NP-MRD: Showing NP-Card for Aspernigrin A (NP0078313)

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Record Information

Version

2.0

Created at

2022-04-28 23:24:43 UTC

Updated at

2022-04-28 23:24:43 UTC

NP-MRD ID

NP0078313

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Aspernigrin A

Description

Aspernigrin A belongs to the class of organic compounds known as nicotinamides. These are heterocyclic aromatic compounds containing a pyridine ring substituted at position 3 by a carboxamide group. Aspernigrin A is found in Aspergillus niger, Cladosporium herbarum IFB-E002 and Pseudopestalotiopsis theae. Aspernigrin A was first documented in 2005 (PMID: 16038560). Aspernigrin A is an extremely weak basic (essentially neutral) compound (based on its pKa) (PMID: 26669099).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 29 30  0  0  0  0  0  0  0  0999 V2000
    4.7543   -0.0017    1.5629 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8975   -1.0467    1.1430 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1543   -2.2360    1.4537 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7163   -0.7336    0.3483 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3849    0.5423   -0.0209 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2898    0.8094   -0.7548 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4398   -0.1569   -1.1800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7496    0.1755   -1.9823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9508    0.4481   -1.1683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3247    1.6615   -0.6901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4706    1.8090    0.0639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2821    0.7261    0.3613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9169   -0.5115   -0.1162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7702   -0.6427   -0.8675 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7556   -1.4514   -0.8185 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8805   -1.7501   -0.0617 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1228   -2.9548    0.2418 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4057    0.8264    2.0838 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7837   -0.0343    1.3564 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0534    1.3508    0.3075 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0587    1.7997   -1.0246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5757    1.1047   -2.6008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0170   -0.6071   -2.7226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6987    2.5139   -0.9161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7820    2.7624    0.4508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1789    0.8234    0.9478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5644   -1.3477    0.1266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5123   -1.6320   -1.2276 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0968   -2.2467   -1.1423 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
  7 15  2  0
 15 16  1  0
 16 17  2  0
 16  4  1  0
 14  9  1  0
  1 18  1  0
  1 19  1  0
  5 20  1  0
  6 21  1  0
  8 22  1  0
  8 23  1  0
 10 24  1  0
 11 25  1  0
 12 26  1  0
 13 27  1  0
 14 28  1  0
 15 29  1  0
M  END

  Mrv1533004171501372D          

 17 18  0  0  0  0            999 V2000
    1.4289    0.0000    0.0000 N   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 O   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
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    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
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   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
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  2  0  0  0  0
  7 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0078313

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC(=O)C1=CNC(CC2=CC=CC=C2)=CC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C13H12N2O2/c14-13(17)11-8-15-10(7-12(11)16)6-9-4-2-1-3-5-9/h1-5,7-8H,6H2,(H2,14,17)(H,15,16)

> <INCHI_KEY>
RUUZDCZRFRLJFC-UHFFFAOYSA-N

> <FORMULA>
C13H12N2O2

> <MOLECULAR_WEIGHT>
228.251

> <EXACT_MASS>
228.089877634

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
23.384453579173737

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-benzyl-4-oxo-1,4-dihydropyridine-3-carboxamide

> <ALOGPS_LOGP>
1.01

> <JCHEM_LOGP>
0.9124512029999999

> <ALOGPS_LOGS>
-3.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.352211234417833

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.957419339591219

> <JCHEM_PKA_STRONGEST_BASIC>
-1.2242057833434559

> <JCHEM_POLAR_SURFACE_AREA>
72.19

> <JCHEM_REFRACTIVITY>
65.95100000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.66e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-benzyl-4-oxo-1H-pyridine-3-carboxamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  N   UNK     0       2.667   0.000   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       5.335  -4.620   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   11                                                  
CONECT    8    7    9                                                       
CONECT    9    8    4   10                                                  
CONECT   10    9                                                            
CONECT   11    7   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

View in JSmol

Synonyms

Value	Source
6-Benzyl-4-oxo-1,4-dihydropyridine-3-carboxamide	MeSH
Aspernigrin a	MeSH

Chemical Formula

C₁₃H₁₂N₂O₂

Average Mass

228.2510 Da

Monoisotopic Mass

228.08988 Da

IUPAC Name

6-benzyl-4-oxo-1,4-dihydropyridine-3-carboxamide

Traditional Name

6-benzyl-4-oxo-1H-pyridine-3-carboxamide

CAS Registry Number

Not Available

SMILES

NC(=O)C1=CNC(CC2=CC=CC=C2)=CC1=O

InChI Identifier

InChI=1S/C13H12N2O2/c14-13(17)11-8-15-10(7-12(11)16)6-9-4-2-1-3-5-9/h1-5,7-8H,6H2,(H2,14,17)(H,15,16)

InChI Key

RUUZDCZRFRLJFC-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
Aspergillus niger	Fungi	KNApSAcK
Cladosporium herbarum IFB-E002	Fungi	KNApSAcK
Pseudopestalotiopsis theae	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as nicotinamides. These are heterocyclic aromatic compounds containing a pyridine ring substituted at position 3 by a carboxamide group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridines and derivatives

Sub Class

Pyridinecarboxylic acids and derivatives

Direct Parent

Nicotinamides

Alternative Parents

Substituents

Nicotinamide
Dihydropyridine
Monocyclic benzene moiety
Hydropyridine
Benzenoid
Heteroaromatic compound
Vinylogous amide
Carboxamide group
Primary carboxylic acid amide
Cyclic ketone
Carboxylic acid derivative
Azacycle
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	1.01	ALOGPS
logP	0.91	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	11.96	ChemAxon
pKa (Strongest Basic)	-1.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	72.19 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	65.95 m³·mol⁻¹	ChemAxon
Polarizability	23.38 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

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00042247

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

11736320

PDB ID

Not Available

ChEBI ID

133846

Good Scents ID

Not Available

References

General References

Ye YH, Zhu HL, Song YC, Liu JY, Tan RX: Structural revision of aspernigrin A, reisolated from Cladosporium herbarum IFB-E002. J Nat Prod. 2005 Jul;68(7):1106-8. doi: 10.1021/np050059p. [PubMed:16038560 ]
Bandara HM, Kumar NS, Jayasinghe L, Masubuti H, Fujimoto Y: A 3-Vinyl Cephem Derivative, a Useful Intermediate in the Synthesis of Cepham Antibiotics, from Aspergillus awamori Associated with Banana Fruit. Nat Prod Commun. 2015 Oct;10(10):1663-6. [PubMed:26669099 ]

Showing NP-Card for Aspernigrin A (NP0078313)

MOL for NP0078313 (Aspernigrin A)

3D MOL for NP0078313 (Aspernigrin A)

3D SDF for NP0078313 (Aspernigrin A)

3D-SDF for NP0078313 (Aspernigrin A)

PDB for NP0078313 (Aspernigrin A)

3D PDB for NP0078313 (Aspernigrin A)

SMILES for NP0078313 (Aspernigrin A)

INCHI for NP0078313 (Aspernigrin A)

Structure for NP0078313 (Aspernigrin A)

3D Structure for NP0078313 (Aspernigrin A)