NP-MRD: Showing NP-Card for Simvastatin (NP0136928)

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Record Information

Version

2.0

Created at

2022-05-30 16:28:41 UTC

Updated at

2022-05-30 16:28:41 UTC

NP-MRD ID

NP0136928

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Simvastatin

Description

Simvastatin, also known as zocor or MK-733, belongs to the class of organic compounds known as delta valerolactones. These are cyclic organic compounds containing an oxan-2- one moiety. Simvastatin is an extremely weak basic (essentially neutral) compound (based on its pKa). In humans, simvastatin is involved in simvastatin action pathway. Simvastatin is a potentially toxic compound. Simvastatin was first documented in 2005 (PMID: 16144183). Compared to the placebo group, those treated with simvastatin experienced a 30% decrease in overall mortality, a 42% reduction in coronary death, a 34% reduction in major coronary events, and a 37% reduction in revascularization procedures (PMID: 16634254) (PMID: 16651050) (PMID: 16864763) (PMID: 16433891).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 04191212132D          

 31 33  0  0  1  0            999 V2000
   -0.7145    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7173    1.6494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1447   -0.8316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0107    1.3303    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1427    0.8155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4245    2.0538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4455    2.8693    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1525    3.2848    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1463    4.1002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4370    4.5025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7572    4.0872    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    0.0416    4.5009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8531    4.5156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4325    2.8866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  2  3  1  0  0  0  0
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 30 27  1  0  0  0  0
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 30 31  1  0  0  0  0
M  END

     RDKit          3D

 68 70  0  0  0  0  0  0  0  0999 V2000
   -3.6399    3.6815   -0.9078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3495    2.2113   -0.9399 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4995   -1.0578    2.3764 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0390   -1.5077   -0.0711 C   0  0  2  0  0  0  0  0  0  0  0  0
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    2.2071    0.6104   -0.8904 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3948    0.8510   -0.0607 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1583    1.6082    1.1976 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8858    2.9176    1.2731 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2646    2.7642    1.1137 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4241    3.7747    0.0811 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9440    3.0330   -1.1009 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0843    3.5934   -2.1817 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2478    1.7105   -0.8974 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3282   -2.0814    0.2948 C   0  0  1  0  0  0  0  0  0  0  0  0
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M  END


  Mrv0541 04191212132D          

 31 33  0  0  1  0            999 V2000
   -0.7145    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  2  1  1  0  0  0  0
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  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
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  3  7  2  0  0  0  0
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 30 27  1  0  0  0  0
 27 28  1  0  0  0  0
 30 29  1  0  0  0  0
 30 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0136928

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12[C@H](C[C@@H](C)C=C1C=C[C@H](C)[C@@H]2CC[C@@H]1C[C@@H](O)CC(=O)O1)OC(=O)C(C)(C)CC

> <INCHI_IDENTIFIER>
InChI=1S/C25H38O5/c1-6-25(4,5)24(28)30-21-12-15(2)11-17-8-7-16(3)20(23(17)21)10-9-19-13-18(26)14-22(27)29-19/h7-8,11,15-16,18-21,23,26H,6,9-10,12-14H2,1-5H3/t15-,16-,18+,19+,20-,21-,23-/m0/s1

> <INCHI_KEY>
RYMZZMVNJRMUDD-HGQWONQESA-N

> <FORMULA>
C25H38O5

> <MOLECULAR_WEIGHT>
418.5662

> <EXACT_MASS>
418.271924326

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
47.85247192642514

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,3R,7S,8S,8aR)-8-{2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl}-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl 2,2-dimethylbutanoate

> <ALOGPS_LOGP>
4.51

> <JCHEM_LOGP>
4.458201216333332

> <ALOGPS_LOGS>
-4.53

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.914537666911102

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8361812244930835

> <JCHEM_POLAR_SURFACE_AREA>
72.83

> <JCHEM_REFRACTIVITY>
117.68339999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.22e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
simvastatin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-12         0                                  
HETATM    1  C   UNK     0      -1.334   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667   0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334  -1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.339   3.079   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.003  -1.552   0.000  0.00  0.00           C+0
HETATM   13  H   UNK     0      -0.020   2.483   0.000  0.00  0.00           H+0
HETATM   14  C   UNK     0       4.000   1.522   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.659   3.834   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.698   5.356   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       4.018   6.132   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.006   7.654   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.682   8.405   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.413   7.629   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.425   6.107   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.078   8.402   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       5.326   8.429   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -2.674   5.388   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -2.671   3.848   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -1.336   3.081   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -5.339   3.844   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -6.671   3.071   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -3.602   1.589   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -4.004   3.076   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -4.400   1.588   0.000  0.00  0.00           C+0
CONECT    1   26    2    5                                                  
CONECT    2    1   13    3    4                                             
CONECT    3    2    6    7                                                  
CONECT    4    2   11    8                                                  
CONECT    5    1    9                                                       
CONECT    6    3   10                                                       
CONECT    7    3    9                                                       
CONECT    8    4   14   10                                                  
CONECT    9    7    5   12                                                  
CONECT   10    8    6                                                       
CONECT   11    4   15                                                       
CONECT   12    9                                                            
CONECT   13    2                                                            
CONECT   14    8                                                            
CONECT   15   11   16                                                       
CONECT   16   15   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   16   20                                                       
CONECT   22   20                                                            
CONECT   23   18                                                            
CONECT   24   25                                                            
CONECT   25   24   30   26                                                  
CONECT   26    1   25                                                       
CONECT   27   30   28                                                       
CONECT   28   27                                                            
CONECT   29   30                                                            
CONECT   30   25   27   29   31                                             
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   66    0
END

