NP-MRD: Showing NP-Card for 2-ethoxy-4-({[(1s)-3-methyl-1-[2-(piperidin-1-yl)phenyl]butyl]-c-hydroxycarbonimidoyl}methyl)benzoic acid (NP0165675)

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Record Information

Version

2.0

Created at

2022-09-03 00:52:58 UTC

Updated at

2022-09-03 00:52:58 UTC

NP-MRD ID

NP0165675

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-ethoxy-4-({[(1s)-3-methyl-1-[2-(piperidin-1-yl)phenyl]butyl]-c-hydroxycarbonimidoyl}methyl)benzoic acid

Description

Repaglinide, also known as prandin or surepost, belongs to the class of organic compounds known as phenylpiperidines. Phenylpiperidines are compounds containing a phenylpiperidine skeleton, which consists of a piperidine bound to a phenyl group. In February 2001 Prandin's patent life was extended to 14 March 2009 in response to Novo Nordisk's patent term restoration application, with U.S. Patent 5,216,167 having been reissued as RE37035. Repaglinide is a strong basic compound (based on its pKa). In humans, repaglinide is involved in repaglinide action pathway. Caution should be taken in people with liver disease and decreased kidney function when using this medication. 2-ethoxy-4-({[(1s)-3-methyl-1-[2-(piperidin-1-yl)phenyl]butyl]-c-hydroxycarbonimidoyl}methyl)benzoic acid is found in Salvia regla. 2-ethoxy-4-({[(1s)-3-methyl-1-[2-(piperidin-1-yl)phenyl]butyl]-c-hydroxycarbonimidoyl}methyl)benzoic acid was first documented in 2000 (PMID: 11060717). Less than 2% is unchanged in the feces.

Structure

MOL 3D MOL SDF PDB SMILES InChI

912
  Mrv0541 02231215062D          

 33 35  0  0  1  0            999 V2000
    5.9370   -0.0495    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    2.4256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    3.6631    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    3.6631    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659   -2.5246    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -1.2870    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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 32 33  1  0  0  0  0
M  END

     RDKit          3D

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M  END

912
  Mrv0541 02231215062D          

 33 35  0  0  1  0            999 V2000
    5.9370   -0.0495    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0165675

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCOC1=C(C=CC(CC(=O)N[C@@H](CC(C)C)C2=CC=CC=C2N2CCCCC2)=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H36N2O4/c1-4-33-25-17-20(12-13-22(25)27(31)32)18-26(30)28-23(16-19(2)3)21-10-6-7-11-24(21)29-14-8-5-9-15-29/h6-7,10-13,17,19,23H,4-5,8-9,14-16,18H2,1-3H3,(H,28,30)(H,31,32)/t23-/m0/s1

> <INCHI_KEY>
FAEKWTJYAYMJKF-QHCPKHFHSA-N

> <FORMULA>
C27H36N2O4

> <MOLECULAR_WEIGHT>
452.5857

> <EXACT_MASS>
452.26750765

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
51.48599953789469

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-ethoxy-4-({[(1S)-3-methyl-1-[2-(piperidin-1-yl)phenyl]butyl]carbamoyl}methyl)benzoic acid

