Norethynodrel

Details

• Internal ID: 5d4817cf-54d9-4bed-aa2d-cd5951fa84f1
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Oxosteroids
• IUPAC Name: (8R,9S,13S,14S,17R)-17-ethynyl-17-hydroxy-13-methyl-1,2,4,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one
• SMILES (Canonical): CC12CCC3C(C1CCC2(C#C)O)CCC4=C3CCC(=O)C4
• SMILES (Isomeric): C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C#C)O)CCC4=C3CCC(=O)C4
• 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
• InChI Key: ICTXHFFSOAJUMG-SLHNCBLASA-N
• Popularity: 1,106 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₆O₂
• Molecular Weight: 298.40 g/mol
• Exact Mass: 298.193280068 g/mol
• Topological Polar Surface Area (TPSA): 37.30 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 3.64
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

• Noretynodrel
• 68-23-5
• Norethinodrel
• Enidrel
• Lynestrol
• 19-Norethynodrel
• SC-4642
• Noretinodrel
• NSC-15432
• Noretynodrelum
• 19-Nor-ethinyl-5,10-testosterone
• DTXSID3021069
• 88181ACA0M
• 17-alpha-Ethynyl-5(10)-estren-17-ol-3-one
• 19-Norpregn-5(10)-en-20-yn-3-one, 17-hydroxy-, (17alpha)-
• 17-alpha-Ethynyl-estr-5(10)-en-3-on-17-beta-ol
• DTXCID60563
• 17-beta-Hydroxy-17-alpha-ethinyl-5(10)-estren-3-one
• (8R,9S,13S,14S,17R)-17-ethynyl-17-hydroxy-13-methyl-1,2,4,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one
• (17-alpha)-17-Hydroxy-19-norpregn-5(10)-en-20-yn-3-one
• 19-Nor-17alpha-pregn-5(10)-en-20-yn-3-one, 17-hydroxy-
• 17-alpha-Ethinyl-17-beta-hydroxy-delta(sup 5(10))-estren-3-one
• 17-alpha-Ethynyl-17-beta-hydroxy-3-oxo-delta(sup 5(10))-estrene
• 17-alpha-Ethynyl-17-beta-hydroxy-delta(sup. 5(10))-estren-3-one
• NSC15432
• (17beta-ethynyl-17-hydroxyestr-5(10)-en-3-one
• (8R,9S,13S,14S,17R)-17-ethynyl-17-hydroxy-13-methyl-1,2,4,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta(a)phenanthren-3-one
• RefChem:854723
• 200-682-1
• 17-Ethinyl-5(10)-estraeneolone
• Norethinynodrel
• Noretynodrel [INN]
• MLS000069824
• Norethynodral
• 17-Hydroxy-19-nor-17alpha-pregn-5(10)-en-20-yn-3-one
• Noretynodrel (INN)
• Norethynodrel (USAN)
• SMR000058915
• Norethynodrel (>90%)
• NORETHYNODREL [USAN]
• (1R,3aS,3bR,9bS,11aS)-1-ethynyl-1-hydroxy-11a-methyl-1H,2H,3H,3aH,3bH,4H,5H,6H,7H,8H,9H,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-one
• (17beta)-17-ethynyl-17-hydroxyestr-5(10)-en-3-one
• Noretinodrel [DCIT]
• Norethindrone EP Impurity D
• Noretynodrelum [INN-Latin]
• CCRIS 486
• 19-Norpregn-5(10)-en-20-yn-3-one, 17-hydroxy-, (17.alpha.)-
• HSDB 2951
• 17alpha-Ethinyl-5,10-estrenolone
• 17-alpha-Ethinyl-5,10-estrenolone
• EINECS 200-682-1
• NSC 15432
• Norethynodrel [Progestins]
• Norethynodrel [USAN:USP]
• CB 8023
• BRN 2389771
• UNII-88181ACA0M
• 17alpha-Ethynyl-5(10)-estren-17-ol-3-one
• CAS-68-23-5
• 17alpha-Ethinyl-5(10)estraen-17beta-ol-3-one
• NCGC00016304-01
