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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (7) Show 7 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-09-22 17:43:42 UTC

HMDB ID

HMDB0000363

Secondary Accession Numbers

HMDB00363

Metabolite Identification

Common Name

17a-Hydroxypregnenolone

Description

17a-Hydroxypregnenolone is a 21-carbon steroid that is converted from pregnenolone by cytochrome P450 17alpha hydroxylase/C17,20 lyase (CYP17, EC 1.14.99.9). 17a-Hydroxypregnenolone is an intermediate in the delta-5 pathway of biosynthesis of gonadal steroid hormones and the adrenal corticosteroids. The first, rate-limiting and hormonally regulated step in the biosynthesis of all steroid hormones is the conversion of cholesterol to pregnenolone. The conversion of cholesterol to pregnenolone is accomplished by the cleavage of the cholesterol side chain, catalyzed by a mitochondrial cytochrome P450 enzyme termed P450scc where scc designates Side Chain Cleavage. All steroid hormones are made from the pregnenolone produced by P450scc; thus, the presence or absence of each of the activities of CYP17 directs this pregnenolone towards its final metabolic pathway. While all cytochrome P450 enzymes can catalyze multiple reactions on a single active site, CYP17 is the only one described to date in which these multiple activities are differentially regulated by a physiologic process. 17a-Hydroxypregnenolone is converted to dehydroepiandrosterone by the 17,20 lyase activity of CYP17. The ratio of the 17,20 lyase to 17 alpha-hydroxylase activity of CYP17 determines the ratio of C21 to C19 steroids produced. This ratio is regulated post-translationally by at least three factors: the abundance of the electron-donating protein P450 oxidoreductase, the presence of cytochrome b5, and the serine phosphorylation of CYP17. (PMID: 12573809 ).

Structure

MOL SDF PDB SMILES InChI

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₂₁H₃₂O₃

Average Molecular Weight

332.477

Monoisotopic Molecular Weight

332.23514489

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

387-79-1

SMILES

Not Available

InChI Identifier

InChI=1S/C21H32O3/c1-13(22)21(24)11-8-18-16-5-4-14-12-15(23)6-9-19(14,2)17(16)7-10-20(18,21)3/h4,15-18,23-24H,5-12H2,1-3H3/t15-,16+,17-,18-,19-,20-,21-/m0/s1

InChI Key

JERGUCIJOXJXHF-TVWVXWENSA-N

Chemical Taxonomy

Classification

Not classified

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 16777916)

Organ substructure

Adrenal cortex (HMDB: HMDB0000363)

Organ

Testicle (HMDB: HMDB0000363)
Testicle (HMDB: HMDB0000363)

Cellular substructure

Organelle

Endoplasmic reticulum (HMDB: HMDB0000363)

Source

Exogenous

Exogenous (HMDB: HMDB0000363)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Endogenous

Endogenous (HMDB: HMDB0000363)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Steroidogenesis (HMDB: HMDB0000363)
Androgen and Estrogen Metabolism (HMDB: HMDB0000363)

Disease pathway

Adrenal Hyperplasia Type 3 or Congenital Adrenal Hyperplasia Due to 21-Hydroxylase Deficiency (HMDB: HMDB0000363)
21-Hydroxylase Deficiency (CYP21) (HMDB: HMDB0000363)
17-beta Hydroxysteroid Dehydrogenase III Deficiency (PathBank: SMP0120437)
Apparent Mineralocorticoid Excess Syndrome (PathBank: SMP0120649)
3-beta-Hydroxysteroid Dehydrogenase Deficiency (PathBank: SMP0120650)
Adrenal Hyperplasia Type 5 or Congenital Adrenal Hyperplasia Due to 17 alpha-Hydroxylase Deficiency (PathBank: SMP0120672)
Aromatase Deficiency (PathBank: SMP0120848)
11-beta-Hydroxylase Deficiency (CYP11B1) (PathBank: SMP0120858)
Corticosterone Methyl Oxidase I Deficiency (CMO I) (PathBank: SMP0120860)
Congenital Lipoid Adrenal Hyperplasia (CLAH) or Lipoid CAH (PathBank: SMP0120470)
17-alpha-Hydroxylase Deficiency (CYP17) (PathBank: SMP0120849)
Corticosterone Methyl Oxidase II Deficiency (CMO II) (PathBank: SMP0120642)

