NP-MRD: Showing NP-Card for 2,4,5-Trihydroxybutyrophenone (NP0337077)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2024-09-11 09:10:29 UTC

Updated at

2024-09-11 09:10:29 UTC

NP-MRD ID

NP0337077

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,4,5-Trihydroxybutyrophenone

Description

1-(2,4,5-Trihydroxyphenyl)-1-butanone, also known as 2',4',5'-trihydroxy-butyrophenone or 5,6,7,8-erythro-tetrahydrobiopterin, belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. 1-(2,4,5-Trihydroxyphenyl)-1-butanone is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061309372D          

 14 14  0  0  0  0            999 V2000
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   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    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   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
    0.7145   -0.4125    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 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  6  4  2  0  0  0  0
  7  3  1  0  0  0  0
  7  6  1  0  0  0  0
  8  5  2  0  0  0  0
  8  6  1  0  0  0  0
  9  4  1  0  0  0  0
 10  5  1  0  0  0  0
 10  9  2  0  0  0  0
 11  7  2  0  0  0  0
 12  8  1  0  0  0  0
 13  9  1  0  0  0  0
 14 10  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0337077

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCC(=O)C1=CC(O)=C(O)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C10H12O4/c1-2-3-7(11)6-4-9(13)10(14)5-8(6)12/h4-5,12-14H,2-3H2,1H3

> <INCHI_KEY>
SRUQARLMFOLRDN-UHFFFAOYSA-N

> <FORMULA>
C10H12O4

> <MOLECULAR_WEIGHT>
196.1999

> <EXACT_MASS>
196.073558872

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
19.717786505586357

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-(2,4,5-trihydroxyphenyl)butan-1-one

> <ALOGPS_LOGP>
1.82

> <JCHEM_LOGP>
2.4153018816666663

> <ALOGPS_LOGS>
-1.92

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.276556785215794

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.983902700382564

> <JCHEM_PKA_STRONGEST_BASIC>
-3.8340689226758142

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
51.631400000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.34e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,4,5-trihydroxybutyrophenone

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+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   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    7                                                       
CONECT    4    6    9                                                       
CONECT    5    8   10                                                       
CONECT    6    4    7    8                                                  
CONECT    7    3    6   11                                                  
CONECT    8    5    6   12                                                  
CONECT    9    4   10   13                                                  
CONECT   10    5    9   14                                                  
CONECT   11    7                                                            
CONECT   12    8                                                            
CONECT   13    9                                                            
CONECT   14   10                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

View in JSmol

Synonyms

Value	Source
1-(2,4,5-Trihydroxyphenyl)butan-1-one	HMDB
2',4',5'-Trihydroxy-butyrophenone	HMDB
2',4',5'-Trihydroxybutyrophenone	HMDB
2',4',5'-Trihydroxybutyrophenone, 8ci	HMDB
2,4,5-Trihydroxybutyrophenone	HMDB
5-Butanoyl-1,2,4-benzeneetriol	HMDB
THBP	HMDB
5,6,7,8-Erythro-tetrahydrobiopterin	HMDB
5,6,7,8-Tetrahydrobiopterin	HMDB
5,6,7,8-Tetrahydrobiopterin, (S-(r,s))-isomer	HMDB
5,6,7,8-Tetrahydrodictyopterin	HMDB
BPH4	HMDB
D-Threo-tetrahydrobiopterin	HMDB
Tetrahydro-6-biopterin	HMDB
5,6,7,8-Tetrahydro-L-erythrobiopterin	HMDB
Sapropterin dihydrochloride	HMDB
Tetrahydrobiopterin	HMDB
6R-BH4	HMDB
6R-L-Erythro-5,6,7,8-tetrahydrobiopterin	HMDB
Kuvan	HMDB
Phenylalanine hydroxylase cofactor	HMDB
Sapropterin	HMDB
1-Butanone, 1-(2,4,5-trihydroxyphenyl)	MeSH
Trihydroxybutyrophenone	MeSH

Chemical Formula

C₁₀H₁₂O₄

Average Mass

196.1999 Da

Monoisotopic Mass

196.07356 Da

IUPAC Name

1-(2,4,5-trihydroxyphenyl)butan-1-one

Traditional Name

2,4,5-trihydroxybutyrophenone

CAS Registry Number

Not Available

SMILES

CCCC(=O)C1=CC(O)=C(O)C=C1O

InChI Identifier

InChI=1S/C10H12O4/c1-2-3-7(11)6-4-9(13)10(14)5-8(6)12/h4-5,12-14H,2-3H2,1H3

InChI Key

SRUQARLMFOLRDN-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alkyl-phenylketones

Alternative Parents

Substituents

Alkyl-phenylketone
Butyrophenone
Hydroxyquinol derivative
Aryl alkyl ketone
Benzoyl
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Polyol
Organic oxide
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	1.82	ALOGPS
logP	2.42	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	7.98	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	51.63 m³·mol⁻¹	ChemAxon
Polarizability	19.72 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0037177

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB016173

KNApSAcK ID

Not Available

Chemspider ID

14286

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15008

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 2,4,5-Trihydroxybutyrophenone (NP0337077)

MOL for NP0337077 (2,4,5-Trihydroxybutyrophenone)

3D MOL for NP0337077 (2,4,5-Trihydroxybutyrophenone)

3D SDF for NP0337077 (2,4,5-Trihydroxybutyrophenone)

3D-SDF for NP0337077 (2,4,5-Trihydroxybutyrophenone)

PDB for NP0337077 (2,4,5-Trihydroxybutyrophenone)

3D PDB for NP0337077 (2,4,5-Trihydroxybutyrophenone)

SMILES for NP0337077 (2,4,5-Trihydroxybutyrophenone)

INCHI for NP0337077 (2,4,5-Trihydroxybutyrophenone)

Structure for NP0337077 (2,4,5-Trihydroxybutyrophenone)

3D Structure for NP0337077 (2,4,5-Trihydroxybutyrophenone)