NP-MRD: Showing NP-Card for 3,6,7,4'-Tetra-O-methyl-5,3'-dihydroxyflavone (NP0052967)

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Record Information

Version

2.0

Created at

2022-04-27 23:49:28 UTC

Updated at

2022-04-27 23:49:28 UTC

NP-MRD ID

NP0052967

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,6,7,4'-Tetra-O-methyl-5,3'-dihydroxyflavone

Description

Casticin, also known as vitexicarpin, belongs to the class of organic compounds known as 7-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone. Thus, casticin is considered to be a flavonoid lipid molecule. Casticin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Casticin has been detected, but not quantified in, fruits and herbs and spices. This could make casticin a potential biomarker for the consumption of these foods. 3,6,7,4'-Tetra-O-methyl-5,3'-dihydroxyflavone is found in Achillea aspleniifolia, Achillea clavennae, Achillea millefolium L. , Achillea sibirica, Achillea sibirica subsp.mongolica, Achillea virescens, Ageratina havanensis, Artemisia abrotanum , Artemisia annua , Artemisia apiacea, Artemisia incanescens, Artemisia judaica, Artemisia scoparia, Artemisia scoparia., Brickellia baccharidea, Brickellia spp., Bromelia pinguin , Callicarpa pilosissima, Chiliadenus montanus, Chrysosplenium japonicum, Chrysosplenium tosaense, Digitalis thapsii, Eremophila mitchellii, Eriodictyon trichocalyx, Helianthus microcephalus, Houttuynia cordata, Laggera alata, Lagophylla glandulosa, Matricaria chamomilla , Parthenium incanum, Parthenium ligulatum, Parthenium spp., Plectranthus cylindraceus, Pluchea sagittalis, Psiadia dentata, Tanacetum polycephalum, Tessaria integrifolia, Veronica officinalis , Veronica orchidea, Veronica teucrium, Vitex agnus-castus , Vitex negundo , Vitex quinata, Vitex rotundifolia and Vitex trifolia . 3,6,7,4'-Tetra-O-methyl-5,3'-dihydroxyflavone was first documented in 2011 (PMID: 21877688). A tetramethoxyflavone that consists of quercetagetin in which the hydroxy groups at positions 3, 6, 7 and 4' have been replaced by methoxy groups (PMID: 22407499) (PMID: 23135489) (PMID: 23464460) (PMID: 23476684).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061305252D          

 27 29  0  0  0  0            999 V2000
    5.0013    2.0625    0.0000 C   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
   -1.4289   -2.4750    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
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    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    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    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
   -0.7145   -0.4125    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
    1.4289   -1.6500    0.0000 C   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
   -0.7145   -1.2375    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
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   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
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  2  0  0  0  0
  9  5  1  0  0  0  0
  9  7  2  0  0  0  0
 10  7  1  0  0  0  0
 11  6  1  0  0  0  0
 11 10  2  0  0  0  0
 12  8  2  0  0  0  0
 13  8  1  0  0  0  0
 14 12  1  0  0  0  0
 15 14  2  0  0  0  0
 16 14  1  0  0  0  0
 17  9  1  0  0  0  0
 18 13  2  0  0  0  0
 18 15  1  0  0  0  0
 19 16  1  0  0  0  0
 19 17  2  0  0  0  0
 20 10  1  0  0  0  0
 21 15  1  0  0  0  0
 22 16  2  0  0  0  0
 23  1  1  0  0  0  0
 23 11  1  0  0  0  0
 24  2  1  0  0  0  0
 24 13  1  0  0  0  0
 25  3  1  0  0  0  0
 25 18  1  0  0  0  0
 26  4  1  0  0  0  0
 26 19  1  0  0  0  0
 27 12  1  0  0  0  0
 27 17  1  0  0  0  0
M  END

