androsterone (CHEBI:16032)

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CHEBI:16032 - androsterone

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ChEBI Name	androsterone

ChEBI ID	CHEBI:16032

Definition	An androstanoid that is 5α-androstane having a hydroxy substituent at the 3α-position and an oxo group at the 17-position. It is a metabolite of dehydroepiandrosterone .

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

Secondary ChEBI IDs	CHEBI:2714, CHEBI:13832, CHEBI:20235

Supplier Information	ChemicalBook:CB91236269, eMolecules:31239572, eMolecules:31225710, ZINC000005965908

Download	Molfile XML SDF

more structures >>

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AOI - Ideal conformer

Mrv1927 06162114533D

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Time for openFile(AOI - Ideal conformer

Mrv1927 06162114533D

51 54 0 0 0 0 999 V2000

-2.3900 1.5190 -0.2610 C 0 0 1 0 0 0 0 0 0 0 0 0

-3.7920 1.4760 0.3490 C 0 0 1 0 0 0 0 0 0 0 0 0

-4.4890 0.1780 -0.0650 C 0 0 1 0 0 0 0 0 0 0 0 0

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-3.6780 -1.0180 0.4370 C 0 0 1 0 0 0 0 0 0 0 0 0

-2.2760 -0.9750 -0.1740 C 0 0 2 0 0 0 0 0 0 0 0 0

-1.4650 -2.1730 0.3240 C 0 0 1 0 0 0 0 0 0 0 0 0

-0.0630 -2.1300 -0.2850 C 0 0 1 0 0 0 0 0 0 0 0 0

0.6350 -0.8350 0.1340 C 0 0 2 0 0 0 0 0 0 0 0 0

-0.1780 0.3640 -0.3760 C 0 0 1 0 0 0 0 0 0 0 0 0

-1.5780 0.3220 0.2390 C 0 0 1 0 0 0 0 0 0 0 0 0

0.4920 1.6870 -0.0210 C 0 0 1 0 0 0 0 0 0 0 0 0

1.9420 1.7350 -0.5330 C 0 0 1 0 0 0 0 0 0 0 0 0

2.6730 0.5530 0.0710 C 0 0 1 0 0 0 0 0 0 0 0 0

2.0110 -0.7490 -0.5020 C 0 0 1 0 0 0 0 0 0 0 0 0

3.0190 -1.8140 -0.0540 C 0 0 1 0 0 0 0 0 0 0 0 0

4.3830 -1.1260 -0.3340 C 0 0 1 0 0 0 0 0 0 0 0 0

4.1210 0.3950 -0.2870 C 0 0 0 0 0 0 0 0 0 0 0 0

4.9130 1.2760 -0.5190 O 0 0 0 0 0 0 0 0 0 0 0 0

2.5190 0.5770 1.5930 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.4670 0.3810 1.7640 C 0 0 0 0 0 0 0 0 0 0 0 0

-2.4660 1.4780 -1.3480 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.8940 2.4430 0.0340 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.7170 1.5170 1.4360 H 0 0 0 0 0 0 0 0 0 0 0 0

-4.3700 2.3290 -0.0070 H 0 0 0 0 0 0 0 0 0 0 0 0

-5.4880 0.1480 0.3700 H 0 0 0 0 0 0 0 0 0 0 0 0

-5.0890 0.8540 -1.8770 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.6030 -0.9760 1.5230 H 0 0 0 0 0 0 0 0 0 0 0 0

-4.1750 -1.9430 0.1430 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.3520 -1.0150 -1.2600 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.3900 -2.1340 1.4110 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.9620 -3.0970 0.0280 H 0 0 0 0 0 0 0 0 0 0 0 0

0.5140 -2.9850 0.0690 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.1380 -2.1680 -1.3720 H 0 0 0 0 0 0 0 0 0 0 0 0

0.7280 -0.8020 1.2190 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.2680 0.2940 -1.4600 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.0720 2.5040 -0.4700 H 0 0 0 0 0 0 0 0 0 0 0 0

