NP-MRD: Showing NP-Card for 2,3-dihydroxy-3-(4-hydroxy-2-imino-7,8-dihydro-1h-pteridin-6-yl)propoxyphosphonic acid (NP0216092)

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Record Information

Version

2.0

Created at

2022-09-05 15:55:34 UTC

Updated at

2022-09-05 15:55:34 UTC

NP-MRD ID

NP0216092

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,3-dihydroxy-3-(4-hydroxy-2-imino-7,8-dihydro-1h-pteridin-6-yl)propoxyphosphonic acid

Description

[2,3-Dihydroxy-3-(4-hydroxy-2-imino-1,2,7,8-tetrahydropteridin-6-yl)propoxy]phosphonic acid belongs to the class of organic compounds known as biopterins and derivatives. These are coenzymes containing a 2-amino-pteridine-4-one derivative. They are mainly synthesized in several parts of the body, including the pineal gland. Based on a literature review very few articles have been published on [2,3-dihydroxy-3-(4-hydroxy-2-imino-1,2,7,8-tetrahydropteridin-6-yl)propoxy]phosphonic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 37  0  0  0  0  0  0  0  0999 V2000
    7.5865   -0.3421   -0.5393 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7904    0.2982   -0.5719 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5710   -0.0147   -0.3053 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1475   -1.2211    0.0558 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8630   -1.5271    0.3308 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4707   -2.8010    0.7036 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9100   -0.5145    0.2316 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3370    0.7269   -0.1386 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6330    0.9698   -0.4000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3783    1.7676   -0.2426 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9456    1.5678   -0.0047 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6233    0.1976    0.4079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7752   -0.1681    0.7194 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8194   -1.5111    1.1607 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7163    0.0153   -0.4359 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7256    1.3295   -0.8677 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1312   -0.2736    0.0773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0163   -0.0793   -0.9888 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6046   -0.3647   -0.5567 P   0  0  0  0  0  5  0  0  0  0  0  0
   -6.3775   -0.7424   -1.7990 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7546   -1.6289    0.5537 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2973    1.0281    0.1235 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5479   -0.7255    0.4944 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7905   -3.3460    0.1728 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9299    1.9397   -0.6835 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6569    2.7356   -0.4971 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6345    2.3472    0.7066 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4862    1.7221   -1.0303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1651    0.4471    1.5666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9739   -2.1059    0.4020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4597   -0.6989   -1.2457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7726    1.9156   -0.0858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1665   -1.3558    0.3277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3656    0.3227    0.9583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5863   -1.5646    1.0739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5945    1.6546    0.4528 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 15  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 21  1  0
 19 22  1  0
 19 20  2  0
 15 13  1  0
 13 14  1  0
 13 12  1  0
 12 23  2  0
 23  7  1  0
  7  8  2  0
  8 10  1  0
 10 11  1  0
  8  9  1  0
  9  3  1  0
  3  2  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
 11 12  1  0
  5  7  1  0
 16 32  1  0
 15 31  1  6
 17 33  1  0
 17 34  1  0
 21 35  1  0
 22 36  1  0
 13 29  1  1
 14 30  1  0
 10 26  1  0
 11 27  1  0
 11 28  1  0
  9 25  1  0
  2  1  1  0
  6 24  1  0
M  END


  Mrv1652309052217552D          

 22 23  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
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -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
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    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
    2.1434   -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
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8743   -4.8395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6993   -3.4105    0.0000 O   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  2  0  0  0  0
  7  8  1  0  0  0  0
  2  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 18 21  1  0  0  0  0
 11 22  2  0  0  0  0
  6 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0216092

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(COP(O)(O)=O)C(O)C1=NC2=C(NC1)NC(=N)N=C2O

> <INCHI_IDENTIFIER>
InChI=1S/C9H14N5O7P/c10-9-13-7-5(8(17)14-9)12-3(1-11-7)6(16)4(15)2-21-22(18,19)20/h4,6,15-16H,1-2H2,(H2,18,19,20)(H4,10,11,13,14,17)

> <INCHI_KEY>
PLSQMGZYOGSOCE-UHFFFAOYSA-N

> <FORMULA>
C9H14N5O7P

> <MOLECULAR_WEIGHT>
335.213

> <EXACT_MASS>
335.063084809

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
28.69214782376976

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[2,3-dihydroxy-3-(4-hydroxy-2-imino-1,2,7,8-tetrahydropteridin-6-yl)propoxy]phosphonic acid

