NP-MRD: Showing NP-Card for (2r)-2-hydroxy-3-(4-hydroxy-2-imino-6-oxo-1,5-dihydropteridin-7-yl)propanoic acid (NP0162023)

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Record Information

Version

2.0

Created at

2022-09-02 20:21:06 UTC

Updated at

2022-09-02 20:21:06 UTC

NP-MRD ID

NP0162023

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r)-2-hydroxy-3-(4-hydroxy-2-imino-6-oxo-1,5-dihydropteridin-7-yl)propanoic acid

Description

(2R)-2-hydroxy-3-(4-hydroxy-2-imino-6-oxo-1,2,5,6-tetrahydropteridin-7-yl)propanoic acid 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. (2r)-2-hydroxy-3-(4-hydroxy-2-imino-6-oxo-1,5-dihydropteridin-7-yl)propanoic acid is found in Ephestia kuehniella. Based on a literature review very few articles have been published on (2R)-2-hydroxy-3-(4-hydroxy-2-imino-6-oxo-1,2,5,6-tetrahydropteridin-7-yl)propanoic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 28 29  0  0  0  0  0  0  0  0999 V2000
    4.6895   -2.7962   -0.8278 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8222   -1.8962   -0.3285 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8183   -1.0811   -0.1190 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0360    0.0732    0.5316 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0762    0.9540    0.7848 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2770    2.1534    1.4554 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7866    0.6869    0.3667 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7710    1.5197    0.5829 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4663    1.2077    0.1525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3605    2.0525    0.3995 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7659    0.0558   -0.5141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1179   -0.3024   -0.9816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0442   -0.8227    0.0643 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5426   -1.9664    0.6906 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5703    0.1544    1.0180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4233    0.0154    2.2647 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2610    1.2804    0.5827 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2954   -0.7822   -0.7233 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5416   -0.4935   -0.3034 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5720   -1.3531   -0.5303 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5504    3.0106    1.0313 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9704    2.4099    1.0914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6375    0.5657   -1.4633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0396   -1.0639   -1.8007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9602   -1.2059   -0.5008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3225   -2.3524    1.1970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0612    2.2139    0.8960 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3667   -2.2376   -1.0370 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 13  1  0
 13 12  1  0
 12 11  1  0
 11 18  2  0
 18 19  1  0
 19  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  7  5  1  0
  5  6  1  0
  5  4  2  0
  4  3  1  0
  3  2  2  0
  3 20  1  0
 13 15  1  0
 15 17  1  0
 15 16  2  0
  9 11  1  0
 20 19  1  0
 14 26  1  0
 13 25  1  6
 12 23  1  0
 12 24  1  0
  8 22  1  0
  6 21  1  0
  2  1  1  0
 20 28  1  0
 17 27  1  0
M  END


  Mrv1652309022222212D          

 19 20  0  0  1  0            999 V2000
    0.0000   -1.6500    0.0000 N   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
    0.7145   -0.4125    0.0000 N   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 N   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
    4.2868   -0.0000    0.0000 O   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
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 N   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 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  4  6  1  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  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 10 17  2  0  0  0  0
 17 18  1  0  0  0  0
  6 18  2  0  0  0  0
 18 19  1  0  0  0  0
  2 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0162023

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@H](CC1=NC2=C(NC1=O)C(O)=NC(=N)N2)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C9H9N5O5/c10-9-13-5-4(7(17)14-9)12-6(16)2(11-5)1-3(15)8(18)19/h3,15H,1H2,(H,12,16)(H,18,19)(H3,10,11,13,14,17)/t3-/m1/s1

> <INCHI_KEY>
CFFJKEIFNMDYED-GSVOUGTGSA-N

> <FORMULA>
C9H9N5O5

> <MOLECULAR_WEIGHT>
267.201

> <EXACT_MASS>
267.06036841

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
23.456208217579945

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-2-hydroxy-3-(4-hydroxy-2-imino-6-oxo-1,2,5,6-tetrahydropteridin-7-yl)propanoic acid

