NP-MRD: Showing NP-Card for (2s)-2-[(3s)-3,8-dihydroxy-2,2-dimethyl-3,4-dihydro-1-benzopyran-6-yl]-5,7-dihydroxy-2,3-dihydro-1-benzopyran-4-one (NP0205640)

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Record Information

Version

2.0

Created at

2022-09-05 01:35:49 UTC

Updated at

2022-09-05 01:35:50 UTC

NP-MRD ID

NP0205640

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-2-[(3s)-3,8-dihydroxy-2,2-dimethyl-3,4-dihydro-1-benzopyran-6-yl]-5,7-dihydroxy-2,3-dihydro-1-benzopyran-4-one

Description

Sigmoidin D, also known as sigmoidin-D, belongs to the class of organic compounds known as 3'-prenylated flavanones. These are flavanones that features a C5-isoprenoid substituent at the 3'-position. (2s)-2-[(3s)-3,8-dihydroxy-2,2-dimethyl-3,4-dihydro-1-benzopyran-6-yl]-5,7-dihydroxy-2,3-dihydro-1-benzopyran-4-one is found in Erythrina abyssinica, Erythrina sigmoidea and Erythrina variegata. (2s)-2-[(3s)-3,8-dihydroxy-2,2-dimethyl-3,4-dihydro-1-benzopyran-6-yl]-5,7-dihydroxy-2,3-dihydro-1-benzopyran-4-one was first documented in 1986 (PMID: 3819737). Based on a literature review very few articles have been published on Sigmoidin D (PMID: 9548845).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052203352D          

 27 30  0  0  1  0            999 V2000
    4.0047   -0.8748    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
    3.4744   -1.7933    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
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.5737   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    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  2  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  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
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
 10  9  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 14 21  1  0  0  0  0
 21 22  1  0  0  0  0
 10 22  1  0  0  0  0
  9 23  1  0  0  0  0
 23 24  2  0  0  0  0
  5 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
  2 26  1  0  0  0  0
 26 27  1  6  0  0  0
M  END

     RDKit          3D

 47 50  0  0  0  0  0  0  0  0999 V2000
   -5.8375   -0.1609   -0.3176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4979    0.3203    0.2203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7118    1.5735    1.0287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6984    0.6624   -0.8994 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3445    0.4069   -0.9457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4266    1.2470   -1.4920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8348    2.4441   -2.0474 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0986    0.8952   -1.4859 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3507   -0.2988   -0.9375 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7937   -0.5662   -0.9893 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2106   -1.7083   -0.0893 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6983   -1.7803   -0.1890 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3367   -2.8063   -0.5082 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4382   -0.5520    0.1120 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7274   -0.6050    0.5941 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3995   -1.7791    0.8262 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3429    0.6223    0.8467 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7039    1.8154    0.6289 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3926    3.0115    0.9083 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4230    1.8194    0.1493 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7631    0.6530   -0.1190 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4724    0.6115   -0.6037 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5901   -1.1270   -0.3943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9236   -0.8057   -0.3842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9848   -1.6630    0.1886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8782   -0.7843    1.0417 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9028   -1.5979    1.5371 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3233    0.6316   -0.9165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6811   -1.0530   -0.9584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4840   -0.3625    0.5605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9814    2.3746    0.7885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6135    1.3620    2.1043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7352    1.9865    0.8819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1440    3.0614   -2.4509 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5961    1.6029   -1.9359 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0830   -0.8200   -2.0274 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7552   -2.6500   -0.4247 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9332   -1.4611    0.9594 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1651   -2.7102    0.7308 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3602    0.5689    1.2266 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8979    3.8745    0.7386 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8950    2.7474   -0.0316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2752   -2.0528    0.0353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5557   -2.4409    0.8508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5891   -2.0628   -0.6351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3057   -0.3897    1.8904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3212   -2.0543    0.7830 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 26  2  1  0
 22 10  1  0
 24  5  1  0
 21 14  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  3 31  1  0
  3 32  1  0
  3 33  1  0
  7 34  1  0
  8 35  1  0
 23 43  1  0
 25 44  1  0
 25 45  1  0
 26 46  1  1
 27 47  1  0
 10 36  1  6
 11 37  1  0
 11 38  1  0
 16 39  1  0
 17 40  1  0
 19 41  1  0
 20 42  1  0
M  END