Role

Biological role

Human metabolite (HMDB: HMDB0000363)

Industrial application

Pharmaceutical industry

Biomarker

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	266 - 271 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Predicted Molecular Properties

Not Available

Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
17a-Hydroxypregnenolone	[H][C@@]12CC[C@](O)(C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C	2657.7	Standard polar	33892256
17a-Hydroxypregnenolone	[H][C@@]12CC[C@](O)(C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C	2730.6	Standard non polar	33892256
17a-Hydroxypregnenolone	[H][C@@]12CC[C@](O)(C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C	2873.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
17a-Hydroxypregnenolone,1TMS,isomer #1	CC(=O)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C	2934.1	Semi standard non polar	33892256
17a-Hydroxypregnenolone,1TMS,isomer #2	CC(=O)[C@@]1(O)CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	2913.3	Semi standard non polar	33892256
17a-Hydroxypregnenolone,1TMS,isomer #3	C=C(O[Si](C)(C)C)[C@@]1(O)CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C	2827.9	Semi standard non polar	33892256
17a-Hydroxypregnenolone,2TMS,isomer #1	CC(=O)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	2961.6	Semi standard non polar	33892256
17a-Hydroxypregnenolone,2TMS,isomer #2	C=C(O[Si](C)(C)C)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C	2958.2	Semi standard non polar	33892256
17a-Hydroxypregnenolone,2TMS,isomer #3	C=C(O[Si](C)(C)C)[C@@]1(O)CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	2855.0	Semi standard non polar	33892256
17a-Hydroxypregnenolone,3TMS,isomer #1	C=C(O[Si](C)(C)C)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	2964.5	Semi standard non polar	33892256
17a-Hydroxypregnenolone,3TMS,isomer #1	C=C(O[Si](C)(C)C)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	2904.0	Standard non polar	33892256
17a-Hydroxypregnenolone,3TMS,isomer #1	C=C(O[Si](C)(C)C)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	3228.3	Standard polar	33892256
17a-Hydroxypregnenolone,1TBDMS,isomer #1	CC(=O)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C	3183.7	Semi standard non polar	33892256
17a-Hydroxypregnenolone,1TBDMS,isomer #2	CC(=O)[C@@]1(O)CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	3170.5	Semi standard non polar	33892256
17a-Hydroxypregnenolone,1TBDMS,isomer #3	C=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O)CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C	3115.1	Semi standard non polar	33892256
17a-Hydroxypregnenolone,2TBDMS,isomer #1	CC(=O)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	3457.9	Semi standard non polar	33892256
17a-Hydroxypregnenolone,2TBDMS,isomer #2	C=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C	3503.7	Semi standard non polar	33892256
17a-Hydroxypregnenolone,2TBDMS,isomer #3	C=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O)CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	3385.0	Semi standard non polar	33892256
17a-Hydroxypregnenolone,3TBDMS,isomer #1	C=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	3724.7	Semi standard non polar	33892256
17a-Hydroxypregnenolone,3TBDMS,isomer #1	C=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	3605.8	Standard non polar	33892256
17a-Hydroxypregnenolone,3TBDMS,isomer #1	C=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	3481.9	Standard polar	33892256

Spectra

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane (predicted from logP)
Endoplasmic reticulum

