MiMeDB: Showing metabocard for Androstenedione (MMDBc0052868)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-05-16 21:07:35 UTC

Update Date

2024-10-09 20:12:58 UTC

Metabolite ID

MMDBc0052868

Metabolite Identification

Common Name

Androstenedione

Description

Androstenedione is a delta-4 19-carbon steroid that is produced not only in the testis, but also in the ovary and the adrenal cortex. Depending on the tissue type, androstenedione can serve as a precursor to testosterone as well as estrone and estradiol. It is the common precursor of male and female sex hormones. Some androstenedione is also secreted into the plasma and may be converted in peripheral tissues to testosterone and estrogens. Androstenedione originates either from the conversion of dehydroepiandrosterone or from 17-hydroxyprogesterone. It is further converted to either testosterone or estrone. The production of adrenal androstenedione is governed by ACTH, while the production of gonadal androstenedione is under control by gonadotropins.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
4-Androstene-3,17-dione	ChEBI
4-ANDROSTENE-3-17-dione	ChEBI
delta(4)-Androsten-3,17-dione	ChEBI
delta(4)-Androstene-3,17-dione	ChEBI
Δ(4)-Androsten-3,17-dione	Generator
Δ(4)-Androstene-3,17-dione	Generator
(4)-Androsten-3,17-dione	HMDB
17-Ketotestosterone	HMDB
3,17-Dioxoandrost-4-ene	HMDB
4-Androsten-3,17-dione	HMDB
4-Androstenedione	HMDB
Androst-4-ene-3,17-dione	HMDB, KEGG
Androstendione	HMDB
D4-Androstene-3,17-dione	HMDB
delta4-Androstenedione	HMDB
Fecundin	HMDB
delta 4 Androstenedione	MeSH, HMDB
delta-4-Androstenedione	MeSH, HMDB
4 Androstene 3,17 dione	MeSH, HMDB
Androstenedione	HMDB
delta4-Androstene-3,17-dione	HMDB
Δ4-Androstene-3,17-dione	HMDB

Molecular Formula

C₁₉H₂₆O₂

Average Mass

286.4085

Monoisotopic Mass

286.193280076

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

Not Available

InChI Identifier

InChI=1S/C19H26O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h11,14-16H,3-10H2,1-2H3/t14-,15-,16-,18-,19-/m0/s1

InChI Key

AEMFNILZOJDQLW-QAGGRKNESA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Androstane steroids

Direct Parent

Androgens and derivatives

Alternative Parents

Substituents

Androgen-skeleton
Oxosteroid
17-oxosteroid
3-oxosteroid
3-oxo-delta-4-steroid
Delta-4-steroid
Cyclohexenone
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

3-oxo Delta(4)-steroid (CHEBI:16422 )
17-oxo steroid (CHEBI:16422 )
androstanoid (CHEBI:16422 )
androstane (C00280 )
C19 steroids (androgens) and derivatives (C00280 )
Androstane and derivatives (C00280 )
Androgens (C00280 )
C19 steroids (androgens) and derivatives (LMST02020007 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Not Available

Spectra

Not Available

Biological Properties

Cellular Locations

Cytoplasm
Endoplasmic reticulum
Extracellular
Membrane

Biospecimen Locations

Adipose Tissue
Adrenal Cortex
Adrenal Gland
Blood
Cerebrospinal Fluid (CSF)
Epidermis
Fibroblasts
Kidney
Liver
Ovary
Placenta
Prostate
Skeletal Muscle
Testis
Urine

Tissue Locations

Adipose Tissue
Adrenal Cortex
Adrenal Gland
Epidermis
Fibroblasts
Kidney
Liver
Ovary
Placenta
Prostate
Skeletal Muscle
Testis