• 17alpha-Ethynyl-estr-5(10)-en-3-on-17beta-ol
• Prestwick_883
• 17-alpha-Ethynyl-17-hydroxyestr-5(10)-en-3-one
• 17alpha-Ethinyl-delta(sup)-5,10-19-nortestosterone
• 17alpha-Ethynyl-17beta-hydroxyestr-5(10)-en-3-one
• Estr-5(10)-en-3-one, 17alpha-ethynyl-17-hydroxy-
• 17-alpha-Ethinyl-delta(super)-5,10-19-nortestosterone
• 17-Hydroxy(17alpha)-19-norpregn-5(10)-en-20-yn-3-one
• 17alpha-Ethynyl-19-nor-5(10)-androsten-17beta-ol-3-one
• 17-alpha-Ethynyl-19-nor-5(10)-androsten-17-beta-ol-3-one
• 17alpha-Ethinyl-17beta-hydroxy-delta(sup 5(10))-estren-3-one
• 17alpha-Ethinyl-19-nor-delta-5(10)-androstene-17beta-ol-3one
• 17alpha-Ethynyl-17beta-hydroxy-delta(sup 5(10))-estren-3-one
• 17alpha-Ethynyl-17beta-hydroxy-3-oxo-delta(sup 5(10))-estrene
• Opera_ID_1052
• Prestwick0_000024
• Prestwick1_000024
• Prestwick2_000024
• Prestwick3_000024
• 17-.alpha.-Ethynyl-17-hydroxyestr-5(10)-en-3-one
• 17.alpha.-Ethinyl-.DELTA.5(10)-19-nortestosterone
• NORETHYNODREL [MI]
• 17-.alpha.-Ethinyl-.DELTA.5(10)-19-nortestosterone
• 17.alpha.-Hydroxy-19-norpregn-5(10)-en-20-yn-3-one
• 5(10)-Estren-3-one, 17alpha-ethynyl-17beta-hydroxy-
• 17.alpha.-Ethinyl-.delta.(sup)-5,10-19-nortestosterone
• CHEMBL1387
• NORETHYNODREL [HSDB]
• SCHEMBL37838
• BSPBio_000087
• NORETHYNODREL [VANDF]
• NORETYNODREL [MART.]
• 13-Methyl-17-ethynyl-17-hydroxy-1,2,3,4,6,7,8,9,11,12,13,14,16,17-tetradecahydro-15H-cyclopenta(a)-phenanthrene-3-one
• 17-.alpha.-Ethynyl-17-.beta.-hydroxy-5(10)-estren-3-one
• 17-.beta.-Hydroxy-17-.alpha.-ethinyl-5(10)-estren-3-one
• BIDD:ER0192
• NORETYNODREL [WHO-DD]
• SPBio_002008
• (17-.alpha.)-17-Hydroxy-19-norpregn-5(10)-en-20-yn-3-one
• 17-.alpha.-Ethynyl-17-.beta.-hydroxy-.DELTA.5(10)-estren-3-one
• 17.alpha.-Ethinyl-17.beta.-hydroxy-.DELTA.5(10)-estren-3-one
• 17.alpha.-Ethynyl-17.beta.-hydroxy-.DELTA.5(10)-estren-3-one
• 17.alpha.-Ethynyl-17.beta.-hydroxy-3-oxo-.DELTA.5(10)-estrene
• BPBio1_000097
• orb1710744
• CHEBI:34895
• 17-Ethynyl-17-hydroxyestr-.DELTA.5(10)-en-3-one, (17.alpha.,17.beta.)-
• HMS1568E09
• HMS2095E09
• HMS2232J10
• HMS3712E09
• NORETHYNODREL [ORANGE BOOK]
• 19-Nor-17-alpha-pregn-5(10)-en-20-yn-3-one, 17-hydroxy-
• HY-B1341
• NORETHYNODREL [USP IMPURITY]
• Tox21_110359
• BDBM50410507
• ENOVID COMPONENT NORETHYNODREL
• AKOS026749810
• CCG-220024
• DB09371
• FN26448
• NCGC00179666-01
• CS-0013090
• NS00006110
• D05207
• G89723
• NORETHISTERONE IMPURITY D [EP IMPURITY]
• WLN: L E5 B666OV MUTJ E1 F1UU1 QQ
• EN300-7481217
• F600857
• SR-01000721945
• Q5659069
• SR-01000721945-2
• BRD-K80334323-001-03-5
• Estr-5(10)-en-3-one,17.alpha.-ethynyl-17-hydroxy-
• 17-hydroxy-19-nor-17alpha-pregn-5(10)en-20-yn-3-one
• 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- 17?-pregn-5(10)-en-20-yn-3-one;(17?)-17-hydroxy-19-norpregn-5(10)-en-20- yn-3-one
• 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

