NP-MRD: Showing NP-Card for 4α-hydroxy-tetrahydrobiopterin (NP0334706)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2024-09-10 19:36:34 UTC

Updated at

2024-09-10 19:36:34 UTC

NP-MRD ID

NP0334706

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4α-hydroxy-tetrahydrobiopterin

Description

4α-Hydroxy-tetrahydrobiopterin 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 4α-hydroxy-tetrahydrobiopterin.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 05252322082D          

 18 19  0  0  0  0            999 V2000
   15.8234  -15.4311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1088  -15.8435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3949  -15.4311    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1088  -16.6685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3949  -17.0811    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8234  -17.0811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8234  -17.9061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5380  -18.3185    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.2525  -17.9061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9672  -18.3185    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.6811  -17.9061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3957  -18.3185    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.6811  -17.0811    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.9672  -16.6685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9672  -15.8435    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.2525  -17.0811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5380  -16.6685    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.2525  -16.2561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  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
  6 17  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 16  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0334706

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(O)C(O)C1CNC2=NC(N)=NC(=O)C2(O)N1

> <INCHI_IDENTIFIER>
InChI=1/C9H15N5O4/c1-3(15)5(16)4-2-11-6-9(18,14-4)7(17)13-8(10)12-6/h3-5,14-16,18H,2H2,1H3,(H3,10,11,12,13,17)

> <INCHI_KEY>
KJKIEFUPAPPGBC-UHFFFAOYNA-N

> <FORMULA>
C9H15N5O4

> <MOLECULAR_WEIGHT>
257.25

> <EXACT_MASS>
257.112403983

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
24.195453908492482

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-6-(1,2-dihydroxypropyl)-4a-hydroxy-4,4a,5,6,7,8-hexahydropteridin-4-one

> <JCHEM_LOGP>
-3.1342584666666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.535559581320525

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.80938663519646

> <JCHEM_PKA_STRONGEST_BASIC>
2.7913203335960866

> <JCHEM_POLAR_SURFACE_AREA>
152.55999999999997

> <JCHEM_REFRACTIVITY>
58.5953

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
4a-hydroxytetrahydrobiopterin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-MAY-23         0                                  
HETATM    1  C   UNK     0      29.537 -28.805   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      28.203 -29.575   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      26.870 -28.805   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      28.203 -31.115   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      26.870 -31.885   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      29.537 -31.885   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      29.537 -33.425   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      30.871 -34.195   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      32.205 -33.425   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      33.539 -34.195   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      34.871 -33.425   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0      36.205 -34.195   0.000  0.00  0.00           N+0
HETATM   13  N   UNK     0      34.871 -31.885   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0      33.539 -31.115   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      33.539 -29.575   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      32.205 -31.885   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0      30.871 -31.115   0.000  0.00  0.00           N+0
HETATM   18  O   UNK     0      32.205 -30.345   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   17                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   16                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16    9   14   17   18                                             
CONECT   17    6   16                                                       
CONECT   18   16                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₉H₁₅N₅O₄

Average Mass

257.2500 Da

Monoisotopic Mass

257.11240 Da

IUPAC Name

2-amino-6-(1,2-dihydroxypropyl)-4a-hydroxy-4,4a,5,6,7,8-hexahydropteridin-4-one

Traditional Name

4a-hydroxytetrahydrobiopterin

CAS Registry Number

Not Available

SMILES

CC(O)C(O)C1CNC2=NC(N)=NC(=O)C2(O)N1

InChI Identifier

InChI=1/C9H15N5O4/c1-3(15)5(16)4-2-11-6-9(18,14-4)7(17)13-8(10)12-6/h3-5,14-16,18H,2H2,1H3,(H3,10,11,12,13,17)

InChI Key

KJKIEFUPAPPGBC-UHFFFAOYNA-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
Hydropyrimidine
1,2,5,6-tetrahydropyrimidine
Imidolactam
1,2-diol
Secondary alcohol
Alkanolamine
Amidine
Carboxylic acid amidine
Secondary aliphatic amine
Azacycle
Secondary amine
Carboximidamide
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Organopnictogen compound
Hydrocarbon derivative
Imine
Organonitrogen compound
Organooxygen compound
Alcohol
Amine
Organic oxygen compound
Organic nitrogen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

tetrahydropterin (CHEBI:15374 )
a small molecule (CPD-5881 )

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	-3.1	ChemAxon
pKa (Strongest Acidic)	9.81	ChemAxon
pKa (Strongest Basic)	2.79	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	152.56 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	58.6 m³·mol⁻¹	ChemAxon
Polarizability	24.2 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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 4α-hydroxy-tetrahydrobiopterin (NP0334706)

MOL for NP0334706 (4α-hydroxy-tetrahydrobiopterin)

3D MOL for NP0334706 (4α-hydroxy-tetrahydrobiopterin)

3D SDF for NP0334706 (4α-hydroxy-tetrahydrobiopterin)

3D-SDF for NP0334706 (4α-hydroxy-tetrahydrobiopterin)

PDB for NP0334706 (4α-hydroxy-tetrahydrobiopterin)

3D PDB for NP0334706 (4α-hydroxy-tetrahydrobiopterin)

SMILES for NP0334706 (4α-hydroxy-tetrahydrobiopterin)

INCHI for NP0334706 (4α-hydroxy-tetrahydrobiopterin)

Structure for NP0334706 (4α-hydroxy-tetrahydrobiopterin)

3D Structure for NP0334706 (4α-hydroxy-tetrahydrobiopterin)