Bovine Metabolome Database: Showing metabocard for Tetrahydrocorticosterone (BMDB0000268)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:27:38 UTC

Update Date

2020-05-21 16:28:51 UTC

BMDB ID

BMDB0000268

Secondary Accession Numbers

BMDB00268

Metabolite Identification

Common Name

Tetrahydrocorticosterone

Description

Tetrahydrocorticosterone 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, tetrahydrocorticosterone is considered to be a steroid lipid molecule. Tetrahydrocorticosterone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(3alpha,5beta,11beta)-3,11,21-Trihydroxypregnan-20-one	HMDB
(3α,5β,11β)-3,11,21-Trihydroxypregnan-20-one	HMDB
3alpha,11beta,21-Trihydroxy-5beta-pregnan-20-one	HMDB
3alpha,5beta-Tetrahydrocorticosterone	HMDB
3α,11β,21-Trihydroxy-5β-pregnan-20-one	HMDB
3α,5β-Tetrahydrocorticosterone	HMDB
5beta-Pregnane-3alpha,11beta,21-triol-20-one	HMDB
5β-Pregnane-3α,11β,21-triol-20-one	HMDB
THB	HMDB
Tetrahydrocorticosterone	HMDB

Chemical Formula

C₂₁H₃₄O₄

Average Molecular Weight

350.4923

Monoisotopic Molecular Weight

350.245709576

IUPAC Name

1-[(1S,2S,5R,7R,10S,11S,14S,15S,17S)-5,17-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-2-hydroxyethan-1-one

Traditional Name

1-[(1S,2S,5R,7R,10S,11S,14S,15S,17S)-5,17-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-2-hydroxyethanone

CAS Registry Number

68-42-8

SMILES

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

InChI Identifier

InChI=1S/C21H34O4/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/h12-17,19,22-24H,3-11H2,1-2H3/t12-,13-,14+,15+,16-,17+,19-,20+,21+/m1/s1

InChI Key

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

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

21-hydroxy steroid (CHEBI:9481 )
C21 steroids (gluco/mineralocorticoids, progestogens) and derivatives (C05476 )
C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030100 )

Ontology

Status

Detected 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	2.07	ALOGPS
logP	1.86	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	13.86	ChemAxon
pKa (Strongest Basic)	-0.25	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	96.2 m³·mol⁻¹	ChemAxon
Polarizability	40 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	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_5) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_6) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_7) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0002-0009000000-cec330110dfc2d03e126	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0592-9077000000-7adca5a0af60b9fda618	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0udi-3490000000-84176a53f54507ead0c6	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive	splash10-01b9-1947000000-cbb72686416e9b705c28	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0fsi-0019000000-3e07505796a0d0ccf759	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0159-0029000000-a684771622b2b677b05e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fmi-3193000000-258bcce49fc0fdfa367c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0009000000-604ddf044ec2555026ca	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-05o1-1029000000-5f7d67b696b8216549c8	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0c2c-4094000000-6414e1ce977710e5f136	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0ue9-0009000000-0aa7b6bcf5326ebfd06d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0g59-1946000000-70f8a3a83793bdccde86	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014l-9360000000-b75838c5554768281848	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0009000000-ce9bde525139d21c8d92	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00kb-0009000000-3c63ef8c1c108dd51eec	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0hg2-1049000000-d6e8731409c9d6502763	View in MoNA

Biological Properties

Cellular Locations

Cell membrane
Cytoplasm
Membrane

Biospecimen Locations

Liver

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Liver	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Liver	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0009850

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

58996

KEGG Compound ID

C05476

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Tetrahydrocorticosterone

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

References

Synthesis Reference

Higashi, Tatsuya; Yokoi, Hiroyuki; Maekubo, Hitoe; Honda, Ayako; Shimada, Kazutake. Studies on neurosteroids. XXIII. Analysis of tetrahydrocorticosterone isomers in the brain of rats exposed to immobilization using LC-MS. Steroids (2007), 72(13), 865-874.

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Dihydrodiol dehydrogenase 3

General function:: Involved in oxidoreductase activity
Specific function:: Not Available
Gene Name:: Not Available
Uniprot ID:: P52898
Molecular weight:: 36784.0

Reactions

Tetrahydrocorticosterone + NADP → 11b,21-Dihydroxy-5b-pregnane-3,20-dione + NADPH	details

Showing metabocard for Tetrahydrocorticosterone (BMDB0000268)

Structure for BMDB0000268 (Tetrahydrocorticosterone)

Enzymes

Reactions