NP-MRD: Showing NP-Card for methyl 6-hydroxy-7-methyl-1h,2h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyridine-4-carboxylate (NP0158731)

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Record Information

Version

2.0

Created at

2022-09-02 16:22:05 UTC

Updated at

2022-09-02 16:22:05 UTC

NP-MRD ID

NP0158731

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 6-hydroxy-7-methyl-1h,2h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyridine-4-carboxylate

Description

Methyl 6-hydroxy-7-methyl-1H,2H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyridine-4-carboxylate belongs to the class of organic compounds known as tetrahydropyridines. These are derivatives of pyridine in which two double bonds in the pyridine moiety are reduced by adding four hydrogen atoms. Methyl 6-hydroxy-7-methyl-1H,2H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyridine-4-carboxylate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 32 33  0  0  0  0  0  0  0  0999 V2000
    4.1865    1.0908    0.0975 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8593    0.6633    0.2762 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5430   -0.6396   -0.1382 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4355   -1.3607   -0.6421 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1702   -1.0845    0.0457 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8626   -2.3119   -0.3423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4642   -2.8380   -0.2012 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5964   -1.9614    0.1329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1701   -0.5641   -0.1126 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1315   -0.2404    0.6339 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2526    1.2222    0.3054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1691    1.7268    0.3935 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4498    2.5398   -0.7263 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0684    0.4999    0.3921 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2336    0.6658   -0.5555 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5873    0.8312   -0.8976 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8102    0.5036    0.8315 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3136    2.1709    0.2689 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6022   -2.9661   -0.7814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6880   -3.8416   -0.3249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4480   -2.1925   -0.5396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8819   -2.1299    1.1904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9486   -0.4202   -1.1788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0032   -0.3808    1.7258 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5753    1.3183   -0.7482 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9284    1.7614    1.0040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2703    2.3088    1.3205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9411    3.3741   -0.5794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4413    0.2810    1.4129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8598    0.4067   -1.5725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6379    1.6790   -0.5698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9864   -0.1118   -0.3057 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 14  1  0
 14 15  1  0
 14 12  1  0
 12 13  1  0
 12 11  1  0
 11 10  1  0
 10  5  1  0
 10  9  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  6 19  1  0
  7 20  1  0
  8 21  1  0
  8 22  1  0
  9 23  1  6
 14 29  1  1
 15 30  1  0
 15 31  1  0
 15 32  1  0
 12 27  1  1
 13 28  1  0
 11 25  1  0
 11 26  1  0
 10 24  1  1
M  END


  Mrv1533004241510282D          

 15 16  0  0  0  0            999 V2000
    3.9934    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5249   -1.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4699    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
  5 15  1  0  0  0  0
  9 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0158731

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=CNCC2C(C)C(O)CC12

> <INCHI_IDENTIFIER>
InChI=1S/C11H17NO3/c1-6-8-4-12-5-9(11(14)15-2)7(8)3-10(6)13/h5-8,10,12-13H,3-4H2,1-2H3

> <INCHI_KEY>
UFTLJHOQQZCDQR-UHFFFAOYSA-N

> <FORMULA>
C11H17NO3

> <MOLECULAR_WEIGHT>
211.261

> <EXACT_MASS>
211.120843411

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
22.49128016236392

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 6-hydroxy-7-methyl-1H,2H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyridine-4-carboxylate

> <ALOGPS_LOGP>
-0.12

> <JCHEM_LOGP>
0.09483694933333284

> <ALOGPS_LOGS>
-1.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.95444608366806

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.926385463393355

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8309989983117445

> <JCHEM_POLAR_SURFACE_AREA>
58.56

> <JCHEM_REFRACTIVITY>
55.6569

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.01e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 6-hydroxy-7-methyl-1H,2H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyridine-4-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       7.454   6.160   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       7.454   4.620   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       6.121   3.850   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       4.787   4.620   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       7.454   0.000   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.322  -0.476   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.846  -1.941   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.877   0.770   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       3.322   2.016   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   15                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   15                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14    5    9                                                  
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

View in JSmol

Synonyms

Value	Source
Methyl 6-hydroxy-7-methyl-1H,2H,4ah,5H,6H,7H,7ah-cyclopenta[c]pyridine-4-carboxylic acid	Generator

Chemical Formula

C₁₁H₁₇NO₃

Average Mass

211.2610 Da

Monoisotopic Mass

211.12084 Da

IUPAC Name

methyl 6-hydroxy-7-methyl-1H,2H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyridine-4-carboxylate

Traditional Name

methyl 6-hydroxy-7-methyl-1H,2H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyridine-4-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=CNCC2C(C)C(O)CC12

InChI Identifier

InChI=1S/C11H17NO3/c1-6-8-4-12-5-9(11(14)15-2)7(8)3-10(6)13/h5-8,10,12-13H,3-4H2,1-2H3

InChI Key

UFTLJHOQQZCDQR-UHFFFAOYSA-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 tetrahydropyridines. These are derivatives of pyridine in which two double bonds in the pyridine moiety are reduced by adding four hydrogen atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridines and derivatives

Sub Class

Hydropyridines

Direct Parent

Tetrahydropyridines

Alternative Parents

Substituents

Tetrahydropyridine
Cyclic alcohol
Methyl ester
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Vinylogous amide
Amino acid or derivatives
Carboxylic acid ester
Secondary alcohol
Azacycle
Allylamine
Carboxylic acid derivative
Secondary amine
Secondary aliphatic amine
Enamine
Monocarboxylic acid or derivatives
Organic oxide
Organonitrogen compound
Organooxygen compound
Amine
Organic nitrogen compound
Organic oxygen compound
Carbonyl group
Alcohol
Organopnictogen compound
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

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	-0.12	ALOGPS
logP	0.095	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	14.93	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	58.56 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	55.66 m³·mol⁻¹	ChemAxon
Polarizability	22.49 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

Not Available

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

73800010

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 6-hydroxy-7-methyl-1h,2h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyridine-4-carboxylate (NP0158731)

MOL for NP0158731 (methyl 6-hydroxy-7-methyl-1h,2h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyridine-4-carboxylate)

3D MOL for NP0158731 (methyl 6-hydroxy-7-methyl-1h,2h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyridine-4-carboxylate)

3D SDF for NP0158731 (methyl 6-hydroxy-7-methyl-1h,2h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyridine-4-carboxylate)

3D-SDF for NP0158731 (methyl 6-hydroxy-7-methyl-1h,2h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyridine-4-carboxylate)

PDB for NP0158731 (methyl 6-hydroxy-7-methyl-1h,2h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyridine-4-carboxylate)

3D PDB for NP0158731 (methyl 6-hydroxy-7-methyl-1h,2h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyridine-4-carboxylate)

SMILES for NP0158731 (methyl 6-hydroxy-7-methyl-1h,2h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyridine-4-carboxylate)

INCHI for NP0158731 (methyl 6-hydroxy-7-methyl-1h,2h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyridine-4-carboxylate)

Structure for NP0158731 (methyl 6-hydroxy-7-methyl-1h,2h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyridine-4-carboxylate)

3D Structure for NP0158731 (methyl 6-hydroxy-7-methyl-1h,2h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyridine-4-carboxylate)