dl-Norgestrel (CED0006519)

Record Information

Version

1.0

Creation Date

2016-05-22 06:17:09 UTC

Update Date

2026-05-14 19:05:43 UTC

Accession Number

CHEM019561

Identification

Common Name

dl-Norgestrel

Class

Small Molecule

Description

dl-Norgestrel is an organic compound with the formula C21H28O2 and an average molecular weight of 312.45 g/mol. dl-Norgestrel belongs to the estrane steroids, a subclass of steroids and steroid derivatives within the organic compounds. It is categorized under the superclass of lipids and lipid-like molecules. This compound is found in healthcare, pharmaceuticals, and veterinary products, specifically within progestogens and estrogens in combination and hormonal contraceptives for systemic use. The recorded route of exposure for this substance is oral. dl-Norgestrel interacts with three protein targets, acting as an agonist or inhibitor of the progesterone receptor (PGR), the androgen receptor (AR), and 3-oxo-5-alpha-steroid 4-dehydrogenase 1 (SRD5A1).

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Ovrette	MeSH
Neogest	MeSH
DL Norgestrel	MeSH
Postinor	MeSH
DL-Norgestrel	MeSH
WY-3707ovrette	ChEMBL
Norgestrel schering brand	MeSH
Wyeth brand OF norgestrel	MeSH
Norgestrel	MeSH
Norgestrel wyeth brand	MeSH
Schering brand OF norgestrel	MeSH

Chemical Formula

C₂₁H₂₈O₂

Average Molecular Mass

312.453 g/mol

Monoisotopic Mass

312.209 g/mol

CAS Registry Number

6533-00-2

IUPAC Name

(1S,2R,10R,11S,14R,15S)-15-ethyl-14-ethynyl-14-hydroxytetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one

Traditional Name

plan b

SMILES

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

InChI Identifier

InChI=1S/C21H28O2/c1-3-20-11-9-17-16-8-6-15(22)13-14(16)5-7-18(17)19(20)10-12-21(20,23)4-2/h2,13,16-19,23H,3,5-12H2,1H3/t16-,17+,18+,19-,20-,21?/m0/s1

InChI Key

WWYNJERNGUHSAO-CULCCENASA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Estrane steroids

Direct Parent

Estrogens and derivatives

Alternative Parents

Substituents

Estrogen-skeleton
3-oxo-delta-4-steroid
3-oxosteroid
17-hydroxysteroid
Oxosteroid
Hydroxysteroid
Delta-4-steroid
Cyclohexenone
Ynone
Cyclic alcohol
Tertiary alcohol
Cyclic ketone
Ketone
Acetylide
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Alcohol
Organooxygen compound
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	0.0058 g/L	ALOGPS
logP	3.25	ALOGPS
logP	3.66	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	17.91	ChemAxon
pKa (Strongest Basic)	-1.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	92.03 m³·mol⁻¹	ChemAxon
Polarizability	36.74 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03di-0179000000-09f92950350c9411f4dc	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0btj-0191000000-7bd7256abde150b22d9f	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0f76-2390000000-84a923da67ade6ef90a8	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03di-0019000000-3f0cb0e2e76214741c6f	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03di-0059000000-f6e5c83ac4c0da584cb2	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-053v-0090000000-6bb0ea8f0fc81b4c6fe2	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
2440.0	Log mg/kg	[1400:4300]	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
322	Progestogens and estrogens in combination	Healthcare, pharmaceuticals & veterinary products	Not Available

Pathways

0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Androgen receptor	P15207	Rattus norvegicus	Predicted (SEA)	0.856341
Click to view 3D structure	Progesterone receptor	Q690N0	Bos taurus	Predicted (SEA)	0.233548
Click to view 3D structure	Sex hormone-binding globulin	P04278	Humans	Predicted (SEA)	0.311397
Click to view 3D structure	Glucocorticoid receptor	P04150	Humans	Predicted (SEA)	2.72472
Click to view 3D structure	Sodium-dependent serotonin transporter	P31645	Humans	Predicted (SEA)	9.10836
Click to view 3D structure	Estrogen receptor	P03372	Humans	Predicted (SEA)	14.0129
Click to view 3D structure	Progesterone receptor	P06401	Humans	Predicted (SEA)	15.8034
Click to view 3D structure	Corticosteroid-binding globulin	P08185	Humans	Predicted (SEA)	14.1686
Click to view 3D structure	Glucocorticoid receptor	Q9N1U3	Sus scrofa	Predicted (SEA)	2.02408
Click to view 3D structure	Sodium-dependent noradrenaline transporter	P23975	Humans	Predicted (SEA)	206.845
Click to view 3D structure	Androgen receptor	P10275	Humans	Predicted (SEA)	54.5723
Click to view 3D structure	Cytochrome P450 2C8	P10632	Humans	Predicted (SEA)	140.44
Click to view 3D structure	Cytochrome P450 2C9	P11712	Humans	Predicted (SEA)	1101.64
Click to view 3D structure	Cytochrome P450 3A4	P08684	Humans	Predicted (SEA)	1401.44
Click to view 3D structure	Glucocorticoid receptor	P06536	Rattus norvegicus	Predicted (SEA)	9.6533
Click to view 3D structure	Mineralocorticoid receptor	P08235	Humans	Predicted (SEA)	37.9904
Click to view 3D structure	Bile salt export pump	O95342	Humans	Predicted (SEA)	55.6622
Click to view 3D structure	Estrogen receptor beta	Q92731	Humans	Predicted (SEA)	173.682
Click to view 3D structure	Cytochrome P450 2C19	P33261	Humans	Predicted (SEA)	1636.47
Click to view 3D structure	Androgen receptor	P19091	Mus musculus	Predicted (SEA)	22.9655
Click to view 3D structure	Steroid 17-alpha-hydroxylase/17,20 lyase	P05093	Humans	Predicted (SEA)	59.2433
Click to view 3D structure	Glucocorticoid receptor	P06537	Mus musculus	Predicted (SEA)	7.70707
Click to view 3D structure	Sodium-dependent dopamine transporter	Q01959	Humans	Predicted (SEA)	1334.02
Click to view 3D structure	Aromatase	P11511	Humans	Predicted (SEA)	231.446
Click to view 3D structure	Glucocorticoid receptor	A0A8C0QLS2	Canis lupus familiaris	Predicted (SEA)	2.25763