NP-MRD: Showing NP-Card for lovastatin acid (NP0214589)

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Record Information

Version

2.0

Created at

2022-09-05 13:56:01 UTC

Updated at

2022-09-05 13:56:01 UTC

NP-MRD ID

NP0214589

Secondary Accession Numbers

None

Natural Product Identification

Common Name

lovastatin acid

Description

Mevinolinic acid, also known as L 154819 or lovastatin acid, belongs to the class of organic compounds known as medium-chain hydroxy acids and derivatives. These are hydroxy acids with a 6 to 12 carbon atoms long side chain. Mevinolinic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). lovastatin acid was first documented in 2001 (PMID: 11372002). A polyketide obtained by hydrolysis of the pyranone ring of lovastatin (PMID: 11831543) (PMID: 12369143) (PMID: 12434405) (PMID: 12927388).

Structure

MOL 3D MOL SDF PDB SMILES InChI

LVA
  Mrv0541 02231217112D          

 38 39  0  0  0  0            999 V2000
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   -0.4265   -0.4632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5869    1.4078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.0468    2.0314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5067    0.4723    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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  1 11  1  0  0  0  0
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  8  4  1  6  0  0  0
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 28 30  1  0  0  0  0
M  END

     RDKit          3D

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M  END

LVA
  Mrv0541 02231217112D          

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 23 37  1  6  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 26 28  1  0  0  0  0
 26 29  1  6  0  0  0
 26 38  1  6  0  0  0
 28 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0214589

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@](O)(CC[C@@]1([H])[C@@]([H])(C)C=CC2=C[C@]([H])(C)C[C@]([H])(OC(=O)[C@@]([H])(C)CC)[C@]12[H])C[C@@]([H])(O)CC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C24H38O6/c1-5-15(3)24(29)30-21-11-14(2)10-17-7-6-16(4)20(23(17)21)9-8-18(25)12-19(26)13-22(27)28/h6-7,10,14-16,18-21,23,25-26H,5,8-9,11-13H2,1-4H3,(H,27,28)/t14-,15-,16-,18+,19+,20-,21-,23-/m0/s1

> <INCHI_KEY>
QLJODMDSTUBWDW-BXMDZJJMSA-N

> <FORMULA>
C24H38O6

> <MOLECULAR_WEIGHT>
422.5549

> <EXACT_MASS>
422.266838948

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
47.46317076360109

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R,5R)-7-[(1S,2S,6R,8S,8aR)-2,6-dimethyl-8-{[(2S)-2-methylbutanoyl]oxy}-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoic acid

