NP-MRD: Showing NP-Card for Calceolarioside B (NP0044202)

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Record Information

Version

1.0

Created at

2021-11-12 23:56:47 UTC

Updated at

2021-11-26 17:46:35 UTC

NP-MRD ID

NP0044202

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Calceolarioside B

Description

Calceolarioside B belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring. Calceolarioside B is found in Aeschynanthus bracteatus , Akebia trifoliata, Calceolaria hypericina, Calceolaria thyrsiflora, Cassinopsis madagascariensis, Digitalis purpurea, Fraxinus insularis, Fraxinus ornus , Lepisorus contortus, Penstemon linarioides, Plantago lanceolata, Plantago major, Primulina sinensis, Prunus grayana and Prunus ssiori. It was first documented in 2015 (PMID: 25641842). Based on a literature review a significant number of articles have been published on Calceolarioside B (PMID: 34498959) (PMID: 34091163) (PMID: 32948420) (PMID: 28326319).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652311132100562D          

 34 36  0  0  1  0            999 V2000
    5.0013   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.8592   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.2881   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.2881   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.8592   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
  5 12  1  0  0  0  0
  2 13  1  0  0  0  0
 13 14  1  0  0  0  0
 15 14  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 21 28  1  0  0  0  0
 17 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
 31 32  1  1  0  0  0
 31 33  1  0  0  0  0
 15 33  1  0  0  0  0
 33 34  1  6  0  0  0
M  END

     RDKit          3D

 60 62  0  0  0  0  0  0  0  0999 V2000
    3.4698    3.5137   -0.5925 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5728    2.2914   -0.3400 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9230    1.6962   -0.2644 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0911    0.4167   -0.0022 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3685   -0.2654    0.0942 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3993   -1.6351    0.3802 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5878   -2.3252    0.4816 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8041   -1.7028    0.3068 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0047   -2.3961    0.4085 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7982   -0.3535    0.0242 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9944    0.2960   -0.1555 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5883    0.3464   -0.0785 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4366    1.5507   -0.1432 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1284    2.1042   -0.2116 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1532    0.9666    0.0625 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1236    1.4691    0.0037 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0549    0.4576    0.2411 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3081    0.9410    0.5262 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7199    0.5046    1.7698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0871    1.0007    2.1414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1306    0.5583    1.1871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7634   -0.6451    1.4436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7547   -1.1571    0.6190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1204   -0.4394   -0.4951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1123   -0.8864   -1.3786 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4817    0.7644   -0.7443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8856    1.4695   -1.8965 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5008    1.2577    0.0836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0599   -0.4076   -1.0259 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0509   -1.3613   -0.9977 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7237   -1.0603   -1.1272 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6124   -1.6301   -2.4076 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4273   -0.1017   -0.9643 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5224   -0.8404   -0.5138 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7990    2.3017   -0.4232 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1904   -0.1574    0.1510 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4618   -2.1395    0.5201 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6261   -3.3904    0.7035 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.9007   -1.9908    0.2909 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9882    1.2828   -0.3622 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5940    1.4135   -0.3024 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9844    2.9609    0.4488 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9072    2.4545   -1.2552 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3411    0.5910    1.0915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6864   -0.1604    1.0763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7116   -0.5979    1.8709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9923    0.8932    2.5113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0488    2.1174    2.2277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3579    0.6083    3.1407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5104   -1.2526    2.3135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2518   -2.0966    0.8153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6054   -1.7398   -1.2541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4600    2.3571   -2.1390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0387    2.1908   -0.1522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1715    0.3096   -1.8681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7581   -2.1223   -1.5738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6660   -1.8528   -0.3494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3172   -2.5766   -2.3412 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7231    0.3259   -1.9477 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2801   -1.2145    0.3720 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
  2 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 26 28  2  0
 17 29  1  0
 29 30  1  0
 29 31  1  0
 31 32  1  0
 31 33  1  0
 33 34  1  0
 12  5  1  0
 33 15  1  0
 28 21  1  0
  3 35  1  0
  4 36  1  0
  6 37  1  0
  7 38  1  0
  9 39  1  0
 11 40  1  0
 12 41  1  0
 14 42  1  0
 14 43  1  0
 15 44  1  1
 17 45  1  1
 19 46  1  0
 19 47  1  0
 20 48  1  0
 20 49  1  0
 22 50  1  0
 23 51  1  0
 25 52  1  0
 27 53  1  0
 28 54  1  0
 29 55  1  6
 30 56  1  0
 31 57  1  1
 32 58  1  0
 33 59  1  6
 34 60  1  0
M  END


