NP-MRD: Showing NP-Card for Cudraflavone B (NP0083959)

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Record Information

Version

2.0

Created at

2022-04-29 04:50:20 UTC

Updated at

2022-04-29 04:50:20 UTC

NP-MRD ID

NP0083959

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cudraflavone B

Description

Cudraflavone B belongs to the class of organic compounds known as 3-prenylated flavones. These are flavones that features a C5-isoprenoid substituent at the 3-position. Cudraflavone B is an extremely weak basic (essentially neutral) compound (based on its pKa). Cudraflavone B is found in Artocarpus altilis, Artocarpus heterophyllus, Brosimum lactescens, Maclura tricuspidata, Morus alba and Morus nigra. Cudraflavone B was first documented in 2011 (PMID: 21319773). An extended flavonoid that consists of a pyranochromane skeleton that is 2H,6H-pyranochromen-6-one substituted by geminal methyl groups at position 2, a 2,4-dihydroxyphenyl group at position 8, a hydroxy group at position 5 and a prenyl group at position 7.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004191522472D          

 31 34  0  0  0  0            999 V2000
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    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
    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
    2.1434   -1.2375    0.0000 O   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
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   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
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9979   -0.8748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5282   -1.7933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   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
   -0.7145   -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 O   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
    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 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 10 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
  8 20  1  0  0  0  0
 20 21  1  0  0  0  0
  5 21  1  0  0  0  0
 21 22  2  0  0  0  0
  6 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  2  0  0  0  0
 23 29  1  0  0  0  0
 29 30  1  0  0  0  0
  2 31  1  0  0  0  0
M  END

     RDKit          3D

 55 58  0  0  0  0  0  0  0  0999 V2000
   -4.3380    3.1659    2.0780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6453    2.8660    0.7699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2679    4.0171   -0.0788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4227    1.6127    0.4499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7362    1.2890   -0.8407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5192    0.5087   -0.6430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4255   -0.8115   -0.3234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5301   -1.7167   -0.2283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5618   -2.5157    0.9296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4927   -3.5016    1.1390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4383   -3.7048    0.1515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3780   -4.7005    0.3680 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4224   -2.9399   -0.9808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4673   -1.9417   -1.1797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5373   -1.2374   -2.3747 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2208   -1.3449   -0.0591 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8987   -0.7185   -0.0797 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0713   -1.3927    0.2141 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2793   -0.7286    0.1941 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2921    0.5894   -0.1174 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0871    1.2780   -0.4181 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1874    2.5929   -0.7187 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8786    0.6259   -0.4011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3086    1.2210   -0.6759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3136    2.4516   -0.9692 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5515    1.3126   -0.1475 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6623    0.6747    0.1286 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7242   -0.7651    0.4771 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.6900   -1.4339   -0.4904 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3691   -0.8493    1.8660 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4771   -1.3883    0.4872 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6865    3.9356    2.5682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3291    3.6184    1.9190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3568    2.2754    2.7183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1819    4.1893   -0.0052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6343    3.9102   -1.1328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7356    4.9563    0.3042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7463    0.8395    1.1368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4261    2.3020   -1.2610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4853    0.9552   -1.5374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8274   -2.3627    1.7052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4796   -4.0952    2.0485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2744   -5.6492    0.0996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1732   -3.0950   -1.7748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2088   -1.3823   -3.0828 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0487   -2.4357    0.4593 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6485    3.3363   -0.9564 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5441    2.3530   -0.3953 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6358    1.1801    0.1179 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4013   -2.1116    0.0243 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3016   -0.6651   -1.0113 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1203   -2.0065   -1.2500 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4682   -0.7167    1.6960 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1883   -1.8439    2.3256 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0455   -0.0021    2.4738 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  1  6
 28 30  1  0
 28 31  1  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 23 24  1  0
 24 25  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 24  6  1  0
 14  8  1  0
 23 17  1  0
 31 19  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  3 35  1  0
  3 36  1  0
  3 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
 18 46  1  0
 26 48  1  0
 27 49  1  0
 29 50  1  0
 29 51  1  0
 29 52  1  0
 30 53  1  0
 30 54  1  0
 30 55  1  0
 22 47  1  0
  9 41  1  0
 10 42  1  0
 12 43  1  0
 13 44  1  0
 15 45  1  0
M  END


  Mrv1533004191522472D          

 31 34  0  0  0  0            999 V2000
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    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
    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
    2.1434   -1.2375    0.0000 O   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
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   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
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9979   -0.8748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5282   -1.7933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   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
   -0.7145   -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 O   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
    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 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 10 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
  8 20  1  0  0  0  0
 20 21  1  0  0  0  0
  5 21  1  0  0  0  0
 21 22  2  0  0  0  0
  6 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  2  0  0  0  0
 23 29  1  0  0  0  0
 29 30  1  0  0  0  0
  2 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0083959

