ContaminantDB: Norethindrone acetate

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-22 03:44:25 UTC

Update Date

2016-11-09 01:15:28 UTC

Accession Number

CHEM016813

Identification

Common Name

Norethindrone acetate

Class

Small Molecule

Description

A 3-oxo Delta(4)-steroid that is norethisterone in which the hydroxy group has been converted to its acetate ester.

Contaminant Sources

STOFF IDENT Compounds
ToxCast & Tox21 Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(17-alpha)-Norethindrone acetate	ChEBI
17-Acetoxy-19-nor-17-alpha-pregn-4-en-20-yn-3-one	ChEBI
17-Acetoxy-19-nor-17alpha-pregn-4-en-20-yn-3-one	ChEBI
17-Acetyloxy(17-alpha)-19-norpregn-4-estren-17-beta-ol-acetate-3-one	ChEBI
17-alpha-Ethinyl-19-nortestosterone acetate	ChEBI
17-alpha-Ethinyl-19-nortestosterone-17-beta-acetate	ChEBI
17-alpha-Ethynyl-17-hydroxyestr-4-en-3-one acetate	ChEBI
17-alpha-Ethynyl-19-nortestosterone acetate	ChEBI
17-Hydroxy-19-nor-17-alpha-pregn-4-en-20-yn-3-one acetate	ChEBI
17-Hydroxy-19-nor-17alpha-pregn-4-en-20-yn-3-one acetate	ChEBI
17alpha-Ethinyl-19-nortestosterone 17beta-acetate	ChEBI
17alpha-Ethinyl-19-nortestosterone-17beta-acetate	ChEBI
17alpha-Ethynyl-17-hydroxyestr-4-en-3-one acetate	ChEBI
17alpha-Ethynyl-17beta-acetoxy-19-norandrost-4-en-3-one	ChEBI
17alpha-Ethynyl-19-nortestosterone acetate	ChEBI
17beta-Acetoxy-19-nor-17alpha-pregn-4-en-20-yn-3-one	ChEBI
17beta-Hydroxy-19-nor-17alpha-pregn-4-en-20-yn-3-one acetate	ChEBI
19-Norethindrone acetate	ChEBI
19-Norethisterone acetate	ChEBI
19-Norethynyltestosterone acetate	ChEBI
Aygestin	ChEBI
Norethindrone 17-acetate	ChEBI
Norethindrone acetate	ChEBI
Norlutate	ChEBI
(17-a)-Norethindrone acetate	Generator
(17-a)-Norethindrone acetic acid	Generator
(17-alpha)-Norethindrone acetic acid	Generator
(17-Α)-norethindrone acetate	Generator
(17-Α)-norethindrone acetic acid	Generator
17-Acetoxy-19-nor-17-a-pregn-4-en-20-yn-3-one	Generator
17-Acetoxy-19-nor-17-α-pregn-4-en-20-yn-3-one	Generator
17-Acetoxy-19-nor-17a-pregn-4-en-20-yn-3-one	Generator
17-Acetoxy-19-nor-17α-pregn-4-en-20-yn-3-one	Generator
17-Acetyloxy(17-a)-19-norpregn-4-estren-17-b-ol-acetate-3-one	Generator
17-Acetyloxy(17-a)-19-norpregn-4-estren-17-b-ol-acetic acid-3-one	Generator
17-Acetyloxy(17-alpha)-19-norpregn-4-estren-17-beta-ol-acetic acid-3-one	Generator
17-Acetyloxy(17-α)-19-norpregn-4-estren-17-β-ol-acetate-3-one	Generator
17-Acetyloxy(17-α)-19-norpregn-4-estren-17-β-ol-acetic acid-3-one	Generator
17-a-Ethinyl-19-nortestosterone acetate	Generator
17-a-Ethinyl-19-nortestosterone acetic acid	Generator
17-alpha-Ethinyl-19-nortestosterone acetic acid	Generator
17-Α-ethinyl-19-nortestosterone acetate	Generator
17-Α-ethinyl-19-nortestosterone acetic acid	Generator
17-a-Ethinyl-19-nortestosterone-17-b-acetate	Generator
17-a-Ethinyl-19-nortestosterone-17-b-acetic acid	Generator
17-alpha-Ethinyl-19-nortestosterone-17-beta-acetic acid	Generator
17-Α-ethinyl-19-nortestosterone-17-β-acetate	Generator
17-Α-ethinyl-19-nortestosterone-17-β-acetic acid	Generator
17-a-Ethynyl-17-hydroxyestr-4-en-3-one acetate	Generator
17-a-Ethynyl-17-hydroxyestr-4-en-3-one acetic acid	Generator
