NP-MRD: Showing NP-Card for Acacetin (NP0043833)

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Record Information

Version

2.0

Created at

2021-06-22 17:24:52 UTC

Updated at

2021-08-20 00:00:44 UTC

NP-MRD ID

NP0043833

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Acacetin

Description

5,7-Dihydroxy-4'-methoxyflavone, also known as 4'-methoxy-5,7-dihydroxyflavone or acacetin, belongs to the class of organic compounds known as 4'-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C4' atom of the flavonoid backbone. Thus, 5,7-dihydroxy-4'-methoxyflavone is considered to be a flavonoid. 5,7-Dihydroxy-4'-methoxyflavone exists in all living organisms, ranging from bacteria to humans. 5,7-Dihydroxy-4'-methoxyflavone is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Acacetin is found in Agastache foeniculum, Agastache rugosa, Alnus glutinosa, Alnus japonica, Apis mellifera, Argyrochosma nivea, Arnica amplexicaulis, Arnica chamissonis, Fridericia chica, Artemisia afra, Artemisia fragrans, Artemisia gmelinii, Artemisia judaica, Artemisia molinieri, Artemisia princeps, Artemisia transiliensis, Baccharis darwinii, Baccharis dracunculifolia, Baccharis patagonica, Baccharis salicifolia, Bahiopsis reticulata, Balsamorhiza deltoidea, Betula pendula, Buddleja davidii, Buddleja officinalis, Calea jamaicensis, Calea ternifolia, Caragana frutex, Carthamus tinctorius, Centaurea cuneifolia, Centaurea pallescens, Chromolaena odorata, Chrysanthemum boreale, Chrysanthemum indicum, Chrysanthemum morifolium, Cirsium japonicum, Cirsium oleraceum, Cirsium rhinoceros, Cistus ladanifer, Cistus laurifolius, Citrus reticulata, Combretum caffrum, Crocus aureus, Crocus heuffelianus, Crocus laevigatus, Cunila lythrifolia, Dracocephalum multicaule, Elsholtzia ciliata, Eriodictyon sessilifolium, Ageratina altissima, Fouquieria splendens, Frullania teneriffae, Garcinia kola, Verbena bipinnatifida, Grindelia camporum, Grindelia hirsutula, Gymnocarpium robertianum, Klasea flavescens, Lawsonia alba , Lepidaploa rufogrisea, Linaria aeruginea, Linaria kurdica, Linaria macroura, Lupinus texensis, Lychnophora ericoides, Lycopus lucidus, Meehania fargesii, Mentha piperita, Microglossa pyrifolia, Micromeria croatica, Mirabilis viscosa, Mosla scabra, Notholaena greggii, Notholaena rigida, Ocimum basilicum L. , Ocimum africanum, Onopordum illyricum, Origanum akhadarense, Origanum boissieri, Origanum hypercifolium, Origanum majorana , Origanum micranthum, Origanum vulgare , Picea neoveitchii, Plazia daphnoides, Pogostemon stellatus, Populus grandidentata, Populus tremula, Populus tremuloides, Salvia dorrii, Salvia sclarea, Scoparia dulcis L. , Sida rhombifolia , Striga asiatica, Tanacetum vulgare, Teucrium japonicum, Tricostularia neesii, Trifolium repens , Turnera diffusa, Valeriana spryginii, Veratrum dahuricum, Verbascum lychnitis, Verbena hybrida, Veronica officinalis , Veronica orchidea, Veronica teucrium, Volkameria inermis, Xanthorrhoea australis and Ziziphora clinopodioides. Acacetin was first documented in 2010 (PMID: 19693651). Based on a literature review a small amount of articles have been published on 5,7-dihydroxy-4'-methoxyflavone (PMID: 21993665) (PMID: 22360797) (PMID: 23325489).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

