NP-MRD: Showing NP-Card for 2-[(5s)-5-hydroxy-4-methyl-5h,6h,7h-cyclopenta[c]pyridin-1-yl]benzene-1,4-diol (NP0327880)

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Record Information

Version

1.0

Created at

2022-09-12 10:51:19 UTC

Updated at

2022-09-12 10:51:19 UTC

NP-MRD ID

NP0327880

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-[(5s)-5-hydroxy-4-methyl-5h,6h,7h-cyclopenta[c]pyridin-1-yl]benzene-1,4-diol

Description

(-)-Ganoapplanatumine A belongs to the class of organic compounds known as phenylpyridines. These are polycyclic aromatic compounds containing a benzene ring linked to a pyridine ring through a CC or CN bond. 2-[(5s)-5-hydroxy-4-methyl-5h,6h,7h-cyclopenta[c]pyridin-1-yl]benzene-1,4-diol is found in Ganoderma applanatum. It was first documented in 2022 (PMID: 36130261). Based on a literature review a significant number of articles have been published on (-)-ganoapplanatumine A (PMID: 36091400) (PMID: 36088383) (PMID: 36109246) (PMID: 36123682).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 34 36  0  0  0  0  0  0  0  0999 V2000
   -3.4748   -1.8611    1.4305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1122   -1.3697    1.1578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9781   -1.7417    1.8375 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2395   -1.2757    1.5348 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4413   -0.3884    0.5148 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7760    0.1060    0.2243 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4520   -0.2136   -0.9271 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7592    0.2085   -1.1764 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4142   -0.1433   -2.3654 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3899    0.9729   -0.2298 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7285    1.3061    0.9372 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4463    0.8805    1.1605 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7996    1.2351    2.3576 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6997   -0.0024   -0.1817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9548   -0.4619    0.1098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9344    0.1748   -0.8012 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4783    1.3233   -0.1558 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1037    0.6744   -1.9436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7685    0.9698   -1.3156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3577   -2.9309    1.7683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0612   -1.8622    0.4996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9899   -1.3562    2.2658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1293   -2.4601    2.6660 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9818   -0.8145   -1.7066 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9511   -1.0156   -2.3634 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4106    1.3337   -0.3424 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1871    1.9117    1.7300 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8393    0.9423    2.5609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7596   -0.5096   -1.0999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7420    2.0107   -0.0892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9869   -0.1277   -2.7130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5361    1.6127   -2.3915 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0662    0.8615   -2.0303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8153    2.0108   -0.9224 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 15  2  1  0
 12  6  1  0
 19 14  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
 16 29  1  6
 17 30  1  0
 18 31  1  0
 18 32  1  0
 19 33  1  0
 19 34  1  0
  7 24  1  0
  9 25  1  0
 10 26  1  0
 11 27  1  0
 13 28  1  0
M  END


  Mrv1652309122212512D          

 19 21  0  0  1  0            999 V2000
    3.2789    2.0625    0.0000 C   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 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8500   -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
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5249    1.8646    0.0000 O   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
    1.7798   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  6 12  1  0  0  0  0
 12 13  1  0  0  0  0
  5 14  1  0  0  0  0
 14 15  2  0  0  0  0
  2 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 14 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0327880

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CN=C(C2=C1[C@@H](O)CC2)C1=CC(O)=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C15H15NO3/c1-8-7-16-15(10-3-5-13(19)14(8)10)11-6-9(17)2-4-12(11)18/h2,4,6-7,13,17-19H,3,5H2,1H3/t13-/m0/s1

> <INCHI_KEY>
YQOMGYYSWFJSPK-ZDUSSCGKSA-N

> <FORMULA>
C15H15NO3

> <MOLECULAR_WEIGHT>
257.289

> <EXACT_MASS>
257.105193347

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
27.30887058696415

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(5S)-5-hydroxy-4-methyl-5H,6H,7H-cyclopenta[c]pyridin-1-yl]benzene-1,4-diol

> <JCHEM_LOGP>
2.471814296666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.91223337516581

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.508214654698428

> <JCHEM_PKA_STRONGEST_BASIC>
4.3681789800802235

> <JCHEM_POLAR_SURFACE_AREA>
73.58000000000001

> <JCHEM_REFRACTIVITY>
72.06500000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
2-[(5S)-5-hydroxy-4-methyl-5H,6H,7H-cyclopenta[c]pyridin-1-yl]benzene-1,4-diol

> <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       6.121   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       7.454   0.000   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.121  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.454  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.454  -4.620   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       8.788  -5.390   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       6.121  -5.390   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.787  -4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.787  -3.080   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       3.453  -2.310   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.787   0.000   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
HETATM   16  C   UNK     0       3.322   2.016   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.846   3.481   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.322  -0.476   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   15                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   14                                                  
CONECT    6    5    7   12                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    6   13                                                  
CONECT   13   12                                                            
CONECT   14    5   15   19                                                  
CONECT   15   14    2   16                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   14                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₅NO₃

