NP-MRD: Showing NP-Card for Pyranonigrin A (NP0007131)

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Record Information

Version

2.0

Created at

2020-12-09 04:00:38 UTC

Updated at

2021-07-15 16:56:45 UTC

NP-MRD ID

NP0007131

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Pyranonigrin A

Provided By

NPAtlas

Description

Pyranonigrin A belongs to the class of organic compounds known as pyranones and derivatives. Pyranones and derivatives are compounds containing a pyran ring which bears a ketone. Pyranonigrin A is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Pyranonigrin A is found in Aspergillus. Pyranonigrin A was first documented in 2007 (PMID: 17604395). Based on a literature review a small amount of articles have been published on Pyranonigrin A (PMID: 24084681).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118373D          

 25 26  0  0  0  0            999 V2000
   -3.9811    0.8124    1.3789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5772    0.6868    0.9061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0731   -0.4683    0.4789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6982   -0.5458    0.0264 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0832    0.4999    0.0219 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3247    0.4810   -0.3749 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9133   -0.6723   -0.8282 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1579   -1.8212   -0.8559 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6530   -2.9046   -1.2635 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1670   -1.7321   -0.4165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9127   -2.8795   -0.4468 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3066   -0.3995   -1.2053 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1175   -1.2426   -1.6570 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5157    0.9799   -0.9516 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3228    1.5773   -0.4361 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4930    2.0496    0.8729 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1722    0.3199    2.3310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2065    1.9110    1.4356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7035    0.4103    0.6314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9009    1.5347    0.8890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6959   -1.3236    0.4774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8594   -3.0097   -0.1778 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4123    1.4821   -1.1185 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9705    2.3977   -1.1128 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6773    1.8567    1.3953 H   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
  3  4  1  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
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
  7 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 10  4  2  0  0  0  0
 15  6  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
  2 20  1  0  0  0  0
  3 21  1  0  0  0  0
 11 22  1  0  0  0  0
 14 23  1  0  0  0  0
 15 24  1  6  0  0  0
 16 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0007131

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C(OC2=C(C(=O)N([H])[C@]2([H])O[H])C1=O)C(\[H])=C(/[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C10H9NO5/c1-2-3-4-6(12)7(13)5-8(16-4)10(15)11-9(5)14/h2-3,10,12,15H,1H3,(H,11,14)/b3-2+/t10-/m1/s1

> <INCHI_KEY>
OALBJWDVDNROSF-VMZHVLLKSA-N

> <FORMULA>
C10H9NO5

> <MOLECULAR_WEIGHT>
223.184

> <EXACT_MASS>
223.048072394

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
20.88585606148316

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(7R)-3,7-dihydroxy-2-[(1E)-prop-1-en-1-yl]-4H,5H,6H,7H-pyrano[2,3-c]pyrrole-4,5-dione

> <ALOGPS_LOGP>
-0.49

> <JCHEM_LOGP>
-0.37900280666666675

> <ALOGPS_LOGS>
-1.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.103373203714668

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.832804695779096

> <JCHEM_PKA_STRONGEST_BASIC>
-2.4098105809600794

> <JCHEM_POLAR_SURFACE_AREA>
95.86

> <JCHEM_REFRACTIVITY>
56.73420000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.78e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(7R)-3,7-dihydroxy-2-[(1E)-prop-1-en-1-yl]-6H,7H-pyrano[2,3-c]pyrrole-4,5-dione

