Bovine Metabolome Database: Showing metabocard for 21-Hydroxy-5b-pregnane-3,11,20-trione (BMDB0006756)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 23:25:36 UTC

Update Date

2020-04-22 15:18:27 UTC

BMDB ID

BMDB0006756

Secondary Accession Numbers

BMDB06756

Metabolite Identification

Common Name

21-Hydroxy-5b-pregnane-3,11,20-trione

Description

21-Hydroxy-5b-pregnane-3,11,20-trione 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, 21-hydroxy-5b-pregnane-3,11,20-trione is considered to be a steroid lipid molecule. 21-Hydroxy-5b-pregnane-3,11,20-trione is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 21-Hydroxy-5b-pregnane-3,11,20-trione can be biosynthesized from 3a,21-dihydroxy-5b-pregnane-11,20-dione; which is mediated by the enzyme aldo-keto reductase family 1 member C4. In cattle, 21-hydroxy-5b-pregnane-3,11,20-trione is involved in the metabolic pathway called the steroidogenesis pathway.

Structure

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

Synonyms

Value	Source
21-Hydroxy-5beta-pregnane-3,11,20-trione	HMDB

Chemical Formula

C₂₁H₃₀O₄

Average Molecular Weight

346.4605

Monoisotopic Molecular Weight

346.214409448

IUPAC Name

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

Traditional Name

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

CAS Registry Number

10417-86-4

SMILES

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

InChI Identifier

InChI=1S/C21H30O4/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/h12,14-16,19,22H,3-11H2,1-2H3/t12-,14+,15+,16?,19-,20+,21+/m1/s1

InChI Key

ZDUVZJUTJOBJHS-HNEBDTNWSA-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-oxosteroid
11-oxosteroid
Oxosteroid
3-oxo-5-beta-steroid
Alpha-hydroxy ketone
Ketone
Cyclic ketone
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 (LMST02030196 )

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	2.63	ALOGPS
logP	2.45	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	13.86	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	71.44 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	94.25 m³·mol⁻¹	ChemAxon
Polarizability	38.67 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	splash10-0fki-1988000000-fba247baf630a7210351	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0udr-2639300000-c9ca38b4ccbbd8f2986e	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	splash10-002b-0019000000-24f7d25b96d058ce27ec	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-016r-0139000000-14964e5f329435527649	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4s-3293000000-fdc80d45785ab54b814f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0009000000-804a5ed2772af86708b7	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-05p2-1029000000-b83f2a0acc0792e5262b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4r-5092000000-c68952d24a29d9931c16	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-002b-0009000000-33bcf2e22dc5313c0e4a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03ys-0049000000-9e885d9932104c564774	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-006t-0193000000-d4a852e1dae01823cdfc	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-002b-0009000000-962664f8be4e6a4a1d65	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03fr-0269000000-d077f7e8c79f38b5e3ed	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-4690000000-b76906ca897f4798e371	View in MoNA