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0192028	Aldo-keto reductase family 1 member C3	Unknown	P42330	Homo sapiens
MMDBp0192107	Cytochrome P450 11B1, mitochondrial	Unknown	P15538	Homo sapiens
MMDBp0192109	Estradiol 17-beta-dehydrogenase 2	Unknown	P37059	Homo sapiens
MMDBp0192114	Estradiol 17-beta-dehydrogenase 8	Unknown	Q92506	Homo sapiens
MMDBp0192197	3-oxo-5-beta-steroid 4-dehydrogenase	Enzyme	P51857	Homo sapiens
MMDBp0192337	3-oxo-5-alpha-steroid 4-dehydrogenase 2	Enzyme	P31213	Homo sapiens
MMDBp0192338	3-oxo-5-alpha-steroid 4-dehydrogenase 1	Enzyme	P18405	Homo sapiens
MMDBp0192466	Testosterone 17-beta-dehydrogenase 3	Enzyme	P37058	Homo sapiens
MMDBp0192630	Cytochrome P450 3A4	Unknown	P08684	Homo sapiens
MMDBp0192647	Cytochrome P450 2C9	Unknown	P11712	Homo sapiens
MMDBp0192649	Cytochrome P450 2C19	Unknown	P33261	Homo sapiens
MMDBp0192653	Steroid 17-alpha-hydroxylase/17,20 lyase	Unknown	P05093	Homo sapiens
MMDBp0193099	Cytochrome P450 2E1	Unknown	P05181	Homo sapiens
MMDBp0193101	Cytochrome P450 3A43	Unknown	Q9HB55	Homo sapiens
MMDBp0193102	Cytochrome P450 1B1	Unknown	Q16678	Homo sapiens
MMDBp0193104	Cytochrome P450 2C18	Unknown	P33260	Homo sapiens
MMDBp0193106	Cytochrome P450 2F1	Unknown	P24903	Homo sapiens
MMDBp0193107	Cytochrome P450 4X1	Unknown	Q8N118	Homo sapiens
MMDBp0193108	Cytochrome P450 2B6	Unknown	P20813	Homo sapiens
MMDBp0193109	Cytochrome P450 3A5	Unknown	P20815	Homo sapiens
MMDBp0193111	Cytochrome P450 2A13	Unknown	Q16696	Homo sapiens
MMDBp0193112	Cytochrome P450 3A7	Unknown	P24462	Homo sapiens
MMDBp0193113	Cytochrome P450 4B1	Unknown	P13584	Homo sapiens
MMDBp0193114	Cytochrome P450 4Z1	Unknown	Q86W10	Homo sapiens
MMDBp0193115	Cytochrome P450 1A2	Unknown	P05177	Homo sapiens
MMDBp0193116	Cytochrome P450 19A1	Unknown	P11511	Homo sapiens
MMDBp0193117	Cytochrome P450 2C8	Unknown	P10632	Homo sapiens
MMDBp0193118	Cytochrome P450 2S1	Unknown	Q96SQ9	Homo sapiens
MMDBp0193120	Cytochrome P450 2J2	Unknown	P51589	Homo sapiens
MMDBp0193121	Cytochrome P450 2A7	Unknown	P20853	Homo sapiens
MMDBp0193122	Cytochrome P450 2A6	Unknown	P11509	Homo sapiens
MMDBp0193167	Androgen receptor	Enzyme	P10275	Homo sapiens
MMDBp0193592	Leptin	Enzyme	P41159	Homo sapiens
MMDBp0193705	17-beta-hydroxysteroid dehydrogenase type 6	Unknown	O14756	Homo sapiens
MMDBp0193970	3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomerase type 1	Unknown	P14060	Homo sapiens
MMDBp0193971	3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomerase type 2	Unknown	P26439	Homo sapiens
MMDBp0193997	Cytochrome P450 11B2, mitochondrial	Unknown	P19099	Homo sapiens
MMDBp0194192	Cytochrome P450, family 1, subfamily A, polypeptide 1	Enzyme	A0N0X8	Homo sapiens
MMDBp0195861	HSD17B3 protein	Enzyme	Q6FH62	Homo sapiens
MMDBp0195862	Mutated cytochrome P-450c11 protein	Enzyme	Q8TDD0	Homo sapiens
MMDBp0195863	Cytochrome P450, family 17, subfamily A, polypeptide 1	Enzyme	Q1HB44	Homo sapiens
MMDBp0195899	Polyprenol reductase	Enzyme	Q9H8P0	Homo sapiens
MMDBp0196019	Cytochrome P450 2D6	Enzyme	Q6NWU0	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
11-beta-hydroxylase deficiency	Increased	Association	Human Blood	HMDB	8933406
21-hydroxylase deficiency		Association	Human Blood	HMDB	11038205
21-hydroxylase deficiency	Increased	Association	Human Blood	HMDB	11826238
Cushing's syndrome	Slight Decrease	Association	Human Blood	HMDB	8384536
Polycystic ovary syndrome	Increased	Association	Human Blood	HMDB	16890572
Rheumatoid arthritis	Decreased	Association	Human Urine	HMDB	15249323
Thyroid cancer		Association	Human Urine	HMDB	14643447

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	1	Human ; Human supragingival plaque
Bacteria	Actinobacteria	3	Human

