Showing Compound 17-Hydroxyprogesterone (FDB021992)

Record Information

Version

1.0

Creation date

2011-09-21 00:06:39 UTC

Update date

2015-10-09 22:28:53 UTC

Primary ID

FDB021992

Secondary Accession Numbers

Not Available

Chemical Information

FooDB 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. [HMDB]

CAS Number

68-96-2

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
17 alpha Hydroxyprogesterone	HMDB
17 alpha-Hydroxyprogesterone	HMDB
17 Hydroxyprogesterone	HMDB
17-alpha-Hydroxyprogesterone	HMDB
17-alpha-hydroxyprogesterone	hmdb
17-Hydroxypregn-4-en-3,20-dione	ChEBI
17-Hydroxypregn-4-ene-3,20-dione	HMDB
17-Hydroxyprogesterone	hmdb
17-Hydroxyprogesterone, (17 alpha)-isomer	HMDB
17-Hydroxyprogesterone, (9 beta, 10 alpha)-isomer	HMDB

Showing 1 to 10 of 42 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.029 g/L	ALOGPS
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	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C21H30O3

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

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

Isomeric 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

Average Molecular Weight

330.4611

Monoisotopic Molecular Weight

330.219494826

Classification

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

Physiological effect

Health effect:

Health condition:

Metabolism and nutrition disorders:

21-hydroxylase deficiency

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Biological location:

Cell and elements:

Extracellular

Tissue and substructures:

Organ and components:

Testicle

Endocrine gland:

Subcellular:

Biofluid and excreta:

Process

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

System process:

Reproduction

Cellular process:

Cell signaling

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
EI-MS	Mass Spectrum (Electron Ionization)	splash10-002f-9731000000-48d2266d41955ffa9ce4	2014-09-20	View Spectrum
GC-MS	17-Hydroxyprogesterone, 2 MEOX; 1 TMS, GC-MS Spectrum	splash10-004l-4911000000-d40ba45835d1ee1b6c41	Spectrum
GC-MS	17-Hydroxyprogesterone, non-derivatized, GC-MS Spectrum	splash10-002o-9651000000-b44110f9abcffa42ce35	Spectrum
GC-MS	17-Hydroxyprogesterone, non-derivatized, GC-MS Spectrum	splash10-004l-4911000000-d40ba45835d1ee1b6c41	Spectrum
Predicted GC-MS	17-Hydroxyprogesterone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0k9f-4595000000-89ccbf45dbf9f474bd2f	Spectrum
Predicted GC-MS	17-Hydroxyprogesterone, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-007c-3249000000-3570f5d248c0ee0716ee	Spectrum
Predicted GC-MS	17-Hydroxyprogesterone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	17-Hydroxyprogesterone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	17-Hydroxyprogesterone, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	17-Hydroxyprogesterone, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	17-Hydroxyprogesterone, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	17-Hydroxyprogesterone, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	17-Hydroxyprogesterone, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-001i-0009000000-a157e4b4aa18bdbc2531	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-052b-5900000000-42494c0ef4b45cfa5cf4	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-052b-9700000000-d8a942a3dfdb061bd5c3	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive	splash10-002o-9651000000-b0c55e50343bf8ab3077	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - , positive	splash10-0a4j-4930000000-c5056c0aac78a148ea92	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-052b-5910000000-fcf792a46552ed6e0028	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 60V, Positive	splash10-052b-6900000000-6970a665800f041e9612	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0532-6966000000-f57233040f10efef4ba9	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-001i-0009000000-0cff8a9a4549636b3f42	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-0a4j-9800000000-3aaefadc8d2e4ad3a522	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 90V, Positive	splash10-0a6s-9600000000-17d56b65d46a46d9f653	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0029000000-0af1b9a61aa5a9d514a4	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0lzi-0295000000-0510776f8fa0d9ddcb6a	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00li-3970000000-1655d52be304b45389ae	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0009000000-bc250df2e599669d113e	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-002r-0097000000-41db31593b4f58cd4bc4	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0bti-0092000000-464375e5c4a93d5d20b3	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01q9-0019000000-bf0f51dc62b5855371a3	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0922000000-6997f50bd7502e7518f2	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0cdi-3910000000-051d81ed4aaf877bebaf	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0039000000-8b733a2d2a661578ddbe	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004r-0049000000-1387b7ed039fc5504c87	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00kr-0091000000-dc494a2f8f424f99a574	2021-09-23	View Spectrum

NMR

Type	Description		View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, experimental)		Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)		Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB00374

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

36989

KNApSAcK ID

Not Available

HET ID

3QZ

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

17-Hydroxyprogesterone

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

Anatidae	Expected but not quantified	Not Available	HMDB
Beefalo	Expected but not quantified	Not Available	HMDB
Bison	Expected but not quantified	Not Available	HMDB
Buffalo	Expected but not quantified	Not Available	HMDB
Cattle (Beef, Veal)	Expected but not quantified	Not Available	HMDB
Chicken	Expected but not quantified	Not Available	HMDB
Columbidae (Dove, Pigeon)	Expected but not quantified	Not Available	HMDB
Deer	Expected but not quantified	Not Available	HMDB
Domestic goat	Expected but not quantified	Not Available	HMDB
Domestic pig	Expected but not quantified	Not Available	HMDB