> <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      -3.981   0.812   1.379  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.577   0.687   0.906  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.073  -0.468   0.479  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.698  -0.546   0.026  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.083   0.500   0.022  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.325   0.481  -0.375  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.913  -0.672  -0.828  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.158  -1.821  -0.856  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.653  -2.905  -1.264  0.00  0.00           O+0
HETATM   10  C   UNK     0      -0.167  -1.732  -0.417  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.913  -2.880  -0.447  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.307  -0.400  -1.205  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.117  -1.243  -1.657  0.00  0.00           O+0
HETATM   14  N   UNK     0       3.516   0.980  -0.952  0.00  0.00           N+0
HETATM   15  C   UNK     0       2.323   1.577  -0.436  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.493   2.050   0.873  0.00  0.00           O+0
HETATM   17  H   UNK     0      -4.172   0.320   2.331  0.00  0.00           H+0
HETATM   18  H   UNK     0      -4.207   1.911   1.436  0.00  0.00           H+0
HETATM   19  H   UNK     0      -4.704   0.410   0.631  0.00  0.00           H+0
HETATM   20  H   UNK     0      -1.901   1.535   0.889  0.00  0.00           H+0
HETATM   21  H   UNK     0      -2.696  -1.324   0.477  0.00  0.00           H+0
HETATM   22  H   UNK     0      -1.859  -3.010  -0.178  0.00  0.00           H+0
HETATM   23  H   UNK     0       4.412   1.482  -1.119  0.00  0.00           H+0
HETATM   24  H   UNK     0       1.970   2.398  -1.113  0.00  0.00           H+0
HETATM   25  H   UNK     0       1.677   1.857   1.395  0.00  0.00           H+0
CONECT    1    2   17   18   19                                             
CONECT    2    1    3   20                                                  
CONECT    3    2    4   21                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   15                                                  
CONECT    7    6    8   12                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11    4                                                  
CONECT   11   10   22                                                       
CONECT   12    7   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   23                                                  
CONECT   15   14   16    6   24                                             
CONECT   16   15   25                                                       
CONECT   17    1                                                            
CONECT   18    1                                                            
CONECT   19    1                                                            
CONECT   20    2                                                            
CONECT   21    3                                                            
CONECT   22   11                                                            
CONECT   23   14                                                            
CONECT   24   15                                                            
CONECT   25   16                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   52    0
END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(7R)-3,7-Dihydroxy-2-((1E)-prop-1-enyl)-6,7-dihydropyrano(2,3-c)pyrrole-4,5-dione	MeSH

Chemical Formula

C₁₀H₉NO₅

Average Mass

223.1840 Da

Monoisotopic Mass

223.04807 Da

IUPAC Name

(7R)-3,7-dihydroxy-2-[(1E)-prop-1-en-1-yl]-4H,5H,6H,7H-pyrano[2,3-c]pyrrole-4,5-dione

Traditional Name

(7R)-3,7-dihydroxy-2-[(1E)-prop-1-en-1-yl]-6H,7H-pyrano[2,3-c]pyrrole-4,5-dione

CAS Registry Number

Not Available

SMILES

C\C=C\C1=C(O)C(=O)C2=C(O1)[C@@H](O)NC2=O

InChI Identifier

InChI=1S/C10H9NO5/c1-2-3-4-6(12)7(13)5-8(16-4)10(15)11-9(5)14/h2-3,10,12,15H,1H3,(H,11,14)/b3-2+/t10-/m1/s1

InChI Key

OALBJWDVDNROSF-VMZHVLLKSA-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	NPAtlas	17604395

Species Where Detected

Species Name	Source	Reference
Aspergillus niger LL-LV3020	KNApSAcK Database	22123792

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyranones and derivatives. Pyranones and derivatives are compounds containing a pyran ring which bears a ketone.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrans

Sub Class

Pyranones and derivatives

Direct Parent

Pyranones and derivatives

Alternative Parents

Substituents

Pyranone
Heteroaromatic compound
Carboxamide group
Lactam
Secondary carboxylic acid amide
Oxacycle
Azacycle
Alkanolamine
Carboxylic acid derivative
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	-0.49	ALOGPS
logP	-0.38	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	8.83	ChemAxon
pKa (Strongest Basic)	-2.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	95.86 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	56.73 m³·mol⁻¹	ChemAxon
Polarizability	20.89 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

NPA012801

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00040123

Chemspider ID

23076409

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16756786

PDB ID

Not Available

ChEBI ID

133779

Good Scents ID

Not Available

References

General References

Schlingmann G, Taniguchi T, He H, Bigelis R, Yang HY, Koehn FE, Carter GT, Berova N: Reassessing the structure of pyranonigrin. J Nat Prod. 2007 Jul;70(7):1180-7. doi: 10.1021/np070175n. Epub 2007 Jun 30. [PubMed:17604395 ]
Riko R, Nakamura H, Shindo K: Studies on pyranonigrins-isolation of pyranonigrin E and biosynthetic studies on pyranonigrin A. J Antibiot (Tokyo). 2014 Feb;67(2):179-81. doi: 10.1038/ja.2013.91. Epub 2013 Oct 2. [PubMed:24084681 ]

Showing NP-Card for Pyranonigrin A (NP0007131)

MOL for NP0007131 (Pyranonigrin A)

3D MOL for NP0007131 (Pyranonigrin A)

3D SDF for NP0007131 (Pyranonigrin A)

3D-SDF for NP0007131 (Pyranonigrin A)

PDB for NP0007131 (Pyranonigrin A)

3D PDB for NP0007131 (Pyranonigrin A)

SMILES for NP0007131 (Pyranonigrin A)

INCHI for NP0007131 (Pyranonigrin A)

Structure for NP0007131 (Pyranonigrin A)

3D Structure for NP0007131 (Pyranonigrin A)