNSPECIFIED
Defined Stereocenters	7 / 7
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]1(CC[C@@]2([H])C3=CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C

InChI

InChIKey=UCTLRSWJYQTBFZ-DDPQNLDTSA-N

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

HIDE SMILES / InChI

Molecular Formula	C27H44O
Molecular Weight	384.6377
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	7 / 7
E/Z Centers	0
Optical Activity	UNSPECIFIED

Approval Year

PubMed

Title	Date	PubMed
Cholesterol 7alpha-hydroxylase. 2. Biochemical properties and participation of endogenous cholesterol in the assay in vitro.	1975 Jun 16	1175606
[Biochemical diagnosis of Smith-Lemli-Opitz syndrome in a patient with congenital adrenal hyperplasia].	2000 Nov	11141372
Comparative behavior of sterols in phosphatidylcholine-sterol monolayer films.	2001 Apr 2	11286977
A little cholesterol in time...	2001 Dec	11767236
Expression of Sonic Hedgehog downstream genes is modified in rat embryos exposed in utero to a distal inhibitor of cholesterol biosynthesis.	2001 Feb	11169843
Frequency gradients of DHCR7 mutations in patients with Smith-Lemli-Opitz syndrome in Europe: evidence for different origins of common mutations.	2001 Jan	11175299
Fatty acid steryl, stanyl, and steroid esters by esterification and transesterification in vacuo using Candida rugosa lipase as catalyst.	2001 Jan	11170561
Carrier frequency of the common mutation IVS8-1G>C in DHCR7 and estimate of the expected incidence of Smith-Lemli-Opitz syndrome.	2001 Jan	11161831
Neutral sterols of rat epididymis. High concentrations of dehydrocholesterols in rat caput epididymidis.	2001 Jul	11441136
[Smith-Lemli-Opitz syndrome].	2001 Jul	11412481
The interactions of amphotericin B with various sterols in relation to its possible use in anticancer therapy.	2001 Jul 2	11429202
Incidence of Smith-Lemli-Opitz syndrome in Ontario, Canada.	2001 Jul 22	11471166
Woc (without children) gene control of ecdysone biosynthesis in Drosophila melanogaster.	2001 Jul 5	11476936
The Smith-Lemli-Opitz syndrome: a novel metabolic way of understanding developmental biology, embryogenesis, and dysmorphology.	2001 Jun	11453964
Mutations in the human DHCR7 gene.	2001 Mar	11241839
Biochemical, phenotypic and neurophysiological characterization of a genetic mouse model of RSH/Smith--Lemli--Opitz syndrome.	2001 Mar 15	11230174
Effects of treatment with deoxycholic acid and chenodeoxycholic acid on the hepatic synthesis of cholesterol and bile acids in healthy subjects.	2001 May	11343248
Observations on serum 25-hydroxyvitamin D and calcium concentrations from wild-caught and captive neotropical bats, Artibeus jamaicensis.	2001 May	11316428
Novel mutation in the Delta7-dehydrocholesterol reductase gene in an Australian patient with Smith-Lemli-Opitz syndrome.	2001 Nov 1	11746018
A cholesterol-lowering drug reduces beta-amyloid pathology in a transgenic mouse model of Alzheimer's disease.	2001 Oct	11592856
A rapid screening procedure for cholesterol and dehydrocholesterol by electrospray ionization tandem mass spectrometry.	2001 Oct	11590227
Adrenal insufficiency and hypertension in a newborn infant with Smith-Lemli-Opitz syndrome.	2001 Oct 15	11745994
7-Dehydrocholesterol-dependent proteolysis of HMG-CoA reductase suppresses sterol biosynthesis in a mouse model of Smith-Lemli-Opitz/RSH syndrome.	2001 Sep	11560960
Smith-Lemli-Opitz (RHS) syndrome: holoprosencephaly and homozygous IVS8-1G-->C genotype.	2001 Sep 15	11562938
Cholesterol catabolism in patients with acute myelogenous leukemia and hypocholesterolemia: suppressed levels of a circulating marker for bile acid synthesis.	2001 Sep 20	11463495