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Blood	Detected and Quantified	0.12				uM	Newborn (0-30 days old)	Female	11-beta-hydroxylase deficiency	HMDB	8933406
Human Blood	Detected and Quantified			0.00360	0.0227	uM	Children (1-13 years old)	Both	11-beta-hydroxylase deficiency	HMDB	8933406
Human Blood	Detected and Quantified	0.00663				uM	Adolescent (13-18 years old)	Female	21-hydroxylase deficiency	HMDB	11038205
Human Blood	Detected and Quantified			0	0.00244	uM	Adult (>18 years old)	Female	21-hydroxylase deficiency	HMDB	11038205
Human Blood	Detected and Quantified			0.00154	0.0174	uM	Adult (>18 years old)	Female	21-hydroxylase deficiency	HMDB	11826238
Human Blood	Detected and Quantified	0.0017				uM	Adult (>18 years old)	Male	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	HMDB	12050224
Human Blood	Detected and Quantified	0.0041				uM	Adolescent (13-18 years old)	Male	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	HMDB	12050224
Human Blood	Detected and Quantified			0.000270	0.0480	uM	Children (1-13 years old)	Both	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	HMDB	12050224
Human Blood	Detected and Quantified	0.000570	0.000200			uM	Children (1-13 years old)	Both	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	HMDB	12050224
Human Blood	Detected and Quantified			0.000698	0.0583	uM	Newborn (0-30 days old)	Male	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	HMDB	27476613
Human Blood	Detected and Quantified	0.000810	0.00140			uM	Children (1-13 years old)	Not Specified	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	HMDB	12050224
Human Blood	Detected and Quantified	0.00103	0.00100			uM	Infant (0-1 year old)	Not Specified	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	HMDB	12050224
Human Blood	Detected and Quantified	0.00137	0.000800			uM	Newborn (0-30 days old)	Not Specified	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	HMDB	12050224
Human Blood	Detected and Quantified			0.00175	0.0770	uM	Newborn (0-30 days old)	Both	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	HMDB	12050224
Human Blood	Detected and Quantified			0.00279	0.00454	uM	Adult (>18 years old)	Female	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	HMDB	7951484
Human Blood	Detected and Quantified	0.00380	0.00100			uM	Adult (>18 years old)	Male	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	HMDB	12050224
Human Blood	Detected and Quantified	0.00430	0.00180			uM	Adult (>18 years old)	Female	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	HMDB	12050224
Human Blood	Detected and Quantified	0.000873				uM	Newborn (0-30 days old)	Female	Adrenal insufficiency, congenital, with 46,XY sex reversal, partial or complete	HMDB	18182448
Human Blood	Detected and Quantified	0.517				uM	Infant (0-1 year old)	Both	Congenital Adrenal Hyperplasia, due to 21-Hydroxylase-Deficiency (CAH)	HMDB	19390483
Human Blood	Detected and Quantified	0.0031	0.0030			uM	Adult (>18 years old)	Both	Cushing's syndrome	HMDB	8384536
Human Blood	Detected and Quantified	0.0090	0.0065			uM	Adult (>18 years old)	Both	Cushing's syndrome	HMDB	8384536
Human Blood	Detected and Quantified	<0.00003				uM	Adult (>18 years old)	Female	Lipoid Adrenal Hyperplasia	HMDB	9077535
Human Blood	Detected and Quantified	<0.00003				uM	Adolescent (13-18 years old)	Female	Lipoid Adrenal Hyperplasia	HMDB	9077535
Human Blood	Detected and Quantified	0.0066	0.0038			uM	Adult (>18 years old)	Female	Polycystic ovary syndrome (PCOS)	HMDB	16890572
Human Blood	Detected and Quantified	0.0090	0.0046			uM	Adult (>18 years old)	Female	Polycystic ovary syndrome (PCOS)	HMDB	16890572
Human Urine	Detected and Quantified	0.0017	0.00034			umol/mmol creatinine	Adult (>18 years old)	Both	Rheumatoid arthritis	HMDB	15249323
Human Urine	Detected and Quantified	0.0025	0.00071			umol/mmol creatinine	Adult (>18 years old)	Both	Rheumatoid arthritis	HMDB	15249323