  Mrv1652309052203352D          

 27 30  0  0  1  0            999 V2000
    4.0047   -0.8748    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
    3.4744   -1.7933    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
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.5737   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    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  2  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  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
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
 10  9  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 14 21  1  0  0  0  0
 21 22  1  0  0  0  0
 10 22  1  0  0  0  0
  9 23  1  0  0  0  0
 23 24  2  0  0  0  0
  5 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
  2 26  1  0  0  0  0
 26 27  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0205640

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)OC2=C(O)C=C(C=C2C[C@@H]1O)[C@@H]1CC(=O)C2=C(O)C=C(O)C=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C20H20O7/c1-20(2)17(25)5-10-3-9(4-14(24)19(10)27-20)15-8-13(23)18-12(22)6-11(21)7-16(18)26-15/h3-4,6-7,15,17,21-22,24-25H,5,8H2,1-2H3/t15-,17-/m0/s1

> <INCHI_KEY>
ASQDBJSRWIDYKK-RDJZCZTQSA-N

> <FORMULA>
C20H20O7

> <MOLECULAR_WEIGHT>
372.373

> <EXACT_MASS>
372.120902984

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
38.562631327569605

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-2-[(3S)-3,8-dihydroxy-2,2-dimethyl-3,4-dihydro-2H-1-benzopyran-6-yl]-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-4-one

> <JCHEM_LOGP>
2.7841420419999996

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.338006223708298

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.8619128771169295

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3205604191868145

> <JCHEM_POLAR_SURFACE_AREA>
116.45000000000002

> <JCHEM_REFRACTIVITY>
96.08209999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-[(3S)-3,8-dihydroxy-2,2-dimethyl-3,4-dihydro-1-benzopyran-6-yl]-5,7-dihydroxy-2,3-dihydro-1-benzopyran-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       7.475  -1.633   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.485  -3.347   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       9.336  -2.310   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      12.003  -0.770   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      13.337  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.337  -4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.670  -5.390   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      16.004  -4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      17.338  -5.390   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      18.672  -4.620   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      17.338  -6.930   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      18.672  -7.700   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      20.005  -6.930   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      18.672  -9.240   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      17.338 -10.010   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      17.338 -11.550   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      16.004  -9.240   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      16.004  -7.700   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      14.670  -6.930   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      12.003  -5.390   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4   26                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   24                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   23                                                  
CONECT   10    9   11   22                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   21                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   14   22                                                  
CONECT   22   21   10                                                       
CONECT   23    9   24                                                       
CONECT   24   23    5   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25    2   27                                                  
CONECT   27   26                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   60    0
END

View in JSmol

Synonyms

Value	Source
Sigmoidin-D	MeSH

Chemical Formula

C₂₀H₂₀O₇

Average Mass

372.3730 Da

Monoisotopic Mass

372.12090 Da

IUPAC Name

(2S)-2-[(3S)-3,8-dihydroxy-2,2-dimethyl-3,4-dihydro-2H-1-benzopyran-6-yl]-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

(2S)-2-[(3S)-3,8-dihydroxy-2,2-dimethyl-3,4-dihydro-1-benzopyran-6-yl]-5,7-dihydroxy-2,3-dihydro-1-benzopyran-4-one

CAS Registry Number

Not Available

SMILES

CC1(C)OC2=C(O)C=C(C=C2C[C@@H]1O)[C@@H]1CC(=O)C2=C(O)C=C(O)C=C2O1

InChI Identifier

InChI=1S/C20H20O7/c1-20(2)17(25)5-10-3-9(4-14(24)19(10)27-20)15-8-13(23)18-12(22)6-11(21)7-16(18)26-15/h3-4,6-7,15,17,21-22,24-25H,5,8H2,1-2H3/t15-,17-/m0/s1

InChI Key

ASQDBJSRWIDYKK-RDJZCZTQSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Erythrina abyssinica	LOTUS Database	35616633
Erythrina sigmoidea	LOTUS Database	35616633
Erythrina variegata	LOTUS Database	35616633

