Norelgestromin (CED0012428)

Record Information

Version

1.0

Creation Date

2016-05-22 05:57:00 UTC

Update Date

2026-05-14 18:23:05 UTC

Accession Number

CHEM019253

Identification

Common Name

Norelgestromin

Class

Small Molecule

Description

Norelgestromin is an organic compound with the formula C21H29NO2 and an average molecular weight of 327.47 g/mol. Norelgestromin belongs to the estrane steroids, a subclass of steroids and steroid derivatives within the organic compounds. This compound is found in or released from two recorded sources: building and construction (sunshades awnings or outside screens) and healthcare, pharmaceuticals and veterinary products, specifically hormonal contraceptives for systemic use. Recorded exposure routes include transdermal and topical application. Norelgestromin interacts with three recorded protein targets, acting as an agonist, binder, or partial agonist of the progesterone receptor (PGR), albumin (ALB), and the androgen receptor (AR).

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
17-Deacetylnorgestimate	MeSH
LNGO	MeSH
Levonorgestrel oxime	MeSH
Levonorgestrel oxime, (3E,17alpha)-isomer	MeSH
Levonorgestrel oxime, (3Z,17alpha)-isomer	MeSH
Progestin norelgestromin	MeSH
Evra	KEGG
Norelgestromin	MeSH

Chemical Formula

C₂₁H₂₉NO₂

Average Molecular Mass

327.468 g/mol

Monoisotopic Mass

327.220 g/mol

CAS Registry Number

53016-31-2

IUPAC Name

(1S,2R,5E,10R,11S,14R,15S)-15-ethyl-14-ethynyl-5-(hydroxyimino)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-14-ol

Traditional Name

Evra

SMILES

[H][C@@]12CC[C@@](O)(C#C)[C@@]1(CC)CC[C@]1([H])[C@@]3([H])CC\C(C=C3CC[C@@]21[H])=N/O

InChI Identifier

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/b22-15+/t16-,17+,18+,19-,20-,21-/m0/s1

InChI Key

ISHXLNHNDMZNMC-VTKCIJPMSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as estrane steroids. These are steroids with a structure based on the estrane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Estrane steroids

Direct Parent

Estrane steroids

Alternative Parents

Substituents

Estrane-skeleton
Hydroxysteroid
17-hydroxysteroid
Delta-4-steroid
Ynone
Cyclic alcohol
Ketoxime
Tertiary alcohol
Oxime
Acetylide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Alcohol
Hydrocarbon derivative
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

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	0.006 g/L	ALOGPS
logP	3.18	ALOGPS
logP	3.67	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	11.47	ChemAxon
pKa (Strongest Basic)	3.12	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	52.82 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	95.85 m³·mol⁻¹	ChemAxon
Polarizability	38.48 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	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	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-0119000000-eafaa72c8f9b8ea1cad7	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-01r2-0296000000-e386e81d7b0d60c80103	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-7491000000-bdde4b8c9d61e8c283ec	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-0019000000-85f89b950caf07fc4ef8	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-0029000000-6a210c16af2f7f9fc3a3	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-053s-1093000000-30353260e85e32a4b2b8	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
2187.0	Log mg/kg	[1200:3900]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
317	Hormonal contraceptives for systemic use	Healthcare, pharmaceuticals & veterinary products	Not Available
502	Sunshades Awnings Or Outside Screens	Building & Construction	Not Available

Pathways

3 pathways

Norelgestromin Action Pathway

Norelgestromin Drug Metabolism

Norelgestromin Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Androgen receptor	P15207	Rattus norvegicus	Predicted (SEA)	4.98235
Click to view 3D structure	Progesterone receptor	Q690N0	Bos taurus	Predicted (SEA)	1.86838
Click to view 3D structure	Sodium-dependent serotonin transporter	P31645	Humans	Predicted (SEA)	32.3853
Click to view 3D structure	Sex hormone-binding globulin	P04278	Humans	Predicted (SEA)	4.35956
Click to view 3D structure	Glucocorticoid receptor	P04150	Humans	Predicted (SEA)	10.9767
Click to view 3D structure	Estrogen receptor	P03372	Humans	Predicted (SEA)	31.3732
Click to view 3D structure	Sodium-dependent noradrenaline transporter	P23975	Humans	Predicted (SEA)	274.496
Click to view 3D structure	Progesterone receptor	P06401	Humans	Predicted (SEA)	54.1831
Click to view 3D structure	Bile salt export pump	O95342	Humans	Predicted (SEA)	258.07
Click to view 3D structure	Cytochrome P450 2C8	P10632	Humans	Predicted (SEA)	1325.38
Click to view 3D structure	Corticosteroid-binding globulin	P08185	Humans	Predicted (SEA)	28.3371
Click to view 3D structure	Glucocorticoid receptor	Q9N1U3	Sus scrofa	Predicted (SEA)	2.72472
Click to view 3D structure	Cytochrome P450 2C9	P11712	Humans	Predicted (SEA)	5174.64
Click to view 3D structure	Estrogen receptor beta	Q92731	Humans	Predicted (SEA)	820.142
Click to view 3D structure	Cytochrome P450 2C19	P33261	Humans	Predicted (SEA)	4470.96
Click to view 3D structure	Sodium-dependent dopamine transporter	Q01959	Humans	Predicted (SEA)	2640.88
Click to view 3D structure	Androgen receptor	P10275	Humans	Predicted (SEA)	595.702
Click to view 3D structure	Glucocorticoid receptor	P06536	Rattus norvegicus	Predicted (SEA)	25.8459
Click to view 3D structure	Cytochrome P450 3A4	P08684	Humans	Predicted (SEA)	6408.31
Click to view 3D structure	Steroid 17-alpha-hydroxylase/17,20 lyase	P05093	Humans	Predicted (SEA)	226.463
Click to view 3D structure	Mineralocorticoid receptor	P08235	Humans	Predicted (SEA)	345.573
Click to view 3D structure	3-oxo-5-alpha-steroid 4-dehydrogenase 1	P18405	Humans	Predicted (SEA)	29.2713
Click to view 3D structure	Polyunsaturated fatty acid lipoxygenase ALOX15	P12530	Oryctolagus cuniculus	Predicted (SEA)	337.71
Click to view 3D structure	3-oxo-5-alpha-steroid 4-dehydrogenase 2	P31213	Humans	Predicted (SEA)	49.1229
Click to view 3D structure	Acetylcholinesterase	P22303	Humans	Predicted (SEA)	5058.8