Bovine Metabolome Database: Showing metabocard for 3a-Hydroxy-5b-pregnane-20-one (BMDB0006759)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 23:25:40 UTC

Update Date

2020-04-22 15:18:29 UTC

BMDB ID

BMDB0006759

Secondary Accession Numbers

BMDB06759

Metabolite Identification

Common Name

3a-Hydroxy-5b-pregnane-20-one

Description

3a-Hydroxy-5b-pregnane-20-one belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety. 3a-Hydroxy-5b-pregnane-20-one is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). 3a-Hydroxy-5b-pregnane-20-one can be converted into 5a-pregnane-3,20-dione; which is catalyzed by the enzyme aldo-keto reductase family 1 member C4. In cattle, 3a-hydroxy-5b-pregnane-20-one 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-Hydroxy-5beta-pregnane-20-one	HMDB

Chemical Formula

C₂₁H₃₄O₂

Average Molecular Weight

318.4935

Monoisotopic Molecular Weight

318.255880332

IUPAC Name

1-[(2S,5R,7R,14S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]ethan-1-one

Traditional Name

pregnanolone

CAS Registry Number

Not Available

SMILES

[H][C@]12CCC3C4CC[C@H](C(C)=O)[C@@]4(C)CCC3[C@@]1(C)CC[C@@H](O)C2

InChI Identifier

InChI=1S/C21H34O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h14-19,23H,4-12H2,1-3H3/t14-,15-,16?,17-,18?,19?,20+,21-/m1/s1

InChI Key

AURFZBICLPNKBZ-KCZNCWLVSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Pregnane steroids

Direct Parent

Gluco/mineralocorticoids, progestogins and derivatives

Alternative Parents

Substituents

Progestogin-skeleton
20-oxosteroid
3-hydroxysteroid
Hydroxysteroid
3-alpha-hydroxysteroid
Oxosteroid
Cyclic alcohol
Ketone
Secondary alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

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	4.28	ALOGPS
logP	3.99	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	18.3	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	92.91 m³·mol⁻¹	ChemAxon
Polarizability	38.36 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	splash10-11du-0292000000-d5c96280786507060adf	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-01t9-1109000000-2c47b5bb98f082161201	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	splash10-0uxr-0019000000-82b5328b4643c0421b0d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0uxr-1496000000-6fd25d5861771fb104b7	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-002o-2490000000-ba6e2bc4d584ea3d3a4b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0029000000-826f869c8c8e3739b52e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0059000000-699658e7c96cdaee62e8	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0zmr-1092000000-9cb4a247b808ab6f5c27	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0009000000-bbaa566ea695ae62f84e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0019000000-b27ed891ac6811eab39d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-0039000000-ee44f8ffc9f4d431f1b9	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0uxr-0039000000-5b11ff3658bc22f27d0a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0j6v-0984000000-16637ba86fccb8e48e17	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4m-6950000000-17eb447f04784923dcfe	View in MoNA