Bovine Metabolome Database: Showing metabocard for 3a,21-Dihydroxy-5b-pregnane-11,20-dione (BMDB0006755)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 23:25:35 UTC

Update Date

2020-04-22 15:18:27 UTC

BMDB ID

BMDB0006755

Secondary Accession Numbers

BMDB06755

Metabolite Identification

Common Name

3a,21-Dihydroxy-5b-pregnane-11,20-dione

Description

3a,21-Dihydroxy-5b-pregnane-11,20-dione, also known as 3a,21-dihydroxy-5b-pregnane-11,20-dione, 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. Thus, 3a,21-dihydroxy-5b-pregnane-11,20-dione is considered to be a steroid lipid molecule. 3a,21-Dihydroxy-5b-pregnane-11,20-dione is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 3a,21-Dihydroxy-5b-pregnane-11,20-dione participates in a number of enzymatic reactions, within cattle. In particular, 3a,21-Dihydroxy-5b-pregnane-11,20-dione can be biosynthesized from tetrahydrocorticosterone through its interaction with the enzyme corticosteroid 11-beta-dehydrogenase isozyme 1. In addition, 3a,21-Dihydroxy-5b-pregnane-11,20-dione can be converted into 21-hydroxy-5b-pregnane-3,11,20-trione; which is catalyzed by the enzyme aldo-keto reductase family 1 member C4. In cattle, 3a,21-dihydroxy-5b-pregnane-11,20-dione is involved in the metabolic pathway called the steroidogenesis pathway.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
3alpha,21-Dihydroxy-5beta-pregnane-11,20-dione	HMDB
5beta-Pregnane-3alpha,21-diol-11,20-dione	HMDB

Chemical Formula

C₂₁H₃₂O₄

Average Molecular Weight

348.4764

Monoisotopic Molecular Weight

348.230059512

IUPAC Name

(1S,2S,5R,7R,10S,11S,15S)-5-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-17-one

Traditional Name

(1S,2S,5R,7R,10S,11S,15S)-5-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-17-one

CAS Registry Number

566-03-0

SMILES

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

InChI Identifier

InChI=1S/C21H32O4/c1-20-8-7-13(23)9-12(20)3-4-14-15-5-6-16(18(25)11-22)21(15,2)10-17(24)19(14)20/h12-16,19,22-23H,3-11H2,1-2H3/t12-,13-,14+,15+,16?,19-,20+,21+/m1/s1

InChI Key

XWYBFXIUISNTQG-XPYNSANSSA-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
3-hydroxysteroid
11-oxosteroid
Oxosteroid
3-alpha-hydroxysteroid
Cyclic alcohol
Alpha-hydroxy ketone
Ketone
Secondary alcohol
Alcohol
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Carbonyl group
Primary alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030199 )

Ontology

Status

Expected but not Quantified

Origin

Endogenous

Exogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cell membrane
Cytoplasm
Membrane

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.56	ALOGPS
logP	2.25	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	13.86	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	95.28 m³·mol⁻¹	ChemAxon
Polarizability	39.15 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0gbi-1659000000-d6ee4b8ffd9d3279a797	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-004i-1546900000-70b347d6200e4b28a36f	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001j-0019000000-523219bfbad06cd0c269	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01qa-0149000000-6757bdd43ed99db2275b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05fs-4193000000-f57704e37c1e7b7af64c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0009000000-4fc0c91330f741f36c93	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00mk-1039000000-1fc49c3cd7bc3ee2d17a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0abi-4093000000-e75b649ebaa0fab9b66b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-002b-0009000000-1e70a00f7d48eb363ae5	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00kb-0029000000-bf7a15c369bb9b829c41	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00kb-1196000000-48db5959e2974fae3f75	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000t-0009000000-6c24133e55d3a62dc790	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03ea-1669000000-2f3cbbb2b029b2e028f2	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00r7-9870000000-936570017e921a3b2547	View in MoNA