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
Evolution of UV-B regulation and protection in plants.	2002	12575721
Cholesterol storage defect in RSH/Smith-Lemli-Opitz syndrome fibroblasts.	2002 Apr	12051964
Two novel mutations of the human delta7-sterol reductase (DHCR7) gene in children with Smith-Lemli-Opitz syndrome.	2002 Aug	12270273
Stimulative effects of (22E,24R)-ergosta-7,22-diene-3beta,5alpha,6beta-triol from fruiting bodies of Tricholoma auratum, on a mouse osteoblastic cell line, MC3T3-E1.	2002 Aug	12186406
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
Smith-Lemli-Opitz syndrome: carrier frequency and spectrum of DHCR7 mutations in Canada.	2002 Jun	12070263
Novel mutation in the Delta-sterol reductase gene in three Lebanese sibs with Smith-Lemli-Opitz (RSH) syndrome.	2002 Jun 15	12116246
Structure and alternative splicing of the rat 7-dehydrocholesterol reductase gene.	2002 Jun 7	12031495
A colorimetric assay for 7-dehydrocholesterol with potential application to screening for Smith-Lemli-Opitz syndrome.	2002 May	12047895
Simvastatin treatment in the SLO syndrome: a safe approach?	2002 Nov 22	12407710
Cholesterol treatment forever? The first Scandinavian trial of cholesterol supplementation in the cholesterol-synthesis defect Smith-Lemli-Opitz syndrome.	2002 Oct	12366604
Feedback inhibition of the cholesterol biosynthetic pathway in patients with Smith-Lemli-Opitz syndrome as demonstrated by urinary mevalonate excretion.	2002 Oct	12364550
Ternary gradient elution markedly improves silver-ion high performance liquid chromatography of unsaturated sterols.	2002 Oct	12234627
Lathosterolosis, a novel multiple-malformation/mental retardation syndrome due to deficiency of 3beta-hydroxysteroid-delta5-desaturase.	2002 Oct	12189593
Molecular prenatal diagnosis of Smith-Lemli-Opitz syndrome is reliable and efficient.	2002 Sep	12224080
Greenberg dysplasia (hydrops-ectopic calcification-moth-eaten skeletal dysplasia): prenatal ultrasound diagnosis and review of literature.	2002 Sep 1	12210303
Extrarenal sites of calcitriol synthesis: the particular role of the skin.	2003	12899518
Smith-Lemli-Opitz syndrome: a review, case report and dental implications.	2003	12887150
Protein prenyltransferases.	2003	12702202
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
27-Hydroxylation of 7- and 8-dehydrocholesterol in Smith-Lemli-Opitz syndrome: a novel metabolic pathway.	2003 Aug	12906934
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
Identification of natural ligands of retinoic acid receptor-related orphan receptor alpha ligand-binding domain expressed in Sf9 cells--a mass spectrometry approach.	2003 Dec 1	14622968
[Clinical characteristics and diagnosis of Smith-Lemli-Opitz syndrome and tentative phenotype-genotype correlation: report of 45 cases].	2003 Jan	12818773
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
Smith-Lemli-Opitz syndrome and the DHCR7 gene.	2003 May	12914579
Chemical and photolytical transformation of biomedically significant compounds in the presence of deuterated solvents.	2003 May-Jun	12849699
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
What controls variation in human skin color?	2003 Oct	14551921
Diagnosis of Smith-Lemli-Opitz syndrome by ultraviolet spectrophotometry.	2003 Oct	14502364
Identification of three patients with a very mild form of Smith-Lemli-Opitz syndrome.	2003 Sep 15	12949967
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
Effect of clothing varieties on solar photosynthesis of previtamin D3: an in vitro study.	2004 Feb	14738534
Formation of 7-dehydrocholesterol-containing membrane rafts in vitro and in vivo, with relevance to the Smith-Lemli-Opitz syndrome.	2004 Feb	14594996
Antenatal manifestations of Smith-Lemli-Opitz (RSH) syndrome: a retrospective survey of 30 cases.	2004 Feb 1	14735596
Late gestational lung hypoplasia in a mouse model of the Smith-Lemli-Opitz syndrome.	2004 Feb 2	15005800
A novel mutation of the human 7-dehydrocholesterol reductase gene reduces enzyme activity in patients with holoprosencephaly.	2004 Feb 27	15013448
The implications of 7-dehydrosterol-7-reductase deficiency (Smith-Lemli-Opitz syndrome) to neurosteroid production.	2004 Jan	14715377
MRI and 1H MRS findings in Smith-Lemli-Opitz syndrome.	2004 Jan	14605787
Synthesis of vitamin D in skin after burns.	2004 Jan 24	14751703
Founder effect for the T93M DHCR7 mutation in Smith-Lemli-Opitz syndrome.	2004 Mar 1	14981719
[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