6?-Hydroxycortisol

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C21H30O6
Molecular Weight	378.4593
Optical Activity	UNSPECIFIED
Defined Stereocenters	8 / 8
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@]12C[C@H](O)[C@H]3[C@@H](C[C@@H](O)C4=CC(=O)CC[C@]34C)[C@@H]1CC[C@]2(O)C(=O)CO

InChI

InChIKey=GNFTWPCIRXSCQF-UJXAPRPESA-N

InChI=1S/C21H30O6/c1-19-5-3-11(23)7-14(19)15(24)8-12-13-4-6-21(27,17(26)10-22)20(13,2)9-16(25)18(12)19/h7,12-13,15-16,18,22,24-25,27H,3-6,8-10H2,1-2H3/t12-,13-,15+,16-,18+,19-,20-,21-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C21H30O6
Molecular Weight	378.4593
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	8 / 8
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22318698
Curator's Comment: description was created based on several sources, including: https://www.wikigenes.org/e/chem/e/6852390.html / https://www.ncbi.nlm.nih.gov/pubmed/218996

Cortisol is metabolized to form 6β-hydroxycortisol (6β-OHF) catalyzed by CYP3A. The metabolite is then excreted in the urine. Therefore, the urinary excretion ratio 6β-OHF/cortisol has extensively been used as a non-invasive index for evaluating the in vivo CYP3A activity in humans. Measurement of urinary 6β-hydroxycortisol is suggested as a good diagnostic test for hypercortisolemic states.

Originator

Approval Year

Conditions

Condition	Modality	Highest Phase	Product
Hypercortisolemic states 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/218996	Diagnostic	Natural Metabolite	Unknown Approved Use Unknown
Porphyria 2 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12463733	Diagnostic	Natural Metabolite	Unknown Approved Use Unknown
CYP3A4 induction 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12022896 https://www.ncbi.nlm.nih.gov/pubmed/22318698	Diagnostic	Natural Metabolite	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Separation and quantitative determination of 6α-hydroxycortisol and 6β-hydroxycortisol in human urine by high-performance liquid chromatography with ultraviolet absorption detection.	2012-03	22318698
Interindividual and intraindividual variability of the urinary 6beta-Hydroxycortisol/Cortisol ratio in Chinese subjects: implications of its use for evaluating CYP3A activity.	2004-12	15545313
Urinary 6beta-hydroxycortisol: a validated test for evaluating drug induction or drug inhibition mediated through CYP3A in humans and in animals.	2003-12	14605790
Simultaneous determination of 6beta- and 6alpha-hydroxycortisols and 6beta-hydroxycortisone in human urine by stable isotope dilution mass spectrometry.	2000-02-11	10718654
6 beta-Hydroxycortisol excretion in hypercortisolemic states.	1979-03	218996

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Tue Apr 01 23:11:52 GMT 2025` Edited by `admin` on `Tue Apr 01 23:11:52 GMT 2025`
Record UNII	J37WKJ5Y50
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NSC-76163

Preferred Name

English

6?-Hydroxycortisol

Common Name

English

PREGN-4-ENE-3,20-DIONE, 6,11,17,21-TETRAHYDROXY-, (6.BETA.,11.BETA.)-

Systematic Name

English

HYDROCORTISONE IMPURITY D [EP IMPURITY]

Common Name

English

6.BETA.-HYDROXYHYDROCORTISONE

Common Name

English

6.BETA.,11.BETA.,17,21-TETRAHYDROXYPREGN-4-ENE-3,20-DIONE

Systematic Name

English

Code System Code Type Description

NSC

76163