NP-MRD: Showing NP-Card for Centaureidin (NP0044574)

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Record Information

Version

2.0

Created at

2022-02-24 21:07:21 UTC

Updated at

2022-02-24 21:07:22 UTC

NP-MRD ID

NP0044574

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Centaureidin

Description

5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-3,6-dimethoxy-4H-chromen-4-one, also known as 5,7,3'-trihydroxy-3,6,4'-trimethoxyflavone or desmethoxycentaureidine, belongs to the class of organic compounds known as 6-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C6 atom of the flavonoid backbone. Thus, 5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-3,6-dimethoxy-4H-chromen-4-one is considered to be a flavonoid lipid molecule. A trihydroxyflavone that consists of quercetagetin in which the hydroxy groups at positions 3, 6 and 4' have been replaced by methoxy groups. Centaureidin is found in Achillea abrotanoides, Achillea atrata, Achillea clavennae, Achillea collina, Achillea latiloba, Achillea ligustica, Achillea millefolium, Achillea multifida, Aeonium spp., Ajania fruticulosa , Alnus glutinosa , Ambrosia chamissonis, Anthemis ruthenica, Anthemis tinctoria , Artemisia abrotanum , Artemisia alba, Artemisia barrelieri, Artemisia molinieri, Asteriscus sericeus, Baccharis neaei, Baccharis salicina, Baccharis sarothroides, Bahia xylopoda, Brickellia baccharidea, Brickellia cylindracea, Cassia grandis, Centaurea africana, Centaurea bracteata Scop., Centaurea corcubionensis, Centaurea jacea, Centaurea nervosa, Chiliadenus montanus, Chrysanthemum cinerariifolium , Cota altissima, Eremophila mitchellii, Eriophyllum confertiflorum, Eupatorium buniifolium, Eupatorium cannabinum, Grindelia hirsutula, Grindelia robusta, Grindelia tarapacana, Iva frutescens, Pericome caudata, Picradeniopsis schaffneri, Picradeniopsis xylopoda, Pluchea chingoyo, Pluchea sagittalis , Polymnia fruticosa, Smallanthus fruticosus, Stevia berlandieri, Stevia nepetifolia, Stevia origanoides, Stevia rebaudiana and Tanacetum microphyllum. Centaureidin was first documented in 2001 (PMID: 11730880). 5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-3,6-dimethoxy-4H-chromen-4-one is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (PMID: 21877688) (PMID: 12943776) (PMID: 19107850) (PMID: 19639540) (PMID: 20804828) (PMID: 21995542).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652308211921232D          

 26 28  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
   -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
   -0.7145   -0.4125    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   -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
   -1.4289    0.0000    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   -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
  5  4  2  0  0  0  0
  8  4  1  0  0  0  0
  8  6  2  0  0  0  0
  9  6  1  0  0  0  0
 10  7  2  0  0  0  0
 11  5  1  0  0  0  0
 11  9  2  0  0  0  0
 12  7  1  0  0  0  0
 13 12  2  0  0  0  0
 14 13  1  0  0  0  0
 15 13  1  0  0  0  0
 16  8  1  0  0  0  0
 17 10  1  0  0  0  0
 17 14  2  0  0  0  0
 18 15  1  0  0  0  0
 18 16  2  0  0  0  0
 19  9  1  0  0  0  0
 20 10  1  0  0  0  0
 21 14  1  0  0  0  0
 22 15  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 17  1  0  0  0  0
 25  3  1  0  0  0  0
 25 18  1  0  0  0  0
 26 12  1  0  0  0  0
 26 16  1  0  0  0  0
M  END

