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53016-31-2 molecular structure
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15-ethyl-14-ethynyl-5-(hydroxyimino)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-14-ol

ChemBase ID: 4450
Molecular Formular: C21H29NO2
Molecular Mass: 327.46046
Monoisotopic Mass: 327.21982917
SMILES and InChIs

SMILES:
CCC12CCC3C(C1CCC2(C#C)O)CCC1=C/C(=N\O)/CCC31
Canonical SMILES:
O/N=C\1/CCC2C(=C1)CCC1C2CCC2(C1CCC2(O)C#C)CC
InChI:
InChI=1S/C21H29NO2/c1-3-20-11-9-17-16-8-6-15(22-24)13-14(16)5-7-18(17)19(20)10-12-21(20,23)4-2/h2,13,16-19,23-24H,3,5-12H2,1H3
InChIKey:
ISHXLNHNDMZNMC-UHFFFAOYSA-N

Cite this record

CBID:4450 http://www.chembase.cn/molecule-4450.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
15-ethyl-14-ethynyl-5-(hydroxyimino)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-14-ol
IUPAC Traditional name
15-ethyl-14-ethynyl-5-(hydroxyimino)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-14-ol
Brand Name
Orthra Evra
Synonyms
Norelgestromin
CAS Number
53016-31-2
PubChem SID
160967882
99443265
PubChem CID
13752005

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 11.466128  H Acceptors
H Donor LogD (pH = 5.5) 3.6694894 
LogD (pH = 7.4) 3.6712167  Log P 3.6712763 
Molar Refractivity 95.8472 cm3 Polarizability 37.191574 Å3
Polar Surface Area 52.82 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 3.18  LOG S -4.73 
Solubility (Water) 6.05e-03 g/l 

PROPERTIES

PROPERTIES

Bioassay(PubChem)

DETAILS

DETAILS

DrugBank DrugBank
DrugBank - DB06713 external link
Item Information
Drug Groups approved
Description Norelgestromin is a drug used in contraception. Norelgestromin is the active progestin responsible for the progestational activity that occurs in women after application of ORTHO EVRA patch.
Indication Norelgestromin is used for contraception and menopausal hormonal therapy. Norelgestromin may potentially be used in breast cancer treatment due to its inhibitory effect on estrone sulfatase . They convert sulfated steroid precursors to estrogen during pregnancy.
Pharmacology Norelgestromin is used for contraception and menopausal hormonal therapy transdermally or in combination with ethinyl estradiol as a vaginal ring. Norelgestromin, in combination with ethinyl estradiol inhibits ovulation by suppressing gonadotropins.
References
Goa KL, Warner GT, Easthope SE: Transdermal ethinylestradiol/norelgestromin: a review of its use in hormonal contraception. Treat Endocrinol. 2003;2(3):191-206. [Pubmed]
Henzl MR: Norgestimate. From the laboratory to three clinical indications. J Reprod Med. 2001 Jul;46(7):647-61. [Pubmed]
Abrams LS, Skee DM, Wong FA, Anderson NJ, Leese PT: Pharmacokinetics of norelgestromin and ethinyl estradiol from two consecutive contraceptive patches. J Clin Pharmacol. 2001 Nov;41(11):1232-7. [Pubmed]
External Links
Wikipedia

REFERENCES

REFERENCES

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  • • Goa KL, Warner GT, Easthope SE: Transdermal ethinylestradiol/norelgestromin: a review of its use in hormonal contraception. Treat Endocrinol. 2003;2(3):191-206. Pubmed
  • • Henzl MR: Norgestimate. From the laboratory to three clinical indications. J Reprod Med. 2001 Jul;46(7):647-61. Pubmed
  • • Abrams LS, Skee DM, Wong FA, Anderson NJ, Leese PT: Pharmacokinetics of norelgestromin and ethinyl estradiol from two consecutive contraceptive patches. J Clin Pharmacol. 2001 Nov;41(11):1232-7. Pubmed
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