Showing Compound 3b-Allotetrahydrocortisol (FDB021941)

Record Information

Version

1.0

Creation date

2011-09-21 00:05:34 UTC

Update date

2015-07-21 06:56:54 UTC

Primary ID

FDB021941

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

3b-Allotetrahydrocortisol

Description

3b-Allotetrahydrocortisol is one of the tetrahydrometabolites of cortisol. The 11-beta-hydroxysteroid dehydrogenase (11beta-HSD) is responsible for the interconversion of both the hormonally inactive cortisone and the active cortisol, which has implications in the pathogenesis of numerous diseases, as reflected in the ratio of tetrahydrometabolites of cortisol. (PMID: 16310418) The daily excretion of allotetrahydrocortisol is above normal in hyperthyroid patients; In contrast, in hyperthyroidism the excretion is diminished below normal levels to approximately half that of normal subjects. (PMID 13906284) A decreased activity of the enzyme 11beta-HSD produces a pattern of urinary steroid metabolites with an abnormal elevation of tetrahydrocortisol and allo-tetrahydrocortisol compared to tetrahydrocortisone; this pattern of steroid excretion is essential for the diagnosis of the syndrome of apparent mineralocorticoid excess type 1. (PMID: 8834992) [HMDB]

CAS Number

651-43-4

Structure

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

Synonyms

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Showing 1 to 6 of 6 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.47 g/L	ALOGPS
logP	1.38	ALOGPS
logP	1.11	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	12.58	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	97.99 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	97.6 m³·mol⁻¹	ChemAxon
Polarizability	41.04 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C21H34O5

IUPAC name

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

InChI Identifier

InChI=1S/C21H34O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h12-16,18,22-24,26H,3-11H2,1-2H3/t12-,13-,14-,15-,16-,18+,19-,20-,21-/m0/s1

InChI Key

AODPIQQILQLWGS-VSJLKEFSSA-N

Isomeric SMILES

[H][C@@]12CC[C@](O)(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

Average Molecular Weight

366.4917

Monoisotopic Molecular Weight

366.240624198

Classification

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-beta-hydroxysteroid
17-hydroxysteroid
Tertiary alcohol
Alpha-hydroxy ketone
Cyclic alcohol
Ketone
Secondary alcohol
Polyol
Primary alcohol
Alcohol
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Biological location:

Cell and elements:

Extracellular

Tissue and substructures:

Hepatic tissue

Biofluid and excreta:

Urine

Subcellular:

Source:

Biological:

Animal

Process

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

Cellular process:

Cell signaling

Role

Biological role:

Molecular messenger:

Industrial application:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	3b-Allotetrahydrocortisol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-000j-3539000000-d7581fc3650c2eb0185b	Spectrum
Predicted GC-MS	3b-Allotetrahydrocortisol, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-000l-1200139000-f34c6af9d49af972f03b	Spectrum
Predicted GC-MS	3b-Allotetrahydrocortisol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	3b-Allotetrahydrocortisol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	3b-Allotetrahydrocortisol, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	3b-Allotetrahydrocortisol, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	3b-Allotetrahydrocortisol, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	3b-Allotetrahydrocortisol, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	3b-Allotetrahydrocortisol, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	3b-Allotetrahydrocortisol, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	3b-Allotetrahydrocortisol, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	3b-Allotetrahydrocortisol, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	3b-Allotetrahydrocortisol, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	3b-Allotetrahydrocortisol, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	3b-Allotetrahydrocortisol, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	3b-Allotetrahydrocortisol, TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	3b-Allotetrahydrocortisol, TMS_2_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	3b-Allotetrahydrocortisol, TMS_2_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	3b-Allotetrahydrocortisol, TMS_2_10, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	3b-Allotetrahydrocortisol, TMS_3_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	3b-Allotetrahydrocortisol, TMS_3_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	3b-Allotetrahydrocortisol, TMS_3_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	3b-Allotetrahydrocortisol, TMS_3_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	3b-Allotetrahydrocortisol, TMS_3_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	3b-Allotetrahydrocortisol, TMS_3_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0019000000-219c2e57df6b2e844bcc	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001j-0159000000-7edf640b3de80bffb6ca	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01p9-0491000000-e99b45997dbf5cb22885	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0009000000-ee75530daadc541f6363	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0ap1-2039000000-f1d87f34ec8f678f57fc	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9086000000-3ee52cebda012a37fd0f	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0009000000-8339b94cd560c336a8d4	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-2009000000-76e08d0eac5051f615bf	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-100c-0039000000-af1a66b3967a8f31e2d4	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-015a-0009000000-249d6f44172a375b08be	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-1902000000-95c98bcfe0691617e5b5	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00kb-8980000000-ea48ab8fad3384d8e0c6	2021-09-22	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

13628056

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

12444612

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB00314

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

Showing Compound 3b-Allotetrahydrocortisol (FDB021941)

Structure for FDB021941 (3b-Allotetrahydrocortisol)