NP-MRD: Showing NP-Card for 4-Hydroxy-4-(3-pyridyl)-butanoic acid (NP0086709)

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Record Information

Version

2.0

Created at

2022-05-11 16:28:49 UTC

Updated at

2022-05-11 16:28:49 UTC

NP-MRD ID

NP0086709

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-Hydroxy-4-(3-pyridyl)-butanoic acid

Description

4-Hydroxy-4-(3-pyridyl)-butanoic acid, also known as 4-(3-pyridyl)-4-hydroxybutyrate or gamma-(3-pyridyl)-gamma-hydroxybutyric acid, belongs to the class of organic compounds known as pyridines and derivatives. Pyridines and derivatives are compounds containing a pyridine ring, which is a six-member aromatic heterocycle which consists of one nitrogen atom and five carbon atoms. 4-Hydroxy-4-(3-pyridyl)-butanoic acid is a strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02231218562D          

 13 13  0  0  0  0            999 V2000
    2.4488   -6.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1632   -6.4655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7343   -6.4655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7343   -7.2905    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4488   -7.7030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1632   -7.2905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4488   -5.2280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1632   -4.8155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1632   -3.9905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8777   -3.5780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7343   -4.8155    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8777   -2.7531    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5922   -3.9905    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  3  2  0  0  0  0
  5  4  1  0  0  0  0
  6  5  2  0  0  0  0
  6  2  1  0  0  0  0
  7  1  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11  7  1  0  0  0  0
 12 10  1  0  0  0  0
 13 10  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0086709

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(CCC(O)=O)C1=CC=CN=C1

> <INCHI_IDENTIFIER>
InChI=1S/C9H11NO3/c11-8(3-4-9(12)13)7-2-1-5-10-6-7/h1-2,5-6,8,11H,3-4H2,(H,12,13)

> <INCHI_KEY>
STZOZPPVGWNSMC-UHFFFAOYSA-N

> <FORMULA>
C9H11NO3

> <MOLECULAR_WEIGHT>
181.1885

> <EXACT_MASS>
181.073893223

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
18.128114422753406

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-hydroxy-4-(pyridin-3-yl)butanoic acid

> <ALOGPS_LOGP>
0.16

> <JCHEM_LOGP>
-0.8030824915921306

> <ALOGPS_LOGS>
-1.13

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.239066875021791

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.8372639742358543

> <JCHEM_PKA_STRONGEST_BASIC>
4.768085114205285

> <JCHEM_POLAR_SURFACE_AREA>
70.42000000000002

> <JCHEM_REFRACTIVITY>
45.9262

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.36e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-hydroxy-4-(pyridin-3-yl)butanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0       4.571 -11.299   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.905 -12.069   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.237 -12.069   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       3.237 -13.609   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       4.571 -14.379   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.905 -13.609   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.571  -9.759   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.905  -8.989   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.905  -7.449   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.238  -6.679   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.237  -8.989   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       7.238  -5.139   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       8.572  -7.449   0.000  0.00  0.00           O+0
CONECT    1    2    3    7                                                  
CONECT    2    1    6                                                       
CONECT    3    1    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    2                                                       
CONECT    7    1    8   11                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   12   13                                                  
CONECT   11    7                                                            
CONECT   12   10                                                            
CONECT   13   10                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

View in JSmol

Synonyms

Value	Source
4-Hydroxy-4-(3-pyridyl)-butanoate	Generator
4-(3-Pyridyl)-4-hydroxybutyrate	HMDB
4-(3-Pyridyl)-4-hydroxybutyric acid	HMDB
gamma-(3-Pyridyl)-gamma-hydroxybutyrate	HMDB
gamma-(3-Pyridyl)-gamma-hydroxybutyric acid	HMDB
4-HOPC4a	HMDB
4-Hydroxy-4-(3-pyridyl)butanoic acid	HMDB
4-Hydroxy-4-(3-pyridyl)butyric acid	HMDB
g-Hydroxy-3-pyridinebutanoate	HMDB
g-Hydroxy-3-pyridinebutanoic acid	HMDB
gamma-Hydroxy-3-pyridinebutanoic acid	HMDB
Γ-hydroxy-3-pyridinebutanoate	HMDB
Γ-hydroxy-3-pyridinebutanoic acid	HMDB

Chemical Formula

C₉H₁₁NO₃

Average Mass

181.1885 Da

Monoisotopic Mass

181.07389 Da

IUPAC Name

4-hydroxy-4-(pyridin-3-yl)butanoic acid

Traditional Name

4-hydroxy-4-(pyridin-3-yl)butanoic acid

CAS Registry Number

Not Available

SMILES

OC(CCC(O)=O)C1=CC=CN=C1

InChI Identifier

InChI=1S/C9H11NO3/c11-8(3-4-9(12)13)7-2-1-5-10-6-7/h1-2,5-6,8,11H,3-4H2,(H,12,13)

InChI Key

STZOZPPVGWNSMC-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyridines and derivatives. Pyridines and derivatives are compounds containing a pyridine ring, which is a six-member aromatic heterocycle which consists of one nitrogen atom and five carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridines and derivatives

Sub Class

Not Available

Direct Parent

Pyridines and derivatives

Alternative Parents

Substituents

Pyridine
Heteroaromatic compound
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Azacycle
Aromatic alcohol
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
Alcohol
Organopnictogen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

pyridines (CHEBI:82573 )

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	0.16	ALOGPS
logP	-0.8	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	3.84	ChemAxon
pKa (Strongest Basic)	4.77	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	70.42 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	45.93 m³·mol⁻¹	ChemAxon
Polarizability	18.13 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon