NP-MRD: Showing NP-Card for Erythropterin (NP0007221)

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Record Information

Version

2.0

Created at

2020-12-09 04:04:19 UTC

Updated at

2021-07-15 16:57:00 UTC

NP-MRD ID

NP0007221

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Erythropterin

Provided By

NPAtlas

Description

Erythropterin is found in Ephestia kuehniella and Mycobacterium lacticola. Erythropterin was first documented in 1949 (PMID: 17755247). Based on a literature review very few articles have been published on 3-(4-hydroxy-2-imino-6-oxo-1,2,5,6-tetrahydropteridin-7-yl)-2-oxopropanoic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118383D          

 26 27  0  0  0  0            999 V2000
   -4.5952    1.2984    1.3589 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5065    0.5750    0.7841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2871    1.1211    0.6139 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2500    0.4366    0.0678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0335    0.9794   -0.1032 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9932    0.2960   -0.6464 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3273    0.9079   -0.8299 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2198    0.3681    0.2265 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7981   -0.4744    1.0864 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5909    0.8142    0.2680 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0160    1.6330   -0.5659 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4483    0.3304    1.2436 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8232   -1.0239   -1.0570 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7662   -1.6810   -1.5669 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3949   -1.5684   -0.8860 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4187   -0.8718   -0.3391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6689   -1.4283   -0.1636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8322   -2.6331   -0.5361 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6650   -0.7001    0.3854 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1053    1.9829    0.7592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8953    1.1678    2.3491 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7029    0.7435   -1.8419 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2302    2.0030   -0.6408 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9029   -0.5812    1.1134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5591   -2.5605   -1.1844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6071   -1.1347    0.5115 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  2  0  0  0  0
  6  7  1  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  2  0  0  0  0
 10 12  1  0  0  0  0
  6 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19  2  1  0  0  0  0
 16  4  2  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
  7 22  1  0  0  0  0
  7 23  1  0  0  0  0
 12 24  1  0  0  0  0
 15 25  1  0  0  0  0
 19 26  1  0  0  0  0
M  END


  Mrv1652306242118383D          

 26 27  0  0  0  0            999 V2000
   -4.5952    1.2984    1.3589 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5065    0.5750    0.7841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2871    1.1211    0.6139 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2500    0.4366    0.0678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0335    0.9794   -0.1032 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9932    0.2960   -0.6464 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3273    0.9079   -0.8299 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2198    0.3681    0.2265 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7981   -0.4744    1.0864 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5909    0.8142    0.2680 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0160    1.6330   -0.5659 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4483    0.3304    1.2436 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8232   -1.0239   -1.0570 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7662   -1.6810   -1.5669 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3949   -1.5684   -0.8860 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4187   -0.8718   -0.3391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6689   -1.4283   -0.1636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8322   -2.6331   -0.5361 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6650   -0.7001    0.3854 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1053    1.9829    0.7592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8953    1.1678    2.3491 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7029    0.7435   -1.8419 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2302    2.0030   -0.6408 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9029   -0.5812    1.1134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5591   -2.5605   -1.1844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6071   -1.1347    0.5115 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  2  0  0  0  0
  6  7  1  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  2  0  0  0  0
 10 12  1  0  0  0  0
  6 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19  2  1  0  0  0  0
 16  4  2  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
  7 22  1  0  0  0  0
  7 23  1  0  0  0  0
 12 24  1  0  0  0  0
 15 25  1  0  0  0  0
 19 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0007221

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C(=O)C([H])([H])C1=NC2=C(N([H])C1=O)C(=O)N([H])C(=N2)N([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C9H7N5O5/c10-9-13-5-4(7(17)14-9)12-6(16)2(11-5)1-3(15)8(18)19/h1H2,(H,12,16)(H,18,19)(H3,10,11,13,14,17)

> <INCHI_KEY>
LQGDIYYBSGTSQV-UHFFFAOYSA-N

> <FORMULA>
C9H7N5O5

> <MOLECULAR_WEIGHT>
265.185

> <EXACT_MASS>
265.044718345

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
22.93637501153096

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-(2-amino-4,6-dioxo-3,4,5,6-tetrahydropteridin-7-yl)-2-oxopropanoic acid

> <ALOGPS_LOGP>
-1.38

> <JCHEM_LOGP>
-1.2515232606666664

> <ALOGPS_LOGS>
-2.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.234266176054422