Human Urine	Detected and Quantified	0.090	0.073			umol/mmol creatinine	Adult (>18 years old)	Female	Thyroid cancer	HMDB	14643447
Human Blood	Detected and Quantified			0.000900	0.00420	uM	Adult (>18 years old)	Male	X-linked ichthyosis	HMDB	3864567
Human Blood	Detected and Quantified	0.000698				uM	Newborn (0-30 days old)	Female	Normal	HMDB	18182448
Human Blood	Detected and Quantified	<0.00100				uM	Not Specified	Both	Normal	HMDB	8933406
Human Blood	Detected and Quantified	<0.0140				uM	Infant (0-1 year old)	Not Specified	Normal	HMDB	19390483
Human Urine	Detected and Quantified	0.00009		0.00003	0.00077	umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	HMDB	23159298
Human Blood	Detected and Quantified	0.00061	0.00022			uM	Adult (>18 years old)	Female	Normal	HMDB	8478958
Human Urine	Detected and Quantified	0.0007		0	0.0052	umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	HMDB	23159298
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.00101		0.00002	0.002	uM	Adult (>18 years old)	Not Specified	Normal	HMDB	1620285
Human Blood	Detected and Quantified			0.00244	0.00768	uM	Not Specified	Not Specified	Normal	HMDB	11038205
Human Blood	Detected and Quantified	0.00489	0.00196			uM	Adult (>18 years old)	Female	Normal	HMDB	11826238
Human Blood	Detected and Quantified	0.00524	0.00140			uM	Adult (>18 years old)	Female	Normal	HMDB	7951484
Human Urine	Detected and Quantified	0.0068	0.0013			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	15249323
Human Urine	Detected and Quantified	0.090	0.058			umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	14643447
Human Blood	Detected and Quantified	0.001		0.00034	0.00170	uM	Children (1-13 years old)	Female	Normal	HMDB	Mayo Medical Laboratories 2005 Test Catalog
Human Blood	Detected and Quantified	0.0022		0.0010	0.0034	uM	Children (1-13 years old)	Both	Normal	HMDB	Mayo Medical Laboratories 2005 Test Catalog
Human Blood	Detected and Quantified	0.0040		0.0013	0.0066	uM	Children (1-13 years old)	Female	Normal	HMDB	Mayo Medical Laboratories 2005 Test Catalog
Human Blood	Detected and Quantified	0.005		0.0024	0.0070	uM	Adolescent (13-18 years old)	Female	Normal	HMDB	Mayo Medical Laboratories 2005 Test Catalog
Human Blood	Detected and Quantified	0.0057		0.00069	0.01	uM	Adult (>18 years old)	Female	Normal	HMDB	Mayo Medical Laboratories 2005 Test Catalog
Human Blood	Detected and Quantified	0.00315		0.00000	0.00630	uM	Adult (>18 years old)	Female	Normal	HMDB	The Merck Manual, 17th ed. Mark H. Beers, MD, Robert Berkow, MD, eds. Whitehouse Station, NJ: Merck Research Labs, 1999.
Human Blood	Detected and Quantified	0.0059		0.0023	0.0094	uM	Adult (>18 years old)	Both	Normal	HMDB	The Merck Manual, 17th ed. Mark H. Beers, MD, Robert Berkow, MD, eds. Whitehouse Station, NJ: Merck Research Labs, 1999.
Human Blood	Detected and Quantified			0.000978	0.00803	uM	Adult (>18 years old)	Both	Normal	HMDB	Vancouver Coastal Health Lab (http://www.vch.ca/Locations-Services/result?res_id=601)
Human Adipose tissue	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Adrenal cortex	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Adrenal gland	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Epidermis	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Fibroblasts	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Kidney	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Liver	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Ovary	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Placenta	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Prostate	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Skeletal muscle	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Testis	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Urine	Detected but not Quantified						Adult (>18 years old)	Female	Normal	HMDB	19010317
Human Blood	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22944140
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0000053