  Mrv1652311132100562D          

 34 36  0  0  1  0            999 V2000
    5.0013   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.8592   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.2881   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.2881   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.8592   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
  5 12  1  0  0  0  0
  2 13  1  0  0  0  0
 13 14  1  0  0  0  0
 15 14  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 21 28  1  0  0  0  0
 17 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
 31 32  1  1  0  0  0
 31 33  1  0  0  0  0
 15 33  1  0  0  0  0
 33 34  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0044202

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@H]1[C@@H](COC(=O)\C=C\C2=CC=C(O)C(O)=C2)O[C@@H](OCCC2=CC=C(O)C(O)=C2)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C23H26O11/c24-14-4-1-12(9-16(14)26)3-6-19(28)33-11-18-20(29)21(30)22(31)23(34-18)32-8-7-13-2-5-15(25)17(27)10-13/h1-6,9-10,18,20-27,29-31H,7-8,11H2/b6-3+/t18-,20-,21+,22-,23-/m1/s1

> <INCHI_KEY>
LFKQVVDFNHDYNK-FOXCETOMSA-N

> <FORMULA>
C23H26O11

> <MOLECULAR_WEIGHT>
478.45

> <EXACT_MASS>
478.147511657

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
47.20717919246417

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(2R,3S,4S,5R,6R)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

> <ALOGPS_LOGP>
0.80

> <JCHEM_LOGP>
1.5433510393333332

> <ALOGPS_LOGS>
-3.08

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.643773860230727

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.010398812127328

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6490922422252465

> <JCHEM_POLAR_SURFACE_AREA>
186.37

> <JCHEM_REFRACTIVITY>
117.53350000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.96e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3S,4S,5R,6R)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 13-NOV-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-NOV-21         0                                  
HETATM    1  O   UNK     0       9.336  -6.930   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.003 -11.550   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.337 -12.320   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.337 -13.860   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.003 -14.630   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      12.003 -16.170   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      10.669 -13.860   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       9.336 -14.630   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      10.669 -12.320   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      12.003  -6.930   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      12.003  -5.390   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.337  -4.620   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      13.337  -3.080   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      14.670  -2.310   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      14.670  -0.770   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      16.004   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      16.004   1.540   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      17.338   2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      17.338   3.850   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      18.672   4.620   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      20.005   3.850   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      21.339   4.620   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      20.005   2.310   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      21.339   1.540   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      18.672   1.540   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      16.004  -3.080   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      17.338  -2.310   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      16.004  -4.620   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      17.338  -5.390   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      14.670  -5.390   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      14.670  -6.930   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    5                                                       
CONECT   13    2   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   33                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   29                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   28                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   21                                                       
CONECT   29   17   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   15   34                                                  
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₂₆O₁₁

Average Mass

478.4500 Da

Monoisotopic Mass

478.14751 Da

IUPAC Name

[(2R,3S,4S,5R,6R)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

Traditional Name

[(2R,3S,4S,5R,6R)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

O[C@@H]1[C@@H](COC(=O)\C=C\C2=CC=C(O)C(O)=C2)O[C@@H](OCCC2=CC=C(O)C(O)=C2)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C23H26O11/c24-14-4-1-12(9-16(14)26)3-6-19(28)33-11-18-20(29)21(30)22(31)23(34-18)32-8-7-13-2-5-15(25)17(27)10-13/h1-6,9-10,18,20-27,29-31H,7-8,11H2/b6-3+/t18-,20-,21+,22-,23-/m1/s1

