NP-MRD: Showing NP-Card for methyl (4as)-1,6-dihydroxy-7-methyl-4ah,5h,6h,7h,7ah-cyclopenta[c]pyridine-4-carboxylate (NP0321874)

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Record Information

Version

2.0

Created at

2022-09-12 00:18:55 UTC

Updated at

2022-09-12 00:18:55 UTC

NP-MRD ID

NP0321874

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (4as)-1,6-dihydroxy-7-methyl-4ah,5h,6h,7h,7ah-cyclopenta[c]pyridine-4-carboxylate

Description

96861-97-1 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 (4as)-1,6-dihydroxy-7-methyl-4ah,5h,6h,7h,7ah-cyclopenta[c]pyridine-4-carboxylate is found in Strychnos mitis. Based on a literature review very few articles have been published on 96861-97-1.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 31 32  0  0  0  0  0  0  0  0999 V2000
    5.0169    0.2564   -0.0225 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7608   -0.3691    0.2122 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5661    0.1959   -0.1796 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5369    1.3011   -0.7680 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2909   -0.4897    0.0856 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3601   -1.6614    0.7123 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1624   -2.3915    0.9704 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9930   -1.9875    0.5892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0620   -2.8351    0.9670 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1329   -0.8157   -0.1614 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0166    0.1134   -0.0431 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3432    1.0478   -1.1521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7549    1.3898   -0.6974 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5278    1.8729   -1.7437 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2987    0.0968   -0.1298 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9839    0.2524    1.1764 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9061    1.3381   -0.2201 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4864   -0.2285   -0.9174 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6716    0.1247    0.8625 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3121   -2.0785    1.0337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4554   -2.7688    1.9139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1104   -1.1953   -1.2925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1486    0.7702    0.9086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4305    0.5144   -2.1181 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2680    1.9520   -1.2075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6951    2.1037    0.1503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7276    2.8237   -1.5375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0558   -0.2526   -0.8585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3265    0.5007    2.0255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5952   -0.6661    1.3548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7133    1.0856    1.0904 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  2  0
  8  9  1  0
  8 10  1  0
 10 15  1  0
 15 16  1  0
 15 13  1  0
 13 14  1  0
 13 12  1  0
 12 11  1  0
 11  5  1  0
 11 10  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  6 20  1  0
  9 21  1  0
 10 22  1  6
 15 28  1  6
 16 29  1  0
 16 30  1  0
 16 31  1  0
 13 26  1  1
 14 27  1  0
 12 24  1  0
 12 25  1  0
 11 23  1  1
M  END


  Mrv1652309122202182D          

 16 17  0  0  1  0            999 V2000
    2.5645    3.3000    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    2.0625    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    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
    3.2789   -1.2375    0.0000 O   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  2  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  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 16 15  1  6  0  0  0
  5 16  1  0  0  0  0
 10 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0321874

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=CN=C(O)C2C(C)C(O)C[C@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C11H15NO4/c1-5-8(13)3-6-7(11(15)16-2)4-12-10(14)9(5)6/h4-6,8-9,13H,3H2,1-2H3,(H,12,14)/t5?,6-,8?,9?/m1/s1

> <INCHI_KEY>
DLTNCDMAPRTYIV-WFWLUNQWSA-N

> <FORMULA>
C11H15NO4

> <MOLECULAR_WEIGHT>
225.244

> <EXACT_MASS>
225.100107967

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
22.711253409807654

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (4aS)-1,6-dihydroxy-7-methyl-4aH,5H,6H,7H,7aH-cyclopenta[c]pyridine-4-carboxylate

