NP-MRD: Showing NP-Card for drospirenone (NP0249392)

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Record Information

Version

2.0

Created at

2022-09-07 11:56:10 UTC

Updated at

2022-09-07 11:56:10 UTC

NP-MRD ID

NP0249392

Secondary Accession Numbers

None

Natural Product Identification

Common Name

drospirenone

Description

Drospirenone, also known as slynd or DRSP, belongs to the class of organic compounds known as spironolactones and derivatives. These are steroid lactones with a structure based on the spironolactone skeleton. Drospirenone is an extremely weak basic (essentially neutral) compound (based on its pKa). drospirenone is found in Macaca fascicularis. drospirenone was first documented in 2000 (PMID: 11024226). Other activity Drospirenone stimulates the proliferation of MCF-7 breast cancer cells in vitro, an action that is independent of the classical PRs and is instead mediated via the progesterone receptor membrane component-1 (PGRMC1) (PMID: 23577032).

Structure

MOL 3D MOL SDF PDB SMILES InChI

1395
  Mrv0541 02231215282D          

 34 40  0  0  1  0            999 V2000
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    3.6170   -3.0361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8101    3.0361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1514    0.0426    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3593    0.0426    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1146   -0.7108    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3963   -0.7108    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6940    0.6641    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7553   -1.1763    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5842   -0.1221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4095    1.4751    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5023    0.4988    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9747    2.1225    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2005   -0.8947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1312    2.2886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0822    1.1330    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7573   -0.2858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1146   -1.6419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END

1395
  Mrv0541 02231215282D          

 34 40  0  0  1  0            999 V2000
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    3.6170   -3.0361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8101    3.0361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0249392

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12C[C@]1([H])[C@@]1([H])[C@]3([H])[C@]4([H])C[C@]4([H])[C@@]4(CCC(=O)O4)[C@@]3(C)CC[C@]1([H])[C@@]1(C)CCC(=O)C=C21

> <INCHI_IDENTIFIER>
InChI=1S/C24H30O3/c1-22-6-3-12(25)9-17(22)13-10-14(13)20-16(22)4-7-23(2)21(20)15-11-18(15)24(23)8-5-19(26)27-24/h9,13-16,18,20-21H,3-8,10-11H2,1-2H3/t13-,14+,15-,16+,18+,20-,21+,22-,23+,24+/m1/s1

> <INCHI_KEY>
METQSPRSQINEEU-HXCATZOESA-N

> <FORMULA>
C24H30O3

> <MOLECULAR_WEIGHT>
366.4932

> <EXACT_MASS>
366.219494826

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
41.80862815363165

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2R,4R,10R,11S,14S,15S,16S,18S,19S)-10,14-dimethylspiro[hexacyclo[9.8.0.0²,⁴.0⁵,¹⁰.0¹⁴,¹⁹.0¹⁶,¹⁸]nonadecane-15,2'-oxolan]-5-ene-5',7-dione

> <ALOGPS_LOGP>
2.36

> <JCHEM_LOGP>
3.3667613656666666

> <ALOGPS_LOGS>
-5.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.952565524845618

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
101.67719999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.25e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
yasmin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1395                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       6.340  -3.065   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       6.752  -5.667   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      12.712   5.667   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       5.883   0.079   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.404   0.079   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.947  -1.327   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.340  -1.327   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.896   1.240   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.143  -2.196   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.957  -0.228   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.364   2.754   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.404   0.931   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.419   3.962   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.841  -1.670   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.845   4.272   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.487   2.115   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.880  -0.534   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.947  -3.065   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.991   3.641   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.250  -2.492   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.116   1.742   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.404  -4.471   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.944   0.709   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.883  -4.471   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.090   4.900   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      12.244   2.975   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      11.727   4.565   0.000  0.00  0.00           C+0
HETATM   28  H   UNK     0       5.393   1.156   0.000  0.00  0.00           H+0
HETATM   29  H   UNK     0       4.281   1.256   0.000  0.00  0.00           H+0
HETATM   30  H   UNK     0       3.156  -2.206   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0       7.673   2.131   0.000  0.00  0.00           H+0
HETATM   32  H   UNK     0       5.247   2.366   0.000  0.00  0.00           H+0
HETATM   33  H   UNK     0       9.560   0.681   0.000  0.00  0.00           H+0
HETATM   34  H   UNK     0       7.652   5.122   0.000  0.00  0.00           H+0
CONECT    1    9   24                                                       
CONECT    2   24                                                            
CONECT    3   27                                                            
CONECT    4    5    7    8   28                                             
CONECT    5    4    6   10   29                                             
CONECT    6    5    9   10   30                                             
CONECT    7    4    9   14   20                                             
CONECT    8    4   11   12   31                                             
CONECT    9    1    6    7   18                                             
CONECT   10    5    6                                                       
CONECT   11    8   13   15   32                                             
CONECT   12    8   16   17   33                                             
CONECT   13   11   15   19   34                                             
CONECT   14    7   17                                                       
CONECT   15   11   13                                                       
CONECT   16   12   19   21   23                                             
CONECT   17   12   14                                                       
CONECT   18    9   22                                                       
CONECT   19   13   16   25                                                  
CONECT   20    7                                                            
CONECT   21   16   26                                                       
CONECT   22   18   24                                                       
CONECT   23   16                                                            
CONECT   24    1    2   22                                                  
CONECT   25   19   27                                                       
CONECT   26   21   27                                                       
CONECT   27    3   25   26                                                  
CONECT   28    4                                                            
CONECT   29    5                                                            
CONECT   30    6                                                            
CONECT   31    8                                                            
CONECT   32   11                                                            
CONECT   33   12                                                            
CONECT   34   13                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   80    0
END

