NP-MRD: Showing NP-Card for atalantoflavone (NP0039355)

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Record Information

Version

2.0

Created at

2021-06-20 21:48:40 UTC

Updated at

2021-06-30 00:12:38 UTC

NP-MRD ID

NP0039355

Secondary Accession Numbers

None

Natural Product Identification

Common Name

atalantoflavone

Provided By

JEOL Database JEOL Logo

Description

Atalantoflavone, also known as limonianin, belongs to the class of organic compounds known as pyranoflavonoids. Pyranoflavonoids are compounds containing a pyran ring fused to a 2-phenyl-1,4-benzopyran skeleton. Thus, atalantoflavone is considered to be a flavonoid. atalantoflavone is found in Atalantia buxifolia, Citrus limon, Citrus medica, Citrus sinensis, Citrus trifoliata, Severinia buxi and Ulex europaeus. atalantoflavone was first documented in 2013 (PMID: 24066509). Based on a literature review a significant number of articles have been published on Atalantoflavone (PMID: 25114960) (PMID: 30755289) (PMID: 29600742) (PMID: 26715029) (PMID: 25034000) (PMID: 23057815).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202123483D          

 41 44  0  0  0  0            999 V2000
    2.5805   -1.9954   -3.1099 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2517   -1.6574   -2.4239 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0897   -2.2577   -3.2239 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2485   -2.2363   -1.0291 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1305   -1.4950    0.0756 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9984   -0.0497   -0.0694 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9907    0.5035   -1.3558 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8612    1.8830   -1.5356 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7390    2.7195   -0.4323 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6162    4.0591   -0.6834 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7463    2.1814    0.8569 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6197    3.0415    2.0401 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5042    4.2577    1.9336 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6368    2.3864    3.3534 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7612    1.0536    3.4078 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7987    0.3313    4.6938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1019    0.6280    5.7287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0558   -0.0752    6.9352 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8856   -1.0809    7.1119 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8941   -1.7397    8.3048 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7828   -1.4005    6.0998 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7351   -0.6965    4.8926 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8917    0.2372    2.2974 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8761    0.8035    1.0422 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1035   -0.2262   -2.5053 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6068   -1.5936   -4.1296 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7532   -3.0761   -3.1614 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4226   -1.5375   -2.5770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8738   -1.9903   -2.7733 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0723   -1.8601   -4.2455 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1510   -3.3501   -3.2811 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3468   -3.3148   -0.9339 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1285   -1.9449    1.0621 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8556    2.3031   -2.5380 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5390    4.5300    0.1772 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5579    3.0263    4.2227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8588    1.3995    5.6064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7561    0.1590    7.7323 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5975   -2.4093    8.2867 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5203   -2.1865    6.2273 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4434   -0.9529    4.1070 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
  8  9  1  0  0  0  0
 15 23  1  0  0  0  0
  7 25  1  0  0  0  0
  6  5  1  0  0  0  0
  5  4  2  0  0  0  0
  4  2  1  0  0  0  0
  2 25  1  0  0  0  0
 23 24  1  0  0  0  0
  2  1  1  0  0  0  0
 24 11  1  0  0  0  0
  2  3  1  0  0  0  0
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 15 16  1  0  0  0  0
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 12 13  2  0  0  0  0
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  7  6  1  0  0  0  0
 19 20  1  0  0  0  0
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  9 10  1  0  0  0  0
 14 36  1  0  0  0  0
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  1 26  1  0  0  0  0
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  3 31  1  0  0  0  0
 17 37  1  0  0  0  0
 18 38  1  0  0  0  0
 21 40  1  0  0  0  0
 22 41  1  0  0  0  0
 20 39  1  0  0  0  0
 10 35  1  0  0  0  0
M  END

