NP-MRD: Showing NP-Card for 2-Hydroxypseudobaptigenin (NP0045564)

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Record Information

Version

2.0

Created at

2022-03-17 19:31:56 UTC

Updated at

2022-03-17 19:31:56 UTC

NP-MRD ID

NP0045564

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-Hydroxypseudobaptigenin

Description

2-Hydroxypseudobaptigenin, also known as DMI, belongs to the class of organic compounds known as isoflavones. These are polycyclic compounds containing a 2-isoflavene skeleton which bears a ketone group at the C4 carbon atom. Thus, 2-hydroxypseudobaptigenin is considered to be a flavonoid lipid molecule. 2-Hydroxypseudobaptigenin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 2-Hydroxypseudobaptigenin exists in all living organisms, ranging from bacteria to humans. Outside of the human body, 2-Hydroxypseudobaptigenin has been detected, but not quantified in, common pea. This could make 2-hydroxypseudobaptigenin a potential biomarker for the consumption of these foods. 2-Hydroxypseudobaptigenin is found in Paraburkholderia phymatum. A pseudobaptigenin that is pseudobaptigenin substituted by a hydroxy groups at position 2'.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652310051713152D          

 22 25  0  0  0  0            999 V2000
    5.4957   -6.4729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -6.0604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102   -5.2354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -3.9979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102   -6.0604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -5.2354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -3.9979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -4.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -4.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9246   -6.4729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -5.2354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -3.9979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -3.8404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -2.5055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  8  1  1  0  0  0  0
  8  3  2  0  0  0  0
  9  2  1  0  0  0  0
 10  4  2  0  0  0  0
 11  6  2  0  0  0  0
 11 10  1  0  0  0  0
 12  5  2  0  0  0  0
 12 10  1  0  0  0  0
 13  3  1  0  0  0  0
 13  9  2  0  0  0  0
 14  4  1  0  0  0  0
 15  5  1  0  0  0  0
 15 14  2  0  0  0  0
 16  9  1  0  0  0  0
 16 11  1  0  0  0  0
 17  8  1  0  0  0  0
 18 12  1  0  0  0  0
 19 16  2  0  0  0  0
 20  6  1  0  0  0  0
 20 13  1  0  0  0  0
 21  7  1  0  0  0  0
 21 14  1  0  0  0  0
 22  7  1  0  0  0  0
 22 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0045564

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC2=C(C=C1)C(=O)C(=CO2)C1=CC2=C(OCO2)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C16H10O6/c17-8-1-2-9-13(3-8)20-6-11(16(9)19)10-4-14-15(5-12(10)18)22-7-21-14/h1-6,17-18H,7H2

> <INCHI_KEY>
WMDDXGLVVGBJSO-UHFFFAOYSA-N

> <FORMULA>
C16H10O6

> <MOLECULAR_WEIGHT>
298.247

> <EXACT_MASS>
298.047738052

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
29.04461507315746

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-hydroxy-3-(6-hydroxy-2H-1,3-benzodioxol-5-yl)-4H-chromen-4-one

> <ALOGPS_LOGP>
2.72

> <JCHEM_LOGP>
2.353671179

> <ALOGPS_LOGS>
-3.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.914177964902532

