Livestock Metabolome Database: Showing metabocard for Progesterone (LMDB00353)

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

Record Information

Version

1.0

Creation Date

2016-07-13 19:47:57 UTC

Update Date

2016-09-23 18:45:13 UTC

Lmdb

LMDB00353

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Progesterone

Description

The major progestational steroid that is secreted primarily by the corpus luteum and the placenta. Progesterone acts on the uterus, the mammary glands and the brain. It is required in embryo implantation, pregnancy maintenance, and the development of mammary tissue for milk production. Progesterone, converted from pregnenolone, also serves as an intermediate in the biosynthesis of gonadal steroid hormones and adrenal corticosteroids. -- Pubchem; Progesterone is a C-21 steroid hormone involved in the female menstrual cycle, pregnancy (supports gestation) and embryogenesis of animals and other species. Progesterone belongs to a class of hormones called progestagens, and is the major naturally occurring animal progestagen. -- Wikipedia; During implantation and gestation, progesterone appears to decrease the maternal immune response to allow for the acceptance of the pregnancy. Progesterone decreases contractility of the uterine smooth muscle. The fetus metabolizes placental progesterone in the production of adrenal mineralo- and glucosteroids. A drop in progesterone levels is possibly one step that facilitates the onset of labor. In addition progesterone inhibits lactation during pregnancy. The fall in progesterone levels following delivery is one of the triggers for milk production. -- Wikipedia.

Structure

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

Synonyms

Value	Source
(S)-4-Pregnene-3,20-dione	ChEBI
(S)-Pregn-4-en-3,20-dione	ChEBI
(S)-Progesterone	ChEBI
17alpha-Progesterone	ChEBI
4-Pregnene-3,20-dione	ChEBI
Agolutin	ChEBI
Akrolutin	ChEBI
Corpus luteum hormone	ChEBI
Crinone	ChEBI
Delta(4)-Pregnene-3,20-dione	ChEBI
Gelbkoerperhormon	ChEBI
Luteohormone	ChEBI
Progesteron	ChEBI
Prometrium	Kegg
17a-Progesterone	Generator
17Α-progesterone	Generator
Δ(4)-pregnene-3,20-dione	Generator
3,20-Pregnene-4	HMDB
4-Pregnen-3,20-dione	HMDB
beta-Progesterone	HMDB
Bio-luton	HMDB
CIDR	HMDB
Colprosterone	HMDB
Corlutin	HMDB
Corlutina	HMDB
Corluvite	HMDB
Corporin	HMDB
Crinone progesterone gel	HMDB
Curretab	HMDB
Cyclogest	HMDB
Cyclogesterin	HMDB
D4-Pregnene-3,20-dione	HMDB
Delalutin	HMDB
Duraprogen	HMDB
Estima	HMDB
Flavolutan	HMDB
Fologenon	HMDB
Gesterol	HMDB
Gesterol 100	HMDB
Gesterol 50	HMDB
Gestiron	HMDB
Gestone	HMDB
Gestormone	HMDB
Gestron	HMDB
Glanducorpin	HMDB
Gynlutin	HMDB
Gynoluton	HMDB
Gynolutone	HMDB
Hormoflaveine	HMDB
Hormoluton	HMDB
Hydroxyprogesterone caproate	HMDB
Hydroxyprogesterone caproic acid	HMDB
Lingusorbs	HMDB
Lipo-lutin	HMDB
Lucorteum	HMDB
Lucorteum sol	HMDB
Lugesteron	HMDB
Luteal hormone	HMDB
Luteocrin normale	HMDB
Luteodyn	HMDB
Luteogan	HMDB
Luteol	HMDB
Luteopur	HMDB
Luteosan	HMDB
Luteostab	HMDB
Luteovis	HMDB
Luteum	HMDB
Lutex	HMDB
Lutidon	HMDB
Lutociclina	HMDB
Lutocuclin m	HMDB
Lutocyclin	HMDB
Lutocyclin m	HMDB
Lutocylin	HMDB
Lutocylol	HMDB
Lutoform	HMDB
Lutogyl	HMDB
Lutren	HMDB
Lutromone	HMDB
Membrettes	HMDB
Methylpregnone	HMDB
MPA	HMDB
Nalutron	HMDB
Percutacrine	HMDB
Percutacrine luteinique	HMDB
Piaponon	HMDB
Pranone	HMDB
Pregn-4-en-3,20-dione	HMDB
Pregn-4-ene-3,20-dione	HMDB
Pregnene-3,20-dione	HMDB
Pregnenedione	HMDB
Primolut	HMDB
Prochieve	HMDB
Progeffik	HMDB
Progekan	HMDB
Progestan	HMDB
Progestasert	HMDB
Progesterol	HMDB
Progesteronum	HMDB
Progestin	HMDB
Progestogel	HMDB
Progestol	HMDB
Progeston	HMDB
Progestone	HMDB
Progestosol	HMDB
Progestron	HMDB
Progestronol	HMDB
Projestaject	HMDB
Prolets	HMDB
Prolidon	HMDB
Prolutin	HMDB
Proluton	HMDB
Prolutone	HMDB
Prontogest	HMDB
Protormone	HMDB
Syngesterone	HMDB
Syngestrets	HMDB
Synovex S	HMDB
Syntolutan	HMDB
Utrogest	HMDB
Utrogestan	HMDB
Vitarrine	HMDB
Progesterone, (13 alpha,17 alpha)-(+-)-isomer	HMDB
Progesterone, (17 alpha)-isomer	HMDB
Progesterone, (9 beta,10 alpha)-isomer	HMDB