     RDKit          3D

 42 44  0  0  0  0  0  0  0  0999 V2000
    6.1958    2.6830   -0.1126 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9243    1.3284    0.1427 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6054    0.9047    0.2182 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5684    1.7837    0.0481 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2707    1.3348    0.1279 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9323    0.0254    0.3740 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5276   -0.3212    0.3968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3874    0.6422    0.4150 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6675    0.4826    0.4376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4861    1.6256    0.4550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8531    1.5165    0.4796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6407    2.6754    0.4965 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4182    0.2608    0.4871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7966    0.1052    0.5118 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5927    0.0204   -0.6465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6078   -0.8700    0.4698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1459   -2.1575    0.4767 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2398   -0.7713    0.4451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3772   -1.8364    0.4263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8383   -2.9900    0.4320 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0062   -1.5906    0.4012 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7927   -2.7166    0.3739 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0894   -3.2782   -0.9042 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9553   -0.8556    0.5455 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2886   -0.4182    0.4675 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3385   -1.3090    0.6398 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2603    2.9376   -0.0408 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6003    3.3320    0.5793 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8601    2.9261   -1.1498 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7620    2.8325   -0.1496 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4700    2.0776   -0.0155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0551    2.6206    0.4494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2033    3.5720    0.4905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9607    0.2088   -1.5443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1110   -0.9530   -0.7228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3791    0.8208   -0.6298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1502   -2.2441    0.4948 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9664   -3.9593   -0.7601 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3855   -2.4601   -1.5733 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1926   -3.8232   -1.2330 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8184   -1.8894    0.7647 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0999   -2.2730    0.8214 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 25  2  0
 25 26  1  0
 25 24  1  0
 24  6  2  0
  6  5  1  0
  5  4  2  0
  6  7  1  0
  7 21  2  0
 21 22  1  0
 22 23  1  0
 21 19  1  0
 19 20  2  0
 19 18  1  0
 18  9  2  0
  9  8  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 13 16  2  0
 16 17  1  0
  4  3  1  0
  8  7  1  0
 16 18  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
 26 42  1  0
 24 41  1  0
  5 31  1  0
  4 30  1  0
 23 38  1  0
 23 39  1  0
 23 40  1  0
 10 32  1  0
 12 33  1  0
 15 34  1  0
 15 35  1  0
 15 36  1  0
 17 37  1  0
M  END


  Mrv1652308211921232D          

 26 28  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
   -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
   -0.7145   -0.4125    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   -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
   -1.4289    0.0000    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   -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
  5  4  2  0  0  0  0
  8  4  1  0  0  0  0
  8  6  2  0  0  0  0
  9  6  1  0  0  0  0
 10  7  2  0  0  0  0
 11  5  1  0  0  0  0
 11  9  2  0  0  0  0
 12  7  1  0  0  0  0
 13 12  2  0  0  0  0
 14 13  1  0  0  0  0
 15 13  1  0  0  0  0
 16  8  1  0  0  0  0
 17 10  1  0  0  0  0
 17 14  2  0  0  0  0
 18 15  1  0  0  0  0
 18 16  2  0  0  0  0
 19  9  1  0  0  0  0
 20 10  1  0  0  0  0
 21 14  1  0  0  0  0
 22 15  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 17  1  0  0  0  0
 25  3  1  0  0  0  0
 25 18  1  0  0  0  0
 26 12  1  0  0  0  0
 26 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0044574

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=C(C=C1)C1=C(OC)C(=O)C2=C(O1)C=C(O)C(OC)=C2O

> <INCHI_IDENTIFIER>
InChI=1S/C18H16O8/c1-23-11-5-4-8(6-9(11)19)16-18(25-3)15(22)13-12(26-16)7-10(20)17(24-2)14(13)21/h4-7,19-21H,1-3H3

> <INCHI_KEY>
BZXULYMZYPRZOG-UHFFFAOYSA-N

> <FORMULA>
C18H16O8

> <MOLECULAR_WEIGHT>
360.318

> <EXACT_MASS>
360.084517475

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
35.565058333240344

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.88

> <JCHEM_LOGP>
2.2573496436666662

> <ALOGPS_LOGS>
-3.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.443374212159158

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.910400344227807

> <JCHEM_PKA_STRONGEST_BASIC>
-4.430019105582086

> <JCHEM_POLAR_SURFACE_AREA>
114.68

> <JCHEM_REFRACTIVITY>
92.5589

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.30e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
centaureidin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 21-AUG-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-AUG-19         0                                  
HETATM    1  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668   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       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  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.334  -2.310   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       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -2.667   0.000   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  -3.080   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   26  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    5    8                                                       
CONECT    5    4   11                                                       
CONECT    6    8    9                                                       
CONECT    7   10   12                                                       
CONECT    8    4    6   16                                                  
CONECT    9    6   11   19                                                  
CONECT   10    7   17   20                                                  
CONECT   11    5    9   23                                                  
CONECT   12    7   13   26                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13   17   21                                                  
CONECT   15   13   18   22                                                  
CONECT   16    8   18   26                                                  
CONECT   17   10   14   24                                                  
CONECT   18   15   16   25                                                  
CONECT   19    9                                                            
CONECT   20   10                                                            
CONECT   21   14                                                            
CONECT   22   15                                                            
CONECT   23    1   11                                                       
CONECT   24    2   17                                                       
CONECT   25    3   18                                                       
CONECT   26   12   16                                                       
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

