NP-MRD: Showing NP-Card for Sigmoidin A (NP0043971)

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Record Information

Version

1.0

Created at

2021-06-22 17:43:24 UTC

Updated at

2021-06-22 17:43:25 UTC

NP-MRD ID

NP0043971

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Sigmoidin A

Description

Sigmoidin A belongs to the class of organic compounds known as 2'-prenylated flavanones. These are flavanones that features a C5-isoprenoid substituent at the 2'-position. Sigmoidin A is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Sigmoidin A is found in Antiaris toxicaria and Sigmoidea. It was first documented in 1990 (PMID: 2343463). Based on a literature review a significant number of articles have been published on sigmoidin A (PMID: 14994185) (PMID: 19941260) (PMID: 22978690) (PMID: 28614730).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652306222119432D          

 31 33  0  0  1  0            999 V2000
   -4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 13 20  1  0  0  0  0
 20 21  1  0  0  0  0
  9 21  1  0  0  0  0
  8 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 22 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  2  0  0  0  0
  6 30  1  0  0  0  0
 30 31  1  0  0  0  0
M  END

NP0043971
     RDKit          3D

 59 61  0  0  0  0  0  0  0  0999 V2000
    5.2887   -3.0548   -0.9460 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0208   -1.8068   -0.0912 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1399   -0.8654    0.0573 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8299   -1.6694    0.4336 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2592   -0.6306    1.2832 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1250    0.0768    0.6684 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7946   -0.3458    0.8314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2429    0.3025    0.1955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6044   -0.2411    0.0652 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4506   -0.3228    1.2935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8024   -0.7882    0.7052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8005   -0.1312    0.6059 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7036   -2.2038    0.2689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7919   -3.0177    0.3046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0324   -2.5893    0.7189 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6498   -4.3662   -0.1036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3858   -4.7513   -0.5115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2610   -6.1118   -0.9074 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3040   -3.9149   -0.5441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4367   -2.5708   -0.1477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3774   -1.7161   -0.1765 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0408    1.4128   -0.6242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1101    2.1874   -1.1463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8738    3.6136   -1.3479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4013    4.6120   -0.6965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3691    4.6045    0.4084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9542    6.0207   -1.1097 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3193    1.8220   -0.7820 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6329    2.9065   -1.5684 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3782    1.1547   -0.1341 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6483    1.6885   -0.3686 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3182   -3.0218   -1.3177 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5716   -3.1062   -1.7658 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1283   -3.9250   -0.2554 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2468   -0.4130    1.0413 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0983   -0.0978   -0.7583 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1213   -1.4036   -0.1339 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1104   -2.5109    0.1816 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9133   -1.1049    2.2466 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0332    0.1326    1.5572 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5775   -1.1874    1.4484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0851    0.0493   -0.8573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7114    0.6717    1.7115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0754   -1.0445    2.0074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2591   -1.6942    1.0255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4892   -5.0256   -0.0876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0227   -6.7421   -0.1300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3491   -4.2496   -0.8590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4985    1.7247   -2.0556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8864    2.1396   -0.3025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1872    3.8709   -2.1910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0479    5.3170    1.2279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5988    3.6596    0.8800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3386    5.0412    0.0501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8232    6.6829   -1.0437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5060    6.0137   -2.0994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1953    6.2927   -0.3542 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5562    3.2537   -1.6960 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4730    1.3730    0.0689 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
  8 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  2  3
 25 26  1  0
 25 27  1  0
 22 28  1  0
 28 29  1  0
 28 30  2  0
 30 31  1  0
 30  6  1  0
 21  9  1  0
 20 13  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  3 35  1  0
  3 36  1  0
  3 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
  7 41  1  0
  9 42  1  6
 10 43  1  0
 10 44  1  0
 15 45  1  0
 16 46  1  0
 18 47  1  0
 19 48  1  0
 23 49  1  0
 23 50  1  0
 24 51  1  0
 26 52  1  0
 26 53  1  0
 26 54  1  0
 27 55  1  0
 27 56  1  0
 27 57  1  0
 29 58  1  0
 31 59  1  0
M  END


