NP-MRD: Showing NP-Card for (2S)-3'-formyl-4',5,7-trihydroxyflavanone (NP0042870)

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Record Information

Version

1.0

Created at

2021-06-21 00:25:41 UTC

Updated at

2021-06-30 00:18:13 UTC

NP-MRD ID

NP0042870

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2S)-3'-formyl-4',5,7-trihydroxyflavanone

Provided By

JEOL Database JEOL Logo

Description

(S)-3'-Formyl-4',5,7-trihydroxyflavanone belongs to the class of organic compounds known as flavanones. Flavanones are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a ketone at the carbon C3. (2S)-3'-formyl-4',5,7-trihydroxyflavanone is found in Feroniella lucida. It was first documented in 2015 (PMID: 26411007). Based on a literature review a significant number of articles have been published on (S)-3'-Formyl-4',5,7-trihydroxyflavanone (PMID: 33011529) (PMID: 30884485) (PMID: 28075580) (PMID: 26721195).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212102253D          

 34 36  0  0  0  0            999 V2000
   -3.5594   -5.9984   -0.0973 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7837   -5.0950   -0.3947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2130   -3.6851   -0.3530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2959   -2.6907   -0.7140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6668   -1.3347   -0.6766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6999   -0.2344   -1.0810 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7627    0.0041   -2.5833 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7993    1.1044   -2.9225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9672    1.8751   -3.8645 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4259    1.1938   -2.1078 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4415    2.1085   -2.4080 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3582    3.0032   -3.4406 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6101    2.1343   -1.6507 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7573    1.2333   -0.5997 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8871    1.2139    0.1634 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7534    0.3191   -0.2902 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5766    0.3105   -1.0367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3726   -0.6105   -0.6775 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9752   -1.0027   -0.2856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8890   -1.9977    0.0703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5083   -3.3347    0.0372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4547   -4.2537    0.3986 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7449   -5.2997   -0.7028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2879   -2.9648   -1.0199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9654    0.6780   -0.5265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7705    0.3084   -2.8864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4718   -0.8847   -3.1552 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4983    2.8655   -3.8999 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3882    2.8497   -1.8984 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4986    1.8969   -0.1610 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8872   -0.3739    0.5360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2973    0.0369   -0.2528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8984   -1.7311    0.3740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0516   -5.1489    0.3298 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  5 19  1  0  0  0  0
 13 11  1  0  0  0  0
 19 20  2  0  0  0  0
 11 10  2  0  0  0  0
 20 21  1  0  0  0  0
 14 13  2  0  0  0  0
 21  3  2  0  0  0  0
 17 16  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
 16 14  1  0  0  0  0
  8  9  2  0  0  0  0
 17 18  1  0  0  0  0
 11 12  1  0  0  0  0
 10  8  1  0  0  0  0
 14 15  1  0  0  0  0
  8  7  1  0  0  0  0
 21 22  1  0  0  0  0
  7  6  1  0  0  0  0
  3  2  1  0  0  0  0
  6 18  1  0  0  0  0
  2  1  2  0  0  0  0
 17 10  1  0  0  0  0
  2 23  1  0  0  0  0
 13 29  1  0  0  0  0
 16 31  1  0  0  0  0
  7 26  1  0  0  0  0
  7 27  1  0  0  0  0
  6 25  1  1  0  0  0
 19 32  1  0  0  0  0
 20 33  1  0  0  0  0
  4 24  1  0  0  0  0
 12 28  1  0  0  0  0
 15 30  1  0  0  0  0
 22 34  1  0  0  0  0
M  END