Chemical Formula

C₂₁H₃₀O₂

Average Molecular Weight

314.4617

Monoisotopic Molecular Weight

314.224580204

IUPAC Name

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

Traditional Name

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

CAS Registry Number

57-83-0

SMILES

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

InChI Identifier

InChI=1S/C21H30O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h12,16-19H,4-11H2,1-3H3/t16-,17+,18-,19-,20-,21+/m0/s1

InChI Key

RJKFOVLPORLFTN-LEKSSAKUSA-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
Oxosteroid
3-oxosteroid
3-oxo-delta-4-steroid
Delta-4-steroid
Cyclohexenone
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

3-oxo Delta(4)-steroid (CHEBI:17026 )
20-oxo steroid (CHEBI:17026 )
C21-steroid hormone (CHEBI:17026 )
Pregnane and derivatives [Fig] (C00410 )
Progestagens (C00410 )
C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030159 )

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	3.58	ALOGPS
logP	4.15	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	18.92	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	34.14 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	92.71 m³·mol⁻¹	ChemAxon
Polarizability	37.26 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 (Non-derivatized)	splash10-0fbc-5910000000-422e38df6de7e8b0a4b7	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0fbc-5910000000-385f45345742235da8e0	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-024l-6923000000-639c7405f69825de7f90	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0229-2941000000-1e075d8489b79cf4e34a	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0229-3963000000-f35e3d9faf6b2ee87465	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0fbc-5910000000-422e38df6de7e8b0a4b7	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0fbc-5910000000-385f45345742235da8e0	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0f6x-2910000000-1baafb91a3e0b988caa7	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-000g-1590000000-3ebb52b90c541e38c0b4	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-014i-1009000000-0f8b7c3e6c2265c3889f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-052b-8900000000-0b0167121b798e7e7534	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-052b-9400000000-881510cbcecd9cb61f4f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (JEOL JMS-01-SG-2) , Positive	splash10-024l-6923000000-639c7405f69825de7f90	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-52) , Positive	splash10-0229-2941000000-1e075d8489b79cf4e34a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-004i-0950000000-ca28d8dfdf780c201716	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-000i-1900000000-857f6720dd17fb2547d1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-004i-3930000000-fda87095285a83b85ad5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-00kb-7955000000-a22f06eac940cd4f753d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-014i-0139000000-6b47f75a44df3e20fa3b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0aba-0950000000-b26d04d179294aa67cc7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0aba-0920000000-d0a3365efe1f8a589564	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-05aj-0910000000-61d7a07e6be85600e1f1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-014i-0009000000-67c6f0147801f0ece957	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-05mk-8956000000-aa5fe992c41261b62fbf	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-052b-6910000000-5e26497eb2d0150a30ac	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0a4j-8900000000-7ca6fd15f0ccc18bfa31	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-052b-9700000000-523fe1ad11bfcbb46f85	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-054k-9400000000-e3d581bd8685e1d3f35d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0269000000-9aa25f8d44bc44ee4d4c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-06dj-0491000000-c312ac322a549be24fac	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0pbc-2290000000-859101eb546be9ddc938	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0019000000-e021f799bd2d232a0592	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0049000000-55066424591bf87a4a49	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0002-1090000000-e9387b8ab692f5ef9083	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-006x-7931000000-f6ad83adccd7e016fa29	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C 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

Follicular Fluid
Serum

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Follicular Fluid	Detected and Quantified	0.318 +/- 0.00636 uM	Not Available	Porcine	183842	details
Serum	Detected and Quantified	0.000594 uM	Not Available	Bovine	21172370	details
Serum	Detected and Quantified	0.00835 uM	Not Available	Bovine	21172370	details
Serum	Detected and Quantified	0.0464 uM	Not Available	Bovine	21172370	details
Serum	Detected and Quantified	0.0922 uM	Not Available	Bovine	21172370	details