Structure Database (LMSD)
Common Name
medroxyprogesterone
Systematic Name
(6α)-17-hydroxy-6-methylpregn-4-ene-3,20-dione
Synonyms
- 17-Hydroxy-6alpha-methyl-pregn-4-ene-3,20-dione
- 17-Hydroxy-6alpha-methylprogesterone
- 17alpha-Hydroxy-6alpha-methylprogesterone
- 6alpha-Methyl-17alpha-hydroxyprogesterone
- 6alpha-Methyl-4-pregnen-17alpha-ol-3,20-dione
- Medroxyprogesteron
LM ID
LMST02030176
Formula
Exact Mass
Calculate m/z
344.235145
Sum Composition
Status
Curated
3D model of medroxyprogesterone
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Category
Main Class
Sub Class
Biological Context
Medroxyprogesterone is a progesterone receptor agonist (Ki = 241 nM) and a metabolite of medroxyprogesterone 17-acetate .1,2,3 It induces a conformational change in the C-terminal domain of the progesterone receptor (EC50 = 47.3 nM) and increases alkaline phosphatase activity in T47D breast cancer cells (EC50 = 23 nM).1
This information has been provided by Cayman Chemical
References
1. Sturm, G., Häberlein, H., Bauer, T.L., et al. Mass spectrometric and high-performance liquid chromatographic studies of medroxyprogesterone acetate metabolites in human plasma. J. Chromatogr. 562(1-2), 351-362 (1991).
2. Ishihara, M., Kirdani, Y., Osawa, Y., et al. The metabolic fate of medroxyprogesterone acetate in the baboon. J. Steroid Biochem. 7(1), 65-70 (1976).
References
String Representations
InChiKey (Click to copy)
FRQMUZJSZHZSGN-HBNHAYAOSA-N
InChi (Click to copy)
InChI=1S/C22H32O3/c1-13-11-16-17(20(3)8-5-15(24)12-19(13)20)6-9-21(4)18(16)7-10-22(21,25)14(2)23/h12-13,16-18,25H,5-11H2,1-4H3/t13-,16+,17-,18-,20+,21-,22-/m0/s1
SMILES (Click to copy)
C1C[C@@](C(=O)C)(O)[C@@]2(C)CC[C@]3([H])[C@@]4(C)CCC(=O)C=C4[C@@H](C)C[C@@]3([H])[C@@]21[H]
Other Databases
Wikipedia
KEGG ID
HMDB ID
CHEBI ID
PubChem CID
Cayman ID
GuidePharm ID
Calculated Physicochemical Properties
Heavy Atoms
25
Rings
4
Aromatic Rings
0
Rotatable Bonds
1
Van der Waals Molecular Volume
358.17
Topological Polar Surface Area
54.37
Hydrogen Bond Donors
1
Hydrogen Bond Acceptors
3
logP
4.37
Molar Refractivity
97.40
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Updated at
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