     RDKit          3D

 41 44  0  0  0  0  0  0  0  0999 V2000
    2.5805   -1.9954   -3.1099 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2517   -1.6574   -2.4239 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0897   -2.2577   -3.2239 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2485   -2.2363   -1.0291 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1305   -1.4950    0.0756 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9984   -0.0497   -0.0694 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9907    0.5035   -1.3558 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8612    1.8830   -1.5356 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7390    2.7195   -0.4323 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6162    4.0591   -0.6834 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7463    2.1814    0.8569 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6197    3.0415    2.0401 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5042    4.2577    1.9336 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6368    2.3864    3.3534 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7612    1.0536    3.4078 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7987    0.3313    4.6938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1019    0.6280    5.7287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0558   -0.0752    6.9352 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8856   -1.0809    7.1119 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8941   -1.7397    8.3048 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7828   -1.4005    6.0998 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7351   -0.6965    4.8926 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8917    0.2372    2.2974 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8761    0.8035    1.0422 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1035   -0.2262   -2.5053 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6068   -1.5936   -4.1296 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7532   -3.0761   -3.1614 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4226   -1.5375   -2.5770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8738   -1.9903   -2.7733 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0723   -1.8601   -4.2455 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1510   -3.3501   -3.2811 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3468   -3.3148   -0.9339 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1285   -1.9449    1.0621 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8556    2.3031   -2.5380 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5390    4.5300    0.1772 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5579    3.0263    4.2227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8588    1.3995    5.6064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7561    0.1590    7.7323 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5975   -2.4093    8.2867 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5203   -2.1865    6.2273 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4434   -0.9529    4.1070 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 14  1  0
 14 15  2  0
  8  9  1  0
 15 23  1  0
  7 25  1  0
  6  5  1  0
  5  4  2  0
  4  2  1  0
  2 25  1  0
 23 24  1  0
  2  1  1  0
 24 11  1  0
  2  3  1  0
  8  7  2  0
 16 17  2  0
  9 11  2  0
 17 18  1  0
 15 16  1  0
 18 19  2  0
 11 12  1  0
 19 21  1  0
 12 13  2  0
 21 22  2  0
 22 16  1  0
  7  6  1  0
 19 20  1  0
 24  6  2  0
  9 10  1  0
 14 36  1  0
  8 34  1  0
  5 33  1  0
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  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  3 30  1  0
  3 31  1  0
 17 37  1  0
 18 38  1  0
 21 40  1  0
 22 41  1  0
 20 39  1  0
 10 35  1  0
M  END


  Mrv1652306202123483D          

 41 44  0  0  0  0            999 V2000
    2.5805   -1.9954   -3.1099 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2517   -1.6574   -2.4239 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0897   -2.2577   -3.2239 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2485   -2.2363   -1.0291 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1305   -1.4950    0.0756 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9984   -0.0497   -0.0694 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9907    0.5035   -1.3558 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8612    1.8830   -1.5356 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7390    2.7195   -0.4323 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6162    4.0591   -0.6834 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7463    2.1814    0.8569 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6197    3.0415    2.0401 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5042    4.2577    1.9336 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6368    2.3864    3.3534 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7612    1.0536    3.4078 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7987    0.3313    4.6938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1019    0.6280    5.7287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0558   -0.0752    6.9352 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8856   -1.0809    7.1119 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8941   -1.7397    8.3048 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7828   -1.4005    6.0998 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7351   -0.6965    4.8926 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8917    0.2372    2.2974 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8761    0.8035    1.0422 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1035   -0.2262   -2.5053 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6068   -1.5936   -4.1296 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7532   -3.0761   -3.1614 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4226   -1.5375   -2.5770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8738   -1.9903   -2.7733 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0723   -1.8601   -4.2455 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1510   -3.3501   -3.2811 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3468   -3.3148   -0.9339 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1285   -1.9449    1.0621 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8556    2.3031   -2.5380 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5390    4.5300    0.1772 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5579    3.0263    4.2227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8588    1.3995    5.6064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7561    0.1590    7.7323 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5975   -2.4093    8.2867 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5203   -2.1865    6.2273 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4434   -0.9529    4.1070 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
  8  9  1  0  0  0  0
 15 23  1  0  0  0  0
  7 25  1  0  0  0  0
  6  5  1  0  0  0  0
  5  4  2  0  0  0  0
  4  2  1  0  0  0  0
  2 25  1  0  0  0  0
 23 24  1  0  0  0  0
  2  1  1  0  0  0  0
 24 11  1  0  0  0  0
  2  3  1  0  0  0  0
  8  7  2  0  0  0  0
 16 17  2  0  0  0  0
  9 11  2  0  0  0  0
 17 18  1  0  0  0  0
 15 16  1  0  0  0  0
 18 19  2  0  0  0  0
 11 12  1  0  0  0  0
 19 21  1  0  0  0  0
 12 13  2  0  0  0  0
 21 22  2  0  0  0  0
 22 16  1  0  0  0  0
  7  6  1  0  0  0  0
 19 20  1  0  0  0  0
 24  6  2  0  0  0  0
  9 10  1  0  0  0  0
 14 36  1  0  0  0  0
  8 34  1  0  0  0  0
  5 33  1  0  0  0  0
  4 32  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
  3 29  1  0  0  0  0
  3 30  1  0  0  0  0
  3 31  1  0  0  0  0
 17 37  1  0  0  0  0
 18 38  1  0  0  0  0
 21 40  1  0  0  0  0
 22 41  1  0  0  0  0
 20 39  1  0  0  0  0
 10 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0039355