View in JSmol

Synonyms

Value	Source
2,2-Dimethylbutyric acid, 8-ester with (4R,6R)-6-(2-((1S,2S,6R,8S,8ar)-1,2,6,7,8,8a-hexahydro-8-hydroxy-2,6-dimethyl-1-naphthyl)ethyl)tetrahydro-4-hydroxy-2H-pyran-2-one	ChEBI
MK-733	ChEBI
Simvastatina	ChEBI
Simvastatine	ChEBI
Simvastatinum	ChEBI
Zocor	ChEBI
2,2-Dimethylbutyrate, 8-ester with (4R,6R)-6-(2-((1S,2S,6R,8S,8ar)-1,2,6,7,8,8a-hexahydro-8-hydroxy-2,6-dimethyl-1-naphthyl)ethyl)tetrahydro-4-hydroxy-2H-pyran-2-one	Generator
(+)-Simvastatin	HMDB
Cholestat	HMDB
Denan	HMDB
Eucor	HMDB
Kolestevan	HMDB
Lipex	HMDB
Lipinorm	HMDB
Liponorm	HMDB
Lipovas	HMDB
Lodales	HMDB
Modutrol	HMDB
Nor-vastina	HMDB
Pepstatin	HMDB
Rechol	HMDB
Simcor	HMDB
Simovil	HMDB
Simvastatin lactone	HMDB
Simvotin	HMDB
Sinvacor	HMDB
Sinvascor	HMDB
Sivastin	HMDB
Statin	HMDB
Synvinolin	HMDB
Valemia	HMDB
Velostatin	HMDB
Zocord	HMDB

Chemical Formula

C₂₅H₃₈O₅

Average Mass

418.5662 Da

Monoisotopic Mass

418.27192 Da

IUPAC Name

(1S,3R,7S,8S,8aR)-8-{2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl}-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl 2,2-dimethylbutanoate

Traditional Name

simvastatin

CAS Registry Number

Not Available

SMILES

[H][C@]12[C@H](C[C@@H](C)C=C1C=C[C@H](C)[C@@H]2CC[C@@H]1C[C@@H](O)CC(=O)O1)OC(=O)C(C)(C)CC

InChI Identifier

InChI=1S/C25H38O5/c1-6-25(4,5)24(28)30-21-12-15(2)11-17-8-7-16(3)20(23(17)21)10-9-19-13-18(26)14-22(27)29-19/h7-8,11,15-16,18-21,23,26H,6,9-10,12-14H2,1-5H3/t15-,16-,18+,19+,20-,21-,23-/m0/s1

InChI Key

RYMZZMVNJRMUDD-HGQWONQESA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as delta valerolactones. These are cyclic organic compounds containing an oxan-2- one moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Delta valerolactones

Direct Parent

Delta valerolactones

Alternative Parents

Substituents

Delta_valerolactone
Fatty acid ester
Delta valerolactone
Fatty acyl
Oxane
Dicarboxylic acid or derivatives
Secondary alcohol
Carboxylic acid ester
Oxacycle
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

statin (semi-synthetic) (CHEBI:9150 )
fatty acid ester (CHEBI:9150 )
delta-lactone (CHEBI:9150 )
carbobicyclic compound (CHEBI:9150 )

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	4.51	ALOGPS
logP	4.46	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	14.91	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	117.68 m³·mol⁻¹	ChemAxon
Polarizability	47.85 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0005007

DrugBank ID

DB00641

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB023580

KNApSAcK ID

Not Available

Chemspider ID

49179

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Simvastatin

METLIN ID

2443

PubChem Compound

54454

PDB ID

Not Available

ChEBI ID

9150

Good Scents ID

Not Available

References

General References

Mahboobi SK, Shohat EZ, Jellinek SP, Rose M: Systemic infections can decrease the threshold of statin-induced muscle injury. South Med J. 2006 Apr;99(4):403-4. doi: 10.1097/01.smj.0000209273.52754.86. [PubMed:16634254 ]
Antons KA, Williams CD, Baker SK, Phillips PS: Clinical perspectives of statin-induced rhabdomyolysis. Am J Med. 2006 May;119(5):400-9. doi: 10.1016/j.amjmed.2006.02.007. [PubMed:16651050 ]
Tsivgoulis G, Spengos K, Karandreas N, Panas M, Kladi A, Manta P: Presymptomatic neuromuscular disorders disclosed following statin treatment. Arch Intern Med. 2006 Jul 24;166(14):1519-24. doi: 10.1001/archinte.166.14.1519. [PubMed:16864763 ]
Finsterer J, Zuntner G: Rhabdomyolysis from Simvastatin triggered by infection and muscle exertion. South Med J. 2005 Aug;98(8):827-9. doi: 10.1097/01.smj.0000170731.44173.34. [PubMed:16144183 ]
Soininen K, Niemi M, Kilkki E, Strandberg T, Kivisto KT: Muscle symptoms associated with statins: a series of twenty patients. Basic Clin Pharmacol Toxicol. 2006 Jan;98(1):51-4. doi: 10.1111/j.1742-7843.2006.pto_193.x. [PubMed:16433891 ]

Showing NP-Card for Simvastatin (NP0136928)

MOL for NP0136928 (Simvastatin)

3D MOL for NP0136928 (Simvastatin)

3D SDF for NP0136928 (Simvastatin)

3D-SDF for NP0136928 (Simvastatin)

PDB for NP0136928 (Simvastatin)

3D PDB for NP0136928 (Simvastatin)

SMILES for NP0136928 (Simvastatin)

INCHI for NP0136928 (Simvastatin)

Structure for NP0136928 (Simvastatin)

3D Structure for NP0136928 (Simvastatin)