     RDKit          3D

 34 36  0  0  0  0  0  0  0  0999 V2000
   -3.5594   -5.9984   -0.0973 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7837   -5.0950   -0.3947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2130   -3.6851   -0.3530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2959   -2.6907   -0.7140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6668   -1.3347   -0.6766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6999   -0.2344   -1.0810 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7627    0.0041   -2.5833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7993    1.1044   -2.9225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9672    1.8751   -3.8645 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4259    1.1938   -2.1078 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4415    2.1085   -2.4080 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3582    3.0032   -3.4406 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6101    2.1343   -1.6507 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7573    1.2333   -0.5997 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8871    1.2139    0.1634 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7534    0.3191   -0.2902 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5766    0.3105   -1.0367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3726   -0.6105   -0.6775 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9752   -1.0027   -0.2856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8890   -1.9977    0.0703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5083   -3.3347    0.0372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4547   -4.2537    0.3986 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7449   -5.2997   -0.7028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2879   -2.9648   -1.0199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9654    0.6780   -0.5265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7705    0.3084   -2.8864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4718   -0.8847   -3.1552 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4983    2.8655   -3.8999 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3882    2.8497   -1.8984 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4986    1.8969   -0.1610 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8872   -0.3739    0.5360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2973    0.0369   -0.2528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8984   -1.7311    0.3740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0516   -5.1489    0.3298 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0
  5 19  1  0
 13 11  1  0
 19 20  2  0
 11 10  2  0
 20 21  1  0
 14 13  2  0
 21  3  2  0
 17 16  2  0
  3  4  1  0
  4  5  2  0
 16 14  1  0
  8  9  2  0
 17 18  1  0
 11 12  1  0
 10  8  1  0
 14 15  1  0
  8  7  1  0
 21 22  1  0
  7  6  1  0
  3  2  1  0
  6 18  1  0
  2  1  2  0
 17 10  1  0
  2 23  1  0
 13 29  1  0
 16 31  1  0
  7 26  1  0
  7 27  1  0
  6 25  1  1
 19 32  1  0
 20 33  1  0
  4 24  1  0
 12 28  1  0
 15 30  1  0
 22 34  1  0
M  END


  Mrv1652306212102253D          

 34 36  0  0  0  0            999 V2000
   -3.5594   -5.9984   -0.0973 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7837   -5.0950   -0.3947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2130   -3.6851   -0.3530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2959   -2.6907   -0.7140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6668   -1.3347   -0.6766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6999   -0.2344   -1.0810 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7627    0.0041   -2.5833 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7993    1.1044   -2.9225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9672    1.8751   -3.8645 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4259    1.1938   -2.1078 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4415    2.1085   -2.4080 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3582    3.0032   -3.4406 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6101    2.1343   -1.6507 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7573    1.2333   -0.5997 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8871    1.2139    0.1634 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7534    0.3191   -0.2902 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5766    0.3105   -1.0367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3726   -0.6105   -0.6775 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9752   -1.0027   -0.2856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8890   -1.9977    0.0703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5083   -3.3347    0.0372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4547   -4.2537    0.3986 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7449   -5.2997   -0.7028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2879   -2.9648   -1.0199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9654    0.6780   -0.5265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7705    0.3084   -2.8864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4718   -0.8847   -3.1552 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4983    2.8655   -3.8999 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3882    2.8497   -1.8984 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4986    1.8969   -0.1610 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8872   -0.3739    0.5360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2973    0.0369   -0.2528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8984   -1.7311    0.3740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0516   -5.1489    0.3298 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  5 19  1  0  0  0  0
 13 11  1  0  0  0  0
 19 20  2  0  0  0  0
 11 10  2  0  0  0  0
 20 21  1  0  0  0  0
 14 13  2  0  0  0  0
 21  3  2  0  0  0  0
 17 16  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
 16 14  1  0  0  0  0
  8  9  2  0  0  0  0
 17 18  1  0  0  0  0
 11 12  1  0  0  0  0
 10  8  1  0  0  0  0
 14 15  1  0  0  0  0
  8  7  1  0  0  0  0
 21 22  1  0  0  0  0
  7  6  1  0  0  0  0
  3  2  1  0  0  0  0
  6 18  1  0  0  0  0
  2  1  2  0  0  0  0
 17 10  1  0  0  0  0
  2 23  1  0  0  0  0
 13 29  1  0  0  0  0
 16 31  1  0  0  0  0
  7 26  1  0  0  0  0
  7 27  1  0  0  0  0
  6 25  1  1  0  0  0
 19 32  1  0  0  0  0
 20 33  1  0  0  0  0
  4 24  1  0  0  0  0
 12 28  1  0  0  0  0
 15 30  1  0  0  0  0
 22 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0042870

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C(O[H])=C2C(O[C@]([H])(C3=C([H])C(C([H])=O)=C(O[H])C([H])=C3[H])C([H])([H])C2=O)=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C16H12O6/c17-7-9-3-8(1-2-11(9)19)14-6-13(21)16-12(20)4-10(18)5-15(16)22-14/h1-5,7,14,18-20H,6H2/t14-/m0/s1

> <INCHI_KEY>
DOFLNDASWRCTNW-AWEZNQCLSA-N

> <FORMULA>
C16H12O6

> <MOLECULAR_WEIGHT>
300.266

> <EXACT_MASS>
300.063388106

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
29.61858346307882

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-[(2S)-5,7-dihydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-2-yl]-2-hydroxybenzaldehyde

> <ALOGPS_LOGP>
2.54

> <JCHEM_LOGP>
3.1976103949999994

> <ALOGPS_LOGS>
-3.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.438167096543273

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.741167816101615

> <JCHEM_PKA_STRONGEST_BASIC>
-4.948216248943308

> <JCHEM_POLAR_SURFACE_AREA>
104.06000000000002

> <JCHEM_REFRACTIVITY>
77.8738

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.50e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-[(2S)-5,7-dihydroxy-4-oxo-2,3-dihydro-1-benzopyran-2-yl]-2-hydroxybenzaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 34 36  0  0  0  0  0  0  0  0999 V2000
   -3.5594   -5.9984   -0.0973 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7837   -5.0950   -0.3947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2130   -3.6851   -0.3530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2959   -2.6907   -0.7140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6668   -1.3347   -0.6766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6999   -0.2344   -1.0810 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7627    0.0041   -2.5833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7993    1.1044   -2.9225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9672    1.8751   -3.8645 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4259    1.1938   -2.1078 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4415    2.1085   -2.4080 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3582    3.0032   -3.4406 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6101    2.1343   -1.6507 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7573    1.2333   -0.5997 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8871    1.2139    0.1634 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7534    0.3191   -0.2902 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5766    0.3105   -1.0367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3726   -0.6105   -0.6775 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9752   -1.0027   -0.2856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8890   -1.9977    0.0703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5083   -3.3347    0.0372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4547   -4.2537    0.3986 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7449   -5.2997   -0.7028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2879   -2.9648   -1.0199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9654    0.6780   -0.5265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7705    0.3084   -2.8864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4718   -0.8847   -3.1552 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4983    2.8655   -3.8999 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3882    2.8497   -1.8984 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4986    1.8969   -0.1610 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8872   -0.3739    0.5360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2973    0.0369   -0.2528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8984   -1.7311    0.3740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0516   -5.1489    0.3298 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0
  5 19  1  0
 13 11  1  0
 19 20  2  0
 11 10  2  0
 20 21  1  0
 14 13  2  0
 21  3  2  0
 17 16  2  0
  3  4  1  0
  4  5  2  0
 16 14  1  0
  8  9  2  0
 17 18  1  0
 11 12  1  0
 10  8  1  0
 14 15  1  0
  8  7  1  0
 21 22  1  0
  7  6  1  0
  3  2  1  0
  6 18  1  0
  2  1  2  0
 17 10  1  0
  2 23  1  0
 13 29  1  0
 16 31  1  0
  7 26  1  0
  7 27  1  0
  6 25  1  1
 19 32  1  0
 20 33  1  0
  4 24  1  0
 12 28  1  0
 15 30  1  0
 22 34  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  O   UNK     0      -3.559  -5.998  -0.097  0.00  0.00           O+0
HETATM    2  C   UNK     0      -2.784  -5.095  -0.395  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.213  -3.685  -0.353  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.296  -2.691  -0.714  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667  -1.335  -0.677  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.700  -0.234  -1.081  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.763   0.004  -2.583  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.799   1.104  -2.922  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.967   1.875  -3.865  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.426   1.194  -2.108  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.442   2.108  -2.408  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.358   3.003  -3.441  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.610   2.134  -1.651  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.757   1.233  -0.600  0.00  0.00           C+0
HETATM   15  O   UNK     0       3.887   1.214   0.163  0.00  0.00           O+0
HETATM   16  C   UNK     0       1.753   0.319  -0.290  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.577   0.311  -1.037  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.373  -0.611  -0.678  0.00  0.00           O+0
HETATM   19  C   UNK     0      -3.975  -1.003  -0.286  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.889  -1.998   0.070  0.00  0.00           C+0
HETATM   21  C   UNK     0      -4.508  -3.335   0.037  0.00  0.00           C+0
HETATM   22  O   UNK     0      -5.455  -4.254   0.399  0.00  0.00           O+0
HETATM   23  H   UNK     0      -1.745  -5.300  -0.703  0.00  0.00           H+0
HETATM   24  H   UNK     0      -1.288  -2.965  -1.020  0.00  0.00           H+0
HETATM   25  H   UNK     0      -1.965   0.678  -0.527  0.00  0.00           H+0
HETATM   26  H   UNK     0      -2.771   0.308  -2.886  0.00  0.00           H+0
HETATM   27  H   UNK     0      -1.472  -0.885  -3.155  0.00  0.00           H+0
HETATM   28  H   UNK     0       0.498   2.865  -3.900  0.00  0.00           H+0
HETATM   29  H   UNK     0       3.388   2.850  -1.898  0.00  0.00           H+0
HETATM   30  H   UNK     0       4.499   1.897  -0.161  0.00  0.00           H+0
HETATM   31  H   UNK     0       1.887  -0.374   0.536  0.00  0.00           H+0
HETATM   32  H   UNK     0      -4.297   0.037  -0.253  0.00  0.00           H+0
HETATM   33  H   UNK     0      -5.898  -1.731   0.374  0.00  0.00           H+0
HETATM   34  H   UNK     0      -5.052  -5.149   0.330  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    3    1   23                                                  
CONECT    3   21    4    2                                                  
CONECT    4    3    5   24                                                  
CONECT    5    6   19    4                                                  
CONECT    6    5    7   18   25                                             
CONECT    7    8    6   26   27                                             
CONECT    8    9   10    7                                                  
CONECT    9    8                                                            
CONECT   10   11    8   17                                                  
CONECT   11   13   10   12                                                  
CONECT   12   11   28                                                       
CONECT   13   11   14   29                                                  
CONECT   14   13   16   15                                                  
CONECT   15   14   30                                                       
CONECT   16   17   14   31                                                  
CONECT   17   16   18   10                                                  
CONECT   18   17    6                                                       
CONECT   19    5   20   32                                                  
CONECT   20   19   21   33                                                  
CONECT   21   20    3   22                                                  
CONECT   22   21   34                                                       
CONECT   23    2                                                            
CONECT   24    4                                                            
CONECT   25    6                                                            
CONECT   26    7                                                            
CONECT   27    7                                                            
CONECT   28   12                                                            
CONECT   29   13                                                            
CONECT   30   15                                                            
CONECT   31   16                                                            
CONECT   32   19                                                            
CONECT   33   20                                                            
CONECT   34   22                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   72    0
END