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(=O)C2=C(O[H])C([H])=C3OC(C([H])=C([H])C3=C2O1)(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C20H16O5/c1-20(2)8-7-13-17(25-20)10-15(23)18-14(22)9-16(24-19(13)18)11-3-5-12(21)6-4-11/h3-10,21,23H,1-2H3

> <INCHI_KEY>
YEUHAZULDUVZLA-UHFFFAOYSA-N

> <FORMULA>
C20H16O5

> <MOLECULAR_WEIGHT>
336.338

> <EXACT_MASS>
336.099773622

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
35.41825167379645

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-hydroxy-2-(4-hydroxyphenyl)-8,8-dimethyl-4H,8H-pyrano[2,3-f]chromen-4-one

> <ALOGPS_LOGP>
4.37

> <JCHEM_LOGP>
3.910877857333333

> <ALOGPS_LOGS>
-4.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.755201880209922

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.5622294341928615

> <JCHEM_PKA_STRONGEST_BASIC>
-4.8068518556270785

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
95.32639999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.03e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
atalantoflavone

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 41 44  0  0  0  0  0  0  0  0999 V2000
    2.5805   -1.9954   -3.1099 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2517   -1.6574   -2.4239 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0897   -2.2577   -3.2239 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2485   -2.2363   -1.0291 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1305   -1.4950    0.0756 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9984   -0.0497   -0.0694 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9907    0.5035   -1.3558 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8612    1.8830   -1.5356 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7390    2.7195   -0.4323 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6162    4.0591   -0.6834 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7463    2.1814    0.8569 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6197    3.0415    2.0401 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5042    4.2577    1.9336 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6368    2.3864    3.3534 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7612    1.0536    3.4078 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7987    0.3313    4.6938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1019    0.6280    5.7287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0558   -0.0752    6.9352 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8856   -1.0809    7.1119 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8941   -1.7397    8.3048 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7828   -1.4005    6.0998 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7351   -0.6965    4.8926 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8917    0.2372    2.2974 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8761    0.8035    1.0422 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1035   -0.2262   -2.5053 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6068   -1.5936   -4.1296 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7532   -3.0761   -3.1614 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4226   -1.5375   -2.5770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8738   -1.9903   -2.7733 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0723   -1.8601   -4.2455 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1510   -3.3501   -3.2811 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3468   -3.3148   -0.9339 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1285   -1.9449    1.0621 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8556    2.3031   -2.5380 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5390    4.5300    0.1772 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5579    3.0263    4.2227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8588    1.3995    5.6064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7561    0.1590    7.7323 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5975   -2.4093    8.2867 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5203   -2.1865    6.2273 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4434   -0.9529    4.1070 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 14  1  0
 14 15  2  0
  8  9  1  0
 15 23  1  0
  7 25  1  0
  6  5  1  0
  5  4  2  0
  4  2  1  0
  2 25  1  0
 23 24  1  0
  2  1  1  0
 24 11  1  0
  2  3  1  0
  8  7  2  0
 16 17  2  0
  9 11  2  0
 17 18  1  0
 15 16  1  0
 18 19  2  0
 11 12  1  0
 19 21  1  0
 12 13  2  0
 21 22  2  0
 22 16  1  0
  7  6  1  0
 19 20  1  0
 24  6  2  0
  9 10  1  0
 14 36  1  0
  8 34  1  0
  5 33  1  0
  4 32  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  3 30  1  0
  3 31  1  0
 17 37  1  0
 18 38  1  0
 21 40  1  0
 22 41  1  0
 20 39  1  0
 10 35  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0       2.580  -1.995  -3.110  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.252  -1.657  -2.424  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.090  -2.258  -3.224  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.248  -2.236  -1.029  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.131  -1.495   0.076  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.998  -0.050  -0.069  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.991   0.503  -1.356  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.861   1.883  -1.536  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.739   2.720  -0.432  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.616   4.059  -0.683  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.746   2.181   0.857  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.620   3.042   2.040  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.504   4.258   1.934  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.637   2.386   3.353  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.761   1.054   3.408  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.799   0.331   4.694  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.102   0.628   5.729  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.056  -0.075   6.935  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.886  -1.081   7.112  0.00  0.00           C+0
