Nandrolone

Details

• Internal ID: 45f23946-d942-40d5-89fd-e0d0aae3f39c
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Estrane steroids > Estrogens and derivatives
• IUPAC Name: (8R,9S,10R,13S,14S,17S)-17-hydroxy-13-methyl-2,6,7,8,9,10,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-one
• InChI: InChI=1S/C18H26O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h10,13-17,20H,2-9H2,1H3/t13-,14+,15+,16-,17-,18-/m0/s1
• InChI Key: NPAGDVCDWIYMMC-IZPLOLCNSA-N
• Popularity: 4,569 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₆O₂
• Molecular Weight: 274.40 g/mol
• Exact Mass: 274.193280068 g/mol
• Topological Polar Surface Area (TPSA): 37.30 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 3.49
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

• 19-Nortestosterone
• 434-22-0
• 19-Norandrostenolone
• Norandrostenolone
• Nortestosterone
• Menidrabol
• 17beta-Hydroxy-4-estren-3-one
• 4-Estren-17beta-ol-3-one
• Nortestosteronum
• Nandrolon
• Nortestonate
• Nandrolona
• Nandrolonum
• Oestrenolon
• Norandrostenolon
• 17beta-Hydroxy-19-nor-4-androsten-3-one
• 17beta-hydroxyestr-4-en-3-one
• (17beta)-17-hydroxyestr-4-en-3-one
• 17-beta-Hydroestr-4-en-3-one
• Nandrolone cIII
• (17-beta)-17-Hydroxyestr-4-en-3-one
• Nandrolone (INN)
• Nandrolone [INN]
• CHEMBL757
• 6PG9VR430D
• CHEBI:7466
• (8R,9S,10R,13S,14S,17S)-17-hydroxy-13-methyl-2,6,7,8,9,10,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-one
• DTXSID7023350
• NSC 3351
• NSC-3351
• NCGC00159416-02
• U 2410
• (+)-19-Nortestosterone
• Nandrolonum [INN-Latin]
• Nandrolona [INN-Spanish]
• DTXCID403350
• decadura
• decadura (TN)
• CAS-434-22-0
• SMR000058610
• HSDB 3368
• Nandrolone [INN:BAN]
• EINECS 207-101-0
• Estr-4-en-3-one, 17-hydroxy-, (17beta)-
• Estr-4-en-3-one, 17beta-hydroxy-
• 4-Estren-17.beta.-ol-3-one
• UNII-6PG9VR430D
• Nandrolone Base
• Nandrolone, beta
• Estr-4-en-3-one, 17-hydroxy-, (17b)-
• Nandrolone, alpha
• NCGC00164479-01
• 19-nor-testosterone
• BIOBOL
• Estr-4-en-3-one, 17-beta-hydroxy-
• 17.beta.-Nandrolone
• NANDROLONE [MI]
• Nandrolone Decanoic acid
• Estr-4-en-3-one, 17-hydroxy-, (17.beta.)-
• enta[a]phenanthren-3-one
• NANDROLONE [HSDB]
• 17.beta.-Nortestosterone
• NANDROLONE [VANDF]
• EC 207-101-0
• NANDROLONE [MART.]
• Estr-4-en-3-one, 17-hydroxy-, (17-beta)-
• NANDROLONE [WHO-DD]
• SCHEMBL20140
• MLS001423989
• MLS002222325
• 17-Hydroxyestr-4-en-3-one
• Nandrolone(19-nortestosterone)
• GTPL6949
• Nandrolone, 1mg/ml in Methanol
• Deca-Durabolin (decanoate ester)
• NANDROLONE CIII [USP-RS]
• Durabolin (phenylpropionate ester)
• HMS2051I04
• HMS2098E05
• HMS2272P06
• HMS3715E05
• Tox21_113167
• Tox21_113199
• Tox21_201212
• BDBM50080092
• LMST02010044
• AKOS015894933
• Nandrolone 1.0 mg/ml in Acetonitrile
• Tox21_113167_1
• CCG-100835
• CS-1416
• DB13169
• GS-6819
• NC00085
• 4-ESTREN-3-ONE-17.BETA.-OL
• NCGC00159416-03
• NCGC00159416-04
• NCGC00258764-01
• (8R,9S,10R,13S,14S,17S)-17-hydroxy-13-methyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthren-3-one
• AC-15207
• AC-30575
• CPD000058610
• HY-17432
• 19-Nortestosterone, >=99.0% (HPLC)
• C07254
• D08250
• Nandrolone, VETRANAL(TM), analytical standard
• Q421709
• SR-01000781257
• SR-01000781257-3
• W-106227
• NANDROLONE DECANOATE IMPURITY D [EP IMPURITY]
• Nandrolone, British Pharmacopoeia (BP) Reference Standard
• Nandrolone, United States Pharmacopeia (USP) Reference Standard
• (1S,2R,10R,11S,14S,15S)-14-hydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one
• (8~{R},9~{S},10~{R},13~{S},14~{S},17~{S})-13-methyl-17-oxidanyl-2,6,7,8,9,10,11,12,14,15,16,17-dodecahydro-1~{H}-cyclop
• (8~{r},9~{s},10~{r},13~{s},14~{s},17~{s})-13-Methyl-17-Oxidanyl-2,6,7,8,9,10,11,12,14,15,16,17-Dodecahydro-1~{h}-Cyclopenta[a]phenanthren-3-One
• (8R,10R,13S,17S)-17-Hydroxy-13-methyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one
• 6VW

