NP-MRD: Showing NP-Card for calycosin (NP0029697)

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Record Information

Version

2.0

Created at

2021-06-19 21:15:24 UTC

Updated at

2021-06-29 23:57:14 UTC

NP-MRD ID

NP0029697

Secondary Accession Numbers

None

Natural Product Identification

Common Name

calycosin

Provided By

JEOL Database JEOL Logo

Description

Calycosin belongs to the class of organic compounds known as 3'-hydroxy,4'-methoxyisoflavonoids. These are isoflavonoids carrying a methoxy group attached to the C4' atom, as well as a hydroxyl group at the C3'-position of the isoflavonoid backbone. Thus, calycosin is considered to be a flavonoid. calycosin is found in Ammopiptanthus mongolicus, Amorpha fruticosa, Andira surinamensis, Astragalus complanatus, Astragalus laxmannii, Astragalus membranaceus, Astragalus microcephalus, Astragalus membranaceus var. mongholicus, Bolusanthus speciosus, Bowdichia virgilioides, Calicotome villosa, Centrolobium paraense, Centrolobium sclerophyllum, Cicer arietinum, Cyclopia intermedia, Dermatophyllum secundiflorum, Glycyrrhiza uralensis, Hedysarum polybotrys, Maackia amurensis, Machaerium aristulatum, Myroxylon peruiferum, Oxytropis falcata, Pycnanthus angolensis, Sophora moorcroftiana, Spatholobus suberectus, Styphnolobium japonicum, Thermopsis fabacea, Trifolium pratense , Trifolium repens , Trigonella foenum-graecum, Virgilia oroboides and Wisteria brachybotrys. calycosin was first documented in 2000 (PMID: 11025148). Based on a literature review a small amount of articles have been published on Calycosin (PMID: 16286304) (PMID: 16441066) (PMID: 17253088) (PMID: 34303214).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192123153D          

 33 35  0  0  0  0            999 V2000
    3.9498    2.8963    2.0147 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1695    2.4078    0.9293 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2348    1.4517    1.2306 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9564    0.9391    2.4946 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9654   -0.0412    2.6513 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2373   -0.5249    1.5526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8037   -1.5554    1.7350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0176   -1.4086    1.1793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0798   -2.2753    1.2714 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9050   -3.4215    2.0021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9848   -4.2998    2.0807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8580   -5.4774    2.8116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9367   -6.3093    2.8631 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6696   -5.7923    3.4666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5896   -4.9106    3.3872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7117   -3.7246    2.6527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5835   -2.7802    2.5574 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4719   -3.0139    3.1356 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5276   -0.0089    0.2827 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5101    0.9660    0.1378 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7590    1.4465   -1.1203 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5359    2.0928    2.4731 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6520    3.6342    1.6150 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3216    3.4016    2.7556 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4872    1.2698    3.3809 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7726   -0.4305    3.6503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3091   -0.5541    0.5793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9189   -4.0705    1.5762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7094   -7.0890    3.3966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5653   -6.7098    4.0380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6564   -5.1470    3.8944 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0074   -0.3625   -0.6033 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4781    2.0977   -1.0020 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
 10 16  2  0  0  0  0
  6  5  2  0  0  0  0
 14 15  2  0  0  0  0
  5  4  1  0  0  0  0
 15 16  1  0  0  0  0
  4  3  2  0  0  0  0
 12 14  1  0  0  0  0
  3 20  1  0  0  0  0
 10 11  1  0  0  0  0
 20 19  2  0  0  0  0
 19  6  1  0  0  0  0
  7  6  1  0  0  0  0
 12 13  1  0  0  0  0
 11 12  2  0  0  0  0
 17 18  2  0  0  0  0
 10  9  1  0  0  0  0
  3  2  1  0  0  0  0
 16 17  1  0  0  0  0
 20 21  1  0  0  0  0
 17  7  1  0  0  0  0
  2  1  1  0  0  0  0
 13 29  1  0  0  0  0
 14 30  1  0  0  0  0
 15 31  1  0  0  0  0
 11 28  1  0  0  0  0
  8 27  1  0  0  0  0
  5 26  1  0  0  0  0
  4 25  1  0  0  0  0
 19 32  1  0  0  0  0
 21 33  1  0  0  0  0
  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
M  END