View in JSmol

Synonyms

Value	Source
5,7,3'-Trihydroxy-3,6,4'-trimethoxyflavone	ChEBI
5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-3,6-dimethoxy-4H-1-benzopyran-4-one	ChEBI
Desmethoxycentaureidine	ChEBI
Quercetagetin 3,6,4'-trimethyl ether	ChEBI

Chemical Formula

C₁₈H₁₆O₈

Average Mass

360.3180 Da

Monoisotopic Mass

360.08452 Da

IUPAC Name

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

Traditional Name

centaureidin

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=C(C=C1)C1=C(OC)C(=O)C2=C(O1)C=C(O)C(OC)=C2O

InChI Identifier

InChI=1S/C18H16O8/c1-23-11-5-4-8(6-9(11)19)16-18(25-3)15(22)13-12(26-16)7-10(20)17(24-2)14(13)21/h4-7,19-21H,1-3H3

InChI Key

BZXULYMZYPRZOG-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃/CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, CDCl₃/CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, CDCl₃/CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, CDCl₃/CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃/CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, CDCl₃/CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, CDCl₃/CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, CDCl₃/CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, CDCl₃/CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, CDCl₃/CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃/CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃/CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃/CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃/CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃/CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃/CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃/CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃/CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃/CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃/CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

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 abrotanoides	LOTUS Database	35616633
Achillea atrata	Plant	KNApSAcK
Achillea clavennae	Plant	KNApSAcK
Achillea collina	LOTUS Database	35616633
Achillea latiloba	LOTUS Database	35616633
Achillea ligustica	LOTUS Database	35616633
Achillea millefolium	LOTUS Database	35616633
Achillea multifida	Plant	KNApSAcK
Aeonium spp.	Plant	KNApSAcK
Ajania fruticulosa	Plant	KNApSAcK
Alnus glutinosa	Plant	KNApSAcK
Ambrosia chamissonis	Plant	KNApSAcK
Anthemis ruthenica	LOTUS Database	35616633
Anthemis tinctoria	Plant	KNApSAcK
Artemisia abrotanum	Plant	KNApSAcK
Artemisia alba	LOTUS Database	35616633
Artemisia barrelieri	Plant	KNApSAcK
Artemisia molinieri	LOTUS Database	35616633
Asteriscus sericeus	Plant	KNApSAcK
Baccharis neaei	LOTUS Database	35616633
Baccharis salicina	Plant	KNApSAcK
Baccharis sarothroides	Plant	KNApSAcK
Bahia xylopoda	Plant	KNApSAcK
Brickellia baccharidea	LOTUS Database	35616633
Brickellia cylindracea	LOTUS Database	35616633
Cassia grandis	LOTUS Database	35616633
Centaurea africana	LOTUS Database	35616633
Centaurea bracteata Scop.	Plant	KNApSAcK
Centaurea corcubionensis	LOTUS Database	35616633
Centaurea jacea	Plant	KNApSAcK
Centaurea nervosa	LOTUS Database	35616633
Chiliadenus montanus	LOTUS Database	35616633
Chrysanthemum cinerariifolium	Plant	KNApSAcK
Cota altissima	LOTUS Database	35616633
Eremophila mitchellii	LOTUS Database	35616633
Eriophyllum confertiflorum	Plant	KNApSAcK
Eupatorium buniifolium	Plant	KNApSAcK
Eupatorium cannabinum	LOTUS Database	35616633
Grindelia hirsutula	LOTUS Database	35616633
Grindelia robusta	Plant	KNApSAcK
Grindelia tarapacana	Plant	KNApSAcK
Iva frutescens	Plant	KNApSAcK
Pericome caudata	LOTUS Database	35616633
Picradeniopsis schaffneri	LOTUS Database	35616633
Picradeniopsis xylopoda	LOTUS Database	35616633
Pluchea chingoyo	LOTUS Database	35616633
Pluchea sagittalis	Plant	KNApSAcK
Polymnia fruticosa	Plant	KNApSAcK
Smallanthus fruticosus	LOTUS Database	35616633
Stevia berlandieri	Plant	KNApSAcK
Stevia nepetifolia	LOTUS Database	35616633
Stevia origanoides	LOTUS Database	35616633
Stevia rebaudiana	LOTUS Database	35616633
Tanacetum microphyllum	Plant	KNApSAcK
Tanacetum parthenium	Linington's dataset npmrd_submissions_20220207	12943776

