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68-23-5 molecular structure
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(1S,10R,11S,14R,15S)-14-ethynyl-14-hydroxy-15-methyltetracyclo[8.7.0.02,7.011,15]heptadec-2(7)-en-5-one

ChemBase ID: 175618
Molecular Formular: C20H26O2
Molecular Mass: 298.41924
Monoisotopic Mass: 298.19328007
SMILES and InChIs

SMILES:
C1C(=O)CC2=C(C1)[C@@H]1[C@@H](CC2)[C@H]2[C@](CC1)([C@](CC2)(O)C#C)C
Canonical SMILES:
C#C[C@]1(O)CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CCC2=C1CCC(=O)C2
InChI:
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/h1,16-18,22H,4-12H2,2H3/t16-,17-,18+,19+,20+/m1/s1
InChIKey:
ICTXHFFSOAJUMG-SLHNCBLASA-N

Cite this record

CBID:175618 http://www.chembase.cn/molecule-175618.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(1S,10R,11S,14R,15S)-14-ethynyl-14-hydroxy-15-methyltetracyclo[8.7.0.02,7.011,15]heptadec-2(7)-en-5-one
IUPAC Traditional name
norethynodrel
Synonyms
13-Methyl-17-ethynyl-17-hydroxy-1,2,3,4,6,7,8,9,11,12,13,14,16,17-tetradecahydro-15H-cyclopenta[a]phenanthren-3-one
17-Hydroxy-19-nor-17α-pregn-5(10)-en-20-yn-3-one
(17α)-17-hydroxy-19-Norpregn-5(10)-en-20-yn-3-one
Norethynodrel
CAS Number
68-23-5
PubChem SID
164231528
PubChem CID
6231

DATA SOURCES

DATA SOURCES

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Data Source Data ID
TRC N676020 external link Add to cart
PubChem 6231 external link
Data Source Data ID Price
TRC
N676020 external link Add to cart Please log in.
Data Source Data ID
PubChem 6231 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 16.301239  H Acceptors
H Donor LogD (pH = 5.5) 2.813825 
LogD (pH = 7.4) 2.813825  Log P 2.813825 
Molar Refractivity 87.1812 cm3 Polarizability 34.003754 Å3
Polar Surface Area 37.3 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Safety Information Product Information Bioassay(PubChem)
MSDS Link
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Certificate of Analysis
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DETAILS

DETAILS

TRC TRC
Toronto Research Chemicals - N676020 external link
The compound is a progestin used in Enovid, an oral contraceptive, also used in the treatment of endometriosis and hypermenorrhea.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Palmer K., et al.: J. Pharmacol. Exp. Ther., 167, 207 (1969)
  • • Liu, L., et al.: Endocrinology., 151, 5782 (1969)
  • • Sonneveld, E., et al.: Toxicol. in Vitro, 25, 545 (2011)
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PATENTS

PATENTS

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INTERNET

INTERNET

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