NP-MRD: Showing NP-Card for 2-Amino-3-carboxy-1,4-naphthoquinone (NP0138382)

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Record Information

Version

1.0

Created at

2022-05-31 17:57:09 UTC

Updated at

2022-05-31 17:57:09 UTC

NP-MRD ID

NP0138382

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-Amino-3-carboxy-1,4-naphthoquinone

Description

2-Amino-3-carboxy-1,4-naphthoquinone, also known as 2-ACNQ, belongs to the class of organic compounds known as naphthalenecarboxylic acids. Naphthalenecarboxylic acids 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. It was first documented in 2002 (PMID: 12450120). Based on a literature review a small amount of articles have been published on 2-amino-3-carboxy-1,4-naphthoquinone (PMID: 31232690) (PMID: 34546573) (PMID: 17609163) (PMID: 12073135).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652305312219572D          

 16 17  0  0  0  0            999 V2000
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 N   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
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  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
  7 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
  4 15  1  0  0  0  0
 15 16  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0138382

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)C1=C(O)C2=CC=CC=C2C(=O)C1=N

> <INCHI_IDENTIFIER>
InChI=1S/C11H7NO4/c12-8-7(11(15)16)9(13)5-3-1-2-4-6(5)10(8)14/h1-4,12-13H,(H,15,16)

> <INCHI_KEY>
LUUNBSJOKUEDSL-UHFFFAOYSA-N

> <FORMULA>
C11H7NO4

> <MOLECULAR_WEIGHT>
217.18

> <EXACT_MASS>
217.037507709

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
20.085154966596615

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-hydroxy-3-imino-4-oxo-3,4-dihydronaphthalene-2-carboxylic acid

> <JCHEM_LOGP>
0.4774053105767633

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
5.902661393026045

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.392777464697609

> <JCHEM_PKA_STRONGEST_BASIC>
2.7700630328093876

> <JCHEM_POLAR_SURFACE_AREA>
98.44999999999999

> <JCHEM_REFRACTIVITY>
66.60360000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
1-hydroxy-3-imino-4-oxonaphthalene-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 31-MAY-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   31-MAY-22         0                                  
HETATM    1  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       0.000  -3.080   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   15                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    7   13                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    4   16                                                  
CONECT   16   15                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

View in JSmol

Synonyms

Value	Source
2-ACNQ	MeSH

Chemical Formula

C₁₁H₇NO₄

Average Mass

217.1800 Da

Monoisotopic Mass

217.03751 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

173043-38-4

SMILES

OC(=O)C1=C(O)C2=CC=CC=C2C(=O)C1=N

InChI Identifier

InChI=1S/C11H7NO4/c12-8-7(11(15)16)9(13)5-3-1-2-4-6(5)10(8)14/h1-4,12-13H,(H,15,16)

InChI Key

LUUNBSJOKUEDSL-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, 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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthalenecarboxylic acids. Naphthalenecarboxylic acids 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
1-naphthol
Aryl ketone
Quinonimine
O-quinonimine
Vinylogous acid
Ketone
Ketimine
Monocarboxylic acid or derivatives
Enol
Carboxylic acid
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Imine
Carbonyl group
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

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

135418289

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Mevers E, Su L, Pishchany G, Baruch M, Cornejo J, Hobert E, Dimise E, Ajo-Franklin CM, Clardy J: An elusive electron shuttle from a facultative anaerobe. Elife. 2019 Jun 24;8. pii: 48054. doi: 10.7554/eLife.48054. [PubMed:31232690 ]
Min D, Liu DF, Wu J, Cheng L, Zhang F, Cheng ZH, Li WW, Yu HQ: Extracellular electron transfer via multiple electron shuttles in waterborne Aeromonas hydrophila for bioreduction of pollutants. Biotechnol Bioeng. 2021 Dec;118(12):4760-4770. doi: 10.1002/bit.27940. Epub 2021 Sep 27. [PubMed:34546573 ]
Kouya T, Misawa K, Horiuchi M, Nakayama E, Deguchi H, Tanaka T, Taniguchi M: Production of extracellular bifidogenic growth stimulator by anaerobic and aerobic cultivations of several propionibacterial strains. J Biosci Bioeng. 2007 May;103(5):464-71. doi: 10.1263/jbb.103.464. [PubMed:17609163 ]
Yamazaki S, Kaneko T, Taketomo N, Kano K, Ikeda T: Glucose metabolism of lactic acid bacteria changed by quinone-mediated extracellular electron transfer. Biosci Biotechnol Biochem. 2002 Oct;66(10):2100-6. doi: 10.1271/bbb.66.2100. [PubMed:12450120 ]
Yamazaki S, Kaneko T, Taketomo N, Kano K, Ikeda T: 2-Amino-3-carboxy-1,4-naphthoquinone affects the end-product profile of bifidobacteria through the mediated oxidation of NAD(P)H. Appl Microbiol Biotechnol. 2002 Jun;59(1):72-8. doi: 10.1007/s00253-002-0982-z. Epub 2002 Apr 12. [PubMed:12073135 ]

Showing NP-Card for 2-Amino-3-carboxy-1,4-naphthoquinone (NP0138382)

MOL for NP0138382 (2-Amino-3-carboxy-1,4-naphthoquinone)

3D MOL for NP0138382 (2-Amino-3-carboxy-1,4-naphthoquinone)

3D SDF for NP0138382 (2-Amino-3-carboxy-1,4-naphthoquinone)

3D-SDF for NP0138382 (2-Amino-3-carboxy-1,4-naphthoquinone)

PDB for NP0138382 (2-Amino-3-carboxy-1,4-naphthoquinone)

3D PDB for NP0138382 (2-Amino-3-carboxy-1,4-naphthoquinone)

SMILES for NP0138382 (2-Amino-3-carboxy-1,4-naphthoquinone)

INCHI for NP0138382 (2-Amino-3-carboxy-1,4-naphthoquinone)

Structure for NP0138382 (2-Amino-3-carboxy-1,4-naphthoquinone)

3D Structure for NP0138382 (2-Amino-3-carboxy-1,4-naphthoquinone)