NP-MRD: Showing NP-Card for (1r,2r)-1-(4-hydroxy-2-imino-1h-pteridin-6-yl)propane-1,2,3-triol (NP0151650)

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Record Information

Version

2.0

Created at

2022-09-02 07:59:51 UTC

Updated at

2022-09-02 07:59:51 UTC

NP-MRD ID

NP0151650

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2r)-1-(4-hydroxy-2-imino-1h-pteridin-6-yl)propane-1,2,3-triol

Description

Umanopterin 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. A pteridine derivative present in body fluids; elevated levels result from immune system activation, malignant disease, allograft rejection, and viral infections. Umanopterin is an extremely weak basic (essentially neutral) compound (based on its pKa). An elevated level of umanopterin is associated with immune system activation, malignant diseases, allograft rejection, and viral infections. An elevated level of umanopterin is associated with immune system activation, malignant diseases, allograft rejection, and viral infections (http://Www.Online-medical-dictionary.Org/). (1r,2r)-1-(4-hydroxy-2-imino-1h-pteridin-6-yl)propane-1,2,3-triol is found in Tetrahymena pyriformis. (1r,2r)-1-(4-hydroxy-2-imino-1h-pteridin-6-yl)propane-1,2,3-triol was first documented in 1992 (PMID: 1524209). Umanopterin also serves as a precursor in the biosynthesis of biopterin (PMID: 1329838).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 29 30  0  0  0  0  0  0  0  0999 V2000
    5.6727   -0.5868    1.0375 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3423   -0.1786    0.7126 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3680   -1.0751    0.5692 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0956   -0.7699    0.2652 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1166   -1.6615    0.1204 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1180   -1.2374   -0.1847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4145    0.0965   -0.3553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7968    0.5002   -0.6912 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3239   -0.3042   -1.6754 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6819    0.4178    0.5412 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7640   -0.8670    1.0216 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0313    1.0251    0.2412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7428    0.3257   -0.7004 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5536    1.0356   -0.2166 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7966    0.6599    0.0864 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8284    1.5533    0.2427 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6400    2.7856    0.1039 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0663    1.1217    0.5491 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4423    0.0769    1.1574 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8743   -1.6112    1.1594 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3308   -2.6753    0.2476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8878   -1.9949   -0.2940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7875    1.5746   -1.0218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8325   -0.2749   -2.5140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1934    1.0466    1.3131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2014   -1.4955    0.4093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6218    1.0791    1.1694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8735    2.0562   -0.1284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8566   -0.6226   -0.5242 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2 18  2  0
 18 16  1  0
 16 17  2  0
 16 15  1  0
 15 14  2  0
 14  7  1  0
  7  6  2  0
  6  5  1  0
  5  4  1  0
  4  3  2  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
  3  2  1  0
  4 15  1  0
  1 19  1  0
  1 20  1  0
  6 22  1  0
  5 21  1  0
  8 23  1  6
  9 24  1  0
 10 25  1  1
 11 26  1  0
 12 27  1  0
 12 28  1  0
 13 29  1  0
M  END


  Mrv1652303192023122D          

 18 19  0  0  0  0            999 V2000
 9998.202210001.2436    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.053610000.4166    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.769310000.0020    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10002.482910000.4166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.196610000.0020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.7693 9999.1780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.053610001.2416    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7733 9998.7604    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9999.627210000.4122    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6272 9998.7621    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10000.3417 9999.1746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3417 9999.9997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9161 9999.9997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.201710000.4122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.4871 9999.9996    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9997.4871 9999.1747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2016 9998.7621    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9161 9999.1747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0  0  0  0
  2  7  1  1  0  0  0
  3  4  1  0  0  0  0
  3  6  1  1  0  0  0
  4  5  1  0  0  0  0
 11 12  2  0  0  0  0
 13 14  1  0  0  0  0
 18 13  1  0  0  0  0
 12  9  1  0  0  0  0
 10 11  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 12  2  1  0  0  0  0
  1 14  2  0  0  0  0
 16  8  1  0  0  0  0
  9 13  2  0  0  0  0
 18 10  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0151650

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC1=NC(=O)C2=NC(=CNC2=N1)[C@@H](O)[C@H](O)CO

> <INCHI_IDENTIFIER>
InChI=1S/C9H11N5O4/c10-9-13-7-5(8(18)14-9)12-3(1-11-7)6(17)4(16)2-15/h1,4,6,15-17H,2H2,(H3,10,11,13,14,18)/t4-,6-/m1/s1

> <INCHI_KEY>
BMQYVXCPAOLZOK-INEUFUBQSA-N

> <FORMULA>
C9H11N5O4

> <MOLECULAR_WEIGHT>
253.2147

> <EXACT_MASS>
253.081103865

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
23.367358971311564

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-6-[(1R,2R)-1,2,3-trihydroxypropyl]-4,8-dihydropteridin-4-one

> <ALOGPS_LOGP>
-1.90

> <JCHEM_LOGP>
-3.2496949546666665

> <ALOGPS_LOGS>
-2.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.941039152022071