DrugBank ID

DB01536

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

16422

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Schwarz S, Pohl P: Steroid hormones and steroid hormone binding globulins in cerebrospinal fluid studied in individuals with intact and with disturbed blood-cerebrospinal fluid barrier. Neuroendocrinology. 1992 Feb;55(2):174-82. doi: 10.1159/000126112. [PubMed:1620285 ]
Thomson S, Wallace AM, Cook B: A 125I-radioimmunoassay for measuring androstenedione in serum and in blood-spot samples from neonates. Clin Chem. 1989 Aug;35(8):1706-12. [PubMed:2758640 ]
Berkovitz GD, Guerami A, Brown TR, MacDonald PC, Migeon CJ: Familial gynecomastia with increased extraglandular aromatization of plasma carbon19-steroids. J Clin Invest. 1985 Jun;75(6):1763-9. doi: 10.1172/JCI111888. [PubMed:3924954 ]
Schlaghecke R, Kley HK, Kruskemper HL: The measurement of 4-androstene-3, 11, 17-trione (11-oxo-androstenedione) by radioimmunoassay in human plasma. Steroids. 1984 Jul;44(1):23-33. doi: 10.1016/s0039-128x(84)80013-6. [PubMed:6100340 ]
Feldman PS, Kovacs K, Horvath E, Adelson GL: Malignant Leydig cell tumor: clinical, histologic and electron microscopic features. Cancer. 1982 Feb 15;49(4):714-21. doi: 10.1002/1097-0142(19820215)49:4<714::aid-cncr2820490420>3.0.co;2-a. [PubMed:7055782 ]
Egloff M, Savoure N, Tardivel-Lacombe J, Massart C, Nicol M, Degrelle H: Influence of sex hormone binding globulin and serum albumin on the conversion of androstenedione to testosterone by human erythrocytes. Acta Endocrinol (Copenh). 1981 Jan;96(1):136-40. doi: 10.1530/acta.0.0960136. [PubMed:7192922 ]
Atkinson G, Campbell DJ, Cawood ML, Oakey RE: Steroids in human intrauterine fluids of early pregnancy. Clin Endocrinol (Oxf). 1996 Apr;44(4):435-40. doi: 10.1046/j.1365-2265.1996.710532.x. [PubMed:8706310 ]
Riikonen RS: How do cryptogenic and symptomatic infantile spasms differ? Review of biochemical studies in Finnish patients. J Child Neurol. 1996 Sep;11(5):383-8. doi: 10.1177/088307389601100508. [PubMed:8877606 ]
Johansson A, Henriksson A, Olofsson BO, Olsson T: Adrenal steroid dysregulation in dystrophia myotonica. J Intern Med. 1999 Apr;245(4):345-51. doi: 10.1046/j.1365-2796.1999.00455.x. [PubMed:10356596 ]
King DS, Sharp RL, Vukovich MD, Brown GA, Reifenrath TA, Uhl NL, Parsons KA: Effect of oral androstenedione on serum testosterone and adaptations to resistance training in young men: a randomized controlled trial. JAMA. 1999 Jun 2;281(21):2020-8. doi: 10.1001/jama.281.21.2020. [PubMed:10359391 ]
Heikkila R, Aho K, Heliovaara M, Hakama M, Marniemi J, Reunanen A, Knekt P: Serum testosterone and sex hormone-binding globulin concentrations and the risk of prostate carcinoma: a longitudinal study. Cancer. 1999 Jul 15;86(2):312-5. [PubMed:10421267 ]
Zarrilli S, Lombardi G, Paesano L, Di Somma C, Colao A, Mirone V, De Rosa M: Hormonal and seminal evaluation of Leydig cell tumour patients before and after orchiectomy. Andrologia. 2000 May;32(3):147-54. doi: 10.1046/j.1439-0272.2000.00356.x. [PubMed:10863969 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. doi: 10.1038/35036052. [PubMed:11413487 ]
Zarrilli S, Paesano L, Mirone V, Finelli L, De Rosa M: [Evaluation of seminal and hormonal parameters in idiopathic varicocele before and after surgical intervention]. Chir Ital. 1998 Mar-Aug;50(2-4):21-8. [PubMed:11762080 ]
van Vloten WA, van Haselen CW, van Zuuren EJ, Gerlinger C, Heithecker R: The effect of 2 combined oral Contraceptives containing either drospirenone or cyproterone acetate on acne and seborrhea. Cutis. 2002 Apr;69(4 Suppl):2-15. [PubMed:12096825 ]
Jasuja R, Ramaraj P, Mac RP, Singh AB, Storer TW, Artaza J, Miller A, Singh R, Taylor WE, Lee ML, Davidson T, Sinha-Hikim I, Gonzalez-Cadavid N, Bhasin S: Delta-4-androstene-3,17-dione binds androgen receptor, promotes myogenesis in vitro, and increases serum testosterone levels, fat-free mass, and muscle strength in hypogonadal men. J Clin Endocrinol Metab. 2005 Feb;90(2):855-63. doi: 10.1210/jc.2004-1577. Epub 2004 Nov 2. [PubMed:15522925 ]
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Showing metabocard for Androstenedione (MMDBc0052868)

MOL for #<Metabolite:0x00007f46ec3032e0>

3D MOL for #<Metabolite:0x00007f46ec3032e0>

3D SDF for #<Metabolite:0x00007f46ec3032e0>

3D-SDF for #<Metabolite:0x00007f46ec3032e0>

PDB for #<Metabolite:0x00007f46ec3032e0>

3D PDB for #<Metabolite:0x00007f46ec3032e0>

SMILES for #<Metabolite:0x00007f46ec3032e0>

INCHI for #<Metabolite:0x00007f46ec3032e0>

Structure for #<Metabolite:0x00007f46ec3032e0>

3D Structure for #<Metabolite:0x00007f46ec3032e0>