0.4920 1.8080 1.0620 H 0 0 0 0 0 0 0 0 0 0 0 0

1.9530 1.6620 -1.6200 H 0 0 0 0 0 0 0 0 0 0 0 0

2.4150 2.6650 -0.2180 H 0 0 0 0 0 0 0 0 0 0 0 0

1.9280 -0.7120 -1.5880 H 0 0 0 0 0 0 0 0 0 0 0 0

2.9060 -2.0310 1.0090 H 0 0 0 0 0 0 0 0 0 0 0 0

2.9110 -2.7230 -0.6460 H 0 0 0 0 0 0 0 0 0 0 0 0

5.0980 -1.3830 0.4480 H 0 0 0 0 0 0 0 0 0 0 0 0

4.7650 -1.4370 -1.3060 H 0 0 0 0 0 0 0 0 0 0 0 0

1.4610 0.6200 1.8510 H 0 0 0 0 0 0 0 0 0 0 0 0

2.9600 -0.3260 2.0170 H 0 0 0 0 0 0 0 0 0 0 0 0

3.0270 1.4530 1.9960 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.4650 0.3520 2.2020 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.8890 -0.4710 2.1200 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.9690 1.3060 2.0560 H 0 0 0 0 0 0 0 0 0 0 0 0

11 21 1 1 0 0 0

14 20 1 1 0 0 0

2 1 1 0 0 0 0

2 3 1 0 0 0 0

12 13 1 0 0 0 0

12 10 1 0 0 0 0

1 11 1 0 0 0 0

13 14 1 0 0 0 0

11 10 1 0 0 0 0

11 6 1 0 0 0 0

14 18 1 0 0 0 0

14 15 1 0 0 0 0

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5 6 1 0 0 0 0

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15 16 1 0 0 0 0

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17 16 1 0 0 0 0

1 22 1 0 0 0 0

1 23 1 0 0 0 0

2 24 1 0 0 0 0

2 25 1 0 0 0 0

3 26 1 1 0 0 0

4 27 1 0 0 0 0

5 28 1 0 0 0 0

5 29 1 0 0 0 0

6 30 1 6 0 0 0

7 31 1 0 0 0 0

7 32 1 0 0 0 0

8 33 1 0 0 0 0

8 34 1 0 0 0 0

9 35 1 1 0 0 0

10 36 1 6 0 0 0

12 37 1 0 0 0 0

12 38 1 0 0 0 0

13 39 1 0 0 0 0

13 40 1 0 0 0 0

15 41 1 6 0 0 0

16 42 1 0 0 0 0

16 43 1 0 0 0 0

17 44 1 0 0 0 0

17 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): 22 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

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Molfile expand

Wikipedia	License
Lenvatinib, sold under the brand name Lenvima among others, is an anti-cancer medication for the treatment of certain kinds of thyroid cancer and for other cancers as well. It was developed by Eisai Co. and acts as a multiple kinase inhibitor against the VEGFR1, VEGFR2 and VEGFR3 kinases.
Read full article at Wikipedia

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/h12-16,20H,3-11H2,1-2H3/t12-,13+,14-,15-,16-,18-,19-/m0/s1

InChIKey

QGXBDMJGAMFCBF-HLUDHZFRSA-N

SMILES

[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[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
Homo sapiens (NCBI:txid9606)	Found in urine (BTO:0001419). See: David F. Putnam Composition and Concentrative Properties of Human Urine. NASA Contractor Report. July 1971
Homo sapiens (NCBI:txid9606)	Found in cerebrospinal fluid (UBERON:0001359). See: PubMed
Homo sapiens (NCBI:txid9606)	Found in blood (UBERON:0000178). See: PubMed

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). pheromone A semiochemical used in olfactory communication between organisms of the same species eliciting a change in sexual or social behaviour. human urinary metabolite Any metabolite (endogenous or exogenous) found in human urine samples. human blood serum metabolite Any metabolite (endogenous or exogenous) found in human blood serum samples. mouse metabolite Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).

Application(s):	anticonvulsant A drug used to prevent seizures or reduce their severity.