  Mrv1652306222119432D          

 31 33  0  0  1  0            999 V2000
   -4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 13 20  1  0  0  0  0
 20 21  1  0  0  0  0
  9 21  1  0  0  0  0
  8 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 22 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  2  0  0  0  0
  6 30  1  0  0  0  0
 30 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0043971

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC1=CC([C@@H]2CC(=O)C3=C(O)C=C(O)C=C3O2)=C(CC=C(C)C)C(O)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C25H28O6/c1-13(2)5-7-15-9-18(17(8-6-14(3)4)25(30)24(15)29)21-12-20(28)23-19(27)10-16(26)11-22(23)31-21/h5-6,9-11,21,26-27,29-30H,7-8,12H2,1-4H3/t21-/m0/s1

> <INCHI_KEY>
BVHLNRAYBCPKOY-NRFANRHFSA-N

> <FORMULA>
C25H28O6

> <MOLECULAR_WEIGHT>
424.493

> <EXACT_MASS>
424.188588622

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
47.09139448158653

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-[3,4-dihydroxy-2,5-bis(3-methylbut-2-en-1-yl)phenyl]-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-4-one

> <ALOGPS_LOGP>
4.26

> <JCHEM_LOGP>
5.988676727333333

> <ALOGPS_LOGS>
-4.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.876514238841652

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.832139219278123

> <JCHEM_PKA_STRONGEST_BASIC>
-4.950285983077525

> <JCHEM_POLAR_SURFACE_AREA>
107.22000000000001

> <JCHEM_REFRACTIVITY>
121.75629999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.24e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-[3,4-dihydroxy-2,5-bis(3-methylbut-2-en-1-yl)phenyl]-5,7-dihydroxy-2,3-dihydro-1-benzopyran-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

NP0043971
     RDKit          3D

 59 61  0  0  0  0  0  0  0  0999 V2000
    5.2887   -3.0548   -0.9460 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0208   -1.8068   -0.0912 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1399   -0.8654    0.0573 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8299   -1.6694    0.4336 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2592   -0.6306    1.2832 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1250    0.0768    0.6684 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7946   -0.3458    0.8314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2429    0.3025    0.1955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6044   -0.2411    0.0652 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4506   -0.3228    1.2935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8024   -0.7882    0.7052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8005   -0.1312    0.6059 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7036   -2.2038    0.2689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7919   -3.0177    0.3046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0324   -2.5893    0.7189 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6498   -4.3662   -0.1036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3858   -4.7513   -0.5115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2610   -6.1118   -0.9074 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3040   -3.9149   -0.5441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4367   -2.5708   -0.1477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3774   -1.7161   -0.1765 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0408    1.4128   -0.6242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1101    2.1874   -1.1463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8738    3.6136   -1.3479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4013    4.6120   -0.6965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3691    4.6045    0.4084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9542    6.0207   -1.1097 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3193    1.8220   -0.7820 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6329    2.9065   -1.5684 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3782    1.1547   -0.1341 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6483    1.6885   -0.3686 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3182   -3.0218   -1.3177 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5716   -3.1062   -1.7658 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1283   -3.9250   -0.2554 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2468   -0.4130    1.0413 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0983   -0.0978   -0.7583 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1213   -1.4036   -0.1339 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1104   -2.5109    0.1816 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9133   -1.1049    2.2466 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0332    0.1326    1.5572 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5775   -1.1874    1.4484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0851    0.0493   -0.8573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7114    0.6717    1.7115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0754   -1.0445    2.0074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2591   -1.6942    1.0255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4892   -5.0256   -0.0876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0227   -6.7421   -0.1300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3491   -4.2496   -0.8590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4985    1.7247   -2.0556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8864    2.1396   -0.3025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1872    3.8709   -2.1910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0479    5.3170    1.2279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5988    3.6596    0.8800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3386    5.0412    0.0501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8232    6.6829   -1.0437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5060    6.0137   -2.0994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1953    6.2927   -0.3542 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5562    3.2537   -1.6960 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4730    1.3730    0.0689 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
  8 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  2  3
 25 26  1  0
 25 27  1  0
 22 28  1  0
 28 29  1  0
 28 30  2  0
 30 31  1  0
 30  6  1  0
 21  9  1  0
 20 13  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  3 35  1  0
  3 36  1  0
  3 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
  7 41  1  0
  9 42  1  6
 10 43  1  0
 10 44  1  0
 15 45  1  0
 16 46  1  0
 18 47  1  0
 19 48  1  0
 23 49  1  0
 23 50  1  0
 24 51  1  0
 26 52  1  0
 26 53  1  0
 26 54  1  0
 27 55  1  0
 27 56  1  0
 27 57  1  0
 29 58  1  0
 31 59  1  0
M  END