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.181543502791532

> <JCHEM_PKA_STRONGEST_BASIC>
-1.4072930384841507

> <JCHEM_POLAR_SURFACE_AREA>
152.89

> <JCHEM_REFRACTIVITY>
59.35480000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.20e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-amino-6-[(1R,2R)-1,2,3-trihydroxypropyl]-8H-pteridin-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-MAR-20         0                                  
HETATM    1  O   UNK     0    8663.3118668.988   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0    8668.6338667.444   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8669.9698666.670   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8671.3018667.444   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0    8672.6348666.670   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8669.9698665.132   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0    8668.6338668.984   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0    8660.6438664.353   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0    8665.9718667.436   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0    8665.9718664.356   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0    8667.3058665.126   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8667.3058666.666   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8664.6438666.666   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8663.3108667.436   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0    8661.9768666.666   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0    8661.9768665.126   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0    8663.3108664.356   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0    8664.6438665.126   0.000  0.00  0.00           C+0
CONECT    1   14                                                            
CONECT    2    3    7   12                                                  
CONECT    3    2    4    6                                                  
CONECT    4    3    5                                                       
CONECT    5    4                                                            
CONECT    6    3                                                            
CONECT    7    2                                                            
CONECT    8   16                                                            
CONECT    9   12   13                                                       
CONECT   10   11   18                                                       
CONECT   11   12   10                                                       
CONECT   12   11    9    2                                                  
CONECT   13   14   18    9                                                  
CONECT   14   13   15    1                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17    8                                                  
CONECT   17   16   18                                                       
CONECT   18   13   17   10                                                  
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

View in JSmol

Synonyms

Value	Source
2-Amino-6-(1,2,3-trihydroxypropyl)-4(3H)-pteridinone	HMDB
Neopterin, (threo-D)-isomer	HMDB
Neopterin	HMDB
Neopterin, (r, r)-isomer	HMDB
Monapterin	HMDB
Neopterin, (erythro-D)-isomer	HMDB
2-Amino-6-[(1R,2R)-1,2,3-trihydroxypropyl]-4(3H)-pteridinone	HMDB
6-D-Threo-monapterin	HMDB
D-(-)-Monapterin	HMDB
D-6-(Threo-1',2',3'-trihydroxypropyl)pterin	HMDB
D-6-(Threo-1’,2’,3’-trihydroxypropyl)pterin	HMDB
D-Monapterin	HMDB
D-Threo-monapterin	HMDB
D-Threo-neopterin	HMDB
Umanopterin	MeSH

Chemical Formula

C₉H₁₁N₅O₄

Average Mass

253.2147 Da

Monoisotopic Mass

253.08110 Da

IUPAC Name

2-amino-6-[(1R,2R)-1,2,3-trihydroxypropyl]-4,8-dihydropteridin-4-one

Traditional Name

2-amino-6-[(1R,2R)-1,2,3-trihydroxypropyl]-8H-pteridin-4-one

CAS Registry Number

Not Available

SMILES

NC1=NC(=O)C2=NC(=CNC2=N1)[C@@H](O)[C@H](O)CO

InChI Identifier

InChI=1S/C9H11N5O4/c10-9-13-7-5(8(18)14-9)12-3(1-11-7)6(17)4(16)2-15/h1,4,6,15-17H,2H2,(H3,10,11,13,14,18)/t4-,6-/m1/s1

InChI Key

BMQYVXCPAOLZOK-INEUFUBQSA-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
Tetrahymena pyriformis	LOTUS Database	35616633

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
Pyrazine
Pyrimidine
Heteroaromatic compound
Vinylogous amide
Secondary alcohol
Polyol
Azacycle
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Primary amine
Primary alcohol
Alcohol
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Amine
Aromatic alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

neopterins (CHEBI:28670 )

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	-1.9	ALOGPS
logP	-3.2	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	8.18	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	152.89 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	59.35 m³·mol⁻¹	ChemAxon
Polarizability	23.37 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

HMDB ID

HMDB0000877

DrugBank ID

DB02385

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022295

KNApSAcK ID

Not Available

Chemspider ID

392507

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

135460965

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Klein R: Determination of the stereoconfiguration of natural pterins by chiral high-performance liquid chromatography. Anal Biochem. 1992 May 15;203(1):134-40. doi: 10.1016/0003-2697(92)90053-a. [PubMed:1524209 ]
Ogiwara S, Nagatsu T, Teradaira R, Fujita K, Sugimoto T: Diastereomers of neopterin and biopterin in human urine. Biol Chem Hoppe Seyler. 1992 Oct;373(10):1061-5. doi: 10.1515/bchm3.1992.373.2.1061. [PubMed:1329838 ]
LOTUS database [Link]

Showing NP-Card for (1r,2r)-1-(4-hydroxy-2-imino-1h-pteridin-6-yl)propane-1,2,3-triol (NP0151650)

MOL for NP0151650 ((1r,2r)-1-(4-hydroxy-2-imino-1h-pteridin-6-yl)propane-1,2,3-triol)

3D MOL for NP0151650 ((1r,2r)-1-(4-hydroxy-2-imino-1h-pteridin-6-yl)propane-1,2,3-triol)

3D SDF for NP0151650 ((1r,2r)-1-(4-hydroxy-2-imino-1h-pteridin-6-yl)propane-1,2,3-triol)

3D-SDF for NP0151650 ((1r,2r)-1-(4-hydroxy-2-imino-1h-pteridin-6-yl)propane-1,2,3-triol)

PDB for NP0151650 ((1r,2r)-1-(4-hydroxy-2-imino-1h-pteridin-6-yl)propane-1,2,3-triol)

3D PDB for NP0151650 ((1r,2r)-1-(4-hydroxy-2-imino-1h-pteridin-6-yl)propane-1,2,3-triol)

SMILES for NP0151650 ((1r,2r)-1-(4-hydroxy-2-imino-1h-pteridin-6-yl)propane-1,2,3-triol)

INCHI for NP0151650 ((1r,2r)-1-(4-hydroxy-2-imino-1h-pteridin-6-yl)propane-1,2,3-triol)

Structure for NP0151650 ((1r,2r)-1-(4-hydroxy-2-imino-1h-pteridin-6-yl)propane-1,2,3-triol)

3D Structure for NP0151650 ((1r,2r)-1-(4-hydroxy-2-imino-1h-pteridin-6-yl)propane-1,2,3-triol)