     RDKit          3D

 33 35  0  0  0  0  0  0  0  0999 V2000
    3.9498    2.8963    2.0147 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1695    2.4078    0.9293 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2348    1.4517    1.2306 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9564    0.9391    2.4946 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9654   -0.0412    2.6513 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2373   -0.5249    1.5526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8037   -1.5554    1.7350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0176   -1.4086    1.1793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0798   -2.2753    1.2714 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9050   -3.4215    2.0021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9848   -4.2998    2.0807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8580   -5.4774    2.8116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9367   -6.3093    2.8631 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6696   -5.7923    3.4666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5896   -4.9106    3.3872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7117   -3.7246    2.6527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5835   -2.7802    2.5574 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4719   -3.0139    3.1356 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5276   -0.0089    0.2827 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5101    0.9660    0.1378 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7590    1.4465   -1.1203 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5359    2.0928    2.4731 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6520    3.6342    1.6150 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3216    3.4016    2.7556 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4872    1.2698    3.3809 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7726   -0.4305    3.6503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3091   -0.5541    0.5793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9189   -4.0705    1.5762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7094   -7.0890    3.3966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5653   -6.7098    4.0380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6564   -5.1470    3.8944 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0074   -0.3625   -0.6033 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4781    2.0977   -1.0020 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  2  0
  8  9  1  0
 10 16  2  0
  6  5  2  0
 14 15  2  0
  5  4  1  0
 15 16  1  0
  4  3  2  0
 12 14  1  0
  3 20  1  0
 10 11  1  0
 20 19  2  0
 19  6  1  0
  7  6  1  0
 12 13  1  0
 11 12  2  0
 17 18  2  0
 10  9  1  0
  3  2  1  0
 16 17  1  0
 20 21  1  0
 17  7  1  0
  2  1  1  0
 13 29  1  0
 14 30  1  0
 15 31  1  0
 11 28  1  0
  8 27  1  0
  5 26  1  0
  4 25  1  0
 19 32  1  0
 21 33  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
M  END


  Mrv1652306192123153D          

 33 35  0  0  0  0            999 V2000
    3.9498    2.8963    2.0147 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1695    2.4078    0.9293 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2348    1.4517    1.2306 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9564    0.9391    2.4946 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9654   -0.0412    2.6513 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2373   -0.5249    1.5526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8037   -1.5554    1.7350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0176   -1.4086    1.1793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0798   -2.2753    1.2714 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9050   -3.4215    2.0021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9848   -4.2998    2.0807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8580   -5.4774    2.8116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9367   -6.3093    2.8631 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6696   -5.7923    3.4666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5896   -4.9106    3.3872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7117   -3.7246    2.6527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5835   -2.7802    2.5574 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4719   -3.0139    3.1356 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5276   -0.0089    0.2827 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5101    0.9660    0.1378 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7590    1.4465   -1.1203 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5359    2.0928    2.4731 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6520    3.6342    1.6150 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3216    3.4016    2.7556 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4872    1.2698    3.3809 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7726   -0.4305    3.6503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3091   -0.5541    0.5793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9189   -4.0705    1.5762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7094   -7.0890    3.3966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5653   -6.7098    4.0380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6564   -5.1470    3.8944 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0074   -0.3625   -0.6033 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4781    2.0977   -1.0020 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
 10 16  2  0  0  0  0
  6  5  2  0  0  0  0
 14 15  2  0  0  0  0
  5  4  1  0  0  0  0
 15 16  1  0  0  0  0
  4  3  2  0  0  0  0
 12 14  1  0  0  0  0
  3 20  1  0  0  0  0
 10 11  1  0  0  0  0
 20 19  2  0  0  0  0
 19  6  1  0  0  0  0
  7  6  1  0  0  0  0
 12 13  1  0  0  0  0
 11 12  2  0  0  0  0
 17 18  2  0  0  0  0
 10  9  1  0  0  0  0
  3  2  1  0  0  0  0
 16 17  1  0  0  0  0
 20 21  1  0  0  0  0
 17  7  1  0  0  0  0
  2  1  1  0  0  0  0
 13 29  1  0  0  0  0
 14 30  1  0  0  0  0
 15 31  1  0  0  0  0
 11 28  1  0  0  0  0
  8 27  1  0  0  0  0
  5 26  1  0  0  0  0
  4 25  1  0  0  0  0
 19 32  1  0  0  0  0
 21 33  1  0  0  0  0
  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0029697

