Milk Composition Database: Showing metabocard for Aldosterone (BMDB0000037)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:18:48 UTC

Update Date

2020-05-11 20:56:49 UTC

MCDB ID

BMDB0000037

Secondary Accession Numbers

BMDB00037

Metabolite Identification

Common Name

Aldosterone

Description

Aldosterone, also known as aldocorten or delta-aldosterone, belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone. Aldosterone exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Aldosterone exists in all living organisms, ranging from bacteria to humans.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(+)-Aldosterone	ChEBI
(11beta)-11,21-Dihydroxy-3,20-dioxopregn-4-en-18-al	ChEBI
11beta,21-Dihydroxy-3,20-dioxo-4-pregnen-18-al	ChEBI
(11b)-11,21-Dihydroxy-3,20-dioxopregn-4-en-18-al	Generator
(11Β)-11,21-dihydroxy-3,20-dioxopregn-4-en-18-al	Generator
11b,21-Dihydroxy-3,20-dioxo-4-pregnen-18-al	Generator
11Β,21-dihydroxy-3,20-dioxo-4-pregnen-18-al	Generator
Aldosterone, (+-)-isomer	HMDB
Aldosterone, (11 beta,17 alpha)-isomer	HMDB
11beta,21-Dihydroxy-3,20-diketo-4-pregnen-18-al	HMDB
11beta,21-Dihydroxy-3,20-diketopregn-4-ene-18-al	HMDB
11beta,21-Dihydroxypregn-4-ene-3,18,20-trione	HMDB
11Β,21-dihydroxy-3,20-diketo-4-pregnen-18-al	HMDB
11Β,21-dihydroxy-3,20-diketopregn-4-ene-18-al	HMDB
11Β,21-dihydroxypregn-4-ene-3,18,20-trione	HMDB
18-Formyl-11beta,21-dihydroxy-4-pregnene-3,20-dione	HMDB
18-Formyl-11β,21-dihydroxy-4-pregnene-3,20-dione	HMDB
18-Oxocorticosterone	HMDB
Aldosterone	HMDB

Chemical Formula

C₂₁H₂₈O₅

Average Molecular Weight

360.444

Monoisotopic Molecular Weight

360.193674006

IUPAC Name

(1S,2R,10S,11S,14S,15R,17S)-17-hydroxy-14-(2-hydroxyacetyl)-2-methyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-15-carbaldehyde

Traditional Name

(1S,2R,10S,11S,14S,15R,17S)-17-hydroxy-14-(2-hydroxyacetyl)-2-methyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-15-carbaldehyde

CAS Registry Number

52-39-1

SMILES

[H][C@@]12CC[C@H](C(=O)CO)[C@]1(C[C@H](O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C)C=O

InChI Identifier

InChI=1S/C21H28O5/c1-20-7-6-13(24)8-12(20)2-3-14-15-4-5-16(18(26)10-22)21(15,11-23)9-17(25)19(14)20/h8,11,14-17,19,22,25H,2-7,9-10H2,1H3/t14-,15-,16+,17-,19+,20-,21+/m0/s1

InChI Key

PQSUYGKTWSAVDQ-ZVIOFETBSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Hydroxysteroids

Direct Parent

21-hydroxysteroids

Alternative Parents

Substituents

Progestogin-skeleton
21-hydroxysteroid
20-oxosteroid
Pregnane-skeleton
18-oxosteroid
3-oxo-delta-4-steroid
3-oxosteroid
Oxosteroid
11-beta-hydroxysteroid
11-hydroxysteroid
Delta-4-steroid
Cyclohexenone
Cyclic alcohol
Alpha-hydroxy ketone
Ketone
Secondary alcohol
Cyclic ketone
Alcohol
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Carbonyl group
Primary alcohol
Aldehyde
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

3-oxo steroid (CHEBI:27584 )
11beta-hydroxy steroid (CHEBI:27584 )
20-oxo steroid (CHEBI:27584 )
mineralocorticoid (CHEBI:27584 )
21-hydroxy steroid (CHEBI:27584 )
C21-steroid hormone (CHEBI:27584 )
18-oxo steroid (CHEBI:27584 )
Pregnane and derivatives [Fig] (C01780 )
Mineralocorticoids (C01780 )
C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030026 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	166.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.051 mg/mL at 37 °C	Not Available
LogP	1.08	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
logP	1.54	ALOGPS
logP	1.06	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	13.82	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	91.67 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	96.79 m³·mol⁻¹	ChemAxon
Polarizability	38.82 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-06si-0694000000-60e1d35ad11d153b5152	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_5) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_4) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-0596-2961000000-38453356e63a34116d1e	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0596-2961000000-38453356e63a34116d1e	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-00te-0795000000-8d98d67da0a192149a61	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-00dj-0930000000-9939fdefed4cc5aa1223	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-00dj-0940000000-75f24824d5d69e3323b5	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-00dj-0930000000-f7fdb389785258ecb726	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-00te-0795000000-21a3474f31fec88ef12b	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-01ox-0019000000-cd366dadcc06e9631cd2	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-00dj-0960000000-b9db4295ff8d4a972819	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-00dj-0940000000-f4e29f9da2ae7127e9e5	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01ox-0019000000-2c34b91dc8d5030ac25b	2017-07-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01tc-0219000000-9e4b8f664dbb988d46f0	2017-07-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0540-4594000000-185caf2f40c5027fdb0a	2017-07-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0009000000-ba327369eee699ad5a21	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4l-1019000000-f6f3606b25ff21806842	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0pbc-8096000000-deeb08e544bed8419dd5	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0019000000-e1f2d66ea30a0f614786	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00xr-0079000000-04e603b008124e8b4eed	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-3592000000-3c3bd43e2b935cce0195	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0019000000-a156d06f21ba3667752f	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0kmj-2095000000-57e9fe798f41239f2b23	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05fs-1091000000-9060d8f84b530afda73b	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, 100%_DMSO, experimental)	Not Available	2020-02-10	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)	Not Available	2020-02-10	View Spectrum

Concentrations

Status	Value		Reference	Details
Detected but not Quantified	Not Applicable		PMID: 29565828	details

External Links

HMDB ID

HMDB0000037

DrugBank ID

DB04630

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB021883

KNApSAcK ID

Not Available

Chemspider ID

5633

KEGG Compound ID

C01780

BioCyc ID

ALDOSTERONE

BiGG ID

Not Available

Wikipedia Link

Aldosterone

METLIN ID

Not Available

PubChem Compound

5839

PDB ID

Not Available

ChEBI ID

27584

References

Synthesis Reference

Bear, Brian R.; Parnes, Jason S.; Shea, Kenneth J. Progress toward the Total Synthesis of (+)-Aldosterone: Synthesis of the A-D Rings. Organic Letters (2003), 5(10), 1613-1616.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735. [PubMed:29565828 ]

Showing metabocard for Aldosterone (BMDB0000037)

Structure for BMDB0000037 (Aldosterone)