View in JSmol

Synonyms

Value	Source
1,2-Dihydrospirorenone	ChEBI
6beta,7Beta;15beta,16beta-dimethylene-3-oxo-17alpha-pregn-4-ene-21,17-carbolactone	ChEBI
Dehydrospirorenone	ChEBI
Drospirenona	ChEBI
Drospirenonum	ChEBI
Slynd	Kegg
6b,7Beta;15b,16b-dimethylene-3-oxo-17a-pregn-4-ene-21,17-carbolactone	Generator
6Β,7beta;15β,16β-dimethylene-3-oxo-17α-pregn-4-ene-21,17-carbolactone	Generator
6Β,7β,15β,16β-dimethylene-3-oxo-17α-pregn-4-ene-21,17 carbolactone	HMDB
DRSP	HMDB
1,2-Dihydro-spirorenone	HMDB
Dihydrospirorenone	HMDB
6beta,7beta,15beta,16beta-Dimethylen-3-oxo-17alpha-pregn-4-en-21,17-carbolacton	HMDB

Chemical Formula

C₂₄H₃₀O₃

Average Mass

366.4932 Da

Monoisotopic Mass

366.21949 Da

IUPAC Name

(1R,2R,4R,10R,11S,14S,15S,16S,18S,19S)-10,14-dimethylspiro[hexacyclo[9.8.0.0²,⁴.0⁵,¹⁰.0¹⁴,¹⁹.0¹⁶,¹⁸]nonadecane-15,2'-oxolan]-5-ene-5',7-dione

Traditional Name

yasmin

CAS Registry Number

Not Available

SMILES

[H][C@@]12C[C@]1([H])[C@@]1([H])[C@]3([H])[C@]4([H])C[C@]4([H])[C@@]4(CCC(=O)O4)[C@@]3(C)CC[C@]1([H])[C@@]1(C)CCC(=O)C=C21

InChI Identifier

InChI=1S/C24H30O3/c1-22-6-3-12(25)9-17(22)13-10-14(13)20-16(22)4-7-23(2)21(20)15-11-18(15)24(23)8-5-19(26)27-24/h9,13-16,18,20-21H,3-8,10-11H2,1-2H3/t13-,14+,15-,16+,18+,20-,21+,22-,23+,24+/m1/s1

InChI Key

METQSPRSQINEEU-HXCATZOESA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Macaca fascicularis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as spironolactones and derivatives. These are steroid lactones with a structure based on the spironolactone skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid lactones

Direct Parent

Spironolactones and derivatives

Alternative Parents

Substituents

Spironolactone
Cyclohexenone
Gamma butyrolactone
Tetrahydrofuran
Cyclic ketone
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Carbonyl group
Organic oxide
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

3-oxo steroid (CHEBI:50838 )
3-oxo Delta(4)-steroid (CHEBI:50838 )
steroid lactone (CHEBI:50838 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.36	ALOGPS
logP	3.37	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Basic)	-5	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	0	ChemAxon
Refractivity	101.68 m³·mol⁻¹	ChemAxon
Polarizability	41.81 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0015467

DrugBank ID

DB01395

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

62105

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Drospirenone

METLIN ID

Not Available

PubChem Compound

68873

PDB ID

Not Available

ChEBI ID

50838

Good Scents ID

Not Available

References

General References

Krattenmacher R: Drospirenone: pharmacology and pharmacokinetics of a unique progestogen. Contraception. 2000 Jul;62(1):29-38. doi: 10.1016/s0010-7824(00)00133-5. [PubMed:11024226 ]
Wichianpitaya J, Taneepanichskul S: A comparative efficacy of low-dose combined oral contraceptives containing desogestrel and drospirenone in premenstrual symptoms. Obstet Gynecol Int. 2013;2013:487143. doi: 10.1155/2013/487143. Epub 2013 Feb 20. [PubMed:23577032 ]
LOTUS database [Link]

Showing NP-Card for drospirenone (NP0249392)

MOL for NP0249392 (drospirenone)

3D MOL for NP0249392 (drospirenone)

3D SDF for NP0249392 (drospirenone)

3D-SDF for NP0249392 (drospirenone)

PDB for NP0249392 (drospirenone)

3D PDB for NP0249392 (drospirenone)

SMILES for NP0249392 (drospirenone)

INCHI for NP0249392 (drospirenone)

Structure for NP0249392 (drospirenone)

3D Structure for NP0249392 (drospirenone)