> <ALOGPS_LOGP>
-1.52

> <JCHEM_LOGP>
-1.8355329503333329

> <ALOGPS_LOGS>
-2.97

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.474897993330196

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.28317749955005

> <JCHEM_PKA_STRONGEST_BASIC>
-0.9033366396807126

> <JCHEM_POLAR_SURFACE_AREA>
167.46

> <JCHEM_REFRACTIVITY>
79.5802

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.86e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-2-hydroxy-3-(4-hydroxy-2-imino-6-oxo-1,5-dihydropteridin-7-yl)propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  N   UNK     0       0.000  -3.080   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       1.334  -0.770   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       5.335   0.000   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      12.003  -2.310   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      10.669  -4.620   0.000  0.00  0.00           O+0
HETATM   17  N   UNK     0       5.335  -3.080   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       2.667  -3.080   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3   19                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   18                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   17                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   10   18                                                       
CONECT   18   17    6   19                                                  
CONECT   19   18    2                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

View in JSmol

Synonyms

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

Chemical Formula

C₉H₉N₅O₅

Average Mass

267.2010 Da

Monoisotopic Mass

267.06037 Da

IUPAC Name

(2R)-2-hydroxy-3-(4-hydroxy-2-imino-6-oxo-1,2,5,6-tetrahydropteridin-7-yl)propanoic acid

Traditional Name

(2R)-2-hydroxy-3-(4-hydroxy-2-imino-6-oxo-1,5-dihydropteridin-7-yl)propanoic acid

CAS Registry Number

Not Available

SMILES

O[C@H](CC1=NC2=C(NC1=O)C(O)=NC(=N)N2)C(O)=O

InChI Identifier

InChI=1S/C9H9N5O5/c10-9-13-5-4(7(17)14-9)12-6(16)2(11-5)1-3(15)8(18)19/h3,15H,1H2,(H,12,16)(H,18,19)(H3,10,11,13,14,17)/t3-/m1/s1

InChI Key

CFFJKEIFNMDYED-GSVOUGTGSA-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

Species Name	Source	Reference
Ephestia kuehniella	LOTUS Database	35616633

Chemical Taxonomy

Description

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
Hydroxypyrimidine
Alpha-hydroxy acid
Hydroxy acid
Pyrazine
Pyrimidine
Heteroaromatic compound
Secondary alcohol
Lactam
Azacycle
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Alcohol
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	-1.5	ALOGPS
logP	-1.8	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	3.28	ChemAxon
pKa (Strongest Basic)	-0.9	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	167.46 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	79.58 m³·mol⁻¹	ChemAxon
Polarizability	23.46 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

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

163187444

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r)-2-hydroxy-3-(4-hydroxy-2-imino-6-oxo-1,5-dihydropteridin-7-yl)propanoic acid (NP0162023)

MOL for NP0162023 ((2r)-2-hydroxy-3-(4-hydroxy-2-imino-6-oxo-1,5-dihydropteridin-7-yl)propanoic acid)

3D MOL for NP0162023 ((2r)-2-hydroxy-3-(4-hydroxy-2-imino-6-oxo-1,5-dihydropteridin-7-yl)propanoic acid)

3D SDF for NP0162023 ((2r)-2-hydroxy-3-(4-hydroxy-2-imino-6-oxo-1,5-dihydropteridin-7-yl)propanoic acid)

3D-SDF for NP0162023 ((2r)-2-hydroxy-3-(4-hydroxy-2-imino-6-oxo-1,5-dihydropteridin-7-yl)propanoic acid)

PDB for NP0162023 ((2r)-2-hydroxy-3-(4-hydroxy-2-imino-6-oxo-1,5-dihydropteridin-7-yl)propanoic acid)

3D PDB for NP0162023 ((2r)-2-hydroxy-3-(4-hydroxy-2-imino-6-oxo-1,5-dihydropteridin-7-yl)propanoic acid)

SMILES for NP0162023 ((2r)-2-hydroxy-3-(4-hydroxy-2-imino-6-oxo-1,5-dihydropteridin-7-yl)propanoic acid)

INCHI for NP0162023 ((2r)-2-hydroxy-3-(4-hydroxy-2-imino-6-oxo-1,5-dihydropteridin-7-yl)propanoic acid)

Structure for NP0162023 ((2r)-2-hydroxy-3-(4-hydroxy-2-imino-6-oxo-1,5-dihydropteridin-7-yl)propanoic acid)

3D Structure for NP0162023 ((2r)-2-hydroxy-3-(4-hydroxy-2-imino-6-oxo-1,5-dihydropteridin-7-yl)propanoic acid)