> <ALOGPS_LOGP>
3.74

> <JCHEM_LOGP>
3.237715789666665

> <ALOGPS_LOGS>
-3.82

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.890242521747759

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.212298804304482

> <JCHEM_PKA_STRONGEST_BASIC>
-2.721465066718528

> <JCHEM_POLAR_SURFACE_AREA>
104.06

> <JCHEM_REFRACTIVITY>
116.67459999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.41e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R,5R)-7-[(1S,2S,6R,8S,8aR)-2,6-dimethyl-8-{[(2S)-2-methylbutanoyl]oxy}-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: LVA                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       7.269   0.300   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       4.749  -0.573   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       7.773   2.919   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       2.228  -1.447   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      -0.796  -0.865   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -4.829   2.628   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.325   1.173   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.724   0.009   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.821   3.792   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.813   0.882   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.765   1.755   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.308   3.501   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.804   2.046   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.245   0.882   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.333   0.009   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.308  -0.573   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.212   0.300   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.732   1.173   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.292   1.755   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.317  -1.738   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.300   4.665   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.253   2.046   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -4.829  -1.447   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -5.837  -2.611   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.292  -2.320   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.220  -2.611   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -1.300  -3.484   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       1.724  -4.066   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.720  -2.261   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.236  -4.357   0.000  0.00  0.00           C+0
HETATM   31  H   UNK     0       1.011  -0.815   0.000  0.00  0.00           H+0
HETATM   32  H   UNK     0      -1.742   0.676   0.000  0.00  0.00           H+0
HETATM   33  H   UNK     0      -2.665   4.531   0.000  0.00  0.00           H+0
HETATM   34  H   UNK     0      -1.117   1.200   0.000  0.00  0.00           H+0
HETATM   35  H   UNK     0       3.531   0.058   0.000  0.00  0.00           H+0
HETATM   36  H   UNK     0      -1.356  -0.043   0.000  0.00  0.00           H+0
HETATM   37  H   UNK     0      -5.899  -1.241   0.000  0.00  0.00           H+0
HETATM   38  H   UNK     0       0.507  -3.435   0.000  0.00  0.00           H+0
CONECT    1   11                                                            
CONECT    2   14                                                            
CONECT    3   11                                                            
CONECT    4    8                                                            
CONECT    5   16   25                                                       
CONECT    6    7    9                                                       
CONECT    7    6   10   15                                                  
CONECT    8    4   17   18   31                                             
CONECT    9    6   12                                                       
CONECT   10    7   13   16   32                                             
CONECT   11    1    3   22                                                  
CONECT   12    9   13   21   33                                             
CONECT   13   10   12   19   34                                             
CONECT   14    2   18   22   35                                             
CONECT   15    7   23                                                       
CONECT   16    5   10   20   36                                             
CONECT   17    8   19                                                       
CONECT   18    8   14                                                       
CONECT   19   13   17                                                       
CONECT   20   16   23                                                       
CONECT   21   12                                                            
CONECT   22   11   14                                                       
CONECT   23   15   20   24   37                                             
CONECT   24   23                                                            
CONECT   25    5   26   27                                                  
CONECT   26   25   28   29   38                                             
CONECT   27   25                                                            
CONECT   28   26   30                                                       
CONECT   29   26                                                            
CONECT   30   28                                                            
CONECT   31    8                                                            
CONECT   32   10                                                            
CONECT   33   12                                                            
CONECT   34   13                                                            
CONECT   35   14                                                            
CONECT   36   16                                                            
CONECT   37   23                                                            
CONECT   38   26                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   78    0
END

View in JSmol

Synonyms

Value	Source
L 154819	ChEBI
L-154819	ChEBI
Lovastatin acid	ChEBI
MK 819	ChEBI
Monacolinic K acid	ChEBI
MSD 803 acid	ChEBI
Mevinolinate	Generator
(3R,5R)-7-((1R,2R,6S,8R,8As)-2,6-dimethyl-8-{[(2R)-2-methylbutanoyl]oxy}-1,2,6,7,8,8a-hexahydronaphthalen-1-yl)-3,5-dihydroxyheptanoate	Generator
Lovestatin acid	MeSH
Mevinolinic acid, aluminum salt (3:1)	MeSH
Mevinolinic acid, monosodium salt	MeSH
Mevinolinic acid, monosodium salt, (1S-(1alpha(betas,deltas),2alpha,6beta,8beta(r*),8aalpha))-isomer	MeSH
Mevinolinic acid, calcium salt (2:1)	MeSH
Mevinolinic acid, monoammonium salt, 1S-(1alpha(betas),2alpha,6beta,8beta(r),8aalpha)-isomer	MeSH
Mevinolinic acid	MeSH
Mevinolinic acid, (1S-(1alpha(betas,deltas),2alpha,6beta,8beta(r*),8aalpha))-isomer	MeSH

Chemical Formula

C₂₄H₃₈O₆

Average Mass

422.5549 Da

Monoisotopic Mass

422.26684 Da

IUPAC Name

(3R,5R)-7-[(1S,2S,6R,8S,8aR)-2,6-dimethyl-8-{[(2S)-2-methylbutanoyl]oxy}-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoic acid

Traditional Name

(3R,5R)-7-[(1S,2S,6R,8S,8aR)-2,6-dimethyl-8-{[(2S)-2-methylbutanoyl]oxy}-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoic acid

CAS Registry Number

Not Available

SMILES

[H][C@@](O)(CC[C@@]1([H])[C@@]([H])(C)C=CC2=C[C@]([H])(C)C[C@]([H])(OC(=O)[C@@]([H])(C)CC)[C@]12[H])C[C@@]([H])(O)CC(O)=O