17-alpha-Ethynyl-17-hydroxyestr-4-en-3-one acetic acid	Generator
17-Α-ethynyl-17-hydroxyestr-4-en-3-one acetate	Generator
17-Α-ethynyl-17-hydroxyestr-4-en-3-one acetic acid	Generator
17-a-Ethynyl-19-nortestosterone acetate	Generator
17-a-Ethynyl-19-nortestosterone acetic acid	Generator
17-alpha-Ethynyl-19-nortestosterone acetic acid	Generator
17-Α-ethynyl-19-nortestosterone acetate	Generator
17-Α-ethynyl-19-nortestosterone acetic acid	Generator
17-Hydroxy-19-nor-17-a-pregn-4-en-20-yn-3-one acetate	Generator
17-Hydroxy-19-nor-17-a-pregn-4-en-20-yn-3-one acetic acid	Generator
17-Hydroxy-19-nor-17-alpha-pregn-4-en-20-yn-3-one acetic acid	Generator
17-Hydroxy-19-nor-17-α-pregn-4-en-20-yn-3-one acetate	Generator
17-Hydroxy-19-nor-17-α-pregn-4-en-20-yn-3-one acetic acid	Generator
17-Hydroxy-19-nor-17a-pregn-4-en-20-yn-3-one acetate	Generator
17-Hydroxy-19-nor-17a-pregn-4-en-20-yn-3-one acetic acid	Generator
17-Hydroxy-19-nor-17alpha-pregn-4-en-20-yn-3-one acetic acid	Generator
17-Hydroxy-19-nor-17α-pregn-4-en-20-yn-3-one acetate	Generator
17-Hydroxy-19-nor-17α-pregn-4-en-20-yn-3-one acetic acid	Generator
17a-Ethinyl-19-nortestosterone 17b-acetate	Generator
17a-Ethinyl-19-nortestosterone 17b-acetic acid	Generator
17alpha-Ethinyl-19-nortestosterone 17beta-acetic acid	Generator
17Α-ethinyl-19-nortestosterone 17β-acetate	Generator
17Α-ethinyl-19-nortestosterone 17β-acetic acid	Generator
17a-Ethinyl-19-nortestosterone-17b-acetate	Generator
17a-Ethinyl-19-nortestosterone-17b-acetic acid	Generator
17alpha-Ethinyl-19-nortestosterone-17beta-acetic acid	Generator
17Α-ethinyl-19-nortestosterone-17β-acetate	Generator
17Α-ethinyl-19-nortestosterone-17β-acetic acid	Generator
17a-Ethynyl-17-hydroxyestr-4-en-3-one acetate	Generator
17a-Ethynyl-17-hydroxyestr-4-en-3-one acetic acid	Generator
17alpha-Ethynyl-17-hydroxyestr-4-en-3-one acetic acid	Generator
17Α-ethynyl-17-hydroxyestr-4-en-3-one acetate	Generator
17Α-ethynyl-17-hydroxyestr-4-en-3-one acetic acid	Generator
17a-Ethynyl-17b-acetoxy-19-norandrost-4-en-3-one	Generator
17Α-ethynyl-17β-acetoxy-19-norandrost-4-en-3-one	Generator
17a-Ethynyl-19-nortestosterone acetate	Generator
17a-Ethynyl-19-nortestosterone acetic acid	Generator
17alpha-Ethynyl-19-nortestosterone acetic acid	Generator
17Α-ethynyl-19-nortestosterone acetate	Generator
17Α-ethynyl-19-nortestosterone acetic acid	Generator
17b-Acetoxy-19-nor-17a-pregn-4-en-20-yn-3-one	Generator
17Β-acetoxy-19-nor-17α-pregn-4-en-20-yn-3-one	Generator
17b-Hydroxy-19-nor-17a-pregn-4-en-20-yn-3-one acetate	Generator
17b-Hydroxy-19-nor-17a-pregn-4-en-20-yn-3-one acetic acid	Generator
17beta-Hydroxy-19-nor-17alpha-pregn-4-en-20-yn-3-one acetic acid	Generator
17Β-hydroxy-19-nor-17α-pregn-4-en-20-yn-3-one acetate	Generator
17Β-hydroxy-19-nor-17α-pregn-4-en-20-yn-3-one acetic acid	Generator
19-Norethindrone acetic acid	Generator
19-Norethisterone acetic acid	Generator
19-Norethynyltestosterone acetic acid	Generator
Norethindrone 17-acetic acid	Generator
Norethindrone acetic acid	Generator
Norlutic acid	Generator
Norethisterone acetic acid	Generator
Norethindrone acetate, (17alpha)-isomer	MeSH
Norethindrone acetate, (17alpha)-(+-)-isomer	MeSH

