Structure Database (LMSD)

Common Name
progesterone
Systematic Name
pregn-4-ene-3,20-dione
Synonyms
  • (S)-4-Pregnene-3,20-dione
  • (S)-Pregn-4-en-3,20-dione
  • (S)-Progesterone
  • 17alpha-progesterone
  • 4-Pregnene-3,20-dione
  • Agolutin
  • Akrolutin
  • Crinone
  • Delta(4)-pregnene-3,20-dione
  • Gelbkoerperhormon
  • PROGESTERONE
  • Progesteron
  • Progesterone
  • corpus luteum hormone
  • luteohormone
  • progesterone
LM ID
LMST02030159
Formula
C21H30O2
Exact Mass
Calculate m/z
314.22458
Sum Composition
ST 21:3;O2
Status
Curated
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Classification

Category
Main Class
Sub Class
Sterol Lipids [ST]
Steroids [ST02]
C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives [ST0203]

Biological Context

Progesterone, along with pregnenolone, is the biosynthetic precursor of all other steroid hormones. Progesterone is synthesized from cholesterol by the sequential action of desmolase in the mitochondria, which produces pregnenolone, followed by Δ4,5-isomerase in the outer mitochondrial membrane and smooth endoplasmic reticulum of steroid-secreting cells.1 Progesterone activates the human progesterone receptor with an EC50 value of 0.5 nM.2

This information has been provided by Cayman Chemical

References

1. Pedram, B., van Oeveren, A., Mais, D.E., et al. A tissue-selective nonsteroidal progesterone receptor modulator: 7,9-Difluoro-5-(3-methylcyclohex-2-enyl)-2,2,4-trimethyl-1,2-dihydrochromeno[3,4-f]quinoline. J. Med. Chem. 51(13), 3696-3699 (2008).
2. Erickson, G.F. The ovary: Basic principles and concepts. A. Physiology. Endocrinology and Metabolism 973-1015 (1995).

Reactions

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String Representations

InChiKey (Click to copy)
RJKFOVLPORLFTN-LEKSSAKUSA-N
InChi (Click to copy)
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
SMILES (Click to copy)
C1CC2[C@@](C)([C@@]3([H])CC[C@@]4([C@H](CC[C@@]4([H])[C@]13[H])C(=O)C)C)CCC(=O)C=2

Other Databases

Wikipedia
progesterone
KEGG ID
C00410
HMDB ID
HMDB0001830
CHEBI ID
17026
PubChem CID
5994
SwissLipids ID
SLM:000390128
Cayman ID
15876
PDB ID
STR
GuidePharm ID
2377

Calculated Physicochemical Properties

Heavy Atoms 23
Rings 4
Aromatic Rings 0
Rotatable Bonds 1
Van der Waals Molecular Volume 332.08
Topological Polar Surface Area 34.14
Hydrogen Bond Donors 0
Hydrogen Bond Acceptors 2
logP 4.72
Molar Refractivity 90.88

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Updated at
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