NP-MRD: Showing NP-Card for Alpha-Naphthoxyacetic Acid (NP0331708)

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Record Information

Version

1.0

Created at

2023-06-29 20:00:14 UTC

Updated at

2024-04-19 09:49:05 UTC

NP-MRD ID

NP0331708

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Alpha-Naphthoxyacetic Acid

Description

NAPHTHYLOXYACETIC ACID, also known as 1-naphthoxyacetic acid or (1-naphthalenyloxy)acetate, belongs to the class of organic compounds known as phenoxyacetic acid derivatives. Phenoxyacetic acid derivatives are compounds containing an anisole where the methane group is linked to an acetic acid or a derivative. NAPHTHYLOXYACETIC ACID is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI

NOA
  Mrv0541 02241213592D          

 15 16  0  0  0  0            999 V2000
   -0.0733   -2.1497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0733   -1.3247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7878   -0.0872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5023    0.3253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5023    1.1503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7878    1.5628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0733    1.1503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.5628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    1.1503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.3253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -0.0872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0733    0.3253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -2.5622    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7878   -2.5622    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7878   -0.9122    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 13  2  0  0  0  0
  1 14  1  0  0  0  0
  2 15  1  0  0  0  0
  3  4  2  0  0  0  0
  3 12  1  0  0  0  0
  3 15  1  0  0  0  0
  4  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
  7 12  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0331708

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)COC1=CC=CC2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C12H10O3/c13-12(14)8-15-11-7-3-5-9-4-1-2-6-10(9)11/h1-7H,8H2,(H,13,14)

> <INCHI_KEY>
GHRYSOFWKRRLMI-UHFFFAOYSA-N

> <FORMULA>
C12H10O3

> <MOLECULAR_WEIGHT>
202.206

> <EXACT_MASS>
202.062994186

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
20.590784982451627

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(naphthalen-1-yloxy)acetic acid

> <ALOGPS_LOGP>
2.65

> <JCHEM_LOGP>
2.2830346153333334

> <ALOGPS_LOGS>
-2.93

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.048630187880515

> <JCHEM_PKA_STRONGEST_BASIC>
-4.912887795541569

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
55.05600000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.37e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
naphthyloxyacetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: NOA                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -0.137  -4.013   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.137  -2.473   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.471  -0.163   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.804   0.607   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.804   2.147   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.471   2.917   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.137   2.147   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.197   2.917   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.530   2.147   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.530   0.607   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.197  -0.163   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.137   0.607   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.197  -4.783   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -1.471  -4.783   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -1.471  -1.703   0.000  0.00  0.00           O+0
CONECT    1    2   13   14                                                  
CONECT    2    1   15                                                       
CONECT    3    4   12   15                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12    3    7   11                                                  
CONECT   13    1                                                            
CONECT   14    1                                                            
CONECT   15    2    3                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

View in JSmol

Synonyms

Value	Source
(1-Naphthalenyloxy)acetic acid	ChEBI
(1-Naphthyloxy)acetic acid	ChEBI
1-Naphthoxyacetic acid	ChEBI
(1-Naphthalenyloxy)acetate	Generator
(1-Naphthyloxy)acetate	Generator
1-Naphthoxyacetate	Generator
NAPHTHYLOXYACETate	Generator
alpha-Naphthoxyacetic acid	MeSH
1-NOA CPD	MeSH
NAPHTHYLOXYACETIC ACID	ChEBI
1-Naphthyloxyacetate	Generator

Chemical Formula

C₁₂H₁₀O₃

Average Mass

202.2060 Da

Monoisotopic Mass

202.06299 Da

IUPAC Name

2-(naphthalen-1-yloxy)acetic acid

Traditional Name

naphthyloxyacetic acid

CAS Registry Number

Not Available

SMILES

OC(=O)COC1=CC=CC2=CC=CC=C12

InChI Identifier

InChI=1S/C12H10O3/c13-12(14)8-15-11-7-3-5-9-4-1-2-6-10(9)11/h1-7H,8H2,(H,13,14)

InChI Key

GHRYSOFWKRRLMI-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	[¹H, ] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Not Available	Not Available	2023-06-29	View Spectrum
1D NMR	[¹H, ] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Not Available	Not Available	2023-06-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600.133705802 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600.133705802 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenoxyacetic acid derivatives. Phenoxyacetic acid derivatives are compounds containing an anisole where the methane group is linked to an acetic acid or a derivative.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenoxyacetic acid derivatives

Direct Parent

Phenoxyacetic acid derivatives

Alternative Parents

Substituents

Phenoxyacetate
Naphthalene
Alkyl aryl ether
Monocarboxylic acid or derivatives
Ether
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

naphthyloxyacetic acid (CHEBI:44588 )

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	2.65	ALOGPS
logP	2.28	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	4.05	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	55.06 m³·mol⁻¹	ChemAxon
Polarizability	20.59 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

DB08286

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

76313

PDB ID

Not Available

ChEBI ID

44588

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Alpha-Naphthoxyacetic Acid (NP0331708)

MOL for NP0331708 (Alpha-Naphthoxyacetic Acid)

3D MOL for NP0331708 (Alpha-Naphthoxyacetic Acid)

3D SDF for NP0331708 (Alpha-Naphthoxyacetic Acid)

3D-SDF for NP0331708 (Alpha-Naphthoxyacetic Acid)

PDB for NP0331708 (Alpha-Naphthoxyacetic Acid)

3D PDB for NP0331708 (Alpha-Naphthoxyacetic Acid)

SMILES for NP0331708 (Alpha-Naphthoxyacetic Acid)

INCHI for NP0331708 (Alpha-Naphthoxyacetic Acid)

Structure for NP0331708 (Alpha-Naphthoxyacetic Acid)

3D Structure for NP0331708 (Alpha-Naphthoxyacetic Acid)