Chemical Formula

C₂₂H₂₈O₃

Average Molecular Mass

340.456 g/mol

Monoisotopic Mass

340.204 g/mol

CAS Registry Number

51-98-9

IUPAC Name

(1S,2R,10R,11S,14R,15S)-14-ethynyl-15-methyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-14-yl acetate

Traditional Name

ENTA

SMILES

[H][C@@]12CC[C@@](OC(C)=O)(C#C)[C@@]1(C)CC[C@]1([H])[C@@]3([H])CCC(=O)C=C3CC[C@@]21[H]

InChI Identifier

InChI=1S/C22H28O3/c1-4-22(25-14(2)23)12-10-20-19-7-5-15-13-16(24)6-8-17(15)18(19)9-11-21(20,22)3/h1,13,17-20H,5-12H2,2-3H3/t17-,18+,19+,20-,21-,22-/m0/s1

InChI Key

IMONTRJLAWHYGT-ZCPXKWAGSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as steroid esters. Steroid esters are compounds containing a steroid moiety which bears a carboxylic acid ester group.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid esters

Direct Parent

Steroid esters

Alternative Parents

Substituents

Steroid ester
Estrogen-skeleton
3-oxo-delta-4-steroid
3-oxosteroid
Estrane-skeleton
Oxosteroid
Delta-4-steroid
Cyclohexenone
Ynone
Carboxylic acid ester
Cyclic ketone
Ketone
Acetylide
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Organooxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

terminal acetylenic compound (CHEBI:7628 )
acetate ester (CHEBI:7628 )
3-oxo Delta(4)-steroid (CHEBI:7628 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.0054 g/L	ALOGPS
logP	3.58	ALOGPS
logP	3.66	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	19.28	ChemAxon
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.37 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	96.58 m³·mol⁻¹	ChemAxon
Polarizability	39.14 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-03fs-0688900000-2a446c473302d1d611dc	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0006-0649000000-12415d159a756fe43c28	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0089000000-44c99a32c5c2dc49106e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001j-0292000000-71de88f7d107e5dedab6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-076r-1970000000-f85e4555d8f9c5410bec	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000j-1059000000-aa30ee7c931370943740	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000b-3094000000-b084eec62eb3cb52ce8f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052g-3090000000-a0ee824ad37f3d3598b4	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DBSALT000129

HMDB ID

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Norethisterone_acetate

Chemspider ID

Not Available

ChEBI ID

7628

PubChem Compound ID

5832

Kegg Compound ID

C08152

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. https://www.ncbi.nlm.nih.gov/pubmed/?term=19820247

2. https://www.ncbi.nlm.nih.gov/pubmed/?term=22505834

3. https://www.ncbi.nlm.nih.gov/pubmed/?term=22999413

4. https://www.ncbi.nlm.nih.gov/pubmed/?term=484634

Norethindrone acetate (CHEM016813)

Structure for CHEM016813: Norethindrone acetate