Structure Database (LMSD)

Common Name
Norethindrone
Systematic Name
17α-hydroxy-19-norpregn-4-en-20-yn-3-one
Synonyms
LM ID
LMST02030097
Formula
C20H26O2
Exact Mass
Calculate m/z
298.19328
Sum Composition
ST 20:4;O2
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View MassBank spectra

Classification

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

Biological Context

Norethindrone is a synthetic progestin.1 In vivo, norethindrone (0.5 mg/animal per day) inhibits the estrous cycle in female mice. It induces tumor progression and metastasis in a BT474 breast cancer mouse xenograft model.2 Formulations containing norethindrone have been used as oral contraceptives.

This information has been provided by Cayman Chemical

References

1. Liang, Y., Benakanakere, I., Besch-Williford, C., et al. Synthetic progestins induce growth and metastasis of BT-474 human breast cancer xenografts in nude mice. Menopause 17(5), 1040-1047 (2010).
2. Bruce, H.M. Preliminary note on the effect of 19-norethisterone on mating behavior and fertility in the mouse. Proc. Soc. Study Fertility 10, 158-165 (1958).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
synthetic construct (#32630)
Steroids LIV. Synthesis of 19-nor-17alpha-ethynyltestosterone and 19-nor-17alpha-methyltestosterone. 1954.,
Am J Obstet Gynecol, 2006
Pubmed ID: 16389045

String Representations

InChiKey (Click to copy)
VIKNJXKGJWUCNN-XGXHKTLJSA-N
InChi (Click to copy)
InChI=1S/C20H26O2/c1-3-20(22)11-9-18-17-6-4-13-12-14(21)5-7-15(13)16(17)8-10-19(18,20)2/h1,12,15-18,22H,4-11H2,2H3/t15-,16+,17+,18-,19-,20-/m0/s1
SMILES (Click to copy)
[C@@]12([H])CC[C@@](O)(C#C)[C@@]1(C)CC[C@]1([H])[C@@]3([H])CCC(=O)C=C3CC[C@@]21[H]

Other Databases

Wikipedia
Norethindrone
KEGG ID
C05028
HMDB ID
HMDB0014855
CHEBI ID
7627
PubChem CID
6230
Cayman ID
20941
PDB ID
NDR
GuidePharm ID
2880

Calculated Physicochemical Properties

Heavy Atoms 22
Rings 4
Aromatic Rings 0
Rotatable Bonds 0
Van der Waals Molecular Volume 312.14
Topological Polar Surface Area 37.30
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 2
logP 3.78
Molar Refractivity 86.39

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Created at
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Updated at
20th Mar 2024