InChI Identifier

InChI=1S/C24H38O6/c1-5-15(3)24(29)30-21-11-14(2)10-17-7-6-16(4)20(23(17)21)9-8-18(25)12-19(26)13-22(27)28/h6-7,10,14-16,18-21,23,25-26H,5,8-9,11-13H2,1-4H3,(H,27,28)/t14-,15-,16-,18+,19+,20-,21-,23-/m0/s1

InChI Key

QLJODMDSTUBWDW-BXMDZJJMSA-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 medium-chain hydroxy acids and derivatives. These are hydroxy acids with a 6 to 12 carbon atoms long side chain.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Hydroxy acids and derivatives

Sub Class

Medium-chain hydroxy acids and derivatives

Direct Parent

Medium-chain hydroxy acids and derivatives

Alternative Parents

Substituents

Fatty alcohol
Medium-chain hydroxy acid
Medium-chain fatty acid
Beta-hydroxy acid
Branched fatty acid
Hydroxy fatty acid
Fatty acid ester
Fatty acyl
Dicarboxylic acid or derivatives
Secondary alcohol
Carboxylic acid ester
Carboxylic acid derivative
Carboxylic acid
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Carbonyl group
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

polyketide (CHEBI:82985 )
fatty acid ester (CHEBI:82985 )
dihydroxy monocarboxylic acid (CHEBI:82985 )
carbobicyclic compound (CHEBI:82985 )

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	3.74	ALOGPS
logP	3.24	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	4.21	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	104.06 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	116.67 m³·mol⁻¹	ChemAxon
Polarizability	47.46 Å³	ChemAxon
Number of Rings	2	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

Not Available

DrugBank ID

DB03785

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

64727

PDB ID

Not Available

ChEBI ID

82985

Good Scents ID

Not Available

References

General References

Kyrklund C, Backman JT, Kivisto KT, Neuvonen M, Laitila J, Neuvonen PJ: Plasma concentrations of active lovastatin acid are markedly increased by gemfibrozil but not by bezafibrate. Clin Pharmacol Ther. 2001 May;69(5):340-5. doi: 10.1067/mcp.2001.115542. [PubMed:11372002 ]
Sun JX, Niecestro R, Phillips G, Shen J, Lukacsko P, Friedhoff L: Comparative pharmacokinetics of lovastatin extended-release tablets and lovastatin immediate-release tablets in humans. J Clin Pharmacol. 2002 Feb;42(2):198-204. doi: 10.1177/00912700222011111. [PubMed:11831543 ]
Baranova NA, Kreier VG, Egorov NS: [Concentration on Diapak C 16 capsules of lovastatin, mevinolinic acid and other inhibitors of biosynthesis of sterins produced by Penicillium citrinum 89]. Antibiot Khimioter. 2002;47(4):3-6. [PubMed:12369143 ]
Nagasawa K, Nagai K, Sumitani Y, Moriya Y, Muraki Y, Takara K, Ohnishi N, Yokoyama T, Fujimoto S: Monocarboxylate transporter mediates uptake of lovastatin acid in rat cultured mesangial cells. J Pharm Sci. 2002 Dec;91(12):2605-13. doi: 10.1002/jps.10246. [PubMed:12434405 ]
Nagasawa K, Nagai K, Ishimoto A, Fujimoto S: Transport mechanism for lovastatin acid in bovine kidney NBL-1 cells: kinetic evidences imply involvement of monocarboxylate transporter 4. Int J Pharm. 2003 Aug 27;262(1-2):63-73. doi: 10.1016/s0378-5173(03)00318-1. [PubMed:12927388 ]
LOTUS database [Link]

Showing NP-Card for lovastatin acid (NP0214589)

MOL for NP0214589 (lovastatin acid)

3D MOL for NP0214589 (lovastatin acid)

3D SDF for NP0214589 (lovastatin acid)

3D-SDF for NP0214589 (lovastatin acid)

PDB for NP0214589 (lovastatin acid)

3D PDB for NP0214589 (lovastatin acid)

SMILES for NP0214589 (lovastatin acid)

INCHI for NP0214589 (lovastatin acid)

Structure for NP0214589 (lovastatin acid)

3D Structure for NP0214589 (lovastatin acid)