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.7717	77.17%
Blood Brain Barrier	-	0.9500	95.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.7083	70.83%
OATP2B1 inhibitior	-	0.8824	88.24%
OATP1B1 inhibitior	+	0.9339	93.39%
OATP1B3 inhibitior	+	0.9799	97.99%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	+	0.9750	97.50%
BSEP inhibitior	-	0.6934	69.34%
P-glycoprotein inhibitior	-	0.7528	75.28%
P-glycoprotein substrate	-	0.8496	84.96%
CYP3A4 substrate	+	0.7085	70.85%
CYP2C9 substrate	+	1.0000	100.00%
CYP2D6 substrate	-	0.8653	86.53%
CYP3A4 inhibition	-	0.9088	90.88%
CYP2C9 inhibition	-	0.9319	93.19%
CYP2C19 inhibition	+	0.5073	50.73%
CYP2D6 inhibition	-	0.9516	95.16%
CYP1A2 inhibition	-	0.8304	83.04%
CYP2C8 inhibition	-	0.9816	98.16%
CYP inhibitory promiscuity	-	0.8700	87.00%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Warning	0.4674	46.74%
Eye corrosion	-	0.9925	99.25%
Eye irritation	-	0.9790	97.90%
Skin irritation	+	0.6485	64.85%
Skin corrosion	-	0.9524	95.24%
Ames mutagenesis	-	0.9500	95.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5104	51.04%
Micronuclear	-	0.9400	94.00%
Hepatotoxicity	+	0.9625	96.25%
skin sensitisation	-	0.5793	57.93%
Respiratory toxicity	+	0.9556	95.56%
Reproductive toxicity	+	1.0000	100.00%
Mitochondrial toxicity	+	0.9875	98.75%
Nephrotoxicity	-	0.8450	84.50%
Acute Oral Toxicity (c)	III	0.5637	56.37%
Estrogen receptor binding	+	0.9194	91.94%
Androgen receptor binding	+	0.8810	88.10%
Thyroid receptor binding	+	0.8461	84.61%
Glucocorticoid receptor binding	+	0.9245	92.45%
Aromatase binding	-	0.6219	62.19%
PPAR gamma	-	0.6858	68.58%
Honey bee toxicity	-	0.8634	86.34%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.6400	64.00%
Fish aquatic toxicity	+	0.9818	98.18%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3305	P04278	Testis-specific androgen-binding protein	501.19 nM	Kd	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1871	P10275	Androgen Receptor	96.69%	96.43%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.87%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.47%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	94.18%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.66%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.58%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.45%	97.09%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	87.36%	90.71%
CHEMBL241	Q14432	Phosphodiesterase 3A	85.51%	92.94%
CHEMBL2581	P07339	Cathepsin D	83.71%	98.95%
CHEMBL279	P35968	Vascular endothelial growth factor receptor 2	83.01%	95.52%
CHEMBL253	P34972	Cannabinoid CB2 receptor	82.27%	97.25%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	81.03%	94.78%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	80.05%	82.69%

Plants that contains it

• Arabidopsis thaliana

Cross-Links

• PubChem: 9904
• LOTUS: LTS0187647
• wikiData: Q421709