RDKit          3D

34 36  0  0  0  0  0  0  0  0999 V2000
   -3.5594   -5.9984   -0.0973 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7837   -5.0950   -0.3947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2130   -3.6851   -0.3530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2959   -2.6907   -0.7140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6668   -1.3347   -0.6766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6999   -0.2344   -1.0810 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7627    0.0041   -2.5833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7993    1.1044   -2.9225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9672    1.8751   -3.8645 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4259    1.1938   -2.1078 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4415    2.1085   -2.4080 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3582    3.0032   -3.4406 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6101    2.1343   -1.6507 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7573    1.2333   -0.5997 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8871    1.2139    0.1634 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7534    0.3191   -0.2902 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5766    0.3105   -1.0367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3726   -0.6105   -0.6775 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9752   -1.0027   -0.2856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8890   -1.9977    0.0703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5083   -3.3347    0.0372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4547   -4.2537    0.3986 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7449   -5.2997   -0.7028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2879   -2.9648   -1.0199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9654    0.6780   -0.5265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7705    0.3084   -2.8864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4718   -0.8847   -3.1552 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4983    2.8655   -3.8999 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3882    2.8497   -1.8984 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4986    1.8969   -0.1610 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8872   -0.3739    0.5360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2973    0.0369   -0.2528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8984   -1.7311    0.3740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0516   -5.1489    0.3298 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0
  5 19  1  0
 13 11  1  0
 19 20  2  0
 11 10  2  0
 20 21  1  0
 14 13  2  0
 21  3  2  0
 17 16  2  0
  3  4  1  0
  4  5  2  0
 16 14  1  0
  8  9  2  0
 17 18  1  0
 11 12  1  0
 10  8  1  0
 14 15  1  0
  8  7  1  0
 21 22  1  0
  7  6  1  0
  3  2  1  0
  6 18  1  0
  2  1  2  0
 17 10  1  0
  2 23  1  0
 13 29  1  0
 16 31  1  0
  7 26  1  0
  7 27  1  0
  6 25  1  1
 19 32  1  0
 20 33  1  0
  4 24  1  0
 12 28  1  0
 15 30  1  0
 22 34  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Not Available

