NP-MRD: Showing NP-Card for 1-Hydroxy-4-methoxy-2-naphthoic acid (NP0023628)

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Record Information

Version

2.0

Created at

2021-01-06 08:41:46 UTC

Updated at

2021-07-15 17:42:15 UTC

NP-MRD ID

NP0023628

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-Hydroxy-4-methoxy-2-naphthoic acid

Provided By

NPAtlas

Description

1-Hydroxy-4-methoxy-2-naphthoic acid is found in Streptosporangium and Streptosporangium cinnabarium ATCC 31213. 1-Hydroxy-4-methoxy-2-naphthoic acid was first documented in 1997 (PMID: 9510917). Based on a literature review very few articles have been published on 1-hydroxy-4-methoxynaphthalene-2-carboxylic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242120433D          

 26 27  0  0  0  0            999 V2000
   -2.4273   -2.5679    0.5634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1378   -1.2355    0.2752 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8854   -0.6923    0.1533 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2701   -1.4254    0.3067 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5101   -0.8280    0.1732 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7210   -1.6117    0.3373 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8327   -1.0567    0.2135 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6011   -2.9617    0.6286 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6352    0.5217   -0.1180 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9029    1.0532   -0.2374 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4910    1.2615   -0.2729 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5441    2.6087   -0.5633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6486    3.3004   -0.7076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8845    2.7174   -0.5772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9336    1.3736   -0.2876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7628    0.6506   -0.1364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4927   -2.6037    0.9337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8107   -2.9719    1.4003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3451   -3.2469   -0.3091 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1733   -2.4834    0.5350 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3728   -3.4563    1.0265 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0808    2.0072   -0.4436 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4992    3.0981   -0.6724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5990    4.3670   -0.9375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8113    3.3023   -0.6996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8954    0.8797   -0.1774 H   0  0  0  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
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  5  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16  3  1  0  0  0  0
 16 11  1  0  0  0  0
  1 17  1  0  0  0  0
  1 18  1  0  0  0  0
  1 19  1  0  0  0  0
  4 20  1  0  0  0  0
  8 21  1  0  0  0  0
 10 22  1  0  0  0  0
 12 23  1  0  0  0  0
 13 24  1  0  0  0  0
 14 25  1  0  0  0  0
 15 26  1  0  0  0  0
M  END


  Mrv1652306242120433D          

 26 27  0  0  0  0            999 V2000
   -2.4273   -2.5679    0.5634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1378   -1.2355    0.2752 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8854   -0.6923    0.1533 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2701   -1.4254    0.3067 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5101   -0.8280    0.1732 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7210   -1.6117    0.3373 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8327   -1.0567    0.2135 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6011   -2.9617    0.6286 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6352    0.5217   -0.1180 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9029    1.0532   -0.2374 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4910    1.2615   -0.2729 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5441    2.6087   -0.5633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6486    3.3004   -0.7076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8845    2.7174   -0.5772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9336    1.3736   -0.2876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7628    0.6506   -0.1364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4927   -2.6037    0.9337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8107   -2.9719    1.4003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3451   -3.2469   -0.3091 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1733   -2.4834    0.5350 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3728   -3.4563    1.0265 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0808    2.0072   -0.4436 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4992    3.0981   -0.6724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5990    4.3670   -0.9375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8113    3.3023   -0.6996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8954    0.8797   -0.1774 H   0  0  0  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
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  5  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16  3  1  0  0  0  0
 16 11  1  0  0  0  0
  1 17  1  0  0  0  0
  1 18  1  0  0  0  0
  1 19  1  0  0  0  0
  4 20  1  0  0  0  0
  8 21  1  0  0  0  0
 10 22  1  0  0  0  0
 12 23  1  0  0  0  0
 13 24  1  0  0  0  0
 14 25  1  0  0  0  0
 15 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0023628

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C1=C(O[H])C2=C([H])C([H])=C([H])C([H])=C2C(OC([H])([H])[H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C12H10O4/c1-16-10-6-9(12(14)15)11(13)8-5-3-2-4-7(8)10/h2-6,13H,1H3,(H,14,15)

> <INCHI_KEY>
CAXOIULERYZINL-UHFFFAOYSA-N

> <FORMULA>
C12H10O4

> <MOLECULAR_WEIGHT>
218.208

> <EXACT_MASS>
218.057908802

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
21.934126720233735

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-hydroxy-4-methoxynaphthalene-2-carboxylic acid

> <ALOGPS_LOGP>
2.90

> <JCHEM_LOGP>
2.809068893333333

> <ALOGPS_LOGS>
-2.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.38476906846208