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.7849	78.49%
Blood Brain Barrier	-	0.9750	97.50%
Human oral bioavailability	+	0.6714	67.14%
Subcellular localzation	Mitochondria	0.7000	70.00%
OATP2B1 inhibitior	-	0.8656	86.56%
OATP1B1 inhibitior	+	0.9414	94.14%
OATP1B3 inhibitior	+	0.9770	97.70%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	+	0.8250	82.50%
BSEP inhibitior	+	0.8633	86.33%
P-glycoprotein inhibitior	-	0.8631	86.31%
P-glycoprotein substrate	-	0.8560	85.60%
CYP3A4 substrate	+	0.6459	64.59%
CYP2C9 substrate	-	0.8078	80.78%
CYP2D6 substrate	-	0.8360	83.60%
CYP3A4 inhibition	-	0.8333	83.33%
CYP2C9 inhibition	-	0.8688	86.88%
CYP2C19 inhibition	+	0.8994	89.94%
CYP2D6 inhibition	-	0.9386	93.86%
CYP1A2 inhibition	-	0.8440	84.40%
CYP2C8 inhibition	-	0.6551	65.51%
CYP inhibitory promiscuity	-	0.7876	78.76%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8700	87.00%
Carcinogenicity (trinary)	Non-required	0.3890	38.90%
Eye corrosion	-	0.9927	99.27%
Eye irritation	-	0.9541	95.41%
Skin irritation	+	0.6025	60.25%
Skin corrosion	-	0.9451	94.51%
Ames mutagenesis	-	0.9600	96.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5720	57.20%
Micronuclear	-	0.8400	84.00%
Hepatotoxicity	+	0.7502	75.02%
skin sensitisation	-	0.5916	59.16%
Respiratory toxicity	+	0.9000	90.00%
Reproductive toxicity	+	1.0000	100.00%
Mitochondrial toxicity	+	1.0000	100.00%
Nephrotoxicity	-	0.6881	68.81%
Acute Oral Toxicity (c)	III	0.5210	52.10%
Estrogen receptor binding	+	0.9047	90.47%
Androgen receptor binding	+	0.8730	87.30%
Thyroid receptor binding	+	0.7932	79.32%
Glucocorticoid receptor binding	+	0.8970	89.70%
Aromatase binding	+	0.6204	62.04%
PPAR gamma	-	0.5498	54.98%
Honey bee toxicity	-	0.8105	81.05%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.6300	63.00%
Fish aquatic toxicity	+	0.9863	98.63%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293224	P10636	Microtubule-associated protein tau	39810.7 nM	Potency	via CMAUP
CHEMBL1293232	Q16637	Survival motor neuron protein	1778.3 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.57%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.86%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	92.95%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.87%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.47%	95.56%
CHEMBL1871	P10275	Androgen Receptor	89.84%	96.43%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	89.58%	89.05%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.77%	97.25%
CHEMBL259	P32245	Melanocortin receptor 4	86.19%	95.38%
CHEMBL221	P23219	Cyclooxygenase-1	83.65%	90.17%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.45%	99.23%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	82.49%	96.38%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	82.26%	97.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	82.22%	85.14%
CHEMBL2581	P07339	Cathepsin D	82.16%	98.95%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	80.01%	82.69%

Plants that contains it

• Atractylodes lancea

Cross-Links

• PubChem: 6231
• NPASS: NPC150506
• ChEMBL: CHEMBL1387