NP-MRD: Showing NP-Card for (6s,7r)-6-hydroxy-7-methyl-1h,2h,3h,4h,5h,6h,7h-cyclopenta[c]pyridine-4-carboxylic acid (NP0327875)

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Record Information

Version

2.0

Created at

2022-09-12 10:50:49 UTC

Updated at

2022-09-12 10:50:50 UTC

NP-MRD ID

NP0327875

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(6s,7r)-6-hydroxy-7-methyl-1h,2h,3h,4h,5h,6h,7h-cyclopenta[c]pyridine-4-carboxylic acid

Description

Tetrahydrocantleyine belongs to the class of organic compounds known as secondary alcohols. Secondary alcohols are compounds containing a secondary alcohol functional group, with the general structure HOC(R)(R') (R,R'=alkyl, aryl). (6s,7r)-6-hydroxy-7-methyl-1h,2h,3h,4h,5h,6h,7h-cyclopenta[c]pyridine-4-carboxylic acid is found in Alstonia angustifolia, Alstonia rostrata, Strychnos mitis and Strychnos pungens. Based on a literature review very few articles have been published on Tetrahydrocantleyine.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 29 30  0  0  0  0  0  0  0  0999 V2000
    2.5913   -0.4413    1.3407 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4596    0.3611    0.7732 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3688   -0.5020    0.2299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3297    0.2710   -0.5889 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5395    1.3356   -1.1639 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8658    1.1377   -0.4668 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7148    0.3173   -1.1999 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7779    0.0358   -0.8408 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5035    1.1804   -0.2543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2144    1.8993   -0.9880 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4227    1.4873    1.0919 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2774   -1.2671   -0.3161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4624   -1.9430    0.6013 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0612   -1.9038    0.3920 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5792   -0.1062    0.9854 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5698   -0.3007    2.4555 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4035   -1.5098    1.1665 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0443    1.1007    1.4892 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7089    1.1420   -2.2422 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1213    2.3501   -0.9831 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3725    2.0840   -0.2192 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9429    0.7146   -2.0741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9007    0.0758   -1.9415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3848    2.4627    1.3780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5234   -1.9441   -1.1636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2741   -1.0601    0.1754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7896   -2.0516    1.5604 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2049   -2.5494   -0.4778 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4349   -2.3762    1.2805 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  6  1  0
  6  7  1  0
  6  5  1  0
  5  4  1  0
  4  3  2  0
  3 14  1  0
 14 13  1  0
 13 12  1  0
 12  8  1  0
  8  9  1  0
  9 11  1  0
  9 10  2  0
  3  2  1  0
  8  4  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  2 18  1  1
  6 21  1  1
  7 22  1  0
  5 19  1  0
  5 20  1  0
 14 28  1  0
 14 29  1  0
 13 27  1  0
 12 25  1  0
 12 26  1  0
  8 23  1  6
 11 24  1  0
M  END


  Mrv1652309122212502D          

 14 15  0  0  1  0            999 V2000
   -0.3984   -2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -1.3654    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6411   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284   -0.6979    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4534   -0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.3646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.3646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -1.1104    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  1  1  0  0  0
  4  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  8 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  3 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0327875

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1[C@@H](O)CC2=C1CNCC2C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H15NO3/c1-5-7-3-11-4-8(10(13)14)6(7)2-9(5)12/h5,8-9,11-12H,2-4H2,1H3,(H,13,14)/t5-,8?,9+/m1/s1

> <INCHI_KEY>
PZFHWNSLGSDVOX-DVIJTVPPSA-N

> <FORMULA>
C10H15NO3

> <MOLECULAR_WEIGHT>
197.234

> <EXACT_MASS>
197.105193347

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
20.524004173616802

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(6S,7R)-6-hydroxy-7-methyl-1H,2H,3H,4H,5H,6H,7H-cyclopenta[c]pyridine-4-carboxylic acid

> <JCHEM_LOGP>
-3.1961402864821413

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.824209195045295

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.551270351402922

> <JCHEM_PKA_STRONGEST_BASIC>
9.680512158300353

> <JCHEM_POLAR_SURFACE_AREA>
69.56

> <JCHEM_REFRACTIVITY>
51.387800000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(6S,7R)-6-hydroxy-7-methyl-1H,2H,3H,4H,5H,6H,7H-cyclopenta[c]pyridine-4-carboxylic acid

