androst-5-ene-3beta,17beta-diol (CHEBI:2710)

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CHEBI:2710 - androst-5-ene-3β,17β-diol

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ChEBI Name	androst-5-ene-3β,17β-diol

ChEBI ID	CHEBI:2710

ChEBI ASCII Name	androst-5-ene-3beta,17beta-diol

Definition	A 3β-hydroxy-Δ⁵-steroid that is 3β-hydroxyandrost-5-ene carrying an additional hydroxy group at position 17β.

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information	ChemicalBook:CB3353226, eMolecules:594035, Selleckchem:Riluzole(Rilutek), ZINC000000006481

Download	Molfile XML SDF

more structures >>

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The Resolver thinks Mol

B81 - Ideal conformer

Mrv1927 06032115223D

starting HoverWatcher_5

Time for openFile(B81 - Ideal conformer

Mrv1927 06032115223D

51 54 0 0 0 0 999 V2000

2.4440 -1.2930 -0.8970 C 0 0 1 0 0 0 0 0 0 0 0 0

3.8630 -1.3320 -0.3260 C 0 0 1 0 0 0 0 0 0 0 0 0

4.4500 0.0800 -0.3080 C 0 0 2 0 0 0 0 0 0 0 0 0

5.8040 0.0270 0.1440 O 0 0 0 0 0 0 0 0 0 0 0 0

3.6300 0.9620 0.6390 C 0 0 1 0 0 0 0 0 0 0 0 0

2.1740 0.9050 0.2070 C 0 0 0 0 0 0 0 0 0 0 0 0

1.5400 2.0260 0.0300 C 0 0 0 0 0 0 0 0 0 0 0 0

0.1050 2.0960 -0.4030 C 0 0 1 0 0 0 0 0 0 0 0 0

-0.6170 0.8160 0.0350 C 0 0 2 0 0 0 0 0 0 0 0 0

0.1420 -0.3840 -0.5490 C 0 0 1 0 0 0 0 0 0 0 0 0

1.5520 -0.4470 0.0150 C 0 0 1 0 0 0 0 0 0 0 0 0

-0.5820 -1.6990 -0.2770 C 0 0 1 0 0 0 0 0 0 0 0 0

-2.0410 -1.6570 -0.7590 C 0 0 1 0 0 0 0 0 0 0 0 0

-2.7140 -0.4980 -0.0460 C 0 0 1 0 0 0 0 0 0 0 0 0

-2.0260 0.8080 -0.5240 C 0 0 1 0 0 0 0 0 0 0 0 0

-2.9800 1.9010 -0.0530 C 0 0 1 0 0 0 0 0 0 0 0 0

-4.3840 1.2460 -0.0510 C 0 0 1 0 0 0 0 0 0 0 0 0

-4.1800 -0.2500 -0.4190 C 0 0 2 0 0 0 0 0 0 0 0 0

-5.0460 -1.0830 0.3540 O 0 0 0 0 0 0 0 0 0 0 0 0

-2.5640 -0.6420 1.4700 C 0 0 0 0 0 0 0 0 0 0 0 0

1.4890 -1.1270 1.3840 C 0 0 0 0 0 0 0 0 0 0 0 0

2.4660 -0.8530 -1.8950 H 0 0 0 0 0 0 0 0 0 0 0 0

2.0470 -2.3070 -0.9550 H 0 0 0 0 0 0 0 0 0 0 0 0

3.8340 -1.7260 0.6900 H 0 0 0 0 0 0 0 0 0 0 0 0

4.4860 -1.9760 -0.9460 H 0 0 0 0 0 0 0 0 0 0 0 0

4.4180 0.5000 -1.3130 H 0 0 0 0 0 0 0 0 0 0 0 0

6.2400 0.8900 0.1810 H 0 0 0 0 0 0 0 0 0 0 0 0

3.7240 0.5910 1.6600 H 0 0 0 0 0 0 0 0 0 0 0 0

3.9890 1.9890 0.5870 H 0 0 0 0 0 0 0 0 0 0 0 0

2.0710 2.9510 0.2020 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.3740 2.9590 0.0590 H 0 0 0 0 0 0 0 0 0 0 0 0