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	androsterone (CHEBI:16032) has parent hydride 5α-androstane (CHEBI:28859) androsterone (CHEBI:16032) has role androgen (CHEBI:50113) androsterone (CHEBI:16032) has role anticonvulsant (CHEBI:35623) androsterone (CHEBI:16032) has role human blood serum metabolite (CHEBI:85234) androsterone (CHEBI:16032) has role human metabolite (CHEBI:77746) androsterone (CHEBI:16032) has role human urinary metabolite (CHEBI:84087) androsterone (CHEBI:16032) has role mouse metabolite (CHEBI:75771) androsterone (CHEBI:16032) has role pheromone (CHEBI:26013) androsterone (CHEBI:16032) is a 17-oxo steroid (CHEBI:19168) androsterone (CHEBI:16032) is a 3α-hydroxy steroid (CHEBI:36835) androsterone (CHEBI:16032) is a androstanoid (CHEBI:50402) androsterone (CHEBI:16032) is a C₁₉-steroid (CHEBI:131621)

Incoming	androsterone 3-glucosiduronic acid (CHEBI:28832) has functional parent androsterone (CHEBI:16032) androsterone sulfate (CHEBI:83037) has functional parent androsterone (CHEBI:16032)

IUPAC Name

3α-hydroxy-5α-androstan-17-one

Synonyms	Sources
(3α,5α)-3-hydroxyandrostan-17-one	NIST Chemistry WebBook
3-epihydroxyetioallocholan-17-one	ChemIDplus
3alpha-Hydroxy-5alpha-androstan-17-one	KEGG COMPOUND
3α-hydroxyetioallocholan-17-one	NIST Chemistry WebBook
5α-androstane-3α-ol-17-one	NIST Chemistry WebBook
5α-androsterone	NIST Chemistry WebBook
Androkinine	NIST Chemistry WebBook
Androsterone	KEGG COMPOUND
androsterone	UniProt
Androtine	NIST Chemistry WebBook
cis-androsterone	NIST Chemistry WebBook

Manual Xrefs	Databases
5668	ChemSpider
Androsterone	Wikipedia
ANDROSTERONE	MetaCyc
AOI	PDBeChem
C00523	KEGG COMPOUND
FDB021881	FooDB
HMDB0000031	HMDB
LMST02020001	LIPID MAPS
View more database links

Registry Numbers	Types	Sources
2217626	Reaxys Registry Number	Reaxys
53-41-8	CAS Registry Number	NIST Chemistry WebBook
53-41-8	CAS Registry Number	ChemIDplus
700649	Gmelin Registry Number	Gmelin

Citations	Types	Sources
10438974	PubMed citation	Europe PMC
10625505	PubMed citation	Europe PMC
12524453	PubMed citation	Europe PMC
12943709	PubMed citation	Europe PMC
14643063	PubMed citation	Europe PMC
15608121	PubMed citation	Europe PMC
158859	PubMed citation	Europe PMC
15894033	PubMed citation	Europe PMC
15946323	PubMed citation	Europe PMC
15954157	PubMed citation	Europe PMC
16078844	PubMed citation	Europe PMC
16585475	PubMed citation	Europe PMC
16675527	PubMed citation	Europe PMC
17017935	PubMed citation	Europe PMC
17260133	PubMed citation	Europe PMC
17716701	PubMed citation	Europe PMC
19493957	PubMed citation	Europe PMC
20960798	PubMed citation	Europe PMC
24705905	PubMed citation	Europe PMC
26105109	PubMed citation	Europe PMC
2946134	PubMed citation	Europe PMC
30408720	PubMed citation	Europe PMC
3162156	PubMed citation	Europe PMC
3802509	PubMed citation	Europe PMC
6211346	PubMed citation	Europe PMC
7245287	PubMed citation	Europe PMC
79632	PubMed citation	Europe PMC
9188497	PubMed citation	Europe PMC
9699884	PubMed citation	Europe PMC

Last Modified

20 May 2022

General Comment
2011-01-14	Androsterone is made in the liver from the metabolism of testosterone.

CHEBI:16032 - androsterone

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