Pregnanediol 3-glucuronide

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C27H44O8
Molecular Weight	496.6335
Optical Activity	UNSPECIFIED
Defined Stereocenters	14 / 14
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@H](O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](CC[C@]4(C)[C@H]3CC[C@]12C)O[C@@H]5O[C@@H]([C@@H](O)[C@H](O)[C@H]5O)C(O)=O

InChI

InChIKey=ZFFFJLDTCLJDHL-JQYCEVDMSA-N

InChI=1S/C27H44O8/c1-13(28)17-6-7-18-16-5-4-14-12-15(8-10-26(14,2)19(16)9-11-27(17,18)3)34-25-22(31)20(29)21(30)23(35-25)24(32)33/h13-23,25,28-31H,4-12H2,1-3H3,(H,32,33)/t13-,14+,15+,16-,17+,18-,19-,20-,21-,22+,23-,25+,26-,27+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C27H44O8
Molecular Weight	496.6335
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	14 / 14
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/5510160
Curator's Comment: description was created based on several sources, including: https://www.ncbi.nlm.nih.gov/pubmed/6362910 | https://www.ncbi.nlm.nih.gov/pubmed/8918986

Progesterone is reduced at the C-3 and C-20 groups, hydroxylated to polar derivatives at C-6 and C-10, and conjugated almost entirely with glucuronide in human and rabbit liver by UDP glucuonyltransferase. The main metabolite is 5β-Pregnane-3α,20α-diol glucuronide. Glucuronic acid is attached via a glycosidic bond to the substance, and the resulting glucuronide, which has a much higher water solubility than the original substance, is eventually excreted by the kidneys. The assessment of 5β-Pregnane-3α,20α-diol glucuronide may be applied to detecting ovulation, assessing the function of corpus luteum, and monitoring early pregnancy.

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pregnancy 65 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6362910 https://www.ncbi.nlm.nih.gov/pubmed/3817603 https://www.ncbi.nlm.nih.gov/pubmed/8918986	Diagnostic		Natural Metabolite	Unknown Approved Use Unknown
Menopause 4 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19240232	Diagnostic		Natural Metabolite	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
The identification of novel steroid N-acetylglucosaminides in the urine of pregnant women.	1996-08	8918986
Rapid immunochemical assay of pregnanediol-3-glucuronide in urine and its clinical application.	1986	3817603
Direct solid-phase fluoroenzymeimmunoassay of 5 beta-pregnane-3 alpha, 20 alpha-diol-3 alpha-glucuronide in urine.	1984-02	6362910
Metabolism of progesterone and synthetic progestational agents.	1970-10	5510160

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 `Wed Apr 02 08:38:59 GMT 2025` Edited by `admin` on `Wed Apr 02 08:38:59 GMT 2025`
Record UNII	488GK5DQ5X
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

Pregnanediol 3-glucuronide

Common Name

English

5?-Pregnane-3?,20?-diol glucuronide

Preferred Name

English

PREGNANEDIOL GLUCURONIDE

Common Name

English

(3?,5?,20S)-20-Hydroxypregnan-3-yl ?-D-glucopyranosiduronic acid

Systematic Name

English

Pregnanediol-3?-glucuronide

Common Name

English

(2S,3S,4S,5R,6R)-6-{[(1S,3aS,3bR,5aR,7R,9aS,9bS,11aS)-1-[(1S)-1-hydroxyethyl]-9a,11a-dimethyl-hexadecahydro-1H-cyclopenta[a]phenanthren-7-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

Systematic Name

English

Pregnanediol-3?-glucuronoside

Common Name

English

Pregnanediol 3?-monoglucuronide

Common Name

English

?-D-Glucopyranosiduronic acid, (3?,5?,20S)-20-hydroxypregnan-3-yl

Systematic Name

English

Code System Code Type Description

WIKIPEDIA

Pregnanediol glucuronide