0.0550 2.1890 -1.4880 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.6430 0.7520 1.1230 H 0 0 0 0 0 0 0 0 0 0 0 0

0.2100 -0.2560 -1.6290 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.0610 -2.5050 -0.7930 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.5700 -1.8970 0.7950 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.0710 -1.4990 -1.8370 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.5430 -2.5910 -0.5060 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.9690 0.8170 -1.6120 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.7140 2.2270 0.9530 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.9570 2.7460 -0.7410 H 0 0 0 0 0 0 0 0 0 0 0 0

-4.8260 1.3120 0.9430 H 0 0 0 0 0 0 0 0 0 0 0 0

-5.0270 1.7380 -0.7800 H 0 0 0 0 0 0 0 0 0 0 0 0

-4.3390 -0.4120 -1.4850 H 0 0 0 0 0 0 0 0 0 0 0 0

-5.9850 -0.9650 0.1560 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.5060 -0.6400 1.7320 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.0630 0.1900 1.9650 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.0160 -1.5800 1.7920 H 0 0 0 0 0 0 0 0 0 0 0 0

2.4940 -1.1970 1.8010 H 0 0 0 0 0 0 0 0 0 0 0 0

0.8580 -0.5410 2.0520 H 0 0 0 0 0 0 0 0 0 0 0 0

1.0710 -2.1280 1.2730 H 0 0 0 0 0 0 0 0 0 0 0 0

1 11 1 0 0 0 0

1 2 1 0 0 0 0

1 22 1 0 0 0 0

1 23 1 0 0 0 0

2 3 1 0 0 0 0

2 24 1 0 0 0 0

2 25 1 0 0 0 0

3 5 1 0 0 0 0

3 4 1 0 0 0 0

3 26 1 6 0 0 0

4 27 1 0 0 0 0

6 5 1 0 0 0 0

5 28 1 0 0 0 0

5 29 1 0 0 0 0

11 6 1 0 0 0 0

6 7 2 0 0 0 0

8 7 1 0 0 0 0

7 30 1 0 0 0 0

9 8 1 0 0 0 0

8 31 1 0 0 0 0

8 32 1 0 0 0 0

15 9 1 0 0 0 0

10 9 1 0 0 0 0

9 33 1 1 0 0 0

12 10 1 0 0 0 0

10 11 1 0 0 0 0

10 34 1 6 0 0 0

11 21 1 1 0 0 0

13 12 1 0 0 0 0

12 35 1 0 0 0 0

12 36 1 0 0 0 0

13 14 1 0 0 0 0

13 37 1 0 0 0 0

13 38 1 0 0 0 0

18 14 1 0 0 0 0

14 20 1 1 0 0 0

14 15 1 0 0 0 0

15 16 1 0 0 0 0

15 39 1 6 0 0 0

17 16 1 0 0 0 0

16 40 1 0 0 0 0

16 41 1 0 0 0 0

18 17 1 0 0 0 0

17 42 1 0 0 0 0

17 43 1 0 0 0 0

19 18 1 0 0 0 0

18 44 1 6 0 0 0

19 45 1 0 0 0 0

20 46 1 0 0 0 0

20 47 1 0 0 0 0

20 48 1 0 0 0 0

21 49 1 0 0 0 0

21 50 1 0 0 0 0

21 51 1 0 0 0 0

M END): 17 ms

reading 51 atoms

ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false

1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them.

Default Van der Waals type for model set to Babel

51 atoms created

ModelSet: not autobonding; use forceAutobond=true to force automatic bond creation

Script completed

Jmol script terminated

Molfile expand

Formula

C19H30O2

Net Charge

Average Mass

290.447

Monoisotopic Mass

290.22458

InChI

InChI=1S/C19H30O2/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/h3,13-17,20-21H,4-11H2,1-2H3/t13-,14-,15-,16-,17-,18-,19-/m0/s1

InChIKey

QADHLRWLCPCEKT-LOVVWNRFSA-N

SMILES

[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C

Metabolite of Species	Details
Mus musculus (NCBI:txid10090)	Source: BioModels - MODEL1507180067 See: PubMed
Homo sapiens (NCBI:txid9606)	See: DOI

Roles Classification
Biological Role(s):	androgen A sex hormone that stimulates or controls the development and maintenance of masculine characteristics in vertebrates by binding to androgen receptors. human metabolite Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens). mouse metabolite Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).