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C2=C(C([H])=C1[H])C(=O)C(=C([H])O2)C1=C([H])C([H])=C(OC([H])([H])[H])C(O[H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C16H12O5/c1-20-14-5-2-9(6-13(14)18)12-8-21-15-7-10(17)3-4-11(15)16(12)19/h2-8,17-18H,1H3

> <INCHI_KEY>
ZZAJQOPSWWVMBI-UHFFFAOYSA-N

> <FORMULA>
C16H12O5

> <MOLECULAR_WEIGHT>
284.2635

> <EXACT_MASS>
284.068473494

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
28.815471381654447

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-hydroxy-3-(3-hydroxy-4-methoxyphenyl)-4H-chromen-4-one

> <ALOGPS_LOGP>
3.37

> <JCHEM_LOGP>
2.5727664456666663

> <ALOGPS_LOGS>
-3.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.20814141022319

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.477056367920937

> <JCHEM_PKA_STRONGEST_BASIC>
-4.763080973713113

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
76.1652

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.53e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
calycosin

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 33 35  0  0  0  0  0  0  0  0999 V2000
    3.9498    2.8963    2.0147 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1695    2.4078    0.9293 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2348    1.4517    1.2306 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9564    0.9391    2.4946 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9654   -0.0412    2.6513 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2373   -0.5249    1.5526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8037   -1.5554    1.7350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0176   -1.4086    1.1793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0798   -2.2753    1.2714 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9050   -3.4215    2.0021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9848   -4.2998    2.0807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8580   -5.4774    2.8116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9367   -6.3093    2.8631 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6696   -5.7923    3.4666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5896   -4.9106    3.3872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7117   -3.7246    2.6527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5835   -2.7802    2.5574 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4719   -3.0139    3.1356 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5276   -0.0089    0.2827 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5101    0.9660    0.1378 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7590    1.4465   -1.1203 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5359    2.0928    2.4731 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6520    3.6342    1.6150 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3216    3.4016    2.7556 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4872    1.2698    3.3809 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7726   -0.4305    3.6503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3091   -0.5541    0.5793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9189   -4.0705    1.5762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7094   -7.0890    3.3966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5653   -6.7098    4.0380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6564   -5.1470    3.8944 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0074   -0.3625   -0.6033 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4781    2.0977   -1.0020 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  2  0
  8  9  1  0
 10 16  2  0
  6  5  2  0
 14 15  2  0
  5  4  1  0
 15 16  1  0
  4  3  2  0
 12 14  1  0
  3 20  1  0
 10 11  1  0
 20 19  2  0
 19  6  1  0
  7  6  1  0
 12 13  1  0
 11 12  2  0
 17 18  2  0
 10  9  1  0
  3  2  1  0
 16 17  1  0
 20 21  1  0
 17  7  1  0
  2  1  1  0
 13 29  1  0
 14 30  1  0
 15 31  1  0
 11 28  1  0
  8 27  1  0
  5 26  1  0
  4 25  1  0
 19 32  1  0
 21 33  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0       3.950   2.896   2.015  0.00  0.00           C+0
HETATM    2  O   UNK     0       3.170   2.408   0.929  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.235   1.452   1.231  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.956   0.939   2.495  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.965  -0.041   2.651  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.237  -0.525   1.553  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.804  -1.555   1.735  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.018  -1.409   1.179  0.00  0.00           C+0