> <JCHEM_LOGP>
-3.4129815193847417

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.308829903840787

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.2226475682142617

> <JCHEM_PKA_STRONGEST_BASIC>
1.932314526271167

> <JCHEM_POLAR_SURFACE_AREA>
200.07999999999998

> <JCHEM_REFRACTIVITY>
91.5444

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
2,3-dihydroxy-3-(4-hydroxy-2-imino-7,8-dihydro-1H-pteridin-6-yl)propoxyphosphonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  N   UNK     0      -2.667   0.000   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      -1.334  -2.310   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       0.000  -0.000   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0       2.667  -0.000   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       6.668  -6.930   0.000  0.00  0.00           O+0
HETATM   18  P   UNK     0       8.002  -7.700   0.000  0.00  0.00           P+0
HETATM   19  O   UNK     0       9.336  -8.470   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       7.232  -9.034   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       8.772  -6.366   0.000  0.00  0.00           O+0
HETATM   22  N   UNK     0       2.667  -3.080   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   22                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7    2                                                       
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   22                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20   21                                             
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   18                                                            
CONECT   22   11    6                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

View in JSmol

Synonyms

Value	Source
[2,3-Dihydroxy-3-(4-hydroxy-2-imino-1,2,7,8-tetrahydropteridin-6-yl)propoxy]phosphonate	Generator

Chemical Formula

C₉H₁₄N₅O₇P

Average Mass

335.2130 Da

Monoisotopic Mass

335.06308 Da

IUPAC Name

[2,3-dihydroxy-3-(4-hydroxy-2-imino-1,2,7,8-tetrahydropteridin-6-yl)propoxy]phosphonic acid

Traditional Name

2,3-dihydroxy-3-(4-hydroxy-2-imino-7,8-dihydro-1H-pteridin-6-yl)propoxyphosphonic acid

CAS Registry Number

Not Available

SMILES

OC(COP(O)(O)=O)C(O)C1=NC2=C(NC1)NC(=N)N=C2O

InChI Identifier

InChI=1S/C9H14N5O7P/c10-9-13-7-5(8(17)14-9)12-3(1-11-7)6(16)4(15)2-21-22(18,19)20/h4,6,15-16H,1-2H2,(H2,18,19,20)(H4,10,11,13,14,17)

InChI Key

PLSQMGZYOGSOCE-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 biopterins and derivatives. These are coenzymes containing a 2-amino-pteridine-4-one derivative. They are mainly synthesized in several parts of the body, including the pineal gland.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pteridines and derivatives

Sub Class

Pterins and derivatives

Direct Parent

Biopterins and derivatives

Alternative Parents

Substituents

Biopterin
Aminopyrimidine
Pyrimidone
Secondary aliphatic/aromatic amine
Monoalkyl phosphate
Organic phosphoric acid derivative
Phosphoric acid ester
Pyrimidine
Alkyl phosphate
Heteroaromatic compound
Vinylogous amide
1,2-diol
Ketimine
Secondary alcohol
Azacycle
Organic 1,3-dipolar compound
Secondary amine
Propargyl-type 1,3-dipolar organic compound
Amine
Hydrocarbon derivative
Primary amine
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Alcohol
Imine
Organic oxygen compound
Organic nitrogen 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	-3.4	ChemAxon
pKa (Strongest Acidic)	1.22	ChemAxon
pKa (Strongest Basic)	1.93	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	200.08 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	91.54 m³·mol⁻¹	ChemAxon
Polarizability	28.69 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	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

644

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

664

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2,3-dihydroxy-3-(4-hydroxy-2-imino-7,8-dihydro-1h-pteridin-6-yl)propoxyphosphonic acid (NP0216092)

MOL for NP0216092 (2,3-dihydroxy-3-(4-hydroxy-2-imino-7,8-dihydro-1h-pteridin-6-yl)propoxyphosphonic acid)

3D MOL for NP0216092 (2,3-dihydroxy-3-(4-hydroxy-2-imino-7,8-dihydro-1h-pteridin-6-yl)propoxyphosphonic acid)

3D SDF for NP0216092 (2,3-dihydroxy-3-(4-hydroxy-2-imino-7,8-dihydro-1h-pteridin-6-yl)propoxyphosphonic acid)

3D-SDF for NP0216092 (2,3-dihydroxy-3-(4-hydroxy-2-imino-7,8-dihydro-1h-pteridin-6-yl)propoxyphosphonic acid)

PDB for NP0216092 (2,3-dihydroxy-3-(4-hydroxy-2-imino-7,8-dihydro-1h-pteridin-6-yl)propoxyphosphonic acid)

3D PDB for NP0216092 (2,3-dihydroxy-3-(4-hydroxy-2-imino-7,8-dihydro-1h-pteridin-6-yl)propoxyphosphonic acid)

SMILES for NP0216092 (2,3-dihydroxy-3-(4-hydroxy-2-imino-7,8-dihydro-1h-pteridin-6-yl)propoxyphosphonic acid)

INCHI for NP0216092 (2,3-dihydroxy-3-(4-hydroxy-2-imino-7,8-dihydro-1h-pteridin-6-yl)propoxyphosphonic acid)

Structure for NP0216092 (2,3-dihydroxy-3-(4-hydroxy-2-imino-7,8-dihydro-1h-pteridin-6-yl)propoxyphosphonic acid)

3D Structure for NP0216092 (2,3-dihydroxy-3-(4-hydroxy-2-imino-7,8-dihydro-1h-pteridin-6-yl)propoxyphosphonic acid)