HETATM   20  O   UNK     0       0.894  -1.740   8.305  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.783  -1.401   6.100  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.735  -0.697   4.893  0.00  0.00           C+0
HETATM   23  O   UNK     0       0.892   0.237   2.297  0.00  0.00           O+0
HETATM   24  C   UNK     0       0.876   0.804   1.042  0.00  0.00           C+0
HETATM   25  O   UNK     0       1.103  -0.226  -2.505  0.00  0.00           O+0
HETATM   26  H   UNK     0       2.607  -1.594  -4.130  0.00  0.00           H+0
HETATM   27  H   UNK     0       2.753  -3.076  -3.161  0.00  0.00           H+0
HETATM   28  H   UNK     0       3.423  -1.538  -2.577  0.00  0.00           H+0
HETATM   29  H   UNK     0      -0.874  -1.990  -2.773  0.00  0.00           H+0
HETATM   30  H   UNK     0       0.072  -1.860  -4.245  0.00  0.00           H+0
HETATM   31  H   UNK     0       0.151  -3.350  -3.281  0.00  0.00           H+0
HETATM   32  H   UNK     0       1.347  -3.315  -0.934  0.00  0.00           H+0
HETATM   33  H   UNK     0       1.129  -1.945   1.062  0.00  0.00           H+0
HETATM   34  H   UNK     0       0.856   2.303  -2.538  0.00  0.00           H+0
HETATM   35  H   UNK     0       0.539   4.530   0.177  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.558   3.026   4.223  0.00  0.00           H+0
HETATM   37  H   UNK     0      -0.859   1.399   5.606  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.756   0.159   7.732  0.00  0.00           H+0
HETATM   39  H   UNK     0       1.597  -2.409   8.287  0.00  0.00           H+0
HETATM   40  H   UNK     0       2.520  -2.187   6.227  0.00  0.00           H+0
HETATM   41  H   UNK     0       2.443  -0.953   4.107  0.00  0.00           H+0
CONECT    1    2   26   27   28                                             
CONECT    2    4   25    1    3                                             
CONECT    3    2   29   30   31                                             
CONECT    4    5    2   32                                                  
CONECT    5    6    4   33                                                  
CONECT    6    5    7   24                                                  
CONECT    7   25    8    6                                                  
CONECT    8    9    7   34                                                  
CONECT    9    8   11   10                                                  
CONECT   10    9   35                                                       
CONECT   11   24    9   12                                                  
CONECT   12   14   11   13                                                  
CONECT   13   12                                                            
CONECT   14   12   15   36                                                  
CONECT   15   14   23   16                                                  
CONECT   16   17   15   22                                                  
CONECT   17   16   18   37                                                  
CONECT   18   17   19   38                                                  
CONECT   19   18   21   20                                                  
CONECT   20   19   39                                                       
CONECT   21   19   22   40                                                  
CONECT   22   21   16   41                                                  
CONECT   23   15   24                                                       
CONECT   24   23   11    6                                                  
CONECT   25    7    2                                                       
CONECT   26    1                                                            
CONECT   27    1                                                            
CONECT   28    1                                                            
CONECT   29    3                                                            
CONECT   30    3                                                            
CONECT   31    3                                                            
CONECT   32    4                                                            
CONECT   33    5                                                            
CONECT   34    8                                                            
CONECT   35   10                                                            
CONECT   36   14                                                            
CONECT   37   17                                                            
CONECT   38   18                                                            
CONECT   39   20                                                            
CONECT   40   21                                                            
CONECT   41   22                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   88    0
END