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.4345738304511912

> <JCHEM_PKA_STRONGEST_BASIC>
-4.842916462378912

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
58.20850000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.51e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-hydroxy-4-methoxynaphthalene-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0      -2.427  -2.568   0.563  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.138  -1.236   0.275  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.885  -0.692   0.153  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.270  -1.425   0.307  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.510  -0.828   0.173  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.721  -1.612   0.337  0.00  0.00           C+0
HETATM    7  O   UNK     0       3.833  -1.057   0.214  0.00  0.00           O+0
HETATM    8  O   UNK     0       2.601  -2.962   0.629  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.635   0.522  -0.118  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.903   1.053  -0.237  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.491   1.262  -0.273  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.544   2.609  -0.563  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.649   3.300  -0.708  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.885   2.717  -0.577  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.934   1.374  -0.288  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.763   0.651  -0.136  0.00  0.00           C+0
HETATM   17  H   UNK     0      -3.493  -2.604   0.934  0.00  0.00           H+0
HETATM   18  H   UNK     0      -1.811  -2.972   1.400  0.00  0.00           H+0
HETATM   19  H   UNK     0      -2.345  -3.247  -0.309  0.00  0.00           H+0
HETATM   20  H   UNK     0       0.173  -2.483   0.535  0.00  0.00           H+0
HETATM   21  H   UNK     0       3.373  -3.456   1.026  0.00  0.00           H+0
HETATM   22  H   UNK     0       3.081   2.007  -0.444  0.00  0.00           H+0
HETATM   23  H   UNK     0       1.499   3.098  -0.672  0.00  0.00           H+0
HETATM   24  H   UNK     0      -0.599   4.367  -0.938  0.00  0.00           H+0
HETATM   25  H   UNK     0      -2.811   3.302  -0.700  0.00  0.00           H+0
HETATM   26  H   UNK     0      -2.895   0.880  -0.177  0.00  0.00           H+0
CONECT    1    2   17   18   19                                             
CONECT    2    1    3                                                       
CONECT    3    2    4   16                                                  
CONECT    4    3    5   20                                                  
CONECT    5    4    6    9                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6   21                                                       
CONECT    9    5   10   11                                                  
CONECT   10    9   22                                                       
CONECT   11    9   12   16                                                  
CONECT   12   11   13   23                                                  
CONECT   13   12   14   24                                                  
CONECT   14   13   15   25                                                  
CONECT   15   14   16   26                                                  
CONECT   16   15    3   11                                                  
CONECT   17    1                                                            
CONECT   18    1                                                            
CONECT   19    1                                                            
CONECT   20    4                                                            
CONECT   21    8                                                            
CONECT   22   10                                                            
CONECT   23   12                                                            
CONECT   24   13                                                            
CONECT   25   14                                                            
CONECT   26   15                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   54    0
END

View in JSmol View NMR Assignments

Synonyms

Value	Source
1-Hydroxy-4-methoxynaphthalene-2-carboxylate	Generator
1-Hydroxy-4-methoxy-2-naphthoate	Generator
HM-Naphthoic acid	MeSH

Chemical Formula

C₁₂H₁₀O₄

Average Mass

218.2080 Da

Monoisotopic Mass

218.05791 Da

IUPAC Name

1-hydroxy-4-methoxynaphthalene-2-carboxylic acid

Traditional Name

1-hydroxy-4-methoxynaphthalene-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

COC1=CC(C(O)=O)=C(O)C2=CC=CC=C12

InChI Identifier

InChI=1S/C12H10O4/c1-16-10-6-9(12(14)15)11(13)8-5-3-2-4-7(8)10/h2-6,13H,1H3,(H,14,15)

InChI Key

CAXOIULERYZINL-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
Streptosporangium	NPAtlas	9510917
Streptosporangium cinnabarium ATCC 31213	-	KNApSAcK

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as naphthalenecarboxylic acids. These are compounds containing a naphthalene moiety, which bears a carboxylic acid group one or more positions. Naphthalene is a bicyclic compound that is made up of two fused benzene ring.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Naphthalenes

Sub Class

Naphthalenecarboxylic acids and derivatives

Direct Parent

Naphthalenecarboxylic acids

Alternative Parents

Substituents

2-naphthalenecarboxylic acid
M-methoxybenzoic acid or derivatives
1-naphthol
Hydroxybenzoic acid
Salicylic acid or derivatives
Phenol ether
Anisole
Phenol
Alkyl aryl ether
Vinylogous acid
Ether
Carboxylic acid
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	2.9	ALOGPS
logP	2.81	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	2.43	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	58.21 m³·mol⁻¹	ChemAxon
Polarizability	21.93 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

NPAtlas ID

NPA001965

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00016417

Chemspider ID

21376101

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15430821

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Pfefferle C, Breinholt J, Gurtler H, Fiedler HP: 1-Hydroxy-4-methoxy-2-naphthoic acid, a herbicidal compound produced by Streptosporangium cinnabarinum ATCC 31,213. J Antibiot (Tokyo). 1997 Dec;50(12):1067-8. doi: 10.7164/antibiotics.50.1067. [PubMed:9510917 ]

Showing NP-Card for 1-Hydroxy-4-methoxy-2-naphthoic acid (NP0023628)

MOL for NP0023628 (1-Hydroxy-4-methoxy-2-naphthoic acid)

3D MOL for NP0023628 (1-Hydroxy-4-methoxy-2-naphthoic acid)

3D SDF for NP0023628 (1-Hydroxy-4-methoxy-2-naphthoic acid)

3D-SDF for NP0023628 (1-Hydroxy-4-methoxy-2-naphthoic acid)

PDB for NP0023628 (1-Hydroxy-4-methoxy-2-naphthoic acid)

3D PDB for NP0023628 (1-Hydroxy-4-methoxy-2-naphthoic acid)

SMILES for NP0023628 (1-Hydroxy-4-methoxy-2-naphthoic acid)

INCHI for NP0023628 (1-Hydroxy-4-methoxy-2-naphthoic acid)

Structure for NP0023628 (1-Hydroxy-4-methoxy-2-naphthoic acid)

3D Structure for NP0023628 (1-Hydroxy-4-methoxy-2-naphthoic acid)