NP0043833
     RDKit          3D

 33 35  0  0  0  0  0  0  0  0999 V2000
    6.2786    0.0416   -0.3443 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3322   -0.5706    0.5055 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9697   -0.4028    0.3005 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5763    0.3810   -0.7601 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2090    0.5692   -0.9927 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2724   -0.0140   -0.1826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1553    0.1619   -0.3975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6473    0.9211   -1.4229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0167    1.0640   -1.5939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4501    1.7659   -2.5421 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8652    0.4305   -0.7166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2381    0.5057   -0.7954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8414    1.2338   -1.7765 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0443   -0.1729    0.1426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5039   -0.9191    1.1494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3234   -1.5938    2.0821 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1349   -0.9968    1.2316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3200   -0.3273    0.3059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0185   -0.4135    0.4009 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7038   -0.7963    0.8752 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0382   -1.0102    1.1435 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0462   -0.1399   -1.4139 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2833   -0.3730   -0.1661 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2304    1.1397   -0.1876 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2676    0.8594   -1.4233 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9444    1.1947   -1.8398 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0073    1.4398   -2.1405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5578    1.7679   -2.5086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1122   -0.0951    0.0550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6270   -1.1712    2.9365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6996   -1.5753    2.0119 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9992   -1.2864    1.5547 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3971   -1.6179    1.9648 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  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
  6 20  1  0
 20 21  2  0
 21  3  1  0
 19  7  1  0
 18 11  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  5 26  1  0
  8 27  1  0
 13 28  1  0
 14 29  1  0
 16 30  1  0
 17 31  1  0
 20 32  1  0
 21 33  1  0
M  END

  Mrv1652306222119242D          

 21 23  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
   -2.1434   -2.8875    0.0000 O   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 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
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    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   -0.4125    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
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   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
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 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
 18 19  1  0  0  0  0
  9 19  1  0  0  0  0
 16 20  1  0  0  0  0
 14 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0043833

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C16H12O5/c1-20-11-4-2-9(3-5-11)14-8-13(19)16-12(18)6-10(17)7-15(16)21-14/h2-8,17-18H,1H3

> <INCHI_KEY>
DANYIYRPLHHOCZ-UHFFFAOYSA-N

> <FORMULA>
C16H12O5

> <MOLECULAR_WEIGHT>
284.2635

> <EXACT_MASS>
284.068473494

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
28.90078151269683

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,7-dihydroxy-2-(4-methoxyphenyl)-4H-chromen-4-one

> <ALOGPS_LOGP>
3.46

> <JCHEM_LOGP>
2.8525831896666665

> <ALOGPS_LOGS>
-3.70

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.180448958193105

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.5777812570326235

> <JCHEM_PKA_STRONGEST_BASIC>
-4.723975378863438

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
77.3962

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.61e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
acacetin

> <JCHEM_VEBER_RULE>
0

$$$$

NP0043833
     RDKit          3D

 33 35  0  0  0  0  0  0  0  0999 V2000
    6.2786    0.0416   -0.3443 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3322   -0.5706    0.5055 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9697   -0.4028    0.3005 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5763    0.3810   -0.7601 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2090    0.5692   -0.9927 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2724   -0.0140   -0.1826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1553    0.1619   -0.3975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6473    0.9211   -1.4229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0167    1.0640   -1.5939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4501    1.7659   -2.5421 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8652    0.4305   -0.7166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2381    0.5057   -0.7954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8414    1.2338   -1.7765 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0443   -0.1729    0.1426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5039   -0.9191    1.1494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3234   -1.5938    2.0821 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1349   -0.9968    1.2316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3200   -0.3273    0.3059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0185   -0.4135    0.4009 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7038   -0.7963    0.8752 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0382   -1.0102    1.1435 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0462   -0.1399   -1.4139 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2833   -0.3730   -0.1661 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2304    1.1397   -0.1876 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2676    0.8594   -1.4233 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9444    1.1947   -1.8398 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0073    1.4398   -2.1405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5578    1.7679   -2.5086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1122   -0.0951    0.0550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6270   -1.1712    2.9365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6996   -1.5753    2.0119 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9992   -1.2864    1.5547 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3971   -1.6179    1.9648 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  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
  6 20  1  0
 20 21  2  0
 21  3  1  0
 19  7  1  0
 18 11  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  5 26  1  0
  8 27  1  0
 13 28  1  0
 14 29  1  0
 16 30  1  0
 17 31  1  0
 20 32  1  0
 21 33  1  0
M  END