Biospecimen Locations

Blood
Urine

Tissue Locations

Adrenal Cortex
Testis

Pathways

Name	SMPDB/PathBank	KEGG
Steroidogenesis
Androgen and Estrogen Metabolism
17-Beta Hydroxysteroid Dehydrogenase III Deficiency		Not Available
Aromatase deficiency		Not Available
Adrenal Hyperplasia Type 3 or Congenital Adrenal Hyperplasia due to 21-hydroxylase Deficiency		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.00180-0.00451 uM	Newborn (0-30 days old)	Female	Normal	18182448	details
Blood	Detected and Quantified	0.00211-0.0256 uM	Newborn (0-30 days old)	Female	Normal	18182448	details
Blood	Detected and Quantified	0.00902 +/- 0.00361 uM	Adult (>18 years old)	Female	Normal	7951484	details
Blood	Detected and Quantified	0.000300-0.0240 uM	Infant (0-1 year old)	Not Specified	Normal	16439592	details
Blood	Detected and Quantified	0.000782 +/- 0.000993 uM	Children (1-13 years old)	Both	Normal	26079780	details
Blood	Detected and Quantified	0.00656 +/- 0.00562 uM	Children (1-13 years old)	Both	Normal	26079780	details
Blood	Detected and Quantified	0.003 (0.000 - 0.006) uM	Adult (>18 years old)	Female	Normal	16777916	details
Blood	Detected and Quantified	0.006 (0.001-0.012) uM	Adult (>18 years old)	Male	Normal	16777916	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.000271 uM	Newborn (0-30 days old)	Female	Adrenal insufficiency, congenital, with 46,XY sex reversal, partial or complete	18182448	details
Blood	Detected and Quantified	0.00123 uM	Newborn (0-30 days old)	Female	Adrenal insufficiency, congenital, with 46,XY sex reversal, partial or complete	18182448	details
Blood	Detected and Quantified	0.0126 +/- 0.0105 uM	Newborn (0-30 days old)	Not Specified	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	12050224	details
Blood	Detected and Quantified	0.00440 +/- 0.00280 uM	Children (1-13 years old)	Not Specified	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	12050224	details
Blood	Detected and Quantified	0.159 uM	Adult (>18 years old)	Male	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	12050224	details
Blood	Detected and Quantified	0.741 uM	Adolescent (13-18 years old)	Male	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	12050224	details
Blood	Detected and Quantified	0.0264-0.103 uM	Children (1-13 years old)	Both	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	12050224	details
Blood	Detected and Quantified	0.0843-1.262 uM	Newborn (0-30 days old)	Both	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	12050224	details
Blood	Detected and Quantified	0.00230 +/- 0.00200 uM	Children (1-13 years old)	Both	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	12050224	details
Blood	Detected and Quantified	0.00300 +/- 0.00250 uM	Adult (>18 years old)	Female	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	12050224	details
Blood	Detected and Quantified	0.00380 +/- 0.00210 uM	Adult (>18 years old)	Male	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	12050224	details
Blood	Detected and Quantified	0.00896 +/- 0.00770 uM	Infant (0-1 year old)	Not Specified	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	12050224	details
Blood	Detected and Quantified	0.0186 uM	Adult (>18 years old)	Female	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	7951484	details
Blood	Detected and Quantified	0.0120-0.180 uM	Infant (0-1 year old)	Both	Antley-Bixler syndrome with genital anomalies and disordered steroidogenesis	16439592	details
Blood	Detected and Quantified	0.136 +/- 0.129 uM	Children (1-13 years old)	Both	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	26079780	details
Blood	Detected and Quantified	0.00439 +/- 0.00896 uM	Children (1-13 years old)	Both	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	26079780	details
Blood	Detected and Quantified	0.176 +/- 0.186 uM	Children (1-13 years old)	Both	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	26079780	details
Blood	Detected and Quantified	0.0111 +/- 0.0219 uM	Children (1-13 years old)	Both	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	26079780	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

