NP-MRD: Showing NP-Card for Sigmoidin B (NP0043972)

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Record Information

Version

2.0

Created at

2021-06-22 17:43:27 UTC

Updated at

2026-02-07 16:01:05 UTC

NP-MRD ID

NP0043972

Natural Product DOI

https://doi.org/10.57994/5656

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Sigmoidin B

Description

Sigmoidin B 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. Sigmoidin B 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 B is found in Glycyrrhiza glabra , Glycyrrhiza inflata and Sigmoidea. Sigmoidin B was first documented in 1990 (PMID: 2343463). Based on a literature review a small amount of articles have been published on sigmoidin B (PMID: 14994185) (PMID: 30793315) (PMID: 33579846).

Structure

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


  Mrv1652306222119432D          

 26 28  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 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
 23 25  2  0  0  0  0
  6 25  1  0  0  0  0
 25 26  1  0  0  0  0
M  END

NP0043972
     RDKit          3D

 46 48  0  0  0  0  0  0  0  0999 V2000
    4.0631    1.8828   -1.2335 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4173    1.3485    0.1052 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0552    2.2273    1.1192 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1649    0.0912    0.3912 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5260   -0.7950   -0.6234 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2320   -1.3531   -0.1455 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0423   -0.8455   -0.6066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1316   -1.3585   -0.1674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4326   -0.8341   -0.6449 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3461    0.4053   -1.4664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7288    0.6459   -1.9920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0155    0.7715   -3.1946 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7866    0.7309   -0.9921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9609    1.4136   -1.1920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2123    2.0715   -2.3588 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9128    1.4238   -0.1539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6731    0.7697    1.0264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6370    0.7916    2.0521 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4925    0.0954    1.2026 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1597   -2.3804    0.7338 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0498   -2.9078    1.2128 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0288   -3.9443    2.1268 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.4841   -2.8560    1.1948 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9846    1.7776   -1.4290 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3106    2.9555   -1.2753 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6416    1.3054   -1.9835 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5652    1.6527    1.9092 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8117    2.8877    0.6512 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2474    2.8144    1.6288 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4316   -0.2827    1.3787 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3700   -0.2303   -1.5576 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2461   -1.6214   -0.8881 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1029   -0.0173   -1.3351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8865   -1.6659   -1.2647 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.6252    1.5196    2.7503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3020   -0.4226    2.1385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0923   -2.8191    1.1104 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8632   -4.3465    2.4903 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5494   -3.6012    1.8533 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
 23 25  2  0
 25 26  1  0
 25  6  1  0
 21  9  1  0
 20 13  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  3 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  7 36  1  0
  9 37  1  6
 10 38  1  0
 10 39  1  0
 15 40  1  0
 16 41  1  0
 18 42  1  0
 19 43  1  0
 22 44  1  0
 24 45  1  0
 26 46  1  0
M  END


  Mrv1652306222119432D          

 26 28  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 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
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 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
 23 25  2  0  0  0  0
  6 25  1  0  0  0  0
 25 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0043972

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC1=CC(=CC(O)=C1O)[C@@H]1CC(=O)C2=C(O)C=C(O)C=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C20H20O6/c1-10(2)3-4-11-5-12(6-16(24)20(11)25)17-9-15(23)19-14(22)7-13(21)8-18(19)26-17/h3,5-8,17,21-22,24-25H,4,9H2,1-2H3/t17-/m0/s1

> <INCHI_KEY>
SFQIGPZCFNTPOD-KRWDZBQOSA-N

> <FORMULA>
C20H20O6

> <MOLECULAR_WEIGHT>
356.374

> <EXACT_MASS>
356.125988364

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
37.66840591656782

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.02

> <JCHEM_LOGP>
4.260109728

> <ALOGPS_LOGS>
-4.19

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.970658025816329

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.841228414800403

> <JCHEM_PKA_STRONGEST_BASIC>
-4.9502363442561

> <JCHEM_POLAR_SURFACE_AREA>
107.22000000000001

> <JCHEM_REFRACTIVITY>
97.5135

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.30e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