HEADER    PROTEIN                                 22-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-JUN-21         0                                  
HETATM    1  C   UNK     0      -8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   30                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   22                                                  
CONECT    9    8   10   21                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   20                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   13   21                                                  
CONECT   21   20    9                                                       
CONECT   22    8   23   28                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   22   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28    6   31                                                  
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   66    0
END

COMPND    NP0043971
HETATM    1  C1  UNL     1       5.289  -3.055  -0.946  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.021  -1.807  -0.091  1.00  0.00           C  
HETATM    3  C3  UNL     1       6.140  -0.865   0.057  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.830  -1.669   0.434  1.00  0.00           C  
HETATM    5  C5  UNL     1       3.259  -0.631   1.283  1.00  0.00           C  
HETATM    6  C6  UNL     1       2.125   0.077   0.668  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.795  -0.346   0.831  1.00  0.00           C  
HETATM    8  C8  UNL     1      -0.243   0.303   0.196  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.604  -0.241   0.065  1.00  0.00           C  
HETATM   10  C10 UNL     1      -2.451  -0.323   1.294  1.00  0.00           C  
HETATM   11  C11 UNL     1      -3.802  -0.788   0.705  1.00  0.00           C  
HETATM   12  O1  UNL     1      -4.800  -0.131   0.606  1.00  0.00           O  
HETATM   13  C12 UNL     1      -3.704  -2.204   0.269  1.00  0.00           C  
HETATM   14  C13 UNL     1      -4.792  -3.018   0.305  1.00  0.00           C  
HETATM   15  O2  UNL     1      -6.032  -2.589   0.719  1.00  0.00           O  
HETATM   16  C14 UNL     1      -4.650  -4.366  -0.104  1.00  0.00           C  
HETATM   17  C15 UNL     1      -3.386  -4.751  -0.511  1.00  0.00           C  
HETATM   18  O3  UNL     1      -3.261  -6.112  -0.907  1.00  0.00           O  
HETATM   19  C16 UNL     1      -2.304  -3.915  -0.544  1.00  0.00           C  
HETATM   20  C17 UNL     1      -2.437  -2.571  -0.148  1.00  0.00           C  
HETATM   21  O4  UNL     1      -1.377  -1.716  -0.177  1.00  0.00           O  
HETATM   22  C18 UNL     1       0.041   1.413  -0.624  1.00  0.00           C  
HETATM   23  C19 UNL     1      -1.110   2.187  -1.146  1.00  0.00           C  
HETATM   24  C20 UNL     1      -0.874   3.614  -1.348  1.00  0.00           C  
HETATM   25  C21 UNL     1      -1.401   4.612  -0.696  1.00  0.00           C  
HETATM   26  C22 UNL     1      -2.369   4.604   0.408  1.00  0.00           C  
HETATM   27  C23 UNL     1      -0.954   6.021  -1.110  1.00  0.00           C  
HETATM   28  C24 UNL     1       1.319   1.822  -0.782  1.00  0.00           C  