HETATM    9  O   UNK     0      -3.080  -2.275   1.271  0.00  0.00           O+0
HETATM   10  C   UNK     0      -2.905  -3.422   2.002  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.985  -4.300   2.081  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.858  -5.477   2.812  0.00  0.00           C+0
HETATM   13  O   UNK     0      -4.937  -6.309   2.863  0.00  0.00           O+0
HETATM   14  C   UNK     0      -2.670  -5.792   3.467  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.590  -4.911   3.387  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.712  -3.725   2.653  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.584  -2.780   2.557  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.472  -3.014   3.136  0.00  0.00           O+0
HETATM   19  C   UNK     0       0.528  -0.009   0.283  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.510   0.966   0.138  0.00  0.00           C+0
HETATM   21  O   UNK     0       1.759   1.446  -1.120  0.00  0.00           O+0
HETATM   22  H   UNK     0       4.536   2.093   2.473  0.00  0.00           H+0
HETATM   23  H   UNK     0       4.652   3.634   1.615  0.00  0.00           H+0
HETATM   24  H   UNK     0       3.322   3.402   2.756  0.00  0.00           H+0
HETATM   25  H   UNK     0       2.487   1.270   3.381  0.00  0.00           H+0
HETATM   26  H   UNK     0       0.773  -0.431   3.650  0.00  0.00           H+0
HETATM   27  H   UNK     0      -2.309  -0.554   0.579  0.00  0.00           H+0
HETATM   28  H   UNK     0      -4.919  -4.071   1.576  0.00  0.00           H+0
HETATM   29  H   UNK     0      -4.709  -7.089   3.397  0.00  0.00           H+0
HETATM   30  H   UNK     0      -2.565  -6.710   4.038  0.00  0.00           H+0
HETATM   31  H   UNK     0      -0.656  -5.147   3.894  0.00  0.00           H+0
HETATM   32  H   UNK     0       0.007  -0.363  -0.603  0.00  0.00           H+0
HETATM   33  H   UNK     0       2.478   2.098  -1.002  0.00  0.00           H+0
CONECT    1    2   22   23   24                                             
CONECT    2    3    1                                                       
CONECT    3    4   20    2                                                  
CONECT    4    5    3   25                                                  
CONECT    5    6    4   26                                                  
CONECT    6    5   19    7                                                  
CONECT    7    8    6   17                                                  
CONECT    8    7    9   27                                                  
CONECT    9    8   10                                                       
CONECT   10   16   11    9                                                  
CONECT   11   10   12   28                                                  
CONECT   12   14   13   11                                                  
CONECT   13   12   29                                                       
CONECT   14   15   12   30                                                  
CONECT   15   14   16   31                                                  
CONECT   16   10   15   17                                                  
CONECT   17   18   16    7                                                  
CONECT   18   17                                                            
CONECT   19   20    6   32                                                  
CONECT   20    3   19   21                                                  
CONECT   21   20   33                                                       
CONECT   22    1                                                            
CONECT   23    1                                                            
CONECT   24    1                                                            
CONECT   25    4                                                            
CONECT   26    5                                                            
CONECT   27    8                                                            
CONECT   28   11                                                            
CONECT   29   13                                                            
CONECT   30   14                                                            
CONECT   31   15                                                            
CONECT   32   19                                                            
CONECT   33   21                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