NP0043972
     RDKit          3D

 46 48  0  0  0  0  0  0  0  0999 V2000
    4.0631    1.8828   -1.2335 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4173    1.3485    0.1052 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0552    2.2273    1.1192 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1649    0.0912    0.3912 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5260   -0.7950   -0.6234 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2320   -1.3531   -0.1455 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0423   -0.8455   -0.6066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1316   -1.3585   -0.1674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4326   -0.8341   -0.6449 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3461    0.4053   -1.4664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7288    0.6459   -1.9920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0155    0.7715   -3.1946 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7866    0.7309   -0.9921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9609    1.4136   -1.1920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2123    2.0715   -2.3588 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9128    1.4238   -0.1539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6731    0.7697    1.0264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6370    0.7916    2.0521 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4925    0.0954    1.2026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5154    0.0521    0.2085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3373   -0.6333    0.4100 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1597   -2.3804    0.7338 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0498   -2.9078    1.2128 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0288   -3.9443    2.1268 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2476   -2.4036    0.7814 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4841   -2.8560    1.1948 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9846    1.7776   -1.4290 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3106    2.9555   -1.2753 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6416    1.3054   -1.9835 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5652    1.6527    1.9092 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8117    2.8877    0.6512 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2474    2.8144    1.6288 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4316   -0.2827    1.3787 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3700   -0.2303   -1.5576 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2461   -1.6214   -0.8881 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1029   -0.0173   -1.3351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8865   -1.6659   -1.2647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6211    0.3321   -2.3046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1047    1.2674   -0.8149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6211    2.1432   -3.1247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8402    1.9420   -0.2675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6252    1.5196    2.7503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3020   -0.4226    2.1385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0923   -2.8191    1.1104 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8632   -4.3465    2.4903 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5494   -3.6012    1.8533 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
 23 25  2  0
 25 26  1  0
 25  6  1  0
 21  9  1  0
 20 13  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  3 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  7 36  1  0
  9 37  1  6
 10 38  1  0
 10 39  1  0
 15 40  1  0
 16 41  1  0
 18 42  1  0
 19 43  1  0
 22 44  1  0
 24 45  1  0
 26 46  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  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   26  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   25                                                  
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                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23    6   26                                                  
CONECT   26   25                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

COMPND    NP0043972
HETATM    1  C1  UNL     1       4.063   1.883  -1.234  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.417   1.349   0.105  1.00  0.00           C  
HETATM    3  C3  UNL     1       5.055   2.227   1.119  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.165   0.091   0.391  1.00  0.00           C  
HETATM    5  C5  UNL     1       3.526  -0.795  -0.623  1.00  0.00           C  
HETATM    6  C6  UNL     1       2.232  -1.353  -0.146  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.042  -0.846  -0.607  1.00  0.00           C  
HETATM    8  C8  UNL     1      -0.132  -1.359  -0.167  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.433  -0.834  -0.645  1.00  0.00           C  
HETATM   10  C10 UNL     1      -1.346   0.405  -1.466  1.00  0.00           C  
HETATM   11  C11 UNL     1      -2.729   0.646  -1.992  1.00  0.00           C  
HETATM   12  O1  UNL     1      -3.016   0.771  -3.195  1.00  0.00           O  
HETATM   13  C12 UNL     1      -3.787   0.731  -0.992  1.00  0.00           C  
HETATM   14  C13 UNL     1      -4.961   1.414  -1.192  1.00  0.00           C  
HETATM   15  O2  UNL     1      -5.212   2.071  -2.359  1.00  0.00           O  
HETATM   16  C14 UNL     1      -5.913   1.424  -0.154  1.00  0.00           C  
HETATM   17  C15 UNL     1      -5.673   0.770   1.026  1.00  0.00           C  
HETATM   18  O3  UNL     1      -6.637   0.792   2.052  1.00  0.00           O  
HETATM   19  C16 UNL     1      -4.493   0.095   1.203  1.00  0.00           C  
HETATM   20  C17 UNL     1      -3.515   0.052   0.208  1.00  0.00           C  
HETATM   21  O4  UNL     1      -2.337  -0.633   0.410  1.00  0.00           O  
HETATM   22  C18 UNL     1      -0.160  -2.380   0.734  1.00  0.00           C  
HETATM   23  C19 UNL     1       1.050  -2.908   1.213  1.00  0.00           C  
HETATM   24  O5  UNL     1       1.029  -3.944   2.127  1.00  0.00           O  
HETATM   25  C20 UNL     1       2.248  -2.404   0.781  1.00  0.00           C  
HETATM   26  O6  UNL     1       3.484  -2.856   1.195  1.00  0.00           O  
HETATM   27  H1  UNL     1       2.985   1.778  -1.429  1.00  0.00           H  
HETATM   28  H2  UNL     1       4.311   2.956  -1.275  1.00  0.00           H  
HETATM   29  H3  UNL     1       4.642   1.305  -1.983  1.00  0.00           H  
HETATM   30  H4  UNL     1       5.565   1.653   1.909  1.00  0.00           H  
HETATM   31  H5  UNL     1       5.812   2.888   0.651  1.00  0.00           H  
HETATM   32  H6  UNL     1       4.247   2.814   1.629  1.00  0.00           H  
HETATM   33  H7  UNL     1       4.432  -0.283   1.379  1.00  0.00           H  
HETATM   34  H8  UNL     1       3.370  -0.230  -1.558  1.00  0.00           H  
HETATM   35  H9  UNL     1       4.246  -1.621  -0.888  1.00  0.00           H  
HETATM   36  H10 UNL     1       1.103  -0.017  -1.335  1.00  0.00           H  
HETATM   37  H11 UNL     1      -1.887  -1.666  -1.265  1.00  0.00           H  
HETATM   38  H12 UNL     1      -0.621   0.332  -2.305  1.00  0.00           H  
HETATM   39  H13 UNL     1      -1.105   1.267  -0.815  1.00  0.00           H  
HETATM   40  H14 UNL     1      -4.621   2.143  -3.125  1.00  0.00           H  
HETATM   41  H15 UNL     1      -6.840   1.942  -0.267  1.00  0.00           H  
HETATM   42  H16 UNL     1      -6.625   1.520   2.750  1.00  0.00           H  
HETATM   43  H17 UNL     1      -4.302  -0.423   2.139  1.00  0.00           H  
HETATM   44  H18 UNL     1      -1.092  -2.819   1.110  1.00  0.00           H  
HETATM   45  H19 UNL     1       1.863  -4.347   2.490  1.00  0.00           H  
HETATM   46  H20 UNL     1       3.549  -3.601   1.853  1.00  0.00           H  
CONECT    1    2   27   28   29
CONECT    2    3    4    4
CONECT    3   30   31   32
CONECT    4    5   33
CONECT    5    6   34   35
CONECT    6    7    7   25
CONECT    7    8   36
CONECT    8    9   22   22
CONECT    9   10   21   37
CONECT   10   11   38   39
CONECT   11   12   12   13
CONECT   13   14   14   20
CONECT   14   15   16
CONECT   15   40
CONECT   16   17   17   41
CONECT   17   18   19
CONECT   18   42
CONECT   19   20   20   43
CONECT   20   21
CONECT   22   23   44
CONECT   23   24   25   25
CONECT   24   45
CONECT   25   26
CONECT   26   46
END

