Livestock Metabolome Database: Showing metabocard for 17-Hydroxyprogesterone (LMDB00147)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:43:23 UTC

Update Date

2016-07-19 23:06:32 UTC

Lmdb

LMDB00147

Secondary Accession Numbers

None

Metabolite Identification

Common Name

17-Hydroxyprogesterone

Description

It serves as an intermediate in the biosynthesis of hydrocortisone and gonadal steroid hormones. It is derived from progesterone via 17-hydroxylase, a P450c17 enzyme, or from 17-hydroxypregnenolone via 3β-hydroxysteroid dehydrogenase/Δ5-4 isomerase. 17-Hydroxyprogesterone is a natural progestin and in pregnancy increases in the third trimester primarily due to fetal adrenal production. This hormone is primarily produced in the adrenal glands and to some degree in the gonads, specifically the corpus luteum of the ovary. Normal levels are 3-90 ng/dl in children, and in women, 15-70 ng/dl prior to ovulation, and 35-290 ng/dl during the luteal phase. Measurements of levels of 17-hydroxyprogesterone are useful in the evaluation of patients with suspected congenital adrenal hyperplasia as the typical enzymes that are defective, namely 21-hydroxylase and 11β-hydroxylase, lead to a build-up of 17OHP. In contrast, the rare patient with 17α-hydroxylase deficiency will have very low or undetectable levels of 17OHP. 17OHP levels can also be used to measure contribution of progestational activity of the corpus luteum during pregnancy as progesterone but not 17OHP is also contributed by the placenta.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
17-Hydroxypregn-4-en-3,20-dione	ChEBI
17alpha-Hydroxy-4-pregnene-3,20-dione	ChEBI
17alpha-Hydroxy-progesterone	ChEBI
delta(4)-Pregnene-17alpha-ol-3,20-dione	ChEBI
Hidroxiprogesterona	ChEBI
Hydroxyprogesterone	ChEBI
Hydroxyprogesteronum	ChEBI
Pregn-4-ene-3,20-dione-17-ol	ChEBI
17a-Hydroxy-4-pregnene-3,20-dione	Generator
17Α-hydroxy-4-pregnene-3,20-dione	Generator
17a-Hydroxy-progesterone	Generator
17Α-hydroxy-progesterone	Generator
delta(4)-Pregnene-17a-ol-3,20-dione	Generator
Δ(4)-pregnene-17α-ol-3,20-dione	Generator
Δ(4)-pregnene-17a-ol-3,20-dione	HMDB
17-alpha-Hydroxyprogesterone	HMDB
17-Hydroxypregn-4-ene-3,20-dione	HMDB
17-OH Progesterone	HMDB
17-OHP	HMDB
17a-Hydroxypregn-4-ene-3,20-dione	HMDB
17a-Hydroxyprogesterone	HMDB
17alpha-Hydroxyprogesterone	HMDB
D4-Pregnen-17a-ol-3,20-dione	HMDB
Gestageno	HMDB
Gestageno gador	HMDB
Pregn-4-en-17a-ol-3,20-dione	HMDB
Prodix	HMDB
Prodox	HMDB
17 Hydroxyprogesterone	HMDB
17-Hydroxyprogesterone, (17 alpha)-isomer	HMDB
17 alpha Hydroxyprogesterone	HMDB
17 alpha-Hydroxyprogesterone	HMDB
17-Hydroxyprogesterone, (9 beta, 10 alpha)-isomer	HMDB

Chemical Formula

C₂₁H₃₀O₃

Average Molecular Weight

330.4611

Monoisotopic Molecular Weight

330.219494826

IUPAC Name

(1S,2R,10R,11S,14R,15S)-14-acetyl-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one

Traditional Name

(1S,2R,10R,11S,14R,15S)-14-acetyl-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one

CAS Registry Number

68-96-2

SMILES

[H][C@@]12CC[C@](O)(C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C

InChI Identifier

InChI=1S/C21H30O3/c1-13(22)21(24)11-8-18-16-5-4-14-12-15(23)6-9-19(14,2)17(16)7-10-20(18,21)3/h12,16-18,24H,4-11H2,1-3H3/t16-,17+,18+,19+,20+,21+/m1/s1

InChI Key

DBPWSSGDRRHUNT-CEGNMAFCSA-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-oxo-delta-4-steroid
3-oxosteroid
17-hydroxysteroid
Oxosteroid
Hydroxysteroid
Delta-4-steroid
Cyclohexenone
Alpha-hydroxy ketone
Cyclic alcohol
Tertiary alcohol
Cyclic ketone
Ketone
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Alcohol
Organooxygen compound
Organic oxide
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

17alpha-hydroxy steroid (CHEBI:17252 )
Progestagens (C01176 )
C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030161 )

Ontology

Status

Detected and Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

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	2.99	ALOGPS
logP	3.4	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	12.7	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	94.11 m³·mol⁻¹	ChemAxon
Polarizability	37.9 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	View
GC-MS	GC-MS Spectrum - GC-MS (2 MEOX; 1 TMS)	splash10-004l-4911000000-d40ba45835d1ee1b6c41	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-002o-9651000000-b44110f9abcffa42ce35	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-004l-4911000000-d40ba45835d1ee1b6c41	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0k9f-4595000000-89ccbf45dbf9f474bd2f	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-007c-3249000000-3570f5d248c0ee0716ee	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-001i-0009000000-a157e4b4aa18bdbc2531	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-052b-5900000000-42494c0ef4b45cfa5cf4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-052b-9700000000-d8a942a3dfdb061bd5c3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive	splash10-002o-9651000000-b0c55e50343bf8ab3077	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0a4j-4930000000-c5056c0aac78a148ea92	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-052b-5910000000-fcf792a46552ed6e0028	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Positive	splash10-052b-6900000000-6970a665800f041e9612	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0532-6966000000-f57233040f10efef4ba9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-001i-0009000000-0cff8a9a4549636b3f42	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-0a4j-9800000000-3aaefadc8d2e4ad3a522	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Positive	splash10-0a6s-9600000000-17d56b65d46a46d9f653	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0029000000-0af1b9a61aa5a9d514a4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0lzi-0295000000-0510776f8fa0d9ddcb6a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00li-3970000000-1655d52be304b45389ae	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0009000000-bc250df2e599669d113e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-002r-0097000000-41db31593b4f58cd4bc4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0bti-0092000000-464375e5c4a93d5d20b3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01q9-0019000000-bf0f51dc62b5855371a3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0922000000-6997f50bd7502e7518f2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0cdi-3910000000-051d81ed4aaf877bebaf	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0039000000-8b733a2d2a661578ddbe	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004r-0049000000-1387b7ed039fc5504c87	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00kr-0091000000-dc494a2f8f424f99a574	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-002f-9731000000-48d2266d41955ffa9ce4	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Serum

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Serum	Detected and Quantified	0.000395 uM	Not Available	Bovine	21172370	details
Serum	Detected and Quantified	0.000999 uM	Not Available	Bovine	21172370	details
Serum	Detected and Quantified	<0.000675 uM	Not Available	Bovine	21172370	details
Serum	Detected and Quantified	<0.000675 uM	Not Available	Bovine	21172370	details