HEADER    PROTEIN                                 22-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-JUN-21         0                                  
HETATM    1  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+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  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -2.310   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  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    9                                                  
CONECT    7    6    8                                                       
CONECT    8    7    3                                                       
CONECT    9    6   10   19                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   18                                                  
CONECT   14   13   15   21                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   20                                                  
CONECT   17   16   18                                                       
CONECT   18   17   13   19                                                  
CONECT   19   18    9                                                       
CONECT   20   16                                                            
CONECT   21   14                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    NP0043833
HETATM    1  C1  UNL     1       6.279   0.042  -0.344  1.00  0.00           C  
HETATM    2  O1  UNL     1       5.332  -0.571   0.505  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.970  -0.403   0.300  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.576   0.381  -0.760  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.209   0.569  -0.993  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.272  -0.014  -0.183  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.155   0.162  -0.398  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.647   0.921  -1.423  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.017   1.064  -1.594  1.00  0.00           C  
HETATM   10  O2  UNL     1      -2.450   1.766  -2.542  1.00  0.00           O  
HETATM   11  C9  UNL     1      -2.865   0.430  -0.717  1.00  0.00           C  
HETATM   12  C10 UNL     1      -4.238   0.506  -0.795  1.00  0.00           C  
HETATM   13  O3  UNL     1      -4.841   1.234  -1.776  1.00  0.00           O  
HETATM   14  C11 UNL     1      -5.044  -0.173   0.143  1.00  0.00           C  
HETATM   15  C12 UNL     1      -4.504  -0.919   1.149  1.00  0.00           C  
HETATM   16  O4  UNL     1      -5.323  -1.594   2.082  1.00  0.00           O  
HETATM   17  C13 UNL     1      -3.135  -0.997   1.232  1.00  0.00           C  
HETATM   18  C14 UNL     1      -2.320  -0.327   0.306  1.00  0.00           C  
HETATM   19  O5  UNL     1      -1.018  -0.414   0.401  1.00  0.00           O  
HETATM   20  C15 UNL     1       1.704  -0.796   0.875  1.00  0.00           C  
HETATM   21  C16 UNL     1       3.038  -1.010   1.144  1.00  0.00           C  
HETATM   22  H1  UNL     1       6.046  -0.140  -1.414  1.00  0.00           H  
HETATM   23  H2  UNL     1       7.283  -0.373  -0.166  1.00  0.00           H  
HETATM   24  H3  UNL     1       6.230   1.140  -0.188  1.00  0.00           H  
HETATM   25  H4  UNL     1       4.268   0.859  -1.423  1.00  0.00           H  
HETATM   26  H5  UNL     1       1.944   1.195  -1.840  1.00  0.00           H  
HETATM   27  H6  UNL     1       0.007   1.440  -2.140  1.00  0.00           H  
HETATM   28  H7  UNL     1      -4.558   1.768  -2.509  1.00  0.00           H  
HETATM   29  H8  UNL     1      -6.112  -0.095   0.055  1.00  0.00           H  
HETATM   30  H9  UNL     1      -5.627  -1.171   2.936  1.00  0.00           H  
HETATM   31  H10 UNL     1      -2.700  -1.575   2.012  1.00  0.00           H  
HETATM   32  H11 UNL     1       0.999  -1.286   1.555  1.00  0.00           H  
HETATM   33  H12 UNL     1       3.397  -1.618   1.965  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3
CONECT    3    4    4   21
CONECT    4    5   25
CONECT    5    6    6   26
CONECT    6    7   20
CONECT    7    8    8   19
CONECT    8    9   27
CONECT    9   10   10   11
CONECT   11   12   12   18
CONECT   12   13   14
CONECT   13   28
CONECT   14   15   15   29
CONECT   15   16   17
CONECT   16   30
CONECT   17   18   18   31
CONECT   18   19
CONECT   20   21   21   32
CONECT   21   33
END

