NP-MRD: Showing NP-Card for 3'-Formyl-2',4',6'-trihydroxydihydrochalcone (NP0055355)

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Record Information

Version

2.0

Created at

2022-04-28 01:26:01 UTC

Updated at

2022-04-28 01:26:01 UTC

NP-MRD ID

NP0055355

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3'-Formyl-2',4',6'-trihydroxydihydrochalcone

Description

2',4',6'-Trihydroxy-3'-formyldihydrochalcone belongs to the class of organic compounds known as 2'-hydroxy-dihydrochalcones. These are organic compounds containing dihydrochalcone skeleton that carries a hydroxyl group at the 2'-position. Thus, 2',4',6'-trihydroxy-3'-formyldihydrochalcone is considered to be a flavonoid lipid molecule. 3'-Formyl-2',4',6'-trihydroxydihydrochalcone is found in Psidium acutangulum . 3'-Formyl-2',4',6'-trihydroxydihydrochalcone was first documented in 2007 (PMID: 17899027). 2',4',6'-Trihydroxy-3'-formyldihydrochalcone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 35 36  0  0  0  0  0  0  0  0999 V2000
    6.3261    1.1592   -0.4598 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2536    1.5508    0.0341 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0708    0.7187   -0.0540 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1662   -0.4996   -0.6891 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3902   -0.8773   -1.2137 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0464   -1.2620   -0.7634 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7956   -0.8699   -0.2249 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7897   -1.7396   -0.3861 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6908    0.3353    0.4066 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4744    0.8678    1.0069 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5650    2.0443    1.5583 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8508    0.2796    1.0872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6101    0.5431   -0.2093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9663   -0.0089   -0.2261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0766    0.7080    0.2117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3153    0.1221    0.1557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5139   -1.1688   -0.3234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4023   -1.8423   -0.7442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1468   -1.3015   -0.7084 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8650    1.1212    0.4780 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7691    2.3304    1.1096 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2074    2.4964    0.5204 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5669   -1.7419   -1.6941 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1301   -2.2177   -1.2642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1093   -1.8209   -0.1878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4436    0.9176    1.8498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9414   -0.7262    1.4859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0447    0.1946   -1.0886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6586    1.6648   -0.3349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9433    1.7304    0.5941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1901    0.6420    0.4835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4981   -1.6089   -0.3583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5162   -2.8494   -1.1239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3224   -1.9147   -1.0662 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4426    3.0233    1.2632 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0
  4  6  2  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
  9 20  1  0
 20 21  1  0
 20  3  2  0
  3  2  1  0
  2  1  2  0
  3  4  1  0
 19 14  1  0
  5 23  1  0
  6 24  1  0
  8 25  1  0
 12 26  1  0
 12 27  1  0
 13 28  1  0
 13 29  1  0
 15 30  1  0
 16 31  1  0
 17 32  1  0
 18 33  1  0
 19 34  1  0
 21 35  1  0
  2 22  1  0
M  END

  Mrv1533004241507012D          

 21 22  0  0  0  0            999 V2000
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    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   -1.6500    0.0000 O   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
  4  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 11 16  1  0  0  0  0
  6 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
  2 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0055355

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC(O)=C(C(=O)CCC2=CC=CC=C2)C(O)=C1C=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H14O5/c17-9-11-13(19)8-14(20)15(16(11)21)12(18)7-6-10-4-2-1-3-5-10/h1-5,8-9,19-21H,6-7H2

> <INCHI_KEY>
SDPWTOSPDBDEBQ-UHFFFAOYSA-N

> <FORMULA>
C16H14O5

> <MOLECULAR_WEIGHT>
286.283

> <EXACT_MASS>
286.084123551

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
28.8389221199875

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,4,6-trihydroxy-3-(3-phenylpropanoyl)benzaldehyde

> <ALOGPS_LOGP>
3.00

> <JCHEM_LOGP>
5.211608199

> <ALOGPS_LOGS>
-3.44

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.017904782855966

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.791212717151042

> <JCHEM_PKA_STRONGEST_BASIC>
-4.636051365710682

> <JCHEM_POLAR_SURFACE_AREA>
94.83000000000001

> <JCHEM_REFRACTIVITY>
78.3104

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.03e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,4,6-trihydroxy-3-(3-phenylpropanoyl)benzaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       8.002  -7.700   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       6.668 -10.010   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334 -14.630   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.000 -13.860   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.000 -12.320   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   19                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   17                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   11                                                       
CONECT   17    6   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17    2   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₄O₅

