NP-MRD: Showing NP-Card for Aurentiacin (NP0054742)

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Record Information

Version

2.0

Created at

2022-04-28 00:59:53 UTC

Updated at

2022-04-28 00:59:54 UTC

NP-MRD ID

NP0054742

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Aurentiacin

Description

Aurentiacin belongs to the class of organic compounds known as 2'-hydroxychalcones. These are organic compounds containing chalcone skeleton that carries a hydroxyl group at the 2'-position. Thus, aurentiacin is considered to be a flavonoid. Aurentiacin is found in Didymocarpus aurantiaca, Didymocarpus aurentiacum, Didymocarpus podocarpa, Myrica pensylvanica and Syzygium samarangense. Aurentiacin was first documented in 2012 (PMID: 22155221). Based on a literature review very few articles have been published on Aurentiacin (PMID: 29692723).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 40 41  0  0  0  0  0  0  0  0999 V2000
   -5.8695    0.3464    0.0230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7215    1.1475    0.3084 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4667    0.6135    0.1330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2922   -0.6507   -0.3027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0207   -1.1326   -0.4599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8856   -2.4545   -0.9158 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9884   -3.2640   -1.2038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8592   -0.3957   -0.1967 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3902   -1.0440   -0.4117 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2537   -2.3104   -0.8504 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7724   -0.7640   -0.3049 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5207    0.2216    0.0411 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0112    0.1981    0.0438 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7576   -0.8765   -0.3221 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1556   -0.8266   -0.2947 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8230    0.3113    0.1034 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0814    1.3857    0.4692 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7011    1.3256    0.4384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0986    0.8761    0.2411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0471    1.6890    0.5298 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3851    1.3901    0.4094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5498    2.7911    0.8924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7359   -0.0415   -1.0201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9128   -0.5001    0.7344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7909    0.9224    0.0997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1708   -1.2480   -0.5154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6712   -4.1542   -1.7735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4983   -3.6559   -0.2859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7534   -2.7523   -1.8268 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4371   -1.6551   -0.6080 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0676    1.1250    0.3499 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3457   -1.7945   -0.6423 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7531   -1.6779   -0.5845 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8952    0.3393    0.1209 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5757    2.2904    0.7854 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1119    2.2067    0.7386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1754    2.6227    0.8516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0780    2.8791    1.8881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0684    3.4746    0.1620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6135    3.0424    0.9179 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  5  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
  8 19  1  0
 19 20  1  0
 19 21  2  0
 21 22  1  0
 21  3  1  0
 18 13  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  7 27  1  0
  7 28  1  0
  7 29  1  0
 11 30  1  0
 12 31  1  0
 14 32  1  0
 15 33  1  0
 16 34  1  0
 17 35  1  0
 18 36  1  0
 20 37  1  0
 22 38  1  0
 22 39  1  0
 22 40  1  0
M  END


  Mrv1652304282202592D          

 22 23  0  0  0  0            999 V2000
    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
    2.8579   -4.1250    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
    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   -4.1250    0.0000 O   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
    4.2868   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  5  8  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 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
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
  3 19  1  0  0  0  0
 19 20  1  0  0  0  0
  1 21  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0054742

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(OC)=C(C(=O)\C=C\C2=CC=CC=C2)C(O)=C1C

> <INCHI_IDENTIFIER>
InChI=1S/C18H18O4/c1-12-15(21-2)11-16(22-3)17(18(12)20)14(19)10-9-13-7-5-4-6-8-13/h4-11,20H,1-3H3/b10-9+

> <INCHI_KEY>
KHJPPYCLBALJRR-MDZDMXLPSA-N

> <FORMULA>
C18H18O4

> <MOLECULAR_WEIGHT>
298.338

> <EXACT_MASS>
298.12050906

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
32.513780108856224

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-1-(2-hydroxy-4,6-dimethoxy-3-methylphenyl)-3-phenylprop-2-en-1-one

> <ALOGPS_LOGP>
4.06

> <JCHEM_LOGP>
4.434838845333333

> <ALOGPS_LOGS>
-4.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.000343643037844

