NP-MRD: Showing NP-Card for Sapropterin (NP0334661)

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Record Information

Version

2.0

Created at

2024-09-10 19:21:48 UTC

Updated at

2024-09-10 19:21:48 UTC

NP-MRD ID

NP0334661

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Sapropterin

Description

Sapropterin 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. Sapropterin was first documented in 2006 (PMID: 32401468). Based on a literature review a small amount of articles have been published on Sapropterin (PMID: 39275225) (PMID: 39237321) (PMID: 38999811) (PMID: 38801163).

Structure

MOL SDF PDB SMILES InChI

Sebacic acid.mol
  Mrv2104 05252321542D          

 17 18  0  0  0  0            999 V2000
   -1.6500   -0.7145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0625    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    0.7145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -1.4289    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.7145    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0625    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6500    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8875    0.0000    0.0000 N   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  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  1 10  1  0  0  0  0
  5 10  2  0  0  0  0
  4 11  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  6  0  0  0
 12 16  1  6  0  0  0
  7 12  1  0  0  0  0
  2 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0334661

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H](O)[C@H](O)C1CNC2=C(N1)C(=O)N=C(N)N2

> <INCHI_IDENTIFIER>
InChI=1/C9H15N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h3-4,6,12,15-16H,2H2,1H3,(H4,10,11,13,14,17)/t3-,4?,6-/s2

> <INCHI_KEY>
FNKQXYHWGSIFBK-CLGFIFAMNA-N

> <FORMULA>
C9H15N5O3

> <MOLECULAR_WEIGHT>
241.251

> <EXACT_MASS>
241.117489363

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
23.68498016409056

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-1,4,5,6,7,8-hexahydropteridin-4-one

> <JCHEM_LOGP>
-2.6621297606666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.010511203269347

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.51676238081279

> <JCHEM_PKA_STRONGEST_BASIC>
5.405484488413579

> <JCHEM_POLAR_SURFACE_AREA>
132.00000000000003

> <JCHEM_REFRACTIVITY>
68.4334

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-5,6,7,8-tetrahydro-1H-pteridin-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-MAY-23   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Sebacic acid.mol                                  
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-MAY-23         0                                  
HETATM    1  N   UNK     0      -3.080  -1.334   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      -3.850   0.000   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      -3.080   1.334   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      -1.540   1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.770   0.000   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       0.770   0.000   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       1.540  -1.334   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.770  -2.667   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      -0.770  -2.667   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      -1.540  -1.334   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.770   2.667   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.080  -1.334   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.850   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.080   1.334   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.390   0.000   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       3.850  -2.667   0.000  0.00  0.00           O+0
HETATM   17  N   UNK     0      -5.390   0.000   0.000  0.00  0.00           N+0
CONECT    1    2   10                                                       
CONECT    2    1    3   17                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   11                                                  
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    1    5                                                  
CONECT   11    4                                                            
CONECT   12   13   16    7                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   12                                                            
CONECT   17    2                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₉H₁₅N₅O₃

Average Mass

241.2510 Da

Monoisotopic Mass

241.11749 Da

IUPAC Name

2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-1,4,5,6,7,8-hexahydropteridin-4-one

Traditional Name

2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-5,6,7,8-tetrahydro-1H-pteridin-4-one

CAS Registry Number

Not Available

SMILES

C[C@H](O)[C@H](O)C1CNC2=C(N1)C(=O)N=C(N)N2

InChI Identifier

InChI=1/C9H15N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h3-4,6,12,15-16H,2H2,1H3,(H4,10,11,13,14,17)/t3-,4?,6-/s2

InChI Key

FNKQXYHWGSIFBK-CLGFIFAMNA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

This compound 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
Pyrimidine
1,3-aminoalcohol
Vinylogous amide
Heteroaromatic compound
Secondary alcohol
1,2-diol
1,2-aminoalcohol
Secondary amine
Azacycle
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Primary amine
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Amine
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

5,6,7,8-tetrahydrobiopterin (CHEBI:64491 )

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	-2.7	ChemAxon
pKa (Strongest Acidic)	13.52	ChemAxon
pKa (Strongest Basic)	5.41	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	132 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	68.43 m³·mol⁻¹	ChemAxon
Polarizability	23.68 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

Tetrahydrobiopterin

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Pinto A, Ahring K, Almeida MF, Ashmore C, Belanger-Quintana A, Burlina A, Coskun T, Daly A, van Dam E, Dursun A, Evans S, Feillet F, Gizewska M, Gokmen-Ozel H, Hickson M, Hoekstra Y, Ilgaz F, Jackson R, Lesniak A, Loro C, Malicka K, Patalan M, Rocha JC, Sivri S, Rodenburg I, van Spronsen F, Straczek K, Tokatli A, MacDonald A: Longitudinal Dietary Intake Data in Patients with Phenylketonuria from Europe: The Impact of Age and Phenylketonuria Severity. Nutrients. 2024 Aug 31;16(17):2909. doi: 10.3390/nu16172909. [PubMed:39275225 ]
Feillet F, Arnoux JB, Delgado MB, Burlina A, Chabrol B, Kucuksayrac E, Lagler FB, Muntau AC, Olsson D, Paci S, Rutsch F, van Spronsen FJ: Long-term safety of sapropterin in paediatric and adult individuals with phenylalanine hydroxylase deficiency: Final results of the Kuvan(R) Adult Maternal Paediatric European Registry multinational observational study. J Inherit Metab Dis. 2024 Sep 5. doi: 10.1002/jimd.12796. [PubMed:39237321 ]
Pinto A, Ahring K, Almeida MF, Ashmore C, Belanger-Quintana A, Burlina A, Coskun T, Daly A, van Dam E, Dursun A, Evans S, Feillet F, Gizewska M, Gokmen-Ozel H, Hickson M, Hoekstra Y, Ilgaz F, Jackson R, Lesniak A, Loro C, Malicka K, Patalan M, Rocha JC, Sivri S, Rodenburg I, van Spronsen F, Straczek K, Tokatli A, MacDonald A: Blood Phenylalanine Levels in Patients with Phenylketonuria from Europe between 2012 and 2018: Is It a Changing Landscape? Nutrients. 2024 Jun 28;16(13):2064. doi: 10.3390/nu16132064. [PubMed:38999811 ]
Delbreil P, Dhondt S, Kenaan El Rahbani RM, Banquy X, Mitchell JJ, Brambilla D: Current Advances and Material Innovations in the Search for Novel Treatments of Phenylketonuria. Adv Healthc Mater. 2024 May 27:e2401353. doi: 10.1002/adhm.202401353. [PubMed:38801163 ]
Authors unspecified: Sapropterin.. 2006. [PubMed:32401468 ]

Showing NP-Card for Sapropterin (NP0334661)

MOL for NP0334661 (Sapropterin)

3D MOL for NP0334661 (Sapropterin)

3D SDF for NP0334661 (Sapropterin)

3D-SDF for NP0334661 (Sapropterin)

PDB for NP0334661 (Sapropterin)

3D PDB for NP0334661 (Sapropterin)

SMILES for NP0334661 (Sapropterin)

INCHI for NP0334661 (Sapropterin)

Structure for NP0334661 (Sapropterin)

3D Structure for NP0334661 (Sapropterin)