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Pharmaceutical impurity

3,17-Dihydroxy-19-nor-17alpha-pregna-1,3,5(10)-trien-20-yn-6-one (6-Oxoethinylestradiol; 6-Ketoethinylestradiol)

3,17-Dihydroxy-19-nor-17alpha-pregna-1,3,5(10)-trien-20-yn-6-one (6-Oxoethinylestradiol; 6-Ketoethinylestradiol) is listed in the pharmaceutical impurity collection under CAS 38002-18-5. Its represented structure has formula C20H22O3 and a calculated molecular weight of 310.39 g/mol.

2D chemical structure

O H O O H H H H ( S ) ( S ) ( R ) ( S ) ( S )

Chemical identity

Catalog name
3,17-Dihydroxy-19-nor-17alpha-pregna-1,3,5(10)-trien-20-yn-6-one (6-Oxoethinylestradiol; 6-Ketoethinylestradiol)
Common name
3,17-Dihydroxy-19-nor-17alpha-pregna-1,3,5(10)-trien-20-yn-6-one (6-Oxoethinylestradiol; 6-Ketoethinylestradiol)
Chemical name
(8R,9S,13S,14S,17R)-17-ethynyl-3,17-dihydroxy-13-methyl-7,8,9,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-6-one
CAS
38002-18-5
SMILES
C#C[C@]1(O)CC[C@H]2[C@@H]3CC(=O)c4cc(O)ccc4[C@H]3CC[C@@]21C
InChI
InChI=1S/C20H22O3/c1-3-20(23)9-7-17-15-11-18(22)16-10-12(21)4-5-13(16)14(15)6-8-19(17,20)2/h1,4-5,10,14-15,17,21,23H,6-9,11H2,2H3/t14-,15-,17+,19+,20+/m1/s1
InChIKey
QHTAUDUBRNENFJ-VCNAKFCDSA-N
Associated API
Matrix - API Family Ethinylestradiol | Estradiol; Ethinylestradiol

Record ID: Ac5b4ef657b81

Computed properties

C20H22O3 Molecular formula
310.393 g/molMolecular weight
310.1569 DaMonoisotopic exact mass
57.53 ŲTopological polar surface area
3.2528 Calculated LogP (Wildman–Crippen)
87.1331 cm³/molMolar refractivity (Wildman–Crippen)
3 countHydrogen-bond acceptors
2 countHydrogen-bond donors

Descriptors are calculated from the displayed SMILES. Calculated LogP is not a measured partition coefficient or a pH-specific LogD.

Molecular descriptor profile

Descriptor radar

Mol. weight LogP TPSA HBA HBD Rotatable 25 50 75 100

Structural feature counts

0 2 4 Count H-bond acceptors H-bond donors Rotatable bonds Rings Aromatic rings Stereo centers

Element composition

C H O 0 5 10 15 20 Number of atoms

Radar scale: 0–100 percentile within 25,771 distinct represented structures in this release, using the midpoint rank for ties. Larger values indicate a higher descriptor rank, not greater safety or toxicity. Element counts include hydrogen and combine isotopes under each element.

Radar values and percentile reference
DescriptorValuePercentile
Molecular weight310.39347.19
Calculated LogP (Wildman–Crippen)3.252866.46
Topological polar surface area57.5338.00
Hydrogen-bond acceptors333.13
Hydrogen-bond donors264.87
Rotatable bonds (strict)03.45

Complete molecular descriptors

PropertyCalculated valueUnit / type
Molecular formulaC20H22O3dimensionless
Molecular weight310.393g/mol
Monoisotopic exact mass310.1569Da
Topological polar surface area57.53Ų
Calculated LogP (Wildman–Crippen)3.2528dimensionless
Molar refractivity (Wildman–Crippen)87.1331cm³/mol
Hydrogen-bond acceptors3count
Hydrogen-bond donors2count
Rotatable bonds (strict)0count
Heavy atoms23count
Heteroatoms3count
Rings4count
Aromatic rings1count
Aliphatic rings3count
Saturated rings2count
Aromatic heterocycles0count
Aliphatic heterocycles0count
Saturated heterocycles0count
Aromatic carbocycles1count
Aliphatic carbocycles3count
Fraction of sp³ carbon atoms0.55fraction
Formal charge0e
Disconnected components1count
Isotopically specified atoms0count
Potential atom stereocenters5count
Unspecified atom stereocenters0count
Spiro atoms0count
Bridgehead atoms0count
Labute approximate surface area136.2723Ų
Valence electrons120count
Radical electrons0count
Bertz complexity730.8926index
Balaban J1.7728index

Ring categories overlap and should not be summed. No toxicity result, PDE, HBEL or acceptable intake is inferred from these descriptors.

Toxicological services and resources for 3,17-Dihydroxy-19-nor-17alpha-pregna-1,3,5(10)-trien-20-yn-6-one (6-Oxoethinylestradiol; 6-Ketoethinylestradiol)

Qualification and safety assessment of 3,17-Dihydroxy-19-nor-17alpha-pregna-1,3,5(10)-trien-20-yn-6-one (6-Oxoethinylestradiol; 6-Ketoethinylestradiol)

Explore toxicological qualification of 3,17-Dihydroxy-19-nor-17alpha-pregna-1,3,5(10)-trien-20-yn-6-one (6-Oxoethinylestradiol; 6-Ketoethinylestradiol) and ICH M7 mutagenic impurity assessment of 3,17-Dihydroxy-19-nor-17alpha-pregna-1,3,5(10)-trien-20-yn-6-one (6-Oxoethinylestradiol; 6-Ketoethinylestradiol) for evaluation of this impurity in its pharmaceutical context.

Where data gaps need to be addressed, resources include read-across assessment for 3,17-Dihydroxy-19-nor-17alpha-pregna-1,3,5(10)-trien-20-yn-6-one (6-Oxoethinylestradiol; 6-Ketoethinylestradiol) and acceptable intake and limit justification for 3,17-Dihydroxy-19-nor-17alpha-pregna-1,3,5(10)-trien-20-yn-6-one (6-Oxoethinylestradiol; 6-Ketoethinylestradiol). The relevant approach depends on the available evidence, exposure and duration of use.

Related Altox services and technical resources

Other catalogue designations with the same represented structure

These are separate catalogue entries; shared structure does not establish interchangeable pharmacopoeial designations.

Identity sources and calculation method

Identifiers originate from the source catalogues and available public identity records. InChI and InChIKey on this page are generated from the displayed SMILES. RDKit validation checks the molecular representation; it does not independently verify every catalogue assignment.

Discuss an assessment for 3,17-Dihydroxy-19-nor-17alpha-pregna-1,3,5(10)-trien-20-yn-6-one (6-Oxoethinylestradiol; 6-Ketoethinylestradiol)

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