NP0043972
     RDKit          3D

46 48  0  0  0  0  0  0  0  0999 V2000
    4.0631    1.8828   -1.2335 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4173    1.3485    0.1052 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0552    2.2273    1.1192 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1649    0.0912    0.3912 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5260   -0.7950   -0.6234 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2320   -1.3531   -0.1455 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0423   -0.8455   -0.6066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1316   -1.3585   -0.1674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4326   -0.8341   -0.6449 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3461    0.4053   -1.4664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7288    0.6459   -1.9920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0155    0.7715   -3.1946 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7866    0.7309   -0.9921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9609    1.4136   -1.1920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2123    2.0715   -2.3588 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9128    1.4238   -0.1539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6731    0.7697    1.0264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6370    0.7916    2.0521 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4925    0.0954    1.2026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5154    0.0521    0.2085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3373   -0.6333    0.4100 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1597   -2.3804    0.7338 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0498   -2.9078    1.2128 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0288   -3.9443    2.1268 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2476   -2.4036    0.7814 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4841   -2.8560    1.1948 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9846    1.7776   -1.4290 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3106    2.9555   -1.2753 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6416    1.3054   -1.9835 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5652    1.6527    1.9092 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8117    2.8877    0.6512 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2474    2.8144    1.6288 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4316   -0.2827    1.3787 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3700   -0.2303   -1.5576 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2461   -1.6214   -0.8881 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1029   -0.0173   -1.3351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8865   -1.6659   -1.2647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6211    0.3321   -2.3046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1047    1.2674   -0.8149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6211    2.1432   -3.1247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8402    1.9420   -0.2675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6252    1.5196    2.7503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3020   -0.4226    2.1385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0923   -2.8191    1.1104 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8632   -4.3465    2.4903 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5494   -3.6012    1.8533 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
 23 25  2  0
 25 26  1  0
 25  6  1  0
 21  9  1  0
 20 13  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  3 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  7 36  1  0
  9 37  1  6
 10 38  1  0
 10 39  1  0
 15 40  1  0
 16 41  1  0
 18 42  1  0
 19 43  1  0
 22 44  1  0
 24 45  1  0
 26 46  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Value	Source
(2S)- 2-(3,4-Dihydroxy-5-(3-methyl-2-butenyl)phenyl)-2,3-dihydro-5,7-dihydroxy-4H-1-benzopyran-4-one	ChEBI
(2S)-2-[3,4-Dihydroxy-5-(3-methylbut-2-en-1-yl)phenyl]-5,7-dihydroxy-2,3-dihydro-4H-chromen-4-one	ChEBI
5,7,3',4'-Tetrahydroxy-5'-prenylflavone	ChEBI
Sigmoidin-b	MeSH