HETATM   29  O5  UNL     1       1.633   2.907  -1.568  1.00  0.00           O  
HETATM   30  C25 UNL     1       2.378   1.155  -0.134  1.00  0.00           C  
HETATM   31  O6  UNL     1       3.648   1.688  -0.369  1.00  0.00           O  
HETATM   32  H1  UNL     1       6.318  -3.022  -1.318  1.00  0.00           H  
HETATM   33  H2  UNL     1       4.572  -3.106  -1.766  1.00  0.00           H  
HETATM   34  H3  UNL     1       5.128  -3.925  -0.255  1.00  0.00           H  
HETATM   35  H4  UNL     1       6.247  -0.413   1.041  1.00  0.00           H  
HETATM   36  H5  UNL     1       6.098  -0.098  -0.758  1.00  0.00           H  
HETATM   37  H6  UNL     1       7.121  -1.404  -0.134  1.00  0.00           H  
HETATM   38  H7  UNL     1       3.110  -2.511   0.182  1.00  0.00           H  
HETATM   39  H8  UNL     1       2.913  -1.105   2.247  1.00  0.00           H  
HETATM   40  H9  UNL     1       4.033   0.133   1.557  1.00  0.00           H  
HETATM   41  H10 UNL     1       0.578  -1.187   1.448  1.00  0.00           H  
HETATM   42  H11 UNL     1      -2.085   0.049  -0.857  1.00  0.00           H  
HETATM   43  H12 UNL     1      -2.711   0.672   1.711  1.00  0.00           H  
HETATM   44  H13 UNL     1      -2.075  -1.044   2.007  1.00  0.00           H  
HETATM   45  H14 UNL     1      -6.259  -1.694   1.025  1.00  0.00           H  
HETATM   46  H15 UNL     1      -5.489  -5.026  -0.088  1.00  0.00           H  
HETATM   47  H16 UNL     1      -3.023  -6.742  -0.130  1.00  0.00           H  
HETATM   48  H17 UNL     1      -1.349  -4.250  -0.859  1.00  0.00           H  
HETATM   49  H18 UNL     1      -1.498   1.725  -2.056  1.00  0.00           H  
HETATM   50  H19 UNL     1      -1.886   2.140  -0.303  1.00  0.00           H  
HETATM   51  H20 UNL     1      -0.187   3.871  -2.191  1.00  0.00           H  
HETATM   52  H21 UNL     1      -2.048   5.317   1.228  1.00  0.00           H  
HETATM   53  H22 UNL     1      -2.599   3.660   0.880  1.00  0.00           H  
HETATM   54  H23 UNL     1      -3.339   5.041   0.050  1.00  0.00           H  
HETATM   55  H24 UNL     1      -1.823   6.683  -1.044  1.00  0.00           H  
HETATM   56  H25 UNL     1      -0.506   6.014  -2.099  1.00  0.00           H  
HETATM   57  H26 UNL     1      -0.195   6.293  -0.354  1.00  0.00           H  
HETATM   58  H27 UNL     1       2.556   3.254  -1.696  1.00  0.00           H  
HETATM   59  H28 UNL     1       4.473   1.373   0.069  1.00  0.00           H  
CONECT    1    2   32   33   34
CONECT    2    3    4    4
CONECT    3   35   36   37
CONECT    4    5   38
CONECT    5    6   39   40
CONECT    6    7    7   30
CONECT    7    8   41
CONECT    8    9   22   22
CONECT    9   10   21   42
CONECT   10   11   43   44
CONECT   11   12   12   13
CONECT   13   14   14   20
CONECT   14   15   16
CONECT   15   45
CONECT   16   17   17   46
CONECT   17   18   19
CONECT   18   47
CONECT   19   20   20   48
CONECT   20   21
CONECT   22   23   28
CONECT   23   24   49   50
CONECT   24   25   25   51
CONECT   25   26   27
CONECT   26   52   53   54
CONECT   27   55   56   57
CONECT   28   29   30   30
CONECT   29   58
CONECT   30   31
CONECT   31   59
END