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.572530527715365

> <JCHEM_PKA_STRONGEST_BASIC>
-4.568791428155866

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
86.8255

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.46e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
aurentiacin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.667  -7.700   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       6.668 -10.010   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334 -14.630   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.000 -13.860   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.000 -12.320   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       8.002  -7.700   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2    6   21                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   19                                                  
CONECT    4    3    5    9                                                  
CONECT    5    4    6    8                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    5                                                            
CONECT    9    4   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   13                                                       
CONECT   19    3   20                                                       
CONECT   20   19                                                            
CONECT   21    1   22                                                       
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

View in JSmol

Synonyms

Value	Source
2'-Hydroxy-4',6'-dimethoxy-3'-methylchalcone	MeSH

Chemical Formula

C₁₈H₁₈O₄

Average Mass

298.3380 Da

Monoisotopic Mass

298.12051 Da

IUPAC Name

(2E)-1-(2-hydroxy-4,6-dimethoxy-3-methylphenyl)-3-phenylprop-2-en-1-one

Traditional Name

aurentiacin

CAS Registry Number

Not Available

SMILES

COC1=CC(OC)=C(C(=O)\C=C\C2=CC=CC=C2)C(O)=C1C

InChI Identifier

InChI=1S/C18H18O4/c1-12-15(21-2)11-16(22-3)17(18(12)20)14(19)10-9-13-7-5-4-6-8-13/h4-11,20H,1-3H3/b10-9+

InChI Key

KHJPPYCLBALJRR-MDZDMXLPSA-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
Didymocarpus aurantiaca	Plant	KNApSAcK
Didymocarpus aurentiacum	Plant	KNApSAcK
Didymocarpus podocarpa	Plant	KNApSAcK
Myrica pensylvanica	Plant	KNApSAcK
Syzygium samarangense	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2'-hydroxychalcones. These are organic compounds containing chalcone 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'-Hydroxychalcones

Alternative Parents

Substituents

2'-hydroxychalcone
Cinnamylphenol
Cinnamic acid or derivatives
Methoxyphenol
M-dimethoxybenzene
Dimethoxybenzene
Phenoxy compound
O-cresol
Anisole
Phenol ether
Methoxybenzene
Benzoyl
Aryl ketone
Styrene
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Toluene
Phenol
Benzenoid
Monocyclic benzene moiety
Acryloyl-group
Vinylogous acid
Alpha,beta-unsaturated ketone
Enone
Ketone
Ether
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Chalcones and dihydrochalcones (LMPK12120224 )

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	4.06	ALOGPS
logP	4.43	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	7.57	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	86.83 m³·mol⁻¹	ChemAxon
Polarizability	32.51 Å³	ChemAxon
Number of Rings	2	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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00007043

Chemspider ID

9646874

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11472044

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Henley-Smith CJ, Botha FS, Hussein AA, Nkomo M, Meyer D, Lall N: Biological Activities of Heteropyxis natalensis Against Micro-Organisms Involved in Oral Infections. Front Pharmacol. 2018 Apr 10;9:291. doi: 10.3389/fphar.2018.00291. eCollection 2018. [PubMed:29692723 ]
Kim YJ, Kim HC, Ko H, Amor EC, Lee JW, Yang HO: Inhibitory effects of aurentiacin from Syzygium samarangense on lipopolysaccharide-induced inflammatory response in mouse macrophages. Food Chem Toxicol. 2012 Mar;50(3-4):1027-35. doi: 10.1016/j.fct.2011.11.050. Epub 2011 Dec 4. [PubMed:22155221 ]

Showing NP-Card for Aurentiacin (NP0054742)

MOL for NP0054742 (Aurentiacin)

3D MOL for NP0054742 (Aurentiacin)

3D SDF for NP0054742 (Aurentiacin)

3D-SDF for NP0054742 (Aurentiacin)

PDB for NP0054742 (Aurentiacin)

3D PDB for NP0054742 (Aurentiacin)

SMILES for NP0054742 (Aurentiacin)

INCHI for NP0054742 (Aurentiacin)

Structure for NP0054742 (Aurentiacin)

3D Structure for NP0054742 (Aurentiacin)