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 6-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C6 atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

6-O-methylated flavonoids

Alternative Parents

Substituents

3-methoxyflavonoid-skeleton
4p-methoxyflavonoid-skeleton
6-methoxyflavonoid-skeleton
3'-hydroxyflavonoid
5-hydroxyflavonoid
7-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

trihydroxyflavone (CHEBI:69356 )
trimethoxyflavone (CHEBI:69356 )
Flavones and Flavonols (LMPK12113000 )

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	2.88	ALOGPS
logP	2.26	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	6.91	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	114.68 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	92.56 m³·mol⁻¹	ChemAxon
Polarizability	35.57 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

HMDB0130255

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB089073

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Centaureidin

METLIN ID

Not Available

PubChem Compound

5315773

PDB ID

Not Available

ChEBI ID

69356

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 ]
Long C, Sauleau P, David B, Lavaud C, Cassabois V, Ausseil F, Massiot G: Bioactive flavonoids of Tanacetum parthenium revisited. Phytochemistry. 2003 Sep;64(2):567-9. doi: 10.1016/s0031-9422(03)00208-5. [PubMed:12943776 ]
Meng JC, Hu YF, Chen JH, Tan RX: Antifungal highly oxygenated guaianolides and other constituents from Ajania fruticulosa. Phytochemistry. 2001 Dec;58(7):1141-5. doi: 10.1016/s0031-9422(01)00389-2. [PubMed:11730880 ]
Csupor-Loffler B, Hajdu Z, Zupko I, Rethy B, Falkay G, Forgo P, Hohmann J: Antiproliferative effect of flavonoids and sesquiterpenoids from Achillea millefolium s.l. on cultured human tumour cell lines. Phytother Res. 2009 May;23(5):672-6. doi: 10.1002/ptr.2697. [PubMed:19107850 ]
Hajdu Z, Zupko I, Rethy B, Forgo P, Hohmann J: Bioactivity-guided isolation of cytotoxic sesquiterpenes and flavonoids from Anthemis ruthenica. Planta Med. 2010 Jan;76(1):94-6. doi: 10.1055/s-0029-1185942. Epub 2009 Jul 28. [PubMed:19639540 ]
Jachak SM, Gautam R, Selvam C, Madhan H, Srivastava A, Khan T: Anti-inflammatory, cyclooxygenase inhibitory and antioxidant activities of standardized extracts of Tridax procumbens L. Fitoterapia. 2011 Mar;82(2):173-7. doi: 10.1016/j.fitote.2010.08.016. Epub 2010 Sep 8. [PubMed:20804828 ]
Pan E, Gorka AP, Alumasa JN, Slebodnick C, Harinantenaina L, Brodie PJ, Roepe PD, Randrianaivo R, Birkinshaw C, Kingston DG: Antiplasmodial and antiproliferative pseudoguaianolides of Athroisma proteiforme from the Madagascar Dry Forest. J Nat Prod. 2011 Oct 28;74(10):2174-80. doi: 10.1021/np200499d. Epub 2011 Oct 13. [PubMed:21995542 ]
Forgo P, Zupko I, Molnar J, Vasas A, Dombi G, Hohmann J: Bioactivity-guided isolation of antiproliferative compounds from Centaurea jacea L. Fitoterapia. 2012 Jul;83(5):921-5. doi: 10.1016/j.fitote.2012.04.006. Epub 2012 Apr 17. [PubMed:22537643 ]

Showing NP-Card for Centaureidin (NP0044574)

MOL for NP0044574 (Centaureidin)

3D MOL for NP0044574 (Centaureidin)

3D SDF for NP0044574 (Centaureidin)

3D-SDF for NP0044574 (Centaureidin)

PDB for NP0044574 (Centaureidin)

3D PDB for NP0044574 (Centaureidin)

SMILES for NP0044574 (Centaureidin)

INCHI for NP0044574 (Centaureidin)

Structure for NP0044574 (Centaureidin)

3D Structure for NP0044574 (Centaureidin)