Associated Disorders and Diseases

Disease References

Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency
Hattori N, Ishihara T, Moridera K, Hino M, Ikekubo K, Kurahachi H: A case of late-onset congenital adrenal hyperplasia due to partial 3 beta-hydroxysteroid dehydrogenase deficiency. Endocr J. 1993 Feb;40(1):107-9. [PubMed:7951484 ] Lutfallah C, Wang W, Mason JI, Chang YT, Haider A, Rich B, Castro-Magana M, Copeland KC, David R, Pang S: Newly proposed hormonal criteria via genotypic proof for type II 3beta-hydroxysteroid dehydrogenase deficiency. J Clin Endocrinol Metab. 2002 Jun;87(6):2611-22. doi: 10.1210/jcem.87.6.8615. [PubMed:12050224 ] Benkert AR, Young M, Robinson D, Hendrickson C, Lee PA, Strauss KA: Severe Salt-Losing 3beta-Hydroxysteroid Dehydrogenase Deficiency: Treatment and Outcomes of HSD3B2 c.35G>A Homozygotes. J Clin Endocrinol Metab. 2015 Aug;100(8):E1105-15. doi: 10.1210/jc.2015-2098. Epub 2015 Jun 16. [PubMed:26079780 ]
Antley-Bixler syndrome with genital anomalies and disordered steroidogenesis
Fukami M, Hasegawa T, Horikawa R, Ohashi T, Nishimura G, Homma K, Ogata T: Cytochrome P450 oxidoreductase deficiency in three patients initially regarded as having 21-hydroxylase deficiency and/or aromatase deficiency: diagnostic value of urine steroid hormone analysis. Pediatr Res. 2006 Feb;59(2):276-80. doi: 10.1203/01.pdr.0000195825.31504.28. [PubMed:16439592 ]
Adrenal insufficiency, congenital, with 46,XY sex reversal, partial or complete
Kim CJ, Lin L, Huang N, Quigley CA, AvRuskin TW, Achermann JC, Miller WL: Severe combined adrenal and gonadal deficiency caused by novel mutations in the cholesterol side chain cleavage enzyme, P450scc. J Clin Endocrinol Metab. 2008 Mar;93(3):696-702. doi: 10.1210/jc.2007-2330. Epub 2008 Jan 8. [PubMed:18182448 ]

Associated OMIM IDs

201810 (Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency)
201750 (Antley-Bixler syndrome with genital anomalies and disordered steroidogenesis)
613743 (Adrenal insufficiency, congenital, with 46,XY sex reversal, partial or complete)

External Links

Not Available

References

Synthesis Reference

Kaspar, Emanuel; Hiersemann, Wolfgang; Schenck, Martin. Preparation from their esters of steroid alcohols that are sensitive to acids and alkali. (1958), DE 1028572 19580424 CAN 54:74845 AN 1960:74845 CAPLUS

Material Safety Data Sheet (MSDS)

Not Available

General References

Shimozawa K, Saisho S, Yata J, Kambegawa A: Age-related changes in serum 17-hydroxypregnenolone and 17-hydroxypregnenolone sulfate concentrations in human infancy and childhood. Endocrinol Jpn. 1988 Apr;35(2):189-95. [PubMed:3208699 ]
Rodriguez-Rigau LJ, Weiss DB, Smith KD, Steinberger E: Suggestion of abnormal testicular steroidogenesis in some oligospermic men. Acta Endocrinol (Copenh). 1978 Feb;87(2):400-12. [PubMed:580138 ]
Kaufman FR, Costin G, Goebelsmann U, Stanczyk FZ, Zachmann M: Male pseudohermaphroditism due to 17,20-desmolase deficiency. J Clin Endocrinol Metab. 1983 Jul;57(1):32-6. [PubMed:6853680 ]
Miller WL: Androgen biosynthesis from cholesterol to DHEA. Mol Cell Endocrinol. 2002 Dec 30;198(1-2):7-14. [PubMed:12573809 ]

Enzymes

Enzyme Details

1. Cholesterol side-chain cleavage enzyme, mitochondrial

General function:: Involved in monooxygenase activity
Specific function:: Catalyzes the side-chain cleavage reaction of cholesterol to pregnenolone.
Gene Name:: CYP11A1
Uniprot ID:: P05108
Molecular weight:: 60101.87

Reactions

17a,20a-Dihydroxycholesterol + Oxygen + Hydrogen Ion + Reduced adrenal ferredoxin → 17a-Hydroxypregnenolone + 4-Methylpentanal + Water + Oxidized adrenal ferredoxin	details

Enzyme Details

2. Steroid 17-alpha-hydroxylase/17,20 lyase

General function:: Involved in monooxygenase activity
Specific function:: Conversion of pregnenolone and progesterone to their 17-alpha-hydroxylated products and subsequently to dehydroepiandrosterone (DHEA) and androstenedione. Catalyzes both the 17-alpha-hydroxylation and the 17,20-lyase reaction. Involved in sexual development during fetal life and at puberty.
Gene Name:: CYP17A1
Uniprot ID:: P05093
Molecular weight:: 57369.995