     RDKit          3D

 45 47  0  0  0  0  0  0  0  0999 V2000
   -6.4125    2.4912   -1.0381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0779    1.2635   -0.4667 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7742    0.8276   -0.2710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6789    1.5808   -0.6295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4003    1.1172   -0.4213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1216   -0.1272    0.1574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7218   -0.5289    0.2851 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1996    0.3843    0.1027 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4595    0.2018    0.1779 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3493    1.2667   -0.0396 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7072    1.0782    0.0398 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5368    2.1632   -0.1838 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0663    3.4487   -0.4880 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1580   -0.1737    0.3357 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5385   -0.3571    0.4146 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3013   -0.7205   -0.7183 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2947   -1.2485    0.5561 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7713   -2.5004    0.8528 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9404   -1.0560    0.4759 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0391   -2.0770    0.6821 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4177   -3.2303    0.9537 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3308   -1.8031    0.5820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2000   -2.8733    0.7902 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5246   -3.6902   -0.3592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2120   -0.8601    0.5077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5284   -0.3950    0.2985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5829   -1.2214    0.6909 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2132    2.5555   -2.1187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4837    2.6944   -0.7935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8347    3.3103   -0.5175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8865    2.5446   -1.0785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5449    1.7411   -0.7185 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9036    2.2340   -0.2709 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9385    4.1457   -0.3636 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2191    3.7410    0.1473 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7713    3.5029   -1.5735 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3147    0.0539   -1.4882 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8762   -1.6580   -1.1721 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3434   -0.8977   -0.3676 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7882   -2.6336    0.9104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5065   -4.1682   -0.1477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5797   -2.9893   -1.2087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7084   -4.4217   -0.5088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0883   -1.8202    0.9861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5230   -0.8952    0.5442 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 26  2  0
 26 27  1  0
 26 25  1  0
 25  6  2  0
  6  5  1  0
  5  4  2  0
  6  7  1  0
  7 22  2  0
 22 23  1  0
 23 24  1  0
 22 20  1  0
 20 21  2  0
 20 19  1  0
 19 17  2  0
 17 18  1  0
 17 14  1  0
 14 15  1  0
 15 16  1  0
 14 11  2  0
 11 12  1  0
 12 13  1  0
 11 10  1  0
 10  9  2  0
  9  8  1  0
  4  3  1  0
  8  7  1  0
  9 19  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
 27 45  1  0
 25 44  1  0
  5 32  1  0
  4 31  1  0
 24 41  1  0
 24 42  1  0
 24 43  1  0
 18 40  1  0
 16 37  1  0
 16 38  1  0
 16 39  1  0
 13 34  1  0
 13 35  1  0
 13 36  1  0
 10 33  1  0
M  END


  Mrv0541 05061305252D          

 27 29  0  0  0  0            999 V2000
    5.0013    2.0625    0.0000 C   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
   -1.4289   -2.4750    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
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    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    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    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
   -0.7145   -0.4125    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
    1.4289   -1.6500    0.0000 C   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
   -0.7145   -1.2375    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
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   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
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  2  0  0  0  0
  9  5  1  0  0  0  0
  9  7  2  0  0  0  0
 10  7  1  0  0  0  0
 11  6  1  0  0  0  0
 11 10  2  0  0  0  0
 12  8  2  0  0  0  0
 13  8  1  0  0  0  0
 14 12  1  0  0  0  0
 15 14  2  0  0  0  0
 16 14  1  0  0  0  0
 17  9  1  0  0  0  0
 18 13  2  0  0  0  0
 18 15  1  0  0  0  0
 19 16  1  0  0  0  0
 19 17  2  0  0  0  0
 20 10  1  0  0  0  0
 21 15  1  0  0  0  0
 22 16  2  0  0  0  0
 23  1  1  0  0  0  0
 23 11  1  0  0  0  0
 24  2  1  0  0  0  0
 24 13  1  0  0  0  0
 25  3  1  0  0  0  0
 25 18  1  0  0  0  0
 26  4  1  0  0  0  0
 26 19  1  0  0  0  0
 27 12  1  0  0  0  0
 27 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0052967

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C19H18O8/c1-23-11-6-5-9(7-10(11)20)17-19(26-4)16(22)14-12(27-17)8-13(24-2)18(25-3)15(14)21/h5-8,20-21H,1-4H3

> <INCHI_KEY>
PJQLSMYMOKWUJG-UHFFFAOYSA-N

> <FORMULA>
C19H18O8

> <MOLECULAR_WEIGHT>
374.3414

> <EXACT_MASS>
374.100167552

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
37.66345092353501

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-3,6,7-trimethoxy-4H-chromen-4-one

> <ALOGPS_LOGP>
2.71

> <JCHEM_LOGP>
2.4032436996666666

> <ALOGPS_LOGS>
-3.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.585625015829745