NP0043833
     RDKit          3D

33 35  0  0  0  0  0  0  0  0999 V2000
    6.2786    0.0416   -0.3443 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3322   -0.5706    0.5055 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9697   -0.4028    0.3005 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5763    0.3810   -0.7601 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2090    0.5692   -0.9927 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2724   -0.0140   -0.1826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1553    0.1619   -0.3975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6473    0.9211   -1.4229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0167    1.0640   -1.5939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4501    1.7659   -2.5421 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8652    0.4305   -0.7166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2381    0.5057   -0.7954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8414    1.2338   -1.7765 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0443   -0.1729    0.1426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5039   -0.9191    1.1494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3234   -1.5938    2.0821 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1349   -0.9968    1.2316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3200   -0.3273    0.3059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0185   -0.4135    0.4009 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7038   -0.7963    0.8752 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0382   -1.0102    1.1435 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0462   -0.1399   -1.4139 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2833   -0.3730   -0.1661 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2304    1.1397   -0.1876 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2676    0.8594   -1.4233 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9444    1.1947   -1.8398 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0073    1.4398   -2.1405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5578    1.7679   -2.5086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1122   -0.0951    0.0550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6270   -1.1712    2.9365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6996   -1.5753    2.0119 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9992   -1.2864    1.5547 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3971   -1.6179    1.9648 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  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
  6 20  1  0
 20 21  2  0
 21  3  1  0
 19  7  1  0
 18 11  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  5 26  1  0
  8 27  1  0
 13 28  1  0
 14 29  1  0
 16 30  1  0
 17 31  1  0
 20 32  1  0
 21 33  1  0
M  END

View in JSmol

Synonyms

Value	Source
4'-Methoxy-5,7-dihydroxyflavone	ChEBI
5,7-Dihydroxy-2-(4-methoxyphenyl)-4-benzopyrone	ChEBI
Acacetin	ChEBI
Linarigenin	ChEBI
5,7-Dihydroxy-4'-methoxyflavone	KEGG

Chemical Formula

C₁₆H₁₂O₅

Average Mass

284.2635 Da

Monoisotopic Mass

284.06847 Da

IUPAC Name

5,7-dihydroxy-2-(4-methoxyphenyl)-4H-chromen-4-one

Traditional Name

acacetin

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C16H12O5/c1-20-11-4-2-9(3-5-11)14-8-13(19)16-12(18)6-10(17)7-15(16)21-14/h2-8,17-18H,1H3