Effect of the structure of natural sterols and sphingolipids on the formation of ordered sphingolipid/sterol domains (rafts). Comparison of cholesterol to plant, fungal, and disease-associated sterols and comparison of sphingomyelin, cerebrosides, and ceramide.	2001 Sep 7	11432870
Evolution of UV-B regulation and protection in plants.	2002	12575721
Cholesterol storage defect in RSH/Smith-Lemli-Opitz syndrome fibroblasts.	2002 Apr	12051964
Reductive metabolism of an alpha,beta-ketoalkyne, 4-phenyl-3-butyn-2-one, by rat liver preparations.	2002 Apr	11901095
Two novel mutations of the human delta7-sterol reductase (DHCR7) gene in children with Smith-Lemli-Opitz syndrome.	2002 Aug	12270273
Developmental sensitivity of associative learning to cholesterol synthesis inhibitors.	2002 Feb 1	11809505
Smith-Lemli-Opitz syndrome: new mutation with a mild phenotype.	2002 Feb 15	11857552
Brain sterols in the AY-9944 rat model of atypical absence seizures.	2002 Jan	11879380
Unbalanced translocation (3;5)(q26.1;p14): a clinical report.	2002 Jul 15	12116209
Cholesterol induce oligomerization of Vibrio vulnificus cytolysin specifically.	2002 Jul 31	12216116
Ternary gradient elution markedly improves silver-ion high performance liquid chromatography of unsaturated sterols.	2002 Oct	12234627
Demonstration of UVB-induced synthesis of 1 alpha,25-dihydroxyvitamin D3 (calcitriol) in human skin by microdialysis.	2003 Apr	12709817
Yeast-like symbiotes as a sterol source in anobiid beetles (Coleoptera, Anobiidae): possible metabolic pathways from fungal sterols to 7-dehydrocholesterol.	2003 Apr	12655605
Abnormal serotonergic development in a mouse model for the Smith-Lemli-Opitz syndrome: implications for autism.	2003 Dec	14659996
Novel sterols synthesized via the CYP27A1 metabolic pathway.	2003 Dec 1	14622972
Molecular, biochemical, and phenotypic analysis of a hemizygous male with a severe atypical phenotype for X-linked dominant Conradi-Hunermann-Happle syndrome and a mutation in EBP.	2003 Jan 30	12503101
Susceptibilities of phospholipid vesicles containing different sterols to amphotericin B-loaded lysophosphatidylcholine micelles.	2003 Jul	12944378
Lathosterolosis: an inborn error of human and murine cholesterol synthesis due to lathosterol 5-desaturase deficiency.	2003 Jul 1	12812989
Biochemical abnormality associated with Smith-Lemli-Opitz syndrome in an infant with features of Rutledge multiple congenital anomaly syndrome confirms that the latter is a variant of the former.	2003 May-Jun	12717589
Normal cognition and behavior in a Smith-Lemli-Opitz syndrome patient who presented with Hirschsprung disease.	2003 Nov 15	14556255
Versatile photosensitization system for 1O2-mediated oxidation of alkenes based on nafion-supported platinum(II) terpyridyl acetylide complex.	2003 Sep 4	12943392
Effect of sterols on beta-amyloid peptide (AbetaP 1-40) channel formation and their properties in planar lipid membranes.	2004 Apr	15041662
Investigation of completed suicide and genes involved in cholesterol metabolism.	2004 Apr	15023477
The implications of 7-dehydrosterol-7-reductase deficiency (Smith-Lemli-Opitz syndrome) to neurosteroid production.	2004 Jan	14715377
[New relevance of vitamin D3 metabolism in the skin].	2004 May	15069602

Patents

Substance Class	Chemical Created by `admin` on `Fri Dec 15 18:58:27 GMT 2023` Edited by `admin` on `Fri Dec 15 18:58:27 GMT 2023`
Record UNII	BK1IU07GKF
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

7-DEHYDROCHOLESTEROL

Official Name

English

NSC-18159

Code

English

7-DEHYDROCHOLESTEROL [INCI]

Common Name

English

(3.BETA.)-7-DEHYDROCHOLESTEROL [MI]

Common Name

English

9.BETA.,10.ALPHA.-CHOLESTA-5,7-DIEN-3.BETA.-OL

Systematic Name

English

CHOLESTA-5,7-DIEN-3.BETA.-OL

Systematic Name

English

CHOLECALCIFEROL IMPURITY B [EP IMPURITY]

Common Name

English

Classification Tree Code System Code

LOINC

50799-6