Pregnenolone

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Pregnenolone
2D structure for Pregnenolone
Chemical Name	1-[(3S,8S,9S,10R,13S,17S)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanone
Chemical Formula	C₂₁H₃₂O₂
CAS Number	145-13-1
Chemical Information	HMDB00253
Biochemical Taxonomy	Steroids and Steroid Derivatives
Functional Taxonomy	Not Available
Nutritional Taxonomy	Not Available
Metabolic Pathways	Androgen and Estrogen Metabolism C21-Steroid Hormone Metabolism
Biofluid Location	Blood Cerebrospinal Fluid (CSF)
Tissue Location	Adrenal Gland Brain Gonads Kidney Myelin Nerves Neurons Placenta Testes Testis Adrenal Cortex
Normal Biofluid Concentrations	Blood: 0.0008 +/- 0.0008 uM Blood: 0.014 +/- 0.008 umol/L Cerebrospinal Fluid (CSF): 0.00013 (0.000082-0.00019) uM
Normal Tissue Concentrations	Not Available
Diseases / Conditions Related to Nutrition	Depressed pregnant woman Premenstrual dysphoric disorder
Other (Monogenic Disorders)	Lipoid congenital adrenal hyperplasia OMIM: 201710
Abnormal Biofluid Concentrations	Blood (Depressed pregnant woman): 0.068 +/- 0.02 uM Blood (Premenstrual dysphoric disorder): 0.00082 +/- 0.0007 uM
Abnormal Tissue Concentrations	Not Available
Physiological Processes	Not Available

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Introduction

guidelines
Pregnenolone is a derivative of cholesterol, the product of Cytochrome P450 side-chain cleavage (EC 1.14.15.6, CYP11A1); this reaction consists of three consecutive monooxygenations; a 22-hydroxylation, 20-hydroxylation and the cleavage of the C20-C22 bond, yielding pregnenolone. Pregnenolone is the precursor to gonadal steroid hormones and the adrenal corticosteroids. This reaction occurs in steroid hormone-producing tissues such as the adrenal cortex, corpus luteum and placenta. The most notable difference between the placenta and other steroidogenic tissues is that electron supply to CYP11A1 limits the rate at which cholesterol is converted to pregnenolone in the placenta. The limiting component for electron delivery to CYP11A1 is the concentration of adrenodoxin reductase in the mitochondrial matrix which is insufficient to maintain the adrenodoxin pool in a fully reduced state. Pregnenolone is also a neurosteroid, and is produced in the spinal cord; CYP11A1 is the key enzyme catalyzing the conversion of cholesterol into pregnenolone, the rate-limiting step in the biosynthesis of all classes of steroids, and has been localized in sensory networks of the spinal cord dorsal horn. In the adrenal glomerulosa cell angiotensin II, one of the major physiological regulators of mineralocorticoid synthesis, appears to affect most of the cholesterol transfer to the mitochondrial outer membrane and transport to the inner membrane steps and thus to exerts a powerful control over the use of cholesterol for aldosterone production. (PMID: 17222962, 15823613, 16632873, 15134809)