InChI Key

LFKQVVDFNHDYNK-FOXCETOMSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Aeschynanthus bracteatus	Plant	KNApSAcK
Akebia trifoliata	LOTUS Database	35616633
Calceolaria hypericina	Plant	KNApSAcK
Calceolaria thyrsiflora	LOTUS Database	35616633
Cassinopsis madagascariensis	LOTUS Database	35616633
Digitalis purpurea	LOTUS Database	35616633
Fraxinus insularis	LOTUS Database	35616633
Fraxinus ornus	Plant	KNApSAcK
Lepisorus contortus	LOTUS Database	35616633
Penstemon linarioides	LOTUS Database	35616633
Plantago lanceolata	LOTUS Database	35616633
Plantago major	LOTUS Database	35616633
Primulina sinensis	LOTUS Database	35616633
Prunus grayana	LOTUS Database	35616633
Prunus ssiori	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Coumaric acids and derivatives

Alternative Parents

Substituents

Coumaric acid or derivatives
Cinnamic acid ester
Glycosyl compound
O-glycosyl compound
Tyrosol derivative
Catechol
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Phenol
Fatty acyl
Benzenoid
Monocyclic benzene moiety
Oxane
Monosaccharide
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Secondary alcohol
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Polyol
Carboxylic acid derivative
Acetal
Monocarboxylic acid or derivatives
Organooxygen compound
Carbonyl group
Alcohol
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

hydroxycinnamic acid (CHEBI:68345 )

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	0.8	ALOGPS
logP	1.54	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	9.01	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	186.37 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	117.53 m³·mol⁻¹	ChemAxon
Polarizability	47.21 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00033686

Chemspider ID

4437970

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5273567

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Verdan MH, Mera de Souza L, Ernesto de Carvalho J, Vendramini Costa DB, Salvador MJ, Barison A, Alves Stefanello ME: Two new hydronaphthoquinones from Sinningia aggregata (Gesneriaceae) and cytotoxic activity of aggregatin D. Chem Biodivers. 2015 Jan;12(1):148-52. doi: 10.1002/cbdv.201400281. [PubMed:25641842 ]
Winiewski V, Mesquita Fonseca M, Salvador MJ, Lemos de Sa E, Alves Stefanello ME: Three new naphthoquinones from the tubers of Sinningia mauroana. Nat Prod Res. 2021 Sep 9:1-6. doi: 10.1080/14786419.2021.1969564. [PubMed:34498959 ]
Zheng X, Pu P, Ding B, Bo W, Qin D, Liang G: Identification of the functional food ingredients with antithrombotic properties via virtual screen and experimental studies. Food Chem. 2021 Nov 15;362:130237. doi: 10.1016/j.foodchem.2021.130237. Epub 2021 May 29. [PubMed:34091163 ]
Adem S, Eyupoglu V, Sarfraz I, Rasul A, Zahoor AF, Ali M, Abdalla M, Ibrahim IM, Elfiky AA: Caffeic acid derivatives (CAFDs) as inhibitors of SARS-CoV-2: CAFDs-based functional foods as a potential alternative approach to combat COVID-19. Phytomedicine. 2021 May;85:153310. doi: 10.1016/j.phymed.2020.153310. Epub 2020 Aug 22. [PubMed:32948420 ]
Hwang SH, Kwon SH, Kim SB, Lim SS: Inhibitory Activities of Stauntonia hexaphylla Leaf Constituents on Rat Lens Aldose Reductase and Formation of Advanced Glycation End Products and Antioxidant. Biomed Res Int. 2017;2017:4273257. doi: 10.1155/2017/4273257. Epub 2017 Feb 23. [PubMed:28326319 ]
Søren Damtoft and Søren Rosendal Jensen (1994). Three phenylethanoid glucosides of unusual structure from Chirita sinensis (gesneriaceae). Phytochemistry, Volume 37, Issue 2, 1994, Pages 441-443. DOI: Volume 37, Issue 2, 1994, Pages 441-443. Phytochemistry.

Showing NP-Card for Calceolarioside B (NP0044202)

MOL for NP0044202 (Calceolarioside B)

3D MOL for NP0044202 (Calceolarioside B)

3D SDF for NP0044202 (Calceolarioside B)

3D-SDF for NP0044202 (Calceolarioside B)

PDB for NP0044202 (Calceolarioside B)

3D PDB for NP0044202 (Calceolarioside B)

SMILES for NP0044202 (Calceolarioside B)

INCHI for NP0044202 (Calceolarioside B)

Structure for NP0044202 (Calceolarioside B)

3D Structure for NP0044202 (Calceolarioside B)