NP0043971
     RDKit          3D

59 61  0  0  0  0  0  0  0  0999 V2000
    5.2887   -3.0548   -0.9460 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0208   -1.8068   -0.0912 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1399   -0.8654    0.0573 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8299   -1.6694    0.4336 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2592   -0.6306    1.2832 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1250    0.0768    0.6684 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7946   -0.3458    0.8314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2429    0.3025    0.1955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6044   -0.2411    0.0652 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4506   -0.3228    1.2935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8024   -0.7882    0.7052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8005   -0.1312    0.6059 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7036   -2.2038    0.2689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7919   -3.0177    0.3046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0324   -2.5893    0.7189 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6498   -4.3662   -0.1036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3858   -4.7513   -0.5115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2610   -6.1118   -0.9074 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3040   -3.9149   -0.5441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4367   -2.5708   -0.1477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3774   -1.7161   -0.1765 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0408    1.4128   -0.6242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1101    2.1874   -1.1463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8738    3.6136   -1.3479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4013    4.6120   -0.6965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3691    4.6045    0.4084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9542    6.0207   -1.1097 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3193    1.8220   -0.7820 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6329    2.9065   -1.5684 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3782    1.1547   -0.1341 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6483    1.6885   -0.3686 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3182   -3.0218   -1.3177 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5716   -3.1062   -1.7658 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1283   -3.9250   -0.2554 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2468   -0.4130    1.0413 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0983   -0.0978   -0.7583 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1213   -1.4036   -0.1339 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1104   -2.5109    0.1816 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9133   -1.1049    2.2466 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0332    0.1326    1.5572 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5775   -1.1874    1.4484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0851    0.0493   -0.8573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7114    0.6717    1.7115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0754   -1.0445    2.0074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2591   -1.6942    1.0255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4892   -5.0256   -0.0876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0227   -6.7421   -0.1300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3491   -4.2496   -0.8590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4985    1.7247   -2.0556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8864    2.1396   -0.3025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1872    3.8709   -2.1910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0479    5.3170    1.2279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5988    3.6596    0.8800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3386    5.0412    0.0501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8232    6.6829   -1.0437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5060    6.0137   -2.0994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1953    6.2927   -0.3542 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5562    3.2537   -1.6960 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4730    1.3730    0.0689 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
  8 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  2  3
 25 26  1  0
 25 27  1  0
 22 28  1  0
 28 29  1  0
 28 30  2  0
 30 31  1  0
 30  6  1  0
 21  9  1  0
 20 13  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  3 35  1  0
  3 36  1  0
  3 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
  7 41  1  0
  9 42  1  6
 10 43  1  0
 10 44  1  0
 15 45  1  0
 16 46  1  0
 18 47  1  0
 19 48  1  0
 23 49  1  0
 23 50  1  0
 24 51  1  0
 26 52  1  0
 26 53  1  0
 26 54  1  0
 27 55  1  0
 27 56  1  0
 27 57  1  0
 29 58  1  0
 31 59  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Value	Source
(2S)- 2-(3,4-Dihydroxy-2,5-bis(3-methyl-2-butenyl)phenyl)-2,3-dihydro-5,7-dihydroxy-4H-1-benzopyran-4-one	ChEBI
5,7,3',4'-Tetrahydroxy-2',5'-diprenylflavone	ChEBI
Sigmoidin-a	MeSH

Chemical Formula

C₂₅H₂₈O₆

Average Mass

424.4930 Da

Monoisotopic Mass

424.18859 Da

IUPAC Name

(2S)-2-[3,4-dihydroxy-2,5-bis(3-methylbut-2-en-1-yl)phenyl]-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

(2S)-2-[3,4-dihydroxy-2,5-bis(3-methylbut-2-en-1-yl)phenyl]-5,7-dihydroxy-2,3-dihydro-1-benzopyran-4-one

CAS Registry Number

Not Available

SMILES

CC(C)=CCC1=CC([C@@H]2CC(=O)C3=C(O)C=C(O)C=C3O2)=C(CC=C(C)C)C(O)=C1O

InChI Identifier

InChI=1S/C25H28O6/c1-13(2)5-7-15-9-18(17(8-6-14(3)4)25(30)24(15)29)21-12-20(28)23-19(27)10-16(26)11-22(23)31-21/h5-6,9-11,21,26-27,29-30H,7-8,12H2,1-4H3/t21-/m0/s1