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.824787677036765

> <JCHEM_PKA_STRONGEST_BASIC>
-4.3117113436107655

> <JCHEM_POLAR_SURFACE_AREA>
103.68000000000002

> <JCHEM_REFRACTIVITY>
97.04119999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.68e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
casticin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
CONECT    1   23                                                            
CONECT    2   24                                                            
CONECT    3   25                                                            
CONECT    4   26                                                            
CONECT    5    6    9                                                       
CONECT    6    5   11                                                       
CONECT    7    9   10                                                       
CONECT    8   12   13                                                       
CONECT    9    5    7   17                                                  
CONECT   10    7   11   20                                                  
CONECT   11    6   10   23                                                  
CONECT   12    8   14   27                                                  
CONECT   13    8   18   24                                                  
CONECT   14   12   15   16                                                  
CONECT   15   14   18   21                                                  
CONECT   16   14   19   22                                                  
CONECT   17    9   19   27                                                  
CONECT   18   13   15   25                                                  
CONECT   19   16   17   26                                                  
CONECT   20   10                                                            
CONECT   21   15                                                            
CONECT   22   16                                                            
CONECT   23    1   11                                                       
CONECT   24    2   13                                                       
CONECT   25    3   18                                                       
CONECT   26    4   19                                                       
CONECT   27   12   17                                                       
MASTER        0    0    0    0    0    0    0    0   27    0   58    0
END

View in JSmol

Synonyms

Value	Source
3',5-Dihydroxy-3,4',6,7-tetramethoxyflavone	ChEBI
3,6,7,4'-Tetra-O-methyl-5,3'-dihydroxyflavone	ChEBI
5-Hydroxy-2-(3-hydroxy-4-methoxyphenyl)-3,6,7-trimethoxy-4H-1-benzopyran-4-one	ChEBI
Quercetagetin 3,6,7,4'-tetramethyl ether	ChEBI
Vitexicarpin	ChEBI
5-Hydroxy-2-(3-hydroxy-4-methoxyphenyl)-3,6,7-trimethoxy-4H-benzopyran-4-one, 9ci	HMDB
VX-5 CPD	MeSH

Chemical Formula

C₁₉H₁₈O₈

Average Mass

374.3414 Da

Monoisotopic Mass

374.10017 Da

IUPAC Name

5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-3,6,7-trimethoxy-4H-chromen-4-one

Traditional Name

casticin

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C19H18O8/c1-23-11-6-5-9(7-10(11)20)17-19(26-4)16(22)14-12(27-17)8-13(24-2)18(25-3)15(14)21/h5-8,20-21H,1-4H3

InChI Key

PJQLSMYMOKWUJG-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
Achillea aspleniifolia	LOTUS Database	35616633
Achillea clavennae	Plant	KNApSAcK
Achillea millefolium L.	Plant	KNApSAcK
Achillea sibirica	LOTUS Database	35616633
Achillea sibirica subsp.mongolica	Plant	KNApSAcK
Achillea virescens	LOTUS Database	35616633
Ageratina havanensis	Plant	KNApSAcK
Artemisia abrotanum	Plant	KNApSAcK
Artemisia annua	Plant	KNApSAcK
Artemisia apiacea	LOTUS Database	35616633
Artemisia incanescens	LOTUS Database	35616633
Artemisia judaica	LOTUS Database	35616633
Artemisia scoparia	LOTUS Database	35616633
Artemisia scoparia.	Plant	KNApSAcK
Brickellia baccharidea	LOTUS Database	35616633
Brickellia spp.	Plant	KNApSAcK
Bromelia pinguin	Plant	KNApSAcK
Callicarpa pilosissima	Plant	KNApSAcK
Chiliadenus montanus	LOTUS Database	35616633
Chrysosplenium japonicum	Plant	KNApSAcK
Chrysosplenium tosaense	Plant	KNApSAcK
Digitalis thapsii	Plant	KNApSAcK
Eremophila mitchellii	LOTUS Database	35616633
Eriodictyon trichocalyx	Plant	KNApSAcK
Helianthus microcephalus	LOTUS Database	35616633
Houttuynia cordata	LOTUS Database	35616633
Laggera alata	LOTUS Database	35616633
Lagophylla glandulosa	Plant	KNApSAcK
Matricaria chamomilla	Plant	KNApSAcK
Parthenium incanum	Plant	KNApSAcK
Parthenium ligulatum	LOTUS Database	35616633
Parthenium spp.	Plant	KNApSAcK
Plectranthus cylindraceus	LOTUS Database	35616633
Pluchea sagittalis	LOTUS Database	35616633
Psiadia dentata	LOTUS Database	35616633
Tanacetum polycephalum	Plant	KNApSAcK
Tessaria integrifolia	LOTUS Database	35616633
Veronica officinalis	Plant	KNApSAcK
Veronica orchidea	Plant	KNApSAcK
Veronica teucrium	Plant	KNApSAcK
Vitex agnus-castus	Plant	KNApSAcK
Vitex negundo	Plant	KNApSAcK
Vitex quinata	LOTUS Database	35616633
Vitex rotundifolia	Plant	KNApSAcK
Vitex trifolia	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 7-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