InChI Key

DANYIYRPLHHOCZ-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Agastache foeniculum	LOTUS Database	35616633
Agastache rugosa	LOTUS Database	35616633
Alnus glutinosa	LOTUS Database	35616633
Alnus japonica	LOTUS Database	35616633
Apis mellifera	LOTUS Database	35616633
Argyrochosma nivea	LOTUS Database	35616633
Arnica amplexicaulis	LOTUS Database	35616633
Arnica chamissonis	LOTUS Database	35616633
Arrabidaea chica	LOTUS Database	35616633
Artemisia afra	LOTUS Database	35616633
Artemisia fragrans	LOTUS Database	35616633
Artemisia gmelinii	LOTUS Database	35616633
Artemisia judaica	LOTUS Database	35616633
Artemisia minor	KNApSAcK Database	22123792
Artemisia molinieri	LOTUS Database	35616633
Artemisia princeps	LOTUS Database	35616633
Artemisia transiliensis	LOTUS Database	35616633
Artemisia vestita	KNApSAcK Database	22123792
Asphodeline globifera	KNApSAcK Database	22123792
Baccharis darwinii	LOTUS Database	35616633
Baccharis dracunculifolia	LOTUS Database	35616633
Baccharis patagonica	LOTUS Database	35616633
Baccharis salicifolia	LOTUS Database	35616633
Bahiopsis reticulata	LOTUS Database	35616633
Balsamorhiza deltoidea	LOTUS Database	35616633
Betula pendula	LOTUS Database	35616633
Biebersteinia orphanidis	KNApSAcK Database	22123792
Buddleja davidii	LOTUS Database	35616633
Buddleja officinalis	LOTUS Database	35616633
Calea jamaicensis	LOTUS Database	35616633
Calea ternifolia	LOTUS Database	35616633
Callicarpa pilosissima	KNApSAcK Database	22123792
Caragana frutex	LOTUS Database	35616633
Carthamus tinctorius	LOTUS Database	35616633
Centaurea cuneifolia	LOTUS Database	35616633
Centaurea pallescens	LOTUS Database	35616633
Chromolaena odorata	LOTUS Database	35616633
Chrysanthemum boreale	LOTUS Database	35616633
Chrysanthemum indicum	LOTUS Database	35616633
Chrysanthemum leucanthemum	KNApSAcK Database	22123792
Chrysanthemum morifolium	LOTUS Database	35616633
Chrysothamnus nauseosus	KNApSAcK Database	22123792
Cirsium japonicum	LOTUS Database	35616633
Cirsium oleraceum	LOTUS Database	35616633
Cirsium rhinoceros	LOTUS Database	35616633
Cistus ladanifer	LOTUS Database	35616633
Cistus laurifolius	LOTUS Database	35616633
Citrus reticulata	LOTUS Database	35616633
Combretum caffrum	LOTUS Database	35616633
Crocus aureus	Plant	KNApSAcK
Crocus heuffelianus	Plant	KNApSAcK
Crocus laevigatus	Plant	KNApSAcK
Cunila lythrifolia	LOTUS Database	35616633
Dalbergia odorifera	KNApSAcK Database	22123792
Dracocephalum multicaule	LOTUS Database	35616633
Elsholtzia ciliata	LOTUS Database	35616633
Eriodictyon sessilifolium	LOTUS Database	35616633
Eupatorium hookerianum	KNApSAcK Database	22123792
Eupatorium rugosum	LOTUS Database	35616633
Eupatorium tinifolium	KNApSAcK Database	22123792
Fouquieria splendens	LOTUS Database	35616633
Frullania teneriffae	LOTUS Database	35616633
Garcinia kola	LOTUS Database	35616633
Ginkgo biloba	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Glandularia bipinnatifida	Plant	KNApSAcK
Grindelia camporum	LOTUS Database	35616633
Grindelia hirsutula	LOTUS Database	35616633
Gymnocarpium robertianum	LOTUS Database	35616633
Indigofera tetrantha	KNApSAcK Database	22123792
Klasea flavescens	LOTUS Database	35616633
Lawsonia alba	Plant	KNApSAcK
Lepidaploa rufogrisea	LOTUS Database	35616633
Leucas aspera	KNApSAcK Database	22123792
Linaria aeruginea	LOTUS Database	35616633
Linaria kurdica	LOTUS Database	35616633
Linaria macroura	LOTUS Database	35616633
Lupinus texensis	LOTUS Database	35616633
Lychnophora ericoides	LOTUS Database	35616633
Lycopus lucidus	LOTUS Database	35616633
Meehania fargesii	LOTUS Database	35616633
Mentha aquatica	KNApSAcK Database	22123792
Mentha longifolia	KNApSAcK Database	22123792
Mentha piperita	LOTUS Database	35616633
Microglossa pyrifolia	LOTUS Database	35616633
Micromeria croatica	LOTUS Database	35616633
Mirabilis viscosa	LOTUS Database	35616633
Mosla scabra	LOTUS Database	35616633
Notholaena greggii	LOTUS Database	35616633
Notholaena rigida	LOTUS Database	35616633
Nuxia sphaerocephala	KNApSAcK Database	22123792
Ocimum americanum L.var.pilosum (Willd.) Paton	KNApSAcK Database	22123792
Ocimum basilicum	Plant	KNApSAcK
Ocimum basilicum L.	KNApSAcK Database	22123792
Ocimum x citriodorum	LOTUS Database	35616633
Ocimum x citriodorum Vis.	KNApSAcK Database	22123792
Onopordum illyricum	LOTUS Database	35616633
Origanum akhadarense	Plant	KNApSAcK
Origanum boissieri	Plant	KNApSAcK
Origanum hypercifolium	Plant	KNApSAcK
Origanum majorana	Plant	KNApSAcK
Origanum micranthum	Plant	KNApSAcK
Origanum vulgare	Plant	KNApSAcK
Ostrya japonica	KNApSAcK Database	22123792
Picea neoveitchii	LOTUS Database	35616633
Plazia daphnoides	LOTUS Database	35616633
Podocarpus fasciculus	KNApSAcK Database	22123792
Pogostemon stellatus	LOTUS Database	35616633
Populus grandidentata	LOTUS Database	35616633
Populus tremula	LOTUS Database	35616633
Populus tremuloides	LOTUS Database	35616633
Robinia pseudoacacia	KNApSAcK Database	22123792
Salvia dorrii	LOTUS Database	35616633
Salvia nicolsoniana	KNApSAcK Database	22123792
Salvia sclarea	LOTUS Database	35616633
Salvia yosgadensis	KNApSAcK Database	22123792
Satureja montana	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Scoparia dulcis	Plant	KNApSAcK
Scoparia dulcis L.	KNApSAcK Database	22123792
Sida rhombifolia	Plant	KNApSAcK
Striga asiatica	LOTUS Database	35616633
Tanacetum vulgare	LOTUS Database	35616633
Teucrium japonicum	LOTUS Database	35616633
Tricostularia neesii	LOTUS Database	35616633
Trifolium repens	Plant	KNApSAcK
Turnera diffusa	LOTUS Database	35616633
Valeriana chionophila	KNApSAcK Database	22123792
Valeriana fedtschenkoi	KNApSAcK Database	22123792
Valeriana spryginii	Plant	KNApSAcK
Veratrum dahuricum	LOTUS Database	35616633
Verbascum lychnitis	LOTUS Database	35616633
Verbena hybrida	Plant	KNApSAcK
Veronica officinalis	Plant	KNApSAcK
Veronica orchidea	Plant	KNApSAcK
Veronica teucrium	Plant	KNApSAcK
Volkameria inermis	LOTUS Database	35616633
Xanthorrhoea australis	LOTUS Database	35616633
Ziziphora clinopodioides	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 4'-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C4' atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