> <ALOGPS_LOGP>
5.05

> <JCHEM_LOGP>
3.946804454827218

> <ALOGPS_LOGS>
-5.19

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.519066522631515

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.6754997808978898

> <JCHEM_PKA_STRONGEST_BASIC>
4.8184755016238165

> <JCHEM_POLAR_SURFACE_AREA>
78.87

> <JCHEM_REFRACTIVITY>
131.8281

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.94e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
repaglinide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 912                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      11.082  -0.092   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       5.748   4.528   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       9.748   6.838   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       7.081   6.838   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0      13.750  -4.713   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       9.748  -2.402   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      12.416  -5.483   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      15.083  -5.483   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.416  -7.023   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      15.083  -7.023   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.750  -7.793   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.082  -3.172   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.750  -3.172   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.416  -2.402   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.082  -4.713   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.748  -5.483   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      15.083  -2.402   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.416  -0.862   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.748  -7.023   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.415  -4.713   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      15.083  -0.862   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.750  -0.092   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.748  -0.862   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.415  -0.092   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.415   1.448   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.081   2.218   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.748   2.218   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.081   3.758   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       9.748   3.758   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.415   4.528   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.415   6.068   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.414   3.758   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.080   4.528   0.000  0.00  0.00           C+0
CONECT    1   23                                                            
CONECT    2   28   32                                                       
CONECT    3   31                                                            
CONECT    4   31                                                            
CONECT    5    7    8   13                                                  
CONECT    6   12   23                                                       
CONECT    7    5    9                                                       
CONECT    8    5   10                                                       
CONECT    9    7   11                                                       
CONECT   10    8   11                                                       
CONECT   11    9   10                                                       
CONECT   12    6   14   15                                                  
CONECT   13    5   14   17                                                  
CONECT   14   12   13   18                                                  
CONECT   15   12   16                                                       
CONECT   16   15   19   20                                                  
CONECT   17   13   21                                                       
CONECT   18   14   22                                                       
CONECT   19   16                                                            
CONECT   20   16                                                            
CONECT   21   17   22                                                       
CONECT   22   18   21                                                       
CONECT   23    1    6   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25   28                                                       
CONECT   27   25   29                                                       
CONECT   28    2   26   30                                                  
CONECT   29   27   30                                                       
CONECT   30   28   29   31                                                  
CONECT   31    3    4   30                                                  
CONECT   32    2   33                                                       
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

View in JSmol

Synonyms

Value	Source
Prandin	Kegg
Surepost	Kegg
AG-ee 388 ZW	HMDB
AG-ee 623 ZW	HMDB
Glaxo wellcome brand OF replaginide	HMDB
Novo nordisk brand 2 OF repaglinide	HMDB
Repa-glinide	HMDB
2-Ethoxy-4-(2-((3-methyl-1-(2-(1-piperidinyl)phenyl)butyl)amino)-2-oxoethyl)benzoic acid	HMDB
Novo nordisk brand OF repaglinide	HMDB
NovoNorm	HMDB
Repaglinide, (+-)-isomer	HMDB
2-Ethoxy-N-(alpha-(2-methyl-1-propyl)-2-piperidinobenzyl)-4-carbamoylmethylbenzoic acid	HMDB
AG-ee 388	HMDB
GlucoNorm	HMDB

Chemical Formula

C₂₇H₃₆N₂O₄

Average Mass

452.5857 Da

Monoisotopic Mass

452.26751 Da

IUPAC Name

2-ethoxy-4-({[(1S)-3-methyl-1-[2-(piperidin-1-yl)phenyl]butyl]carbamoyl}methyl)benzoic acid

Traditional Name

repaglinide

CAS Registry Number

Not Available

SMILES

CCOC1=C(C=CC(CC(=O)N[C@@H](CC(C)C)C2=CC=CC=C2N2CCCCC2)=C1)C(O)=O

InChI Identifier

InChI=1S/C27H36N2O4/c1-4-33-25-17-20(12-13-22(25)27(31)32)18-26(30)28-23(16-19(2)3)21-10-6-7-11-24(21)29-14-8-5-9-15-29/h6-7,10-13,17,19,23H,4-5,8-9,14-16,18H2,1-3H3,(H,28,30)(H,31,32)/t23-/m0/s1

InChI Key

FAEKWTJYAYMJKF-QHCPKHFHSA-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
Salvia regla	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpiperidines. Phenylpiperidines are compounds containing a phenylpiperidine skeleton, which consists of a piperidine bound to a phenyl group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Piperidines