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC1=C(OC2=CC3=C(C=CC(C)(C)O3)C(O)=C2C1=O)C1=CC=C(O)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C25H24O6/c1-13(2)5-7-17-23(29)21-20(30-24(17)15-8-6-14(26)11-18(15)27)12-19-16(22(21)28)9-10-25(3,4)31-19/h5-6,8-12,26-28H,7H2,1-4H3

> <INCHI_KEY>
XIWCDUHPYMOFIL-UHFFFAOYSA-N

> <FORMULA>
C25H24O6

> <MOLECULAR_WEIGHT>
420.461

> <EXACT_MASS>
420.157288493

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
45.67867380376726

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(2,4-dihydroxyphenyl)-5-hydroxy-8,8-dimethyl-3-(3-methylbut-2-en-1-yl)-4H,8H-pyrano[3,2-g]chromen-4-one

> <ALOGPS_LOGP>
4.89

> <JCHEM_LOGP>
5.218008635000001

> <ALOGPS_LOGS>
-4.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.190410084870043

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.191518937562038

> <JCHEM_PKA_STRONGEST_BASIC>
-4.807809940578825

> <JCHEM_POLAR_SURFACE_AREA>
96.22

> <JCHEM_REFRACTIVITY>
120.86599999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.56e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cudraflavone B

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       5.335  -3.080   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       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       9.336  -2.310   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.196  -1.633   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.186  -3.347   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       6.668  -6.930   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -2.667  -0.000   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   31                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   21                                                  
CONECT    6    5    7   23                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   20                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   17                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14   15                                             
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   12   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   10   18                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18    8   21                                                  
CONECT   21   20    5   22                                                  
CONECT   22   21                                                            
CONECT   23    6   24   29                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   23   30                                                  
CONECT   30   29                                                            
CONECT   31    2                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₂₄O₆

Average Mass

420.4610 Da

Monoisotopic Mass

420.15729 Da

IUPAC Name

2-(2,4-dihydroxyphenyl)-5-hydroxy-8,8-dimethyl-3-(3-methylbut-2-en-1-yl)-4H,8H-pyrano[3,2-g]chromen-4-one

Traditional Name

cudraflavone B

CAS Registry Number

Not Available

SMILES

CC(C)=CCC1=C(OC2=CC3=C(C=CC(C)(C)O3)C(O)=C2C1=O)C1=CC=C(O)C=C1O

InChI Identifier

InChI=1S/C25H24O6/c1-13(2)5-7-17-23(29)21-20(30-24(17)15-8-6-14(26)11-18(15)27)12-19-16(22(21)28)9-10-25(3,4)31-19/h5-6,8-12,26-28H,7H2,1-4H3

InChI Key

XIWCDUHPYMOFIL-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
Artocarpus altilis	LOTUS Database	35616633
Artocarpus heterophyllus	LOTUS Database	35616633
Brosimum lactescens	LOTUS Database	35616633
Maclura tricuspidata	LOTUS Database	35616633
Morus alba	Plant	KNApSAcK
Morus nigra	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3-prenylated flavones. These are flavones that features a C5-isoprenoid substituent at the 3-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavones

Direct Parent

3-prenylated flavones

Alternative Parents

Substituents

3-prenylated flavone
Pyranoflavonoid
Hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
Pyranochromene
2,2-dimethyl-1-benzopyran
Chromone
1-benzopyran
Benzopyran
Resorcinol
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
Pyranone
Phenol
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Pyran
Benzenoid
Vinylogous acid
Heteroaromatic compound
Oxacycle
Organoheterocyclic compound
Ether
Organic oxygen compound
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

trihydroxyflavone (CHEBI:67850 )
extended flavonoid (CHEBI:67850 )
pyranochromane (CHEBI:67850 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	4.89	ALOGPS
logP	5.22	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	7.19	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	96.22 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	120.87 m³·mol⁻¹	ChemAxon
Polarizability	45.68 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5319925

PDB ID

Not Available

ChEBI ID

67850

Good Scents ID

Not Available

References

General References

Hosek J, Bartos M, Chudik S, Dall'Acqua S, Innocenti G, Kartal M, Kokoska L, Kollar P, Kutil Z, Landa P, Marek R, Zavalova V, Zemlicka M, Smejkal K: Natural compound cudraflavone B shows promising anti-inflammatory properties in vitro. J Nat Prod. 2011 Apr 25;74(4):614-9. doi: 10.1021/np100638h. Epub 2011 Feb 14. [PubMed:21319773 ]

Showing NP-Card for Cudraflavone B (NP0083959)

MOL for NP0083959 (Cudraflavone B)

3D MOL for NP0083959 (Cudraflavone B)

3D SDF for NP0083959 (Cudraflavone B)

3D-SDF for NP0083959 (Cudraflavone B)

PDB for NP0083959 (Cudraflavone B)

3D PDB for NP0083959 (Cudraflavone B)

SMILES for NP0083959 (Cudraflavone B)

INCHI for NP0083959 (Cudraflavone B)

Structure for NP0083959 (Cudraflavone B)

3D Structure for NP0083959 (Cudraflavone B)