> <JCHEM_LOGP>
0.29992623499999965

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.943510169566409

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.229951471299354

> <JCHEM_PKA_STRONGEST_BASIC>
3.032831012557037

> <JCHEM_POLAR_SURFACE_AREA>
79.12

> <JCHEM_REFRACTIVITY>
56.305

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (4aS)-1,6-dihydroxy-7-methyl-4aH,5H,6H,7H,7aH-cyclopenta[c]pyridine-4-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0       4.787   6.160   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.787   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       7.454   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  O   UNK     0       6.121  -2.310   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.322  -0.476   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.846  -1.941   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.877   0.770   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       3.322   2.016   0.000  0.00  0.00           C+0
HETATM   16  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   16                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   16                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15    5   10                                                  
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₁H₁₅NO₄

Average Mass

225.2440 Da

Monoisotopic Mass

225.10011 Da

IUPAC Name

methyl (4aS)-1,6-dihydroxy-7-methyl-4aH,5H,6H,7H,7aH-cyclopenta[c]pyridine-4-carboxylate

Traditional Name

methyl (4aS)-1,6-dihydroxy-7-methyl-4aH,5H,6H,7H,7aH-cyclopenta[c]pyridine-4-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=CN=C(O)C2C(C)C(O)C[C@H]12

InChI Identifier

InChI=1S/C11H15NO4/c1-5-8(13)3-6-7(11(15)16-2)4-12-10(14)9(5)6/h4-6,8-9,13H,3H2,1-2H3,(H,12,14)/t5?,6-,8?,9?/m1/s1

InChI Key

DLTNCDMAPRTYIV-WFWLUNQWSA-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
Strychnos mitis	LOTUS Database	35616633

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
Vinylogous amide
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Cyclic alcohol
Secondary carboxylic acid amide
Secondary alcohol
Lactam
Carboxylic acid ester
Carboxamide group
Azacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Alcohol
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	0.3	ChemAxon
pKa (Strongest Acidic)	5.23	ChemAxon
pKa (Strongest Basic)	3.03	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	79.12 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	56.3 m³·mol⁻¹	ChemAxon
Polarizability	22.71 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

155729

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

178920

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (4as)-1,6-dihydroxy-7-methyl-4ah,5h,6h,7h,7ah-cyclopenta[c]pyridine-4-carboxylate (NP0321874)

MOL for NP0321874 (methyl (4as)-1,6-dihydroxy-7-methyl-4ah,5h,6h,7h,7ah-cyclopenta[c]pyridine-4-carboxylate)

3D MOL for NP0321874 (methyl (4as)-1,6-dihydroxy-7-methyl-4ah,5h,6h,7h,7ah-cyclopenta[c]pyridine-4-carboxylate)

3D SDF for NP0321874 (methyl (4as)-1,6-dihydroxy-7-methyl-4ah,5h,6h,7h,7ah-cyclopenta[c]pyridine-4-carboxylate)

3D-SDF for NP0321874 (methyl (4as)-1,6-dihydroxy-7-methyl-4ah,5h,6h,7h,7ah-cyclopenta[c]pyridine-4-carboxylate)

PDB for NP0321874 (methyl (4as)-1,6-dihydroxy-7-methyl-4ah,5h,6h,7h,7ah-cyclopenta[c]pyridine-4-carboxylate)

3D PDB for NP0321874 (methyl (4as)-1,6-dihydroxy-7-methyl-4ah,5h,6h,7h,7ah-cyclopenta[c]pyridine-4-carboxylate)

SMILES for NP0321874 (methyl (4as)-1,6-dihydroxy-7-methyl-4ah,5h,6h,7h,7ah-cyclopenta[c]pyridine-4-carboxylate)

INCHI for NP0321874 (methyl (4as)-1,6-dihydroxy-7-methyl-4ah,5h,6h,7h,7ah-cyclopenta[c]pyridine-4-carboxylate)

Structure for NP0321874 (methyl (4as)-1,6-dihydroxy-7-methyl-4ah,5h,6h,7h,7ah-cyclopenta[c]pyridine-4-carboxylate)

3D Structure for NP0321874 (methyl (4as)-1,6-dihydroxy-7-methyl-4ah,5h,6h,7h,7ah-cyclopenta[c]pyridine-4-carboxylate)