Average Mass

286.2830 Da

Monoisotopic Mass

286.08412 Da

IUPAC Name

2,4,6-trihydroxy-3-(3-phenylpropanoyl)benzaldehyde

Traditional Name

2,4,6-trihydroxy-3-(3-phenylpropanoyl)benzaldehyde

CAS Registry Number

Not Available

SMILES

OC1=CC(O)=C(C(=O)CCC2=CC=CC=C2)C(O)=C1C=O

InChI Identifier

InChI=1S/C16H14O5/c17-9-11-13(19)8-14(20)15(16(11)21)12(18)7-6-10-4-2-1-3-5-10/h1-5,8-9,19-21H,6-7H2

InChI Key

SDPWTOSPDBDEBQ-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
Psidium acutangulum	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2'-hydroxy-dihydrochalcones. These are organic compounds containing dihydrochalcone skeleton that carries a hydroxyl group at the 2'-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Linear 1,3-diarylpropanoids

Sub Class

Chalcones and dihydrochalcones

Direct Parent

2'-Hydroxy-dihydrochalcones

Alternative Parents

Substituents

2'-hydroxy-dihydrochalcone
Cinnamylphenol
Alkyl-phenylketone
Acylphloroglucinol derivative
Butyrophenone
Benzenetriol
Phloroglucinol derivative
Hydroxybenzaldehyde
Phenylketone
Aryl alkyl ketone
Aryl ketone
Benzaldehyde
Benzoyl
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Aryl-aldehyde
Phenol
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Ketone
Polyol
Aldehyde
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

polyphenol (CHEBI:28150 )
benzaldehydes (CHEBI:28150 )
dihydrochalcones (CHEBI:28150 )
dihydrochalcones (C09975 )
Chalcones and dihydrochalcones (LMPK12120487 )

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	ALOGPS
logP	5.21	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	6.79	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	94.83 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	78.31 m³·mol⁻¹	ChemAxon
Polarizability	28.84 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	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

C00007994

Chemspider ID

Not Available

KEGG Compound ID

C09975

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

442546

PDB ID

Not Available

ChEBI ID

28150

Good Scents ID

Not Available

References

General References

Arraez-Roman D, Zurek G, Bassmann C, Almaraz-Abarca N, Quirantes R, Segura-Carretero A, Fernandez-Gutierrez A: Identification of phenolic compounds from pollen extracts using capillary electrophoresis-electrospray time-of-flight mass spectrometry. Anal Bioanal Chem. 2007 Nov;389(6):1909-17. doi: 10.1007/s00216-007-1611-6. Epub 2007 Sep 22. [PubMed:17899027 ]

Showing NP-Card for 3'-Formyl-2',4',6'-trihydroxydihydrochalcone (NP0055355)

MOL for NP0055355 (3'-Formyl-2',4',6'-trihydroxydihydrochalcone)

3D MOL for NP0055355 (3'-Formyl-2',4',6'-trihydroxydihydrochalcone)

3D SDF for NP0055355 (3'-Formyl-2',4',6'-trihydroxydihydrochalcone)

3D-SDF for NP0055355 (3'-Formyl-2',4',6'-trihydroxydihydrochalcone)

PDB for NP0055355 (3'-Formyl-2',4',6'-trihydroxydihydrochalcone)

3D PDB for NP0055355 (3'-Formyl-2',4',6'-trihydroxydihydrochalcone)

SMILES for NP0055355 (3'-Formyl-2',4',6'-trihydroxydihydrochalcone)

INCHI for NP0055355 (3'-Formyl-2',4',6'-trihydroxydihydrochalcone)

Structure for NP0055355 (3'-Formyl-2',4',6'-trihydroxydihydrochalcone)

3D Structure for NP0055355 (3'-Formyl-2',4',6'-trihydroxydihydrochalcone)