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.7041639206031074

> <JCHEM_PKA_STRONGEST_BASIC>
-0.5718565558132832

> <JCHEM_POLAR_SURFACE_AREA>
163.31

> <JCHEM_REFRACTIVITY>
68.22430000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.97e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(2-amino-4,6-dioxo-3,5-dihydropteridin-7-yl)-2-oxopropanoic 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  N   UNK     0      -4.595   1.298   1.359  0.00  0.00           N+0
HETATM    2  C   UNK     0      -3.506   0.575   0.784  0.00  0.00           C+0
HETATM    3  N   UNK     0      -2.287   1.121   0.614  0.00  0.00           N+0
HETATM    4  C   UNK     0      -1.250   0.437   0.068  0.00  0.00           C+0
HETATM    5  N   UNK     0      -0.034   0.979  -0.103  0.00  0.00           N+0
HETATM    6  C   UNK     0       0.993   0.296  -0.646  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.327   0.908  -0.830  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.220   0.368   0.227  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.798  -0.474   1.086  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.591   0.814   0.268  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.016   1.633  -0.566  0.00  0.00           O+0
HETATM   12  O   UNK     0       5.448   0.330   1.244  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.823  -1.024  -1.057  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.766  -1.681  -1.567  0.00  0.00           O+0
HETATM   15  N   UNK     0      -0.395  -1.568  -0.886  0.00  0.00           N+0
HETATM   16  C   UNK     0      -1.419  -0.872  -0.339  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.669  -1.428  -0.164  0.00  0.00           C+0
HETATM   18  O   UNK     0      -2.832  -2.633  -0.536  0.00  0.00           O+0
HETATM   19  N   UNK     0      -3.665  -0.700   0.385  0.00  0.00           N+0
HETATM   20  H   UNK     0      -5.105   1.983   0.759  0.00  0.00           H+0
HETATM   21  H   UNK     0      -4.895   1.168   2.349  0.00  0.00           H+0
HETATM   22  H   UNK     0       2.703   0.744  -1.842  0.00  0.00           H+0
HETATM   23  H   UNK     0       2.230   2.003  -0.641  0.00  0.00           H+0
HETATM   24  H   UNK     0       5.903  -0.581   1.113  0.00  0.00           H+0
HETATM   25  H   UNK     0      -0.559  -2.561  -1.184  0.00  0.00           H+0
HETATM   26  H   UNK     0      -4.607  -1.135   0.511  0.00  0.00           H+0
CONECT    1    2   20   21                                                  
CONECT    2    1    3   19                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   16                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   13                                                  
CONECT    7    6    8   22   23                                             
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   24                                                       
CONECT   13    6   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   25                                                  
CONECT   16   15   17    4                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17    2   26                                                  
CONECT   20    1                                                            
CONECT   21    1                                                            
CONECT   22    7                                                            
CONECT   23    7                                                            
CONECT   24   12                                                            
CONECT   25   15                                                            
CONECT   26   19                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   54    0
END

View in JSmol View NMR Assignments

Synonyms

Value	Source
3-(4-Hydroxy-2-imino-6-oxo-1,2,5,6-tetrahydropteridin-7-yl)-2-oxopropanoate	Generator

Chemical Formula

C₉H₇N₅O₅

Average Mass

265.1850 Da

Monoisotopic Mass

265.04472 Da

IUPAC Name

3-(2-amino-4,6-dioxo-3,4,5,6-tetrahydropteridin-7-yl)-2-oxopropanoic acid

Traditional Name

3-(2-amino-4,6-dioxo-3,5-dihydropteridin-7-yl)-2-oxopropanoic acid

CAS Registry Number

Not Available

SMILES

NC1=NC2=C(NC(=O)C(CC(=O)C(O)=O)=N2)C(=O)N1

InChI Identifier

InChI=1S/C9H7N5O5/c10-9-13-5-4(7(17)14-9)12-6(16)2(11-5)1-3(15)8(18)19/h1H2,(H,12,16)(H,18,19)(H3,10,11,13,14,17)

InChI Key

LQGDIYYBSGTSQV-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
Ephestia kuehniella	LOTUS Database	35616633
Mycobacterium lacticola	NPAtlas	17755247

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as pterins and derivatives. These are polycyclic aromatic compounds containing a pterin moiety, which consist of a pteridine ring bearing a ketone and an amine group to form 2-aminopteridin-4(3H)-one.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pteridines and derivatives

Sub Class

Pterins and derivatives

Direct Parent

Pterins and derivatives

Alternative Parents

Substituents

Pterin
Aminopyrimidine
Pyrimidone
Alpha-keto acid
Keto acid
Pyrimidine
Pyrazine
Alpha-hydroxy ketone
Heteroaromatic compound
Vinylogous amide
Amino acid or derivatives
Amino acid
Ketone
Lactam
Carboxylic acid derivative
Carboxylic acid
Azacycle
Monocarboxylic acid or derivatives
Amine
Hydrocarbon derivative
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Organic oxide
Primary amine
Organopnictogen compound
Organonitrogen compound
Organooxygen 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	-1.4	ALOGPS
logP	-1.3	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	2.7	ChemAxon
pKa (Strongest Basic)	-0.57	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	163.31 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	68.22 m³·mol⁻¹	ChemAxon
Polarizability	22.94 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA006057

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

230925

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

262921

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Crowe MO, Walker A: Pterin-like Pigment Derived from the Tubercle Bacillus. Fluorescence and Absorption Spectral Data for Erythropterin-like Pigment Isolated by Ultrachromatographic Analysis. Science. 1949 Aug 12;110(2850):166-8. doi: 10.1126/science.110.2850.166. [PubMed:17755247 ]

Showing NP-Card for Erythropterin (NP0007221)

MOL for NP0007221 (Erythropterin)

3D MOL for NP0007221 (Erythropterin)

3D SDF for NP0007221 (Erythropterin)

3D-SDF for NP0007221 (Erythropterin)

PDB for NP0007221 (Erythropterin)

3D PDB for NP0007221 (Erythropterin)

SMILES for NP0007221 (Erythropterin)

INCHI for NP0007221 (Erythropterin)

Structure for NP0007221 (Erythropterin)

3D Structure for NP0007221 (Erythropterin)