RDKit          3D

41 44  0  0  0  0  0  0  0  0999 V2000
    2.5805   -1.9954   -3.1099 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2517   -1.6574   -2.4239 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0897   -2.2577   -3.2239 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2485   -2.2363   -1.0291 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1305   -1.4950    0.0756 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9984   -0.0497   -0.0694 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9907    0.5035   -1.3558 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8612    1.8830   -1.5356 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7390    2.7195   -0.4323 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6162    4.0591   -0.6834 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7463    2.1814    0.8569 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6197    3.0415    2.0401 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5042    4.2577    1.9336 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6368    2.3864    3.3534 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7612    1.0536    3.4078 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7987    0.3313    4.6938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1019    0.6280    5.7287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0558   -0.0752    6.9352 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8856   -1.0809    7.1119 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8941   -1.7397    8.3048 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7828   -1.4005    6.0998 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7351   -0.6965    4.8926 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8917    0.2372    2.2974 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8761    0.8035    1.0422 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1035   -0.2262   -2.5053 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6068   -1.5936   -4.1296 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7532   -3.0761   -3.1614 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4226   -1.5375   -2.5770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8738   -1.9903   -2.7733 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0723   -1.8601   -4.2455 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1510   -3.3501   -3.2811 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3468   -3.3148   -0.9339 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1285   -1.9449    1.0621 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8556    2.3031   -2.5380 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5390    4.5300    0.1772 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5579    3.0263    4.2227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8588    1.3995    5.6064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7561    0.1590    7.7323 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5975   -2.4093    8.2867 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5203   -2.1865    6.2273 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4434   -0.9529    4.1070 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 14  1  0
 14 15  2  0
  8  9  1  0
 15 23  1  0
  7 25  1  0
  6  5  1  0
  5  4  2  0
  4  2  1  0
  2 25  1  0
 23 24  1  0
  2  1  1  0
 24 11  1  0
  2  3  1  0
  8  7  2  0
 16 17  2  0
  9 11  2  0
 17 18  1  0
 15 16  1  0
 18 19  2  0
 11 12  1  0
 19 21  1  0
 12 13  2  0
 21 22  2  0
 22 16  1  0
  7  6  1  0
 19 20  1  0
 24  6  2  0
  9 10  1  0
 14 36  1  0
  8 34  1  0
  5 33  1  0
  4 32  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  3 30  1  0
  3 31  1  0
 17 37  1  0
 18 38  1  0
 21 40  1  0
 22 41  1  0
 20 39  1  0
 10 35  1  0
M  END

View in JSmol

Synonyms

Value	Source
5-Hydroxy-2-(4-hydroxyphenyl)-8,8-dimethyl-4H,8H-benzo[1,2-b:3,4-b']dipyran-4-one, 9ci	HMDB
Limonianin	HMDB

Chemical Formula

C₂₀H₁₆O₅

Average Mass

336.3380 Da

Monoisotopic Mass

336.09977 Da

IUPAC Name

5-hydroxy-2-(4-hydroxyphenyl)-8,8-dimethyl-4H,8H-pyrano[2,3-f]chromen-4-one

Traditional Name

atalantoflavone

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(=O)C2=C(O[H])C([H])=C3OC(C([H])=C([H])C3=C2O1)(C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C20H16O5/c1-20(2)8-7-13-17(25-20)10-15(23)18-14(22)9-16(24-19(13)18)11-3-5-12(21)6-4-11/h3-10,21,23H,1-2H3

InChI Key

YEUHAZULDUVZLA-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, acetone-d6, 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
Atalantia buxifolia	LOTUS Database	35616633
Atalantia racemosa	KNApSAcK Database	22123792
Citrus limon	LOTUS Database	35616633
Citrus medica	LOTUS Database	35616633
Citrus sinensis	LOTUS Database	35616633
Citrus trifoliata	LOTUS Database	35616633
Erythrina vogelii	KNApSAcK Database	22123792
Morus mongolica	KNApSAcK Database	22123792
Severinia buxi	JEOL database	Bacher, M., et al, Mag. Reson. Chem. 48, 83 (2010)
Ulex airensis	KNApSAcK Database	22123792
Ulex europaeus	LOTUS Database	35616633
Ulex europaeus subsp. europaeus	KNApSAcK Database	22123792