RDKit          3D

33 35  0  0  0  0  0  0  0  0999 V2000
    3.9498    2.8963    2.0147 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1695    2.4078    0.9293 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2348    1.4517    1.2306 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9564    0.9391    2.4946 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9654   -0.0412    2.6513 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2373   -0.5249    1.5526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8037   -1.5554    1.7350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0176   -1.4086    1.1793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0798   -2.2753    1.2714 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9050   -3.4215    2.0021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9848   -4.2998    2.0807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8580   -5.4774    2.8116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9367   -6.3093    2.8631 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6696   -5.7923    3.4666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5896   -4.9106    3.3872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7117   -3.7246    2.6527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5835   -2.7802    2.5574 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4719   -3.0139    3.1356 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5276   -0.0089    0.2827 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5101    0.9660    0.1378 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7590    1.4465   -1.1203 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5359    2.0928    2.4731 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6520    3.6342    1.6150 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3216    3.4016    2.7556 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4872    1.2698    3.3809 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7726   -0.4305    3.6503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3091   -0.5541    0.5793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9189   -4.0705    1.5762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7094   -7.0890    3.3966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5653   -6.7098    4.0380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6564   -5.1470    3.8944 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0074   -0.3625   -0.6033 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4781    2.0977   -1.0020 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  2  0
  8  9  1  0
 10 16  2  0
  6  5  2  0
 14 15  2  0
  5  4  1  0
 15 16  1  0
  4  3  2  0
 12 14  1  0
  3 20  1  0
 10 11  1  0
 20 19  2  0
 19  6  1  0
  7  6  1  0
 12 13  1  0
 11 12  2  0
 17 18  2  0
 10  9  1  0
  3  2  1  0
 16 17  1  0
 20 21  1  0
 17  7  1  0
  2  1  1  0
 13 29  1  0
 14 30  1  0
 15 31  1  0
 11 28  1  0
  8 27  1  0
  5 26  1  0
  4 25  1  0
 19 32  1  0
 21 33  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
M  END

View in JSmol

Synonyms

Value	Source
3'-Hydroxy-formononetin	ChEBI
7,3'-Dihydroxy-4'-methoxyisoflavone	ChEBI
7-Hydroxy-3-(3-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-one	ChEBI
7-Hydroxy-3-(3-hydroxy-4-methoxyphenyl)chromen-4-one	ChEBI
3'-Hydroxyformononetin	Kegg
Calycosin (old)	ChEBI

Chemical Formula

C₁₆H₁₂O₅

Average Mass

284.2635 Da

Monoisotopic Mass

284.06847 Da

IUPAC Name

7-hydroxy-3-(3-hydroxy-4-methoxyphenyl)-4H-chromen-4-one

Traditional Name

calycosin

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C2=C(C([H])=C1[H])C(=O)C(=C([H])O2)C1=C([H])C([H])=C(OC([H])([H])[H])C(O[H])=C1[H]

InChI Identifier

InChI=1S/C16H12O5/c1-20-14-5-2-9(6-13(14)18)12-8-21-15-7-10(17)3-4-11(15)16(12)19/h2-8,17-18H,1H3

InChI Key

ZZAJQOPSWWVMBI-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Ammopiptanthus mongolicus	LOTUS Database	35616633
Amorpha fruticosa	LOTUS Database	35616633
Andira inermis	KNApSAcK Database	22123792
Andira surinamensis	LOTUS Database	35616633
Astragalus complanatus	LOTUS Database	35616633
Astragalus laxmannii	LOTUS Database	35616633
Astragalus membranaceus	LOTUS Database	35616633
Astragalus microcephalus	LOTUS Database	35616633
Astragalus mongholicus	JEOL database	Du, X., et al, Magn. Reson. Chem. 44, 708(2006)
Baptisia spp.	KNApSAcK Database	22123792
Bolusanthus speciosus	LOTUS Database	35616633
Bowdichia nitida	KNApSAcK Database	22123792
Bowdichia virgilioides	LOTUS Database	35616633
Calicotome villosa	LOTUS Database	35616633
Centrolobium paraense	LOTUS Database	35616633
Centrolobium sclerophyllum	LOTUS Database	35616633
Cicer arietinum	LOTUS Database	35616633
Cyclopia intermedia	LOTUS Database	35616633
Dalbergia parviflora	KNApSAcK Database	22123792
Dermatophyllum secundiflorum	LOTUS Database	35616633
Erycibe expansa	KNApSAcK Database	22123792
Erythrina latissima	KNApSAcK Database	22123792
Glycyrrhiza pallidiflora	KNApSAcK Database	22123792
Glycyrrhiza uralensis	LOTUS Database	35616633
Hedysarum polybotrys	LOTUS Database	35616633
Maackia amurensis	LOTUS Database	35616633
Machaerium aristulatum	LOTUS Database	35616633
Machaerium mucronulatum	KNApSAcK Database	22123792
Machaerium vestitum	KNApSAcK Database	22123792
Machaerium villosum	KNApSAcK Database	22123792
Medicago truncatula	KNApSAcK Database	22123792
Melilotus messanensis	KNApSAcK Database	22123792
Millettia laurentii	KNApSAcK Database	22123792
Myroxylon balsamum	KNApSAcK Database	22123792
Myroxylon peruiferum	LOTUS Database	35616633
Oxytropis falcata	LOTUS Database	35616633
Psorothamnus arborescens	KNApSAcK Database	22123792
Pycnanthus angolensis	LOTUS Database	35616633
Sophora flavescens	KNApSAcK Database	22123792
Sophora fraseri	KNApSAcK Database	22123792
Sophora moorcroftiana	LOTUS Database	35616633
Sophora secundiflora	KNApSAcK Database	22123792
Spatholobus suberectus	LOTUS Database	35616633
Styphnolobium japonicum	LOTUS Database	35616633
Thermopsis lupinoides	LOTUS Database	35616633
Trifolium pratense	Plant	KNApSAcK
Trifolium repens	Plant	KNApSAcK
Trigonella foenum-graecum	LOTUS Database	35616633
Virgilia oroboides	LOTUS Database	35616633
Wisteria brachybotrys	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3'-hydroxy,4'-methoxyisoflavonoids. These are isoflavonoids carrying a methoxy group attached to the C4' atom, as well as a hydroxyl group at the C3'-position of the isoflavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

