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

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

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
[New relevance of vitamin D3 metabolism in the skin].	2004-05	15069602
Effect of sterols on beta-amyloid peptide (AbetaP 1-40) channel formation and their properties in planar lipid membranes.	2004-04	15041662
Investigation of completed suicide and genes involved in cholesterol metabolism.	2004-04	15023477
Founder effect for the T93M DHCR7 mutation in Smith-Lemli-Opitz syndrome.	2004-03-01	14981719
A novel mutation of the human 7-dehydrocholesterol reductase gene reduces enzyme activity in patients with holoprosencephaly.	2004-02-27	15013448
Late gestational lung hypoplasia in a mouse model of the Smith-Lemli-Opitz syndrome.	2004-02-02	15005800
Antenatal manifestations of Smith-Lemli-Opitz (RSH) syndrome: a retrospective survey of 30 cases.	2004-02-01	14735596
Effect of clothing varieties on solar photosynthesis of previtamin D3: an in vitro study.	2004-02	14738534
Formation of 7-dehydrocholesterol-containing membrane rafts in vitro and in vivo, with relevance to the Smith-Lemli-Opitz syndrome.	2004-02	14594996
Synthesis of vitamin D in skin after burns.	2004-01-24	14751703
The implications of 7-dehydrosterol-7-reductase deficiency (Smith-Lemli-Opitz syndrome) to neurosteroid production.	2004-01	14715377
MRI and 1H MRS findings in Smith-Lemli-Opitz syndrome.	2004-01	14605787
Novel sterols synthesized via the CYP27A1 metabolic pathway.	2003-12-01	14622972
Identification of natural ligands of retinoic acid receptor-related orphan receptor alpha ligand-binding domain expressed in Sf9 cells--a mass spectrometry approach.	2003-12-01	14622968
Abnormal serotonergic development in a mouse model for the Smith-Lemli-Opitz syndrome: implications for autism.	2003-12	14659996
Normal cognition and behavior in a Smith-Lemli-Opitz syndrome patient who presented with Hirschsprung disease.	2003-11-15	14556255
What controls variation in human skin color?	2003-10	14551921
Diagnosis of Smith-Lemli-Opitz syndrome by ultraviolet spectrophotometry.	2003-10	14502364
Identification of three patients with a very mild form of Smith-Lemli-Opitz syndrome.	2003-09-15	12949967
Versatile photosensitization system for 1O2-mediated oxidation of alkenes based on nafion-supported platinum(II) terpyridyl acetylide complex.	2003-09-04	12943392
27-Hydroxylation of 7- and 8-dehydrocholesterol in Smith-Lemli-Opitz syndrome: a novel metabolic pathway.	2003-08	12906934
Chemical and photolytical transformation of biomedically significant compounds in the presence of deuterated solvents.	2003-07-10	12849699
Lathosterolosis: an inborn error of human and murine cholesterol synthesis due to lathosterol 5-desaturase deficiency.	2003-07-01	12812989
Susceptibilities of phospholipid vesicles containing different sterols to amphotericin B-loaded lysophosphatidylcholine micelles.	2003-07	12944378
Smith-Lemli-Opitz syndrome and the DHCR7 gene.	2003-05	12914579
Demonstration of UVB-induced synthesis of 1 alpha,25-dihydroxyvitamin D3 (calcitriol) in human skin by microdialysis.	2003-04	12709817
Yeast-like symbiotes as a sterol source in anobiid beetles (Coleoptera, Anobiidae): possible metabolic pathways from fungal sterols to 7-dehydrocholesterol.	2003-04	12655605
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.	2003-01-30	12503101
[Clinical characteristics and diagnosis of Smith-Lemli-Opitz syndrome and tentative phenotype-genotype correlation: report of 45 cases].	2003-01	12818773
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
Simvastatin treatment in the SLO syndrome: a safe approach?	2002-11-22	12407710
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.	2002-11-06	12717589
Cholesterol treatment forever? The first Scandinavian trial of cholesterol supplementation in the cholesterol-synthesis defect Smith-Lemli-Opitz syndrome.	2002-10	12366604
Feedback inhibition of the cholesterol biosynthetic pathway in patients with Smith-Lemli-Opitz syndrome as demonstrated by urinary mevalonate excretion.	2002-10	12364550
Ternary gradient elution markedly improves silver-ion high performance liquid chromatography of unsaturated sterols.	2002-10	12234627
Lathosterolosis, a novel multiple-malformation/mental retardation syndrome due to deficiency of 3beta-hydroxysteroid-delta5-desaturase.	2002-10	12189593
Greenberg dysplasia (hydrops-ectopic calcification-moth-eaten skeletal dysplasia): prenatal ultrasound diagnosis and review of literature.	2002-09-01	12210303
Molecular prenatal diagnosis of Smith-Lemli-Opitz syndrome is reliable and efficient.	2002-09	12224080
Two novel mutations of the human delta7-sterol reductase (DHCR7) gene in children with Smith-Lemli-Opitz syndrome.	2002-08	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.	2002-08	12186406
Cholesterol induce oligomerization of Vibrio vulnificus cytolysin specifically.	2002-07-31	12216116
Unbalanced translocation (3;5)(q26.1;p14): a clinical report.	2002-07-15	12116209
Novel mutation in the Delta-sterol reductase gene in three Lebanese sibs with Smith-Lemli-Opitz (RSH) syndrome.	2002-06-15	12116246
Structure and alternative splicing of the rat 7-dehydrocholesterol reductase gene.	2002-06-07	12031495
Smith-Lemli-Opitz syndrome: carrier frequency and spectrum of DHCR7 mutations in Canada.	2002-06	12070263
A colorimetric assay for 7-dehydrocholesterol with potential application to screening for Smith-Lemli-Opitz syndrome.	2002-05	12047895
Cholesterol storage defect in RSH/Smith-Lemli-Opitz syndrome fibroblasts.	2002-04	12051964
Evolution of UV-B regulation and protection in plants.	2002	12575721

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:28:10 GMT 2025` Edited by `admin` on `Mon Mar 31 19:28:10 GMT 2025`
Record UNII	BK1IU07GKF
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NSC-18159

Preferred Name

English

7-DEHYDROCHOLESTEROL

Official 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