Application(s):	radiation protective agent Any compound that is able to protect normal cells from the damage caused by radiation therapy.

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	androst-5-ene-3β,17β-diol (CHEBI:2710) has parent hydride androstane (CHEBI:35509) androst-5-ene-3β,17β-diol (CHEBI:2710) has role androgen (CHEBI:50113) androst-5-ene-3β,17β-diol (CHEBI:2710) has role human metabolite (CHEBI:77746) androst-5-ene-3β,17β-diol (CHEBI:2710) has role mouse metabolite (CHEBI:75771) androst-5-ene-3β,17β-diol (CHEBI:2710) has role radiation protective agent (CHEBI:66987) androst-5-ene-3β,17β-diol (CHEBI:2710) is a 17β-hydroxy steroid (CHEBI:35343) androst-5-ene-3β,17β-diol (CHEBI:2710) is a 3β-hydroxy-Δ⁵-steroid (CHEBI:1722)

Incoming	androstenediol 3-sulfate(1−) (CHEBI:190287) has functional parent androst-5-ene-3β,17β-diol (CHEBI:2710)

IUPAC Name

androst-5-ene-3β,17β-diol

Synonyms	Sources
(3β,17β)-androst-5-ene-3,17-diol	ChemIDplus
3beta,17beta-Dihydroxy-5-androstene	KEGG COMPOUND
3β,17β-dihydroxyandrost-5-ene	ChemIDplus
3beta,17beta-Dihydroxyandrost-5-ene	KEGG COMPOUND
5-androstenediol	ChEBI
androst-5-en-3β,17β-diol	UniProt
Androst-5-ene-3beta,17beta-diol	KEGG COMPOUND
androst-5-enediol	ChemIDplus
Androstenediol	KEGG COMPOUND
hermaphrodiol	ChemIDplus

Manual Xrefs	Databases
10188	ChemSpider
214	DrugCentral
B81	PDBeChem
C04295	KEGG COMPOUND
D00179	KEGG DRUG
DB01524	DrugBank
FDB023228	FooDB
HMDB0003818	HMDB
LMST02020005	LIPID MAPS
WO9963973	Patent
View more database links

Registry Number	Type	Source
521-17-5	CAS Registry Number	ChemIDplus

Citations

Wu T, Liu W, Fan T, Zhong H, Zhou H, Guo W, Zhu X (2020)
5-Androstenediol prevents radiation injury in mice by promoting NF-κB signaling and inhibiting AIM2 inflammasome activation.
Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie 121, 109597 [PubMed:31726369]
[show Abstract]

Plaza F, Gabler F, Romero C, Vantman D, Valladares L, Vega M (2010)
The conversion of dehydroepiandrosterone into androst-5-ene-3beta,17beta-diol (androstenediol) is increased in endometria from untreated women with polycystic ovarian syndrome.
Steroids 75, 810-817 [PubMed:20620158]
[show Abstract]

Marwah A, Gomez FE, Marwah P, Ntambi JM, Fox BG, Lardy H (2006)
Redox reactions of dehydroepiandrosterone and its metabolites in differentiating 3T3-L1 adipocytes: A liquid chromatographic-mass spectrometric study.
Archives of biochemistry and biophysics 456, 1-7 [PubMed:17078923]
[show Abstract]

Padgett DA, MacCallum RC, Loria RM, Sheridan JF (2000)
Androstenediol-induced restoration of responsiveness to influenza vaccination in mice.
The journals of gerontology. Series A, Biological sciences and medical sciences 55, B418-24 [PubMed:10995038]
[show Abstract]

Ball WJ, Kasturi R, Dey P, Tabet M, O'Donnell S, Hudson D, Fishwild D (1999)
Isolation and characterization of human monoclonal antibodies to digoxin.
Journal of immunology (Baltimore, Md. : 1950) 163, 2291-2298 [PubMed:10438974]
[show Abstract]

Last Modified

17 January 2023

CHEBI:2710 - androst-5-ene-3β,17β-diol

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