Chemical Formula

C₁₆H₁₂O₆

Average Mass

300.2660 Da

Monoisotopic Mass

300.06339 Da

IUPAC Name

5-[(2S)-5,7-dihydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-2-yl]-2-hydroxybenzaldehyde

Traditional Name

5-[(2S)-5,7-dihydroxy-4-oxo-2,3-dihydro-1-benzopyran-2-yl]-2-hydroxybenzaldehyde

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C(O[H])=C2C(O[C@]([H])(C3=C([H])C(C([H])=O)=C(O[H])C([H])=C3[H])C([H])([H])C2=O)=C1[H]

InChI Identifier

InChI=1S/C16H12O6/c17-7-9-3-8(1-2-11(9)19)14-6-13(21)16-12(20)4-10(18)5-15(16)22-14/h1-5,7,14,18-20H,6H2/t14-/m0/s1

InChI Key

DOFLNDASWRCTNW-AWEZNQCLSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, 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, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, chcl3, 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
Feroniella lucida	JEOL database	Sriyatep, T., et al. J. Tetrahedron 70, 1458 (2014)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavanones. Flavanones are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a ketone at the carbon C3.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

Flavanones

Alternative Parents

Substituents

4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavanone
Hydroxyflavonoid
Chromone
Benzopyran
Chromane
1-benzopyran
Hydroxybenzaldehyde
Aryl ketone
Benzaldehyde
Benzoyl
Aryl alkyl ketone
Aryl-aldehyde
Phenol
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Ketone
Oxacycle
Organoheterocyclic compound
Ether
Organic oxygen compound
Aldehyde
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

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	2.54	ALOGPS
logP	3.2	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	7.74	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	104.06 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	77.87 m³·mol⁻¹	ChemAxon
Polarizability	29.62 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

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

102127187

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Hu Z, Wu Z, Su Q, Li M, Wu S, Meng R, Ding W, Li C: Metabolites with phytopathogenic fungi inhibitory activities from the mangrove endophytic fungus Botryosphaeria ramose. Bioorg Chem. 2020 Nov;104:104300. doi: 10.1016/j.bioorg.2020.104300. Epub 2020 Sep 22. [PubMed:33011529 ]
Subramanian M, Thotakura B, Chandra Sekaran SP, Jyothi AK, Sundaramurthi I: Naringin (4',5,7-Trihydroxyflavanone 7-Rhamnoglucoside) Attenuates beta-Cell Dysfunction in Diabetic Rats through Upregulation of PDX-1. Cells Tissues Organs. 2018;206(3):133-143. doi: 10.1159/000496506. Epub 2019 Mar 18. [PubMed:30884485 ]
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Showing NP-Card for (2S)-3'-formyl-4',5,7-trihydroxyflavanone (NP0042870)

MOL for NP0042870 ((2S)-3'-formyl-4',5,7-trihydroxyflavanone)

3D MOL for NP0042870 ((2S)-3'-formyl-4',5,7-trihydroxyflavanone)

3D SDF for NP0042870 ((2S)-3'-formyl-4',5,7-trihydroxyflavanone)

3D-SDF for NP0042870 ((2S)-3'-formyl-4',5,7-trihydroxyflavanone)

PDB for NP0042870 ((2S)-3'-formyl-4',5,7-trihydroxyflavanone)

3D PDB for NP0042870 ((2S)-3'-formyl-4',5,7-trihydroxyflavanone)

SMILES for NP0042870 ((2S)-3'-formyl-4',5,7-trihydroxyflavanone)

INCHI for NP0042870 ((2S)-3'-formyl-4',5,7-trihydroxyflavanone)

Structure for NP0042870 ((2S)-3'-formyl-4',5,7-trihydroxyflavanone)

3D Structure for NP0042870 ((2S)-3'-formyl-4',5,7-trihydroxyflavanone)