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

3'-prenylated flavanones

Alternative Parents

Substituents

3'-prenylated flavanone
Pyranoflavonoid
3'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavanone
Hydroxyflavonoid
2,2-dimethyl-1-benzopyran
Chromone
Chromane
Benzopyran
1-benzopyran
Aryl ketone
Aryl alkyl ketone
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Vinylogous acid
Secondary alcohol
Ketone
Organoheterocyclic compound
Oxacycle
Ether
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Organooxygen compound
Organic oxide
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	2.78	ChemAxon
pKa (Strongest Acidic)	7.86	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	116.45 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	96.08 m³·mol⁻¹	ChemAxon
Polarizability	38.56 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00008457

Chemspider ID

114575

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

129362

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Moriyasu M, Ichimaru M, Nishiyama Y, Kato A, Mathenge SG, Juma FD, Nganga JN: Minor Flavanones from Erythrina abyssinica. J Nat Prod. 1998 Feb 27;61(2):185-8. doi: 10.1021/np9703048. [PubMed:9548845 ]
Promsattha R, Tempesta MS, Fomum ZT, Ayafor JF, Mbafor JT: Sigmoidin D: a new prenylated flavanone from Erythrina sigmoidea. J Nat Prod. 1986 Sep-Oct;49(5):932-3. doi: 10.1021/np50047a032. [PubMed:3819737 ]
LOTUS database [Link]

Showing NP-Card for (2s)-2-[(3s)-3,8-dihydroxy-2,2-dimethyl-3,4-dihydro-1-benzopyran-6-yl]-5,7-dihydroxy-2,3-dihydro-1-benzopyran-4-one (NP0205640)

MOL for NP0205640 ((2s)-2-[(3s)-3,8-dihydroxy-2,2-dimethyl-3,4-dihydro-1-benzopyran-6-yl]-5,7-dihydroxy-2,3-dihydro-1-benzopyran-4-one)

3D MOL for NP0205640 ((2s)-2-[(3s)-3,8-dihydroxy-2,2-dimethyl-3,4-dihydro-1-benzopyran-6-yl]-5,7-dihydroxy-2,3-dihydro-1-benzopyran-4-one)

3D SDF for NP0205640 ((2s)-2-[(3s)-3,8-dihydroxy-2,2-dimethyl-3,4-dihydro-1-benzopyran-6-yl]-5,7-dihydroxy-2,3-dihydro-1-benzopyran-4-one)

3D-SDF for NP0205640 ((2s)-2-[(3s)-3,8-dihydroxy-2,2-dimethyl-3,4-dihydro-1-benzopyran-6-yl]-5,7-dihydroxy-2,3-dihydro-1-benzopyran-4-one)

PDB for NP0205640 ((2s)-2-[(3s)-3,8-dihydroxy-2,2-dimethyl-3,4-dihydro-1-benzopyran-6-yl]-5,7-dihydroxy-2,3-dihydro-1-benzopyran-4-one)

3D PDB for NP0205640 ((2s)-2-[(3s)-3,8-dihydroxy-2,2-dimethyl-3,4-dihydro-1-benzopyran-6-yl]-5,7-dihydroxy-2,3-dihydro-1-benzopyran-4-one)

SMILES for NP0205640 ((2s)-2-[(3s)-3,8-dihydroxy-2,2-dimethyl-3,4-dihydro-1-benzopyran-6-yl]-5,7-dihydroxy-2,3-dihydro-1-benzopyran-4-one)

INCHI for NP0205640 ((2s)-2-[(3s)-3,8-dihydroxy-2,2-dimethyl-3,4-dihydro-1-benzopyran-6-yl]-5,7-dihydroxy-2,3-dihydro-1-benzopyran-4-one)

Structure for NP0205640 ((2s)-2-[(3s)-3,8-dihydroxy-2,2-dimethyl-3,4-dihydro-1-benzopyran-6-yl]-5,7-dihydroxy-2,3-dihydro-1-benzopyran-4-one)

3D Structure for NP0205640 ((2s)-2-[(3s)-3,8-dihydroxy-2,2-dimethyl-3,4-dihydro-1-benzopyran-6-yl]-5,7-dihydroxy-2,3-dihydro-1-benzopyran-4-one)