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyranoflavonoids. Pyranoflavonoids are compounds containing a pyran ring fused to a 2-phenyl-1,4-benzopyran skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Pyranoflavonoids

Direct Parent

Pyranoflavonoids

Alternative Parents

Not Available

Substituents

Not Available

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

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	4.37	ALOGPS
logP	3.91	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	7.56	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	95.33 m³·mol⁻¹	ChemAxon
Polarizability	35.42 Å³	ChemAxon
Number of Rings	4	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

HMDB0030450

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB002316

KNApSAcK ID

C00004052

Chemspider ID

24693595

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14162621

PDB ID

Not Available

ChEBI ID

603782

Good Scents ID

rw1820061

References

General References

Ahmed SA, Kamel EM: Cytotoxic activities of flavonoids from Centaurea scoparia. ScientificWorldJournal. 2014;2014:274207. doi: 10.1155/2014/274207. Epub 2014 Jun 11. [PubMed:25114960 ]
Lemos da Silva LA, Hoehr de Moraes M, Scotti MT, Scotti L, de Jesus Souza R, Nantchouang Ouete JL, Biavatti MW, Steindel M, Sandjo LP: Antiprotozoal investigation of 20 plant metabolites on Trypanosoma cruzi and Leishmania amazonensis amastigotes. Atalantoflavone alters the mitochondrial membrane potential. Parasitology. 2019 Jun;146(7):849-856. doi: 10.1017/S0031182019000052. Epub 2019 Feb 13. [PubMed:30755289 ]
Posri P, Suthiwong J, Takomthong P, Wongsa C, Chuenban C, Boonyarat C, Yenjai C: A new flavonoid from the leaves of Atalantia monophylla (L.) DC. Nat Prod Res. 2019 Apr;33(8):1115-1121. doi: 10.1080/14786419.2018.1457667. Epub 2018 Mar 30. [PubMed:29600742 ]
Djeussi DE, Sandjo LP, Noumedem JA, Omosa LK, T Ngadjui B, Kuete V: Antibacterial activities of the methanol extracts and compounds from Erythrina sigmoidea against Gram-negative multi-drug resistant phenotypes. BMC Complement Altern Med. 2015 Dec 30;15:453. doi: 10.1186/s12906-015-0978-8. [PubMed:26715029 ]
Kuete V, Sandjo LP, Djeussi DE, Zeino M, Kwamou GM, Ngadjui B, Efferth T: Cytotoxic flavonoids and isoflavonoids from Erythrina sigmoidea towards multi-factorial drug resistant cancer cells. Invest New Drugs. 2014 Dec;32(6):1053-62. doi: 10.1007/s10637-014-0137-y. Epub 2014 Jul 19. [PubMed:25034000 ]
Ouete JL, Sandjo LP, Kapche DW, Liermann JC, Opatz T, Simo IK, Ngadjui BT: A new flavone from the roots of Milicia excelsa (Moraceae). Z Naturforsch C J Biosci. 2013 Jul-Aug;68(7-8):259-63. [PubMed:24066509 ]
Ndemangou B, Sielinou VT, Vardamides JC, Ali MS, Lateef M, Iqbal L, Afza N, Nkengfack AE: Urease inhibitory isoflavonoids from different parts of Calopogonium mucunoides (Fabaceae). J Enzyme Inhib Med Chem. 2013 Dec;28(6):1156-61. doi: 10.3109/14756366.2012.719025. Epub 2012 Oct 11. [PubMed:23057815 ]
Bacher, M., et al. (2010). Bacher, M., et al, Mag. Reson. Chem. 48, 83 (2010). Mag. Reson. Chem..

Showing NP-Card for atalantoflavone (NP0039355)

MOL for NP0039355 (atalantoflavone)

3D MOL for NP0039355 (atalantoflavone)

3D SDF for NP0039355 (atalantoflavone)

3D-SDF for NP0039355 (atalantoflavone)

PDB for NP0039355 (atalantoflavone)

3D PDB for NP0039355 (atalantoflavone)

SMILES for NP0039355 (atalantoflavone)

INCHI for NP0039355 (atalantoflavone)

Structure for NP0039355 (atalantoflavone)

3D Structure for NP0039355 (atalantoflavone)