O-methylated isoflavonoids

Direct Parent

3'-hydroxy,4'-methoxyisoflavonoids

Alternative Parents

Substituents

4p-o-methylisoflavone
3'-hydroxy,4'-methoxyisoflavonoid
Isoflavone
Hydroxyisoflavonoid
Chromone
Methoxyphenol
1-benzopyran
Benzopyran
Phenoxy compound
Phenol ether
Anisole
Methoxybenzene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
Phenol
Pyran
Monocyclic benzene moiety
Benzenoid
Heteroaromatic compound
Ether
Organoheterocyclic compound
Oxacycle
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

methoxyisoflavone (CHEBI:17793 )
7-hydroxyisoflavones (CHEBI:17793 )
isoflavones (C01562 )
Isoflavonoids (C01562 )
Isoflavonoids (LMPK12050056 )
an isoflavone (CPD-9539 )

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	3.37	ALOGPS
logP	2.57	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	6.48	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	76.17 m³·mol⁻¹	ChemAxon
Polarizability	28.82 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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Calycosin

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

17793

Good Scents ID

Not Available

References

General References

Kraft C, Jenett-Siems K, Siems K, Gupta MP, Bienzle U, Eich E: Antiplasmodial activity of isoflavones from Andira inermis. J Ethnopharmacol. 2000 Nov;73(1-2):131-5. doi: 10.1016/s0378-8741(00)00285-3. [PubMed:11025148 ]
Juck DB, De Rezende LC, David JP, De Queiroz LP, David JM: Two new isoflavonoids from Bowdichia virgilioides. Nat Prod Res. 2006 Jan;20(1):27-30. doi: 10.1080/14786410500160942. [PubMed:16286304 ]
Salem MM, Werbovetz KA: Isoflavonoids and other compounds from Psorothamnus arborescens with antiprotozoal activities. J Nat Prod. 2006 Jan;69(1):43-9. doi: 10.1021/np0502600. [PubMed:16441066 ]
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Showing NP-Card for calycosin (NP0029697)

MOL for NP0029697 (calycosin)

3D MOL for NP0029697 (calycosin)

3D SDF for NP0029697 (calycosin)

3D-SDF for NP0029697 (calycosin)

PDB for NP0029697 (calycosin)

3D PDB for NP0029697 (calycosin)

SMILES for NP0029697 (calycosin)

INCHI for NP0029697 (calycosin)

Structure for NP0029697 (calycosin)

3D Structure for NP0029697 (calycosin)