Bovine Metabolome Database: Showing metabocard for Alloepipregnanolone (BMDB0001455)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:46:14 UTC

Update Date

2020-04-22 15:08:17 UTC

BMDB ID

BMDB0001455

Secondary Accession Numbers

BMDB01455

Metabolite Identification

Common Name

Alloepipregnanolone

Description

Alloepipregnanolone, also known as eltanolone, 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. Thus, alloepipregnanolone is considered to be a steroid. Based on a literature review very few articles have been published on Alloepipregnanolone.

Structure

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

Synonyms

Value	Source
(3beta,5alpha)-3-Hydroxypregnan-20-one	ChEBI
3beta-Hydroxy-5alpha-pregnane-20-one	ChEBI
5alpha-Pregnan-3beta-ol-20-one	ChEBI
Allopregnan-3beta-ol-20-one	ChEBI
Epiallopregnanolone	Kegg
3beta-Hydroxy-5alpha-pregnan-20-one	Kegg
(3b,5a)-3-Hydroxypregnan-20-one	Generator
(3Β,5α)-3-hydroxypregnan-20-one	Generator
3b-Hydroxy-5a-pregnane-20-one	Generator
3Β-hydroxy-5α-pregnane-20-one	Generator
5a-Pregnan-3b-ol-20-one	Generator
5Α-pregnan-3β-ol-20-one	Generator
Allopregnan-3b-ol-20-one	Generator
Allopregnan-3β-ol-20-one	Generator
3b-Hydroxy-5a-pregnan-20-one	Generator
3Β-hydroxy-5α-pregnan-20-one	Generator
3 Hydroxypregnan 20 one	MeSH
3 alpha Hydroxy 5 alpha pregnan 20 one	MeSH
3 alpha Hydroxy 5 beta pregnan 20 one	MeSH
3 alpha, 5 beta Tetrahydroprogesterone	MeSH
3 alpha, 5 beta-Tetrahydroprogesterone	MeSH
3 alpha-Hydroxy-5 alpha-pregnan-20-one	MeSH
3 alpha-Hydroxy-5 beta-pregnan-20-one	MeSH
3-Hydroxypregnan-20-one	MeSH
3beta Hydroxy 5alpha pregnan 20 one	MeSH
Allopregnan 3 beta ol 20 one	MeSH
Allopregnan-3 beta-ol-20-one	MeSH
Eltanolone	MeSH
Epipregnanolone	MeSH
Pregnan 3alpha ol 20 one	MeSH
Pregnan-3alpha-ol-20-one	MeSH
Pregnanolone	MeSH
Pregnanolone, (3alpha)-isomer	MeSH
Pregnanolone, (3alpha, 5beta, 17-alpha)-isomer	MeSH
Pregnanolone, (3alpha,5alpha)-isomer	MeSH
Pregnanolone, (3alpha,5beta)-isomer	MeSH
Pregnanolone, (3beta)-isomer	MeSH
Pregnanolone, (3beta, 5alpha)-isomer	MeSH
Pregnanolone, (3beta, 5alpha, 17alpha)-isomer	MeSH
Pregnanolone, (3beta, 5alpha, 8alpha, 17beta)-isomer	MeSH
Pregnanolone, (3beta, 5beta)-isomer	MeSH
Pregnanolone, (3beta, 5beta, 17alpha)-isomer	MeSH
Pregnanolone, (3beta, 5beta,14beta)-isomer	MeSH
Pregnanolone, (5alpha)-isomer	MeSH
Sepranolone	MeSH
alpha-Hydroxy-5 alpha-pregnan-20-one, 3	MeSH
alpha-Hydroxy-5 beta-pregnan-20-one, 3	MeSH
alpha-Pregnan-20-one, 3 alpha-hydroxy-5	MeSH
beta-Ol-20-one, allopregnan-3	MeSH
beta-Pregnan-20-one, 3 alpha-hydroxy-5	MeSH
3-deoxo-3b-Hydroxy-5a-dihydroprogesterone	HMDB
3b-Allopregnanolone	HMDB
3b-Hydroxy-5a,17b-pregnan-20-one	HMDB
3b-Hydroxy-5a-tetrahydroprogesterone	HMDB
5a-Dihydropregnenolone	HMDB
5a-Pregnane-3b-ol-20-one	HMDB
Allopregnanolone	HMDB, MeSH
Isopregnanolone	HMDB

Chemical Formula

C₂₁H₃₄O₂

Average Molecular Weight

318.4935

Monoisotopic Molecular Weight

318.255880332

IUPAC Name

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

Traditional Name

isopregnanolone

CAS Registry Number

516-55-2

SMILES

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

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+/m0/s1

InChI Key

AURFZBICLPNKBZ-FZCSVUEKSA-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-beta-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

3-hydroxy-5alpha-pregnan-20-one (CHEBI:11909 )
C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030173 )

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	194.5 °C	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	38.72 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	splash10-1174-0292000000-fb2c0f3a1cfddb10cb08	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-004i-2139000000-ab8a6de8f5a129af086e	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-0129000000-90e5fcb36022dd1ba688	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0uxr-0396000000-4c39fe7ccd8e0c86e179	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-2490000000-7ac55935cc0d4da95860	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0029000000-fa09e69c9c0b6736d2e7	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0069000000-d1d57e3e1a99da4ed11f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0zg0-1193000000-44d1597a59ac11f16a41	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0gb9-0029000000-87d0f95f5dbd34be3481	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0i0v-1985000000-41959912f77ca2ce0a84	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052b-6950000000-e08ac95bf48862f7a6a8	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-0019000000-2f80b71569ae462f9c19	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-0039000000-8ffa894a38bb04888d3b	View in MoNA

Biological Properties

Cellular Locations

Cell membrane
Cytoplasm
Membrane

Biospecimen Locations

Not Available

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0001455

DrugBank ID

DB12972

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022634

KNApSAcK ID

Not Available

Chemspider ID

83761

KEGG Compound ID

C15484

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

92787

PDB ID

Not Available

ChEBI ID

11909

References

Synthesis Reference

Kametani, Tetsuji; Suzuki, Koji; Nemoto, Hideo. Efficient synthesis of a pregnane-type steroid. Total synthesis of (+)-5a-dihydropregnenolone [(+)-3b-hydroxy-5a-pregnan-20-one]. Journal of the Chemical Society, Perkin Transactions 1. 1980, p.2805-2807

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Alloepipregnanolone (BMDB0001455)

Structure for BMDB0001455 (Alloepipregnanolone)