4'-O-methylated flavonoids

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

dihydroxyflavone (CHEBI:15335 )
monomethoxyflavone (CHEBI:15335 )
flavones (C01470 )
Flavones and Flavonols (C01470 )
Flavones and Flavonols (LMPK12110468 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	263.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Boiling Point	518.57 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	71.1 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	2.443 (est)	The Good Scents Company Information System

Predicted Properties

Property	Value	Source
logP	3.46	ALOGPS
logP	2.85	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	6.58	ChemAxon
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	77.4 m³·mol⁻¹	ChemAxon
Polarizability	28.9 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

HMDB0132457

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Acacetin

METLIN ID

Not Available

PubChem Compound

5280442

PDB ID

Not Available

ChEBI ID

15335

Good Scents ID

rw1504411

References

General References

Shen KH, Hung SH, Yin LT, Huang CS, Chao CH, Liu CL, Shih YW: Acacetin, a flavonoid, inhibits the invasion and migration of human prostate cancer DU145 cells via inactivation of the p38 MAPK signaling pathway. Mol Cell Biochem. 2010 Jan;333(1-2):279-91. doi: 10.1007/s11010-009-0229-8. Epub 2009 Aug 20. [PubMed:19693651 ]
Watanabe K, Kanno S, Tomizawa A, Yomogida S, Ishikawa M: Acacetin induces apoptosis in human T cell leukemia Jurkat cells via activation of a caspase cascade. Oncol Rep. 2012 Jan;27(1):204-9. doi: 10.3892/or.2011.1498. Epub 2011 Oct 12. [PubMed:21993665 ]
Lopez-Martinez S, Navarrete-Vazquez G, Estrada-Soto S, Leon-Rivera I, Rios MY: Chemical constituents of the hemiparasitic plant Phoradendron brachystachyum DC Nutt (Viscaceae). Nat Prod Res. 2013;27(2):130-6. doi: 10.1080/14786419.2012.662646. Epub 2012 Feb 23. [PubMed:22360797 ]
Nugroho A, Lim SC, Choi J, Park HJ: Identification and quantification of the sedative and anticonvulsant flavone glycoside from Chrysanthemum boreale. Arch Pharm Res. 2013 Jan;36(1):51-60. doi: 10.1007/s12272-013-0015-8. [PubMed:23325489 ]

Showing NP-Card for Acacetin (NP0043833)

MOL for NP0043833 (Acacetin)

3D MOL for NP0043833 (Acacetin)

3D SDF for NP0043833 (Acacetin)

3D-SDF for NP0043833 (Acacetin)

PDB for NP0043833 (Acacetin)

3D PDB for NP0043833 (Acacetin)

SMILES for NP0043833 (Acacetin)

INCHI for NP0043833 (Acacetin)

Structure for NP0043833 (Acacetin)

3D Structure for NP0043833 (Acacetin)