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.471157130361519

> <JCHEM_PKA_STRONGEST_BASIC>
-4.645752566050498

> <JCHEM_POLAR_SURFACE_AREA>
85.22000000000001

> <JCHEM_REFRACTIVITY>
75.4689

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.49e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-hydroxypseudobaptigenin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-OCT-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-OCT-17         0                                  
HETATM    1  C   UNK     0      10.259 -12.083   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.925 -11.313   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.592  -9.773   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.924  -7.463   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.924  -4.383   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.925  -6.693   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.220  -5.923   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.592 -11.313   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.925  -9.773   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.258  -6.693   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.591  -7.463   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.258  -5.153   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.259  -9.003   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.590  -6.693   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.590  -5.153   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.591  -9.003   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      12.926 -12.083   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       7.591  -4.383   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       6.258  -9.773   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      10.259  -7.463   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       2.126  -7.169   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       2.126  -4.677   0.000  0.00  0.00           O+0
CONECT    1    2    8                                                       
CONECT    2    1    9                                                       
CONECT    3    8   13                                                       
CONECT    4   10   14                                                       
CONECT    5   12   15                                                       
CONECT    6   11   20                                                       
CONECT    7   21   22                                                       
CONECT    8    1    3   17                                                  
CONECT    9    2   13   16                                                  
CONECT   10    4   11   12                                                  
CONECT   11    6   10   16                                                  
CONECT   12    5   10   18                                                  
CONECT   13    3    9   20                                                  
CONECT   14    4   15   21                                                  
CONECT   15    5   14   22                                                  
CONECT   16    9   11   19                                                  
CONECT   17    8                                                            
CONECT   18   12                                                            
CONECT   19   16                                                            
CONECT   20    6   13                                                       
CONECT   21    7   14                                                       
CONECT   22    7   15                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

View in JSmol

Synonyms

Value	Source
DMI	ChEBI

Chemical Formula

C₁₆H₁₀O₆

Average Mass

298.2470 Da

Monoisotopic Mass

298.04774 Da

IUPAC Name

7-hydroxy-3-(6-hydroxy-2H-1,3-benzodioxol-5-yl)-4H-chromen-4-one

Traditional Name

2-hydroxypseudobaptigenin

CAS Registry Number

21495-84-1

SMILES

OC1=CC2=C(C=C1)C(=O)C(=CO2)C1=CC2=C(OCO2)C=C1O

InChI Identifier

InChI=1S/C16H10O6/c17-8-1-2-9-13(3-8)20-6-11(16(9)19)10-4-14-15(5-12(10)18)22-7-21-14/h1-6,17-18H,7H2

InChI Key

WMDDXGLVVGBJSO-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Paraburkholderia phymatum	-	KNApSAcK
Pisum sativum	FooDB	KNAPSACK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoflavones. These are polycyclic compounds containing a 2-isoflavene skeleton which bears a ketone group at the C4 carbon atom.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Isoflav-2-enes

Direct Parent

Isoflavones

Alternative Parents

Substituents

Isoflavone
Hydroxyisoflavonoid
Chromone
Benzopyran
1-benzopyran
Benzodioxole
Pyranone
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Pyran
Heteroaromatic compound
Oxacycle
Organoheterocyclic compound
Acetal
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

benzodioxoles (CHEBI:80393 )
hydroxyisoflavone (CHEBI:80393 )
isoflavones (C16226 )
Isoflavonoids (LMPK12050082 )
a small molecule (CPD-3629 )

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	2.72	ALOGPS
logP	2.35	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	6.47	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	85.22 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	75.47 m³·mol⁻¹	ChemAxon
Polarizability	29.04 Å³	ChemAxon
Number of Rings	4	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

HMDB0150599

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB001445

KNApSAcK ID

C00000649

Chemspider ID

Not Available

KEGG Compound ID

C16226

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

23724666

PDB ID

Not Available

ChEBI ID

80393

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 2-Hydroxypseudobaptigenin (NP0045564)

MOL for NP0045564 (2-Hydroxypseudobaptigenin)

3D MOL for NP0045564 (2-Hydroxypseudobaptigenin)

3D SDF for NP0045564 (2-Hydroxypseudobaptigenin)

3D-SDF for NP0045564 (2-Hydroxypseudobaptigenin)

PDB for NP0045564 (2-Hydroxypseudobaptigenin)

3D PDB for NP0045564 (2-Hydroxypseudobaptigenin)

SMILES for NP0045564 (2-Hydroxypseudobaptigenin)

INCHI for NP0045564 (2-Hydroxypseudobaptigenin)

Structure for NP0045564 (2-Hydroxypseudobaptigenin)

3D Structure for NP0045564 (2-Hydroxypseudobaptigenin)