Sub Class

Phenylpiperidines

Direct Parent

Phenylpiperidines

Alternative Parents

Substituents

Phenylpiperidine
Phenylacetamide
Benzoic acid or derivatives
Benzoic acid
Phenoxy compound
Benzoyl
Phenol ether
Tertiary aliphatic/aromatic amine
Dialkylarylamine
Aniline or substituted anilines
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Amino acid
Tertiary amine
Carboxamide group
Amino acid or derivatives
Secondary carboxylic acid amide
Monocarboxylic acid or derivatives
Ether
Carboxylic acid
Carboxylic acid derivative
Azacycle
Organonitrogen compound
Hydrocarbon derivative
Carbonyl group
Amine
Organic oxide
Organopnictogen compound
Organooxygen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

piperidines (CHEBI:8805 )

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	5.05	ALOGPS
logP	3.95	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	3.68	ChemAxon
pKa (Strongest Basic)	4.82	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	78.87 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	131.83 m³·mol⁻¹	ChemAxon
Polarizability	51.49 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0015048

DrugBank ID

DB00912

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

59377

KEGG Compound ID

C07670

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Repaglinide

METLIN ID

Not Available

PubChem Compound

65981

PDB ID

Not Available

ChEBI ID

348669

Good Scents ID

Not Available

References

General References

Massi-Benedetti M, Damsbo P: Pharmacology and clinical experience with repaglinide. Expert Opin Investig Drugs. 2000 Apr;9(4):885-98. doi: 10.1517/13543784.9.4.885. [PubMed:11060717 ]
LOTUS database [Link]

Showing NP-Card for 2-ethoxy-4-({[(1s)-3-methyl-1-[2-(piperidin-1-yl)phenyl]butyl]-c-hydroxycarbonimidoyl}methyl)benzoic acid (NP0165675)

MOL for NP0165675 (2-ethoxy-4-({[(1s)-3-methyl-1-[2-(piperidin-1-yl)phenyl]butyl]-c-hydroxycarbonimidoyl}methyl)benzoic acid)

3D MOL for NP0165675 (2-ethoxy-4-({[(1s)-3-methyl-1-[2-(piperidin-1-yl)phenyl]butyl]-c-hydroxycarbonimidoyl}methyl)benzoic acid)

3D SDF for NP0165675 (2-ethoxy-4-({[(1s)-3-methyl-1-[2-(piperidin-1-yl)phenyl]butyl]-c-hydroxycarbonimidoyl}methyl)benzoic acid)

3D-SDF for NP0165675 (2-ethoxy-4-({[(1s)-3-methyl-1-[2-(piperidin-1-yl)phenyl]butyl]-c-hydroxycarbonimidoyl}methyl)benzoic acid)

PDB for NP0165675 (2-ethoxy-4-({[(1s)-3-methyl-1-[2-(piperidin-1-yl)phenyl]butyl]-c-hydroxycarbonimidoyl}methyl)benzoic acid)

3D PDB for NP0165675 (2-ethoxy-4-({[(1s)-3-methyl-1-[2-(piperidin-1-yl)phenyl]butyl]-c-hydroxycarbonimidoyl}methyl)benzoic acid)

SMILES for NP0165675 (2-ethoxy-4-({[(1s)-3-methyl-1-[2-(piperidin-1-yl)phenyl]butyl]-c-hydroxycarbonimidoyl}methyl)benzoic acid)

INCHI for NP0165675 (2-ethoxy-4-({[(1s)-3-methyl-1-[2-(piperidin-1-yl)phenyl]butyl]-c-hydroxycarbonimidoyl}methyl)benzoic acid)

Structure for NP0165675 (2-ethoxy-4-({[(1s)-3-methyl-1-[2-(piperidin-1-yl)phenyl]butyl]-c-hydroxycarbonimidoyl}methyl)benzoic acid)

3D Structure for NP0165675 (2-ethoxy-4-({[(1s)-3-methyl-1-[2-(piperidin-1-yl)phenyl]butyl]-c-hydroxycarbonimidoyl}methyl)benzoic acid)