> <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      -0.744  -4.013   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.268  -2.549   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.197  -2.073   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.197  -0.533   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.268  -0.057   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.173  -1.303   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.713  -1.303   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.530   0.237   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.530   1.777   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.197   2.547   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       3.864   2.547   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.864  -0.533   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       3.864  -2.073   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       2.530  -2.843   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4   14                                                  
CONECT    4    3    5    8                                                  
CONECT    5    4    6                                                       
CONECT    6    5    2    7                                                  
CONECT    7    6                                                            
CONECT    8    4    9   12                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    8   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    3                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₀H₁₅NO₃

Average Mass

197.2340 Da

Monoisotopic Mass

197.10519 Da

IUPAC Name

(6S,7R)-6-hydroxy-7-methyl-1H,2H,3H,4H,5H,6H,7H-cyclopenta[c]pyridine-4-carboxylic acid

Traditional Name

(6S,7R)-6-hydroxy-7-methyl-1H,2H,3H,4H,5H,6H,7H-cyclopenta[c]pyridine-4-carboxylic acid

CAS Registry Number

Not Available

SMILES

C[C@H]1[C@@H](O)CC2=C1CNCC2C(O)=O

InChI Identifier

InChI=1S/C10H15NO3/c1-5-7-3-11-4-8(10(13)14)6(7)2-9(5)12/h5,8-9,11-12H,2-4H2,1H3,(H,13,14)/t5-,8?,9+/m1/s1

InChI Key

PZFHWNSLGSDVOX-DVIJTVPPSA-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
Alstonia angustifolia	LOTUS Database	35616633
Alstonia rostrata	LOTUS Database	35616633
Strychnos mitis	LOTUS Database	35616633
Strychnos pungens	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as secondary alcohols. Secondary alcohols are compounds containing a secondary alcohol functional group, with the general structure HOC(R)(R') (R,R'=alkyl, aryl).

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Secondary alcohols

Alternative Parents

Substituents

Amino acid or derivatives
Secondary alcohol
Amino acid
Carboxylic acid derivative
Carboxylic acid
Secondary aliphatic amine
Monocarboxylic acid or derivatives
Secondary amine
Organoheterocyclic compound
Azacycle
Carbonyl group
Organonitrogen compound
Organic oxide
Amine
Organic nitrogen 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	-3.2	ChemAxon
pKa (Strongest Acidic)	3.55	ChemAxon
pKa (Strongest Basic)	9.68	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	69.56 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	51.39 m³·mol⁻¹	ChemAxon
Polarizability	20.52 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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

101415891

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (6s,7r)-6-hydroxy-7-methyl-1h,2h,3h,4h,5h,6h,7h-cyclopenta[c]pyridine-4-carboxylic acid (NP0327875)

MOL for NP0327875 ((6s,7r)-6-hydroxy-7-methyl-1h,2h,3h,4h,5h,6h,7h-cyclopenta[c]pyridine-4-carboxylic acid)

3D MOL for NP0327875 ((6s,7r)-6-hydroxy-7-methyl-1h,2h,3h,4h,5h,6h,7h-cyclopenta[c]pyridine-4-carboxylic acid)

3D SDF for NP0327875 ((6s,7r)-6-hydroxy-7-methyl-1h,2h,3h,4h,5h,6h,7h-cyclopenta[c]pyridine-4-carboxylic acid)

3D-SDF for NP0327875 ((6s,7r)-6-hydroxy-7-methyl-1h,2h,3h,4h,5h,6h,7h-cyclopenta[c]pyridine-4-carboxylic acid)

PDB for NP0327875 ((6s,7r)-6-hydroxy-7-methyl-1h,2h,3h,4h,5h,6h,7h-cyclopenta[c]pyridine-4-carboxylic acid)

3D PDB for NP0327875 ((6s,7r)-6-hydroxy-7-methyl-1h,2h,3h,4h,5h,6h,7h-cyclopenta[c]pyridine-4-carboxylic acid)

SMILES for NP0327875 ((6s,7r)-6-hydroxy-7-methyl-1h,2h,3h,4h,5h,6h,7h-cyclopenta[c]pyridine-4-carboxylic acid)

INCHI for NP0327875 ((6s,7r)-6-hydroxy-7-methyl-1h,2h,3h,4h,5h,6h,7h-cyclopenta[c]pyridine-4-carboxylic acid)

Structure for NP0327875 ((6s,7r)-6-hydroxy-7-methyl-1h,2h,3h,4h,5h,6h,7h-cyclopenta[c]pyridine-4-carboxylic acid)

3D Structure for NP0327875 ((6s,7r)-6-hydroxy-7-methyl-1h,2h,3h,4h,5h,6h,7h-cyclopenta[c]pyridine-4-carboxylic acid)