NP-MRD: Showing NP-Card for Prudomestin (NP0046037)

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Record Information

Version

2.0

Created at

2022-03-17 19:47:22 UTC

Updated at

2022-03-17 19:47:22 UTC

NP-MRD ID

NP0046037

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Prudomestin

Description

Prudomestin belongs to the class of organic compounds known as flavonols. Flavonols are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-position. Thus, prudomestin is considered to be a flavonoid lipid molecule. Prudomestin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Prudomestin has been detected, but not quantified in, european plums and fruits. Prudomestin is found in Calceolaria irazeunsis, Pityrogramma triangularis, Zanthoxylum acanthopodium and Zanthoxylum integrifoliolum. This could make prudomestin a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241217382D          

 24 26  0  0  0  0            999 V2000
   -2.7143   -0.4328    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0328   -0.8091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0325   -1.6587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3113   -2.1061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3510   -2.8836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5718    0.3462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2927    0.7472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0137    0.2996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9741   -0.4778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2531   -0.8788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5718   -0.5024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1306   -0.4554    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8509   -0.9034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8120   -1.6805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5327   -2.1292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0915   -2.9310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0910   -2.0815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5905   -1.7052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5905   -0.8565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3118   -0.4081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2722    0.3693    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9216    0.8577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7347    0.7007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7347    1.5493    0.0000 C   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
  2 20  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4 18  2  0  0  0  0
  6  7  2  0  0  0  0
  6 11  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 23  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 13  1  0  0  0  0
 12 13  1  0  0  0  0
 12 19  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 17  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 23 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0046037

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(C=C1)C1=C(O)C(=O)C2=C(O)C=C(O)C(OC)=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C17H14O7/c1-22-9-5-3-8(4-6-9)15-14(21)13(20)12-10(18)7-11(19)16(23-2)17(12)24-15/h3-7,18-19,21H,1-2H3

> <INCHI_KEY>
HLSIOUXODPWHFI-UHFFFAOYSA-N

> <FORMULA>
C17H14O7

> <MOLECULAR_WEIGHT>
330.2889

> <EXACT_MASS>
330.073952802

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
32.52951888277514

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,5,7-trihydroxy-8-methoxy-2-(4-methoxyphenyl)-4H-chromen-4-one

> <ALOGPS_LOGP>
2.29

> <JCHEM_LOGP>
2.448087576

> <ALOGPS_LOGS>
-3.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.03937072620772

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.966828285806991

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9327842631549705

> <JCHEM_POLAR_SURFACE_AREA>
105.45000000000002

> <JCHEM_REFRACTIVITY>
85.82679999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.10e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
prudomestin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0      -5.067  -0.808   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -3.794  -1.510   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.794  -3.096   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.448  -3.931   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -2.522  -5.383   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.934   0.646   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.280   1.395   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.626   0.559   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.552  -0.892   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.206  -1.640   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.934  -0.938   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.244  -0.850   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.588  -1.686   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.516  -3.137   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.861  -3.975   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       0.171  -5.471   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.170  -3.885   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.102  -3.183   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.102  -1.599   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.449  -0.762   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -2.375   0.689   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -3.587   1.601   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.972   1.308   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       6.972   2.892   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   20                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   18                                                  
CONECT    5    4                                                            
CONECT    6    7   11                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   23                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11    6   10   13                                                  
CONECT   12   13   19                                                       
CONECT   13   11   12   14                                                  
CONECT   14   13   15   17                                                  
CONECT   15   14                                                            
CONECT   16   17                                                            
CONECT   17   14   16   18                                                  
CONECT   18    4   17   19                                                  
CONECT   19   12   18   20                                                  
CONECT   20    2   19   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23    8   24                                                       
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Value	Source
3,5,7-Trihydroxy-8-methoxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one	HMDB
5,7-Dihydroxy-4',8-dimethoxyflavonol	HMDB
Herbacetin 8,4'-dimethyl ether	HMDB

Chemical Formula

C₁₇H₁₄O₇

Average Mass

330.2889 Da

Monoisotopic Mass

330.07395 Da

IUPAC Name

3,5,7-trihydroxy-8-methoxy-2-(4-methoxyphenyl)-4H-chromen-4-one

Traditional Name

prudomestin

CAS Registry Number

3443-28-5

SMILES

COC1=CC=C(C=C1)C1=C(O)C(=O)C2=C(O)C=C(O)C(OC)=C2O1

InChI Identifier

InChI=1S/C17H14O7/c1-22-9-5-3-8(4-6-9)15-14(21)13(20)12-10(18)7-11(19)16(23-2)17(12)24-15/h3-7,18-19,21H,1-2H3

InChI Key

HLSIOUXODPWHFI-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
Calceolaria irazeunsis	Plant	KNApSAcK
Pityrogramma triangularis	Plant	KNApSAcK
Prunus domestica	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Zanthoxylum acanthopodium	LOTUS Database	35616633
Zanthoxylum integrifoliolum	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonols. Flavonols are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavones

Direct Parent

Flavonols

Alternative Parents

Substituents

3-hydroxyflavone
8-methoxyflavonoid-skeleton
4p-methoxyflavonoid-skeleton
Hydroxyflavonoid
7-hydroxyflavonoid
5-hydroxyflavonoid
3-hydroxyflavonoid
Chromone
1-benzopyran
Benzopyran
Methoxybenzene
Phenoxy compound
Anisole
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
Monocyclic benzene moiety
Benzenoid
Pyran
Vinylogous acid
Heteroaromatic compound
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavones and Flavonols (LMPK12113159 )

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	2.29	ALOGPS
logP	2.45	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	6.97	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	105.45 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	85.83 m³·mol⁻¹	ChemAxon
Polarizability	32.53 Å³	ChemAxon
Number of Rings	3	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

HMDB0030811

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB002765

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

10404353

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Prudomestin (NP0046037)

MOL for NP0046037 (Prudomestin)

3D MOL for NP0046037 (Prudomestin)

3D SDF for NP0046037 (Prudomestin)

3D-SDF for NP0046037 (Prudomestin)

PDB for NP0046037 (Prudomestin)

3D PDB for NP0046037 (Prudomestin)

SMILES for NP0046037 (Prudomestin)

INCHI for NP0046037 (Prudomestin)

Structure for NP0046037 (Prudomestin)

3D Structure for NP0046037 (Prudomestin)