Average Mass

257.2890 Da

Monoisotopic Mass

257.10519 Da

IUPAC Name

2-[(5S)-5-hydroxy-4-methyl-5H,6H,7H-cyclopenta[c]pyridin-1-yl]benzene-1,4-diol

Traditional Name

2-[(5S)-5-hydroxy-4-methyl-5H,6H,7H-cyclopenta[c]pyridin-1-yl]benzene-1,4-diol

CAS Registry Number

Not Available

SMILES

CC1=CN=C(C2=C1[C@@H](O)CC2)C1=CC(O)=CC=C1O

InChI Identifier

InChI=1S/C15H15NO3/c1-8-7-16-15(10-3-5-13(19)14(8)10)11-6-9(17)2-4-12(11)18/h2,4,6-7,13,17-19H,3,5H2,1H3/t13-/m0/s1

InChI Key

YQOMGYYSWFJSPK-ZDUSSCGKSA-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
Ganoderma applanatum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpyridines. These are polycyclic aromatic compounds containing a benzene ring linked to a pyridine ring through a CC or CN bond.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridines and derivatives

Sub Class

Phenylpyridines

Direct Parent

Phenylpyridines

Alternative Parents

Substituents

2-phenylpyridine
Hydroquinone
1-hydroxy-2-unsubstituted benzenoid
Methylpyridine
Phenol
Benzenoid
Monocyclic benzene moiety
Heteroaromatic compound
Secondary alcohol
Azacycle
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	2.47	ChemAxon
pKa (Strongest Acidic)	8.51	ChemAxon
pKa (Strongest Basic)	4.37	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	73.58 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	72.06 m³·mol⁻¹	ChemAxon
Polarizability	27.31 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	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

78440683

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139583117

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Yuksel S, Bonus M, Schwabe T, Pfleger C, Zimmer T, Enke U, Sass I, Gohlke H, Benndorf K, Kusch J: Uncoupling of Voltage- and Ligand-Induced Activation in HCN2 Channels by Glycine Inserts. Front Physiol. 2022 Aug 25;13:895324. doi: 10.3389/fphys.2022.895324. eCollection 2022. [PubMed:36091400 ]
Peter A, Balogh A, Csanadi Z, Danko K, Griger Z: Subclinical systolic and diastolic myocardial dysfunction in polyphasic polymyositis/dermatomyositis: a 2-year longitudinal study. Arthritis Res Ther. 2022 Sep 10;24(1):219. doi: 10.1186/s13075-022-02906-7. [PubMed:36088383 ]
Dagdigian PJ: Theoretical investigation of rotationally inelastic collisions of OH(X(2)Pi) with hydrogen atoms. J Chem Phys. 2022 Sep 14;157(10):104305. doi: 10.1063/5.0110724. [PubMed:36109246 ]
Vranic M, Perochon A, Benbow H, Doohan FM: Comprehensive analysis of pathogen-responsive wheat NAC transcription factors: new candidates for crop improvement. G3 (Bethesda). 2022 Sep 21. pii: 6709347. doi: 10.1093/g3journal/jkac247. [PubMed:36130261 ]
Regidor PA, Richter WH, Koytchev R, Kirkov V, Colli E: Evaluation of the food effect on a drospirenone only contraceptive containing 4 mg administered with and without high-fat breakfast in a randomised trial. BMC Womens Health. 2022 Sep 19;22(1):381. doi: 10.1186/s12905-022-01960-2. [PubMed:36123682 ]
LOTUS database [Link]

Showing NP-Card for 2-[(5s)-5-hydroxy-4-methyl-5h,6h,7h-cyclopenta[c]pyridin-1-yl]benzene-1,4-diol (NP0327880)

MOL for NP0327880 (2-[(5s)-5-hydroxy-4-methyl-5h,6h,7h-cyclopenta[c]pyridin-1-yl]benzene-1,4-diol)

3D MOL for NP0327880 (2-[(5s)-5-hydroxy-4-methyl-5h,6h,7h-cyclopenta[c]pyridin-1-yl]benzene-1,4-diol)

3D SDF for NP0327880 (2-[(5s)-5-hydroxy-4-methyl-5h,6h,7h-cyclopenta[c]pyridin-1-yl]benzene-1,4-diol)

3D-SDF for NP0327880 (2-[(5s)-5-hydroxy-4-methyl-5h,6h,7h-cyclopenta[c]pyridin-1-yl]benzene-1,4-diol)

PDB for NP0327880 (2-[(5s)-5-hydroxy-4-methyl-5h,6h,7h-cyclopenta[c]pyridin-1-yl]benzene-1,4-diol)

3D PDB for NP0327880 (2-[(5s)-5-hydroxy-4-methyl-5h,6h,7h-cyclopenta[c]pyridin-1-yl]benzene-1,4-diol)

SMILES for NP0327880 (2-[(5s)-5-hydroxy-4-methyl-5h,6h,7h-cyclopenta[c]pyridin-1-yl]benzene-1,4-diol)

INCHI for NP0327880 (2-[(5s)-5-hydroxy-4-methyl-5h,6h,7h-cyclopenta[c]pyridin-1-yl]benzene-1,4-diol)

Structure for NP0327880 (2-[(5s)-5-hydroxy-4-methyl-5h,6h,7h-cyclopenta[c]pyridin-1-yl]benzene-1,4-diol)

3D Structure for NP0327880 (2-[(5s)-5-hydroxy-4-methyl-5h,6h,7h-cyclopenta[c]pyridin-1-yl]benzene-1,4-diol)