7-O-methylated flavonoids

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

dihydroxyflavone (CHEBI:69355 )
tetramethoxyflavone (CHEBI:69355 )
Flavones and Flavonols (LMPK12113010 )

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	2.71	ALOGPS
logP	2.4	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	8.82	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	103.68 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	97.04 m³·mol⁻¹	ChemAxon
Polarizability	37.66 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

HMDB0030660

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB002570

KNApSAcK ID

C00004705

Chemspider ID

4474632

KEGG Compound ID

Not Available

BioCyc ID

CPD-14856

BiGG ID

Not Available

Wikipedia Link

Casticin

METLIN ID

Not Available

PubChem Compound

5315263

PDB ID

Not Available

ChEBI ID

69355

Good Scents ID

Not Available

References

General References

Barnes EC, Carroll AR, Davis RA: Mitchellenes A-E, cyclic sesquiterpenes from the Australian plant Eremophila mitchellii. J Nat Prod. 2011 Sep 23;74(9):1888-93. doi: 10.1021/np2003676. Epub 2011 Aug 30. [PubMed:21877688 ]
Ling Y, Zhu J, Fan M, Wu B, Qin L, Huang C: Metabolism studies of casticin in rats using HPLC-ESI-MS(n). Biomed Chromatogr. 2012 Dec;26(12):1502-8. doi: 10.1002/bmc.2724. Epub 2012 Mar 8. [PubMed:22407499 ]
Tang SY, Zhong MZ, Yuan GJ, Hou SP, Yin LL, Jiang H, Yu ZUpsilon: Casticin, a flavonoid, potentiates TRAIL-induced apoptosis through modulation of anti-apoptotic proteins and death receptor 5 in colon cancer cells. Oncol Rep. 2013 Feb;29(2):474-80. doi: 10.3892/or.2012.2127. Epub 2012 Nov 7. [PubMed:23135489 ]
Meng FM, Yang JB, Yang CH, Jiang Y, Zhou YF, Yu B, Yang H: Vitexicarpin induces apoptosis in human prostate carcinoma PC-3 cells through G2/M phase arrest. Asian Pac J Cancer Prev. 2012;13(12):6369-74. doi: 10.7314/apjcp.2012.13.12.6369. [PubMed:23464460 ]
Zhang B, Liu L, Zhao S, Wang X, Liu L, Li S: Vitexicarpin acts as a novel angiogenesis inhibitor and its target network. Evid Based Complement Alternat Med. 2013;2013:278405. doi: 10.1155/2013/278405. Epub 2013 Feb 12. [PubMed:23476684 ]

Showing NP-Card for 3,6,7,4'-Tetra-O-methyl-5,3'-dihydroxyflavone (NP0052967)

MOL for NP0052967 (3,6,7,4'-Tetra-O-methyl-5,3'-dihydroxyflavone)

3D MOL for NP0052967 (3,6,7,4'-Tetra-O-methyl-5,3'-dihydroxyflavone)

3D SDF for NP0052967 (3,6,7,4'-Tetra-O-methyl-5,3'-dihydroxyflavone)

3D-SDF for NP0052967 (3,6,7,4'-Tetra-O-methyl-5,3'-dihydroxyflavone)

PDB for NP0052967 (3,6,7,4'-Tetra-O-methyl-5,3'-dihydroxyflavone)

3D PDB for NP0052967 (3,6,7,4'-Tetra-O-methyl-5,3'-dihydroxyflavone)

SMILES for NP0052967 (3,6,7,4'-Tetra-O-methyl-5,3'-dihydroxyflavone)

INCHI for NP0052967 (3,6,7,4'-Tetra-O-methyl-5,3'-dihydroxyflavone)

Structure for NP0052967 (3,6,7,4'-Tetra-O-methyl-5,3'-dihydroxyflavone)

3D Structure for NP0052967 (3,6,7,4'-Tetra-O-methyl-5,3'-dihydroxyflavone)