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360-70-3 molecular structure
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(1S,2R,10R,11S,14S,15S)-15-methyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-14-yl decanoate

ChemBase ID: 6404
Molecular Formular: C28H44O3
Molecular Mass: 428.64716
Monoisotopic Mass: 428.32904527
SMILES and InChIs

SMILES:
O([C@@H]1[C@@]2([C@H]([C@H]3[C@H](CC2)[C@@H]2C(=CC(=O)CC2)CC3)CC1)C)C(=O)CCCCCCCCC
Canonical SMILES:
CCCCCCCCCC(=O)O[C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CCC2=CC(=O)CC[C@H]12
InChI:
InChI=1S/C28H44O3/c1-3-4-5-6-7-8-9-10-27(30)31-26-16-15-25-24-13-11-20-19-21(29)12-14-22(20)23(24)17-18-28(25,26)2/h19,22-26H,3-18H2,1-2H3/t22-,23+,24+,25-,26-,28-/m0/s1
InChIKey:
JKWKMORAXJQQSR-MOPIKTETSA-N

Cite this record

CBID:6404 http://www.chembase.cn/molecule-6404.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(1S,2R,10R,11S,14S,15S)-15-methyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-14-yl decanoate
(1S,2R,10R,11S,14S,15S)-15-methyl-5-oxotetracyclo[8.7.0.02,7.011,15]heptadec-6-en-14-yl decanoate
IUPAC Traditional name
nandrolone decanoate
Brand Name
Deca-Durabol
Deca-durabolin
Deca Durabolin
Retabolil
Synonyms
Norandrostenolone decanoate
Nortestosterone decanoate
Nandrolone decanoate
17β-Hydroxy-19-nor-4-androsten-3-one 17-decanoate
17β-Hydroxy-4-estren-3-one 17-decanoate
4-Estren-17β-ol-3-one 17-decanoate
Decadurabolin
Nandrolone decanoate
19-Nortestosterone 17-decanoate
17β-Hydroxy-19-norandrost-4-en-3-one 17-Decanoate
17β-Hydroxyestr-4-en-3-one 17-Decanoate
17β-Hydroxyestr-4-en-3-one Decanoate
17β-Nandrolone laureate
17β-Nortestosterone laureate
19-Nor-17β-hydroxy-3-ketoandrost-4-ene 17-Decanoate
19-Norandrostenolone Decanoate
19-Nortestosterone 17β-Decanoate
19-Nortestosterone Decanoate
Anabolicum
Anabolin Forte
Deca-Durabol
Deca-Durabolin
Deca-Hybolin
Decanofort
Extraboline
Hybolin Decanoate
Nandrobolic LA
Retabolil
19-Nortestosterone 17-decanoate
CAS Number
360-70-3
EC Number
206-639-3
MDL Number
MFCD00135100
PubChem SID
160969711
PubChem CID
9677

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 19.278885  H Acceptors
H Donor LogD (pH = 5.5) 7.319018 
LogD (pH = 7.4) 7.319018  Log P 7.319018 
Molar Refractivity 125.9401 cm3 Polarizability 49.98545 Å3
Polar Surface Area 43.37 Å2 Rotatable Bonds 10 
Lipinski's Rule of Five false 
Log P 5.96  LOG S -6.44 
Solubility (Water) 1.57e-04 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
3.09 mg/mL at 25 oC [YALKOWSKY,SH & HE,Y (2003)] expand Show data source
45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: soluble0.8 mg/mL expand Show data source
DMSO: soluble10 mg/mL expand Show data source
ethanol: soluble5 mg/mL expand Show data source
H2O: insoluble expand Show data source
Apperance
white to light yellow powder expand Show data source
Hydrophobicity(logP)
2.62 [HANSCH,C ET AL. (1995)] expand Show data source
RTECS
KG7967000 expand Show data source
European Hazard Symbols
Harmful Harmful (Xn) expand Show data source
MSDS Link
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
40 expand Show data source
Safety Statements
22-36 expand Show data source
GHS Pictograms
GHS08 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H351 expand Show data source
GHS Precautionary statements
P281 expand Show data source
Personal Protective Equipment
Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges expand Show data source
Drug Control
USDEA Schedule III; Home Office Schedule 4.2; regulated under CDSA - not available from Sigma-Aldrich Canada expand Show data source
Storage Temperature
-20°C expand Show data source
2-8°C expand Show data source
Purity
98% expand Show data source
Certificate of Analysis
Download expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Sigma Aldrich Sigma Aldrich TRC TRC
DrugBank - DB08804 external link
Item Information
Drug Groups illicit; approved
Description C18 steroid with androgenic and anabolic properties. It is generally prepared from alkyl ethers of estradiol to resemble testosterone but less one carbon at the 19 position. It is a schedule III drug in the U.S.
Indication For the treatment of refractory deficient red cell production anemias, breast carcinoma, hereditary angioedema, antithrombin III deficiency, fibrinogen excess, growth failure and Turner's syndrome. It is also indicated in the prophylaxis of hereditary angioedema.
Pharmacology Nandrolone is an anabolic steroid occurring naturally in the human body, albeit in small quantities. Nandrolone increases production and urinary excretion of erythropoietin. It may also have a direct action on bone marrow. Nandrolone binds to the androgen receptor to a greater degree than testosterone, but due to its inability to act on the muscle in ways unmediated by the receptor, has less overall effect on muscle growth.
Affected Organisms
Humans and other mammals
Biotransformation Nandrolone is unusual in that unlike most anabolic steroids, it is not broken down into the more reactive DHT by the enzyme 5α-reductase, but rather into a less effective product known as Dihydronandrolone.
Protein Binding 58%
External Links
Wikipedia
Drugs.com
Sigma Aldrich - N6633 external link
Biochem/physiol Actions
Anabolic steroid with a stimulatory effect on bone mass, muscle ultrastructure, and immune response.
Toronto Research Chemicals - N315020 external link
Nandrolone Decanoate is an anabolic steroid. Nandrolone decanoate is used in the treatment of osteoporosis in postmenopausal women. Nandrolone Decanoate is also used for some aplastic anemias.Controlled Substance.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Dhem, A. et al.: Curr. Med. Res. Opin., 6, 606 (1980)
  • • Lippi, G. et al.: Scand. J. Clin. Lab. Invest., 57, 507 (1980)
  • • Frisoli, A. et al.: J. Gerontol. Ser. A Biol. Sci. Med. Sci., 60A, 648 (1980)
  • • Sheashaa, H. et al.: Nephron, 99, c102 (1980)
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PATENTS

PATENTS

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INTERNET

INTERNET

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