Reactions

Pregnenolone + Reduced acceptor + Oxygen → 17a-Hydroxypregnenolone + Acceptor + Water	details
17a-Hydroxypregnenolone + Reduced acceptor + Oxygen → Dehydroepiandrosterone + Acetic acid + Acceptor + Water	details

Enzyme Details

3. 3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomerase type 1

General function:: Involved in 3-beta-hydroxy-delta5-steroid dehydrogenase activity
Specific function:: 3-beta-HSD is a bifunctional enzyme, that catalyzes the oxidative conversion of Delta(5)-ene-3-beta-hydroxy steroid, and the oxidative conversion of ketosteroids. The 3-beta-HSD enzymatic system plays a crucial role in the biosynthesis of all classes of hormonal steroids. Efficiently catalyzes the transformation of pregnenolone to progesterone, 17-alpha-hydroxypregnenolone to 17-alpha-hydroxyprogesterone, DHEA to 4-androstenedione, dihydrotestosterone to 5-alpha-androstane-3 beta,17 beta-diol, dehydroepiandrosterone to androstenedione and 5-alpha-androstan-3 beta,17 beta-diol to 5-alpha-dihydrotestosterone.
Gene Name:: HSD3B1
Uniprot ID:: P14060
Molecular weight:: 42251.25

Reactions

17a-Hydroxypregnenolone + NAD → 17-Hydroxyprogesterone + NADH + Hydrogen Ion	details

Enzyme Details

4. 3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomerase type 2

General function:: Involved in 3-beta-hydroxy-delta5-steroid dehydrogenase activity
Specific function:: 3-beta-HSD is a bifunctional enzyme, that catalyzes the oxidative conversion of Delta(5)-ene-3-beta-hydroxy steroid, and the oxidative conversion of ketosteroids. The 3-beta-HSD enzymatic system plays a crucial role in the biosynthesis of all classes of hormonal steroids.
Gene Name:: HSD3B2
Uniprot ID:: P26439
Molecular weight:: 42051.845

Reactions

17a-Hydroxypregnenolone + NAD → 17-Hydroxyprogesterone + NADH + Hydrogen Ion	details

Enzyme Details

5. Cytochrome P450 21-hydroxylase

General function:: Involved in monooxygenase activity
Specific function:: Not Available
Gene Name:: P450-CYP21B
Uniprot ID:: Q16874
Molecular weight:: 56000.9

Enzyme Details

6. Cytochrome P450, family 21, subfamily A, polypeptide 2

General function:: Involved in monooxygenase activity
Specific function:: Not Available
Gene Name:: CYP21A2
Uniprot ID:: Q08AG9
Molecular weight:: 55972.9

Enzyme Details

7. Steroid 21-hydroxylase

General function:: Not Available
Specific function:: Specifically catalyzes the 21-hydroxylation of steroids. Required for the adrenal synthesis of mineralocorticoids and glucocorticoids.
Gene Name:: CYP21A2
Uniprot ID:: P08686
Molecular weight:: 56000.94

Reactions

17a-Hydroxypregnenolone + NADPH + Hydrogen Ion + Oxygen → 17alpha,21-Dihydroxypregnenolone + NADP + Water	details

Showing metabocard for 17a-Hydroxypregnenolone (HMDB0000363)

MOL for HMDB0000363 (17a-Hydroxypregnenolone)

3D MOL for HMDB0000363 (17a-Hydroxypregnenolone)

3D SDF for HMDB0000363 (17a-Hydroxypregnenolone)

3D-SDF for HMDB0000363 (17a-Hydroxypregnenolone)

PDB for HMDB0000363 (17a-Hydroxypregnenolone)

3D PDB for HMDB0000363 (17a-Hydroxypregnenolone)

SMILES for HMDB0000363 (17a-Hydroxypregnenolone)

INCHI for HMDB0000363 (17a-Hydroxypregnenolone)

Structure for HMDB0000363 (17a-Hydroxypregnenolone)

3D Structure for HMDB0000363 (17a-Hydroxypregnenolone)

Predicted Kovats Retention Indices

Underivatized

Derivatized

Enzymes

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