Chemical Formula

C₂₀H₂₀O₆

Average Mass

356.3740 Da

Monoisotopic Mass

356.12599 Da

IUPAC Name

(2S)-2-[3,4-dihydroxy-5-(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-5-(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(=CC(O)=C1O)[C@@H]1CC(=O)C2=C(O)C=C(O)C=C2O1

InChI Identifier

InChI=1S/C20H20O6/c1-10(2)3-4-11-5-12(6-16(24)20(11)25)17-9-15(23)19-14(22)7-13(21)8-18(19)26-17/h3,5-8,17,21-22,24-25H,4,9H2,1-2H3/t17-/m0/s1

InChI Key

SFQIGPZCFNTPOD-KRWDZBQOSA-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

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 300.13, Dimethylsulfoxide-d6, simulated)	[email protected]	Not Available	Not Available	2026-02-07	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75.47, Dimethylsulfoxide-d6, simulated)	[email protected]	Not Available	Not Available	2026-02-07	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Erythrina abyssinica	KNApSAcK Database	22123792
Erythrina latissima	KNApSAcK Database	22123792
Erythrina sigmoidea		Not Available
Erythrina sigmoidea	KNApSAcK Database	22123792
Glycyrrhiza glabra	Plant	KNApSAcK
Glycyrrhiza inflata	LOTUS Database	35616633
Glycyrrhiza uralensis	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 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
Flavanone
3'-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Hydroxyflavonoid
Chromone
Benzopyran
Chromane
1-benzopyran
Catechol
Aryl ketone
Aryl alkyl ketone
1-hydroxy-2-unsubstituted benzenoid
Phenol
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Vinylogous acid
Ketone
Organoheterocyclic compound
Oxacycle
Ether
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

tetrahydroxyflavanone (CHEBI:66483 )

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	3.02	ALOGPS
logP	4.26	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	7.84	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	3	ChemAxon
Refractivity	97.51 m³·mol⁻¹	ChemAxon
Polarizability	37.67 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

C00008318

Chemspider ID

65964

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

73205

PDB ID

Not Available

ChEBI ID

66483

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 ]
Koch K, Schulz G, Doring W, Buchter C, Havermann S, Mutiso PC, Passreiter C, Watjen W: Abyssinone V, a prenylated flavonoid isolated from the stem bark of Erythrina melanacantha increases oxidative stress and decreases stress resistance in Caenorhabditis elegans. J Pharm Pharmacol. 2019 Jun;71(6):1007-1016. doi: 10.1111/jphp.13074. Epub 2019 Feb 21. [PubMed:30793315 ]
Wang YZ, Meng L, Zhuang QS, Shen L: Screening Traditional Chinese Medicine Combination for Cotreatment of Alzheimer's Disease and Type 2 Diabetes Mellitus by Network Pharmacology. J Alzheimers Dis. 2021;80(2):787-797. doi: 10.3233/JAD-201336. [PubMed:33579846 ]
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.
DOI: 10.1002/mrc.1260310211

Showing NP-Card for Sigmoidin B (NP0043972)

MOL for NP0043972 (Sigmoidin B)

3D MOL for NP0043972 (Sigmoidin B)

3D SDF for NP0043972 (Sigmoidin B)

3D-SDF for NP0043972 (Sigmoidin B)

PDB for NP0043972 (Sigmoidin B)

3D PDB for NP0043972 (Sigmoidin B)

SMILES for NP0043972 (Sigmoidin B)

INCHI for NP0043972 (Sigmoidin B)

Structure for NP0043972 (Sigmoidin B)

3D Structure for NP0043972 (Sigmoidin B)