InChI Key

BVHLNRAYBCPKOY-NRFANRHFSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 75.47 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300.13 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Dimethylsulfoxide-d6, 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, 50 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, dmso, 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
Antiaris toxicaria	LOTUS Database	35616633
Erythrina abyssinica	KNApSAcK Database	22123792
Erythrina latissima	KNApSAcK Database	22123792
Erythrina sigmoidea	KNApSAcK Database	22123792
Sigmoidea	Linigton's dataset	Jean-Claude Ndom, J. Tanyi Mbafor, Z. Tanee Fomum, Marie-Th√©r√®se Martin, Bernard Bodo 1H and 13...

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2'-prenylated flavanones. These are flavanones that features a C5-isoprenoid substituent at the 2'-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

2'-prenylated flavanones

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

tetrahydroxyflavanone (CHEBI:66482 )

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	4.26	ALOGPS
logP	5.99	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	7.83	ChemAxon
pKa (Strongest Basic)	-5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	107.22 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	121.76 m³·mol⁻¹	ChemAxon
Polarizability	47.09 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

C00008319

Chemspider ID

65963

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

73204

PDB ID

Not Available

ChEBI ID

66482

Good Scents ID

Not Available

References

General References

Njamen D, Mbafor JT, Fomum ZT, Kamanyi A, Mbanya JC, Recio MC, Giner RM, Manez S, Rios JL: Anti-inflammatory activities of two flavanones, sigmoidin A and sigmoidin B, from Erythrina sigmoidea. Planta Med. 2004 Feb;70(2):104-7. doi: 10.1055/s-2004-815484. [PubMed:14994185 ]
Biyiti L, Pesando D, Puiseux-Dao S, Girard JP, Payan P: Effect of antibacterial plant flavanones on the intracellular calcium compartment involved in the first cleavage of sea urchin eggs. Toxicon. 1990;28(3):275-83. doi: 10.1016/0041-0101(90)90063-d. [PubMed:2343463 ]
Habtemariam S, Dagne E: Comparative antioxidant, prooxidant and cytotoxic activity of sigmoidin A and eriodictyol. Planta Med. 2010 Apr;76(6):589-94. doi: 10.1055/s-0029-1240604. Epub 2009 Nov 25. [PubMed:19941260 ]
Habtemariam S: The anti-obesity potential of sigmoidin A. Pharm Biol. 2012 Dec;50(12):1519-22. doi: 10.3109/13880209.2012.688838. Epub 2012 Sep 14. [PubMed:22978690 ]
Zarev Y, Foubert K, Lucia de Almeida V, Anthonissen R, Elgorashi E, Apers S, Ionkova I, Verschaeve L, Pieters L: Antigenotoxic prenylated flavonoids from stem bark of Erythrina latissima. Phytochemistry. 2017 Sep;141:140-146. doi: 10.1016/j.phytochem.2017.06.003. Epub 2017 Jun 12. [PubMed:28614730 ]
Jean-Claude Ndom, J. Tanyi Mbafor, Z. Tanee Fomum, Marie-Thérèse Martin, Bernard Bodo (1993). Jean-Claude Ndom, J. Tanyi Mbafor, Z. Tanee Fomum, Marie-Thérèse Martin, Bernard Bodo 1H and 13C NMR spectral assignment of the prenylflavanones sigmoidins A, B and C, by two-dimensional NMR techniques. DOI: 10.1002/mrc.1260310211. Magnetic Resonance in Chemistry.

Showing NP-Card for Sigmoidin A (NP0043971)

MOL for NP0043971 (Sigmoidin A)

3D MOL for NP0043971 (Sigmoidin A)

3D SDF for NP0043971 (Sigmoidin A)

3D-SDF for NP0043971 (Sigmoidin A)

PDB for NP0043971 (Sigmoidin A)

3D PDB for NP0043971 (Sigmoidin A)

SMILES for NP0043971 (Sigmoidin A)

INCHI for NP0043971 (Sigmoidin A)

Structure for NP0043971 (Sigmoidin A)

3D Structure for NP0043971 (Sigmoidin A)