NP-MRD: Showing NP-Card for 6,14-dihydroxy-7-methoxy-13-[(3,4,5-trihydroxyoxan-2-yl)oxy]-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4,6,8(16),11,13-hexaene-3,10-dione (NP0282673)

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Record Information

Version

2.0

Created at

2022-09-09 09:36:30 UTC

Updated at

2022-09-09 09:36:30 UTC

NP-MRD ID

NP0282673

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6,14-dihydroxy-7-methoxy-13-[(3,4,5-trihydroxyoxan-2-yl)oxy]-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4,6,8(16),11,13-hexaene-3,10-dione

Description

Ducheside A belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety. 6,14-dihydroxy-7-methoxy-13-[(3,4,5-trihydroxyoxan-2-yl)oxy]-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4,6,8(16),11,13-hexaene-3,10-dione is found in Aphananthe aspera, Castanopsis fissa and Platycarya strobilacea. Ducheside A is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251507222D          

 32 36  0  0  0  0            999 V2000
    5.5539    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7289    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3164   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5539   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3164   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4914   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4914   -2.9684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6039   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6039   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2211   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6336   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4586   -0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8711    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4586    1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8711    2.0329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6336    1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2211    2.0329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2211    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6039    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4914   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   -0.8250    0.0000 C   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
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 16 23  1  0  0  0  0
 23 24  1  0  0  0  0
 14 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
  3 30  1  0  0  0  0
 30 31  2  0  0  0  0
  7 31  1  0  0  0  0
 31 32  1  0  0  0  0
 11 32  1  0  0  0  0
 26 32  2  0  0  0  0
M  END

     RDKit          3D

 48 52  0  0  0  0  0  0  0  0999 V2000
    5.7147    2.8613   -0.7862 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2668    1.7222   -1.5047 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7527    0.6094   -0.8583 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5765   -0.4479   -0.4553 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9342   -0.3533   -0.7215 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0354   -1.5391    0.1844 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6779   -1.5574    0.4120 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0692   -2.6167    1.0462 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8078   -3.5788    1.4148 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7745   -2.6240    1.2580 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9856   -1.6204    0.8765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3706   -1.6604    1.1147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8447   -2.7927    1.7642 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2583   -0.6456    0.7434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5520   -0.6822    0.9699 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7625   -0.9587    1.3045 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4169    0.0148    2.1418 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1532    1.2469    1.5604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8319    1.4388    0.2385 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1557    2.4475   -0.4469 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9296    0.2093   -0.5951 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0169    0.2787   -1.6632 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7649   -1.0692    0.1384 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3238   -2.0636   -0.7323 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6736    0.4722    0.0833 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6703    0.5083   -0.1509 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2950    1.5720   -0.7901 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5759    2.5397   -1.1647 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6016    1.5756   -1.0020 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3865    0.5859   -0.6268 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8551   -0.5119    0.0146 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5005   -0.5226    0.2378 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1515    2.9898    0.1750 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4935    3.7579   -1.4145 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8013    2.8326   -0.6078 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5248   -1.1197   -0.4283 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6999   -2.3324    0.4794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8168   -2.8751    1.9623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9148   -1.9592    1.8347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5061    2.0212    2.2822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0574    1.3977    1.4720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8630    1.8392    0.4408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4711    2.0036   -1.0068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9445    0.1848   -1.0912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4434    0.7206   -2.4556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7179   -1.4147    0.5912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0384   -2.1612   -1.4185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3233    1.2765   -0.2196 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 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
 19 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 14 25  2  0
 25 26  1  0
 26 32  2  0
 32 31  1  0
 31 30  2  0
 30 29  1  0
 29 27  1  0
 27 28  2  0
 30  3  1  0
 31  7  1  0
 32 11  1  0
 23 16  1  0
 27 26  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  5 36  1  0
  6 37  1  0
 13 38  1  0
 16 39  1  1
 18 40  1  0
 18 41  1  0
 19 42  1  1
 20 43  1  0
 21 44  1  6
 22 45  1  0
 23 46  1  1
 24 47  1  0
 25 48  1  0
M  END


  Mrv1533004251507222D          

 32 36  0  0  0  0            999 V2000
    5.5539    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7289    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3164   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5539   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3164   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4914   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4914   -2.9684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6039   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6039   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2211   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6336   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4586   -0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8711    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4586    1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8711    2.0329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6336    1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2211    2.0329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2211    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6039    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4914   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   -0.8250    0.0000 C   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
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 16 23  1  0  0  0  0
 23 24  1  0  0  0  0
 14 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
  3 30  1  0  0  0  0
 30 31  2  0  0  0  0
  7 31  1  0  0  0  0
 31 32  1  0  0  0  0
 11 32  1  0  0  0  0
 26 32  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0282673

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=C2C(=O)OC3=C(O)C(OC4OCC(O)C(O)C4O)=CC4=C3C2=C1OC4=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H16O12/c1-28-15-7(21)2-5-11-10-6(19(27)32-17(11)15)3-9(13(24)16(10)31-18(5)26)30-20-14(25)12(23)8(22)4-29-20/h2-3,8,12,14,20-25H,4H2,1H3

> <INCHI_KEY>
VAXNJGHUQUHOGC-UHFFFAOYSA-N

> <FORMULA>
C20H16O12

> <MOLECULAR_WEIGHT>
448.336

> <EXACT_MASS>
448.064175955

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
41.28643130422436

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7,13-dihydroxy-14-methoxy-6-[(3,4,5-trihydroxyoxan-2-yl)oxy]-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4(16),5,7,11,13-hexaene-3,10-dione

> <ALOGPS_LOGP>
0.48

> <JCHEM_LOGP>
0.17408332266666676

> <ALOGPS_LOGS>
-2.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.582370902726506

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.17094549056504

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5265985239784365

> <JCHEM_POLAR_SURFACE_AREA>
181.44

> <JCHEM_REFRACTIVITY>
101.27179999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.15e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7,13-dihydroxy-14-methoxy-6-[(3,4,5-trihydroxyoxan-2-yl)oxy]-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4(16),5,7,11,13-hexaene-3,10-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0      10.367   1.127   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       8.827   1.127   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       8.057  -0.206   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.827  -1.540   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      10.367  -1.540   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       8.057  -2.874   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.517  -2.874   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.747  -4.207   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.517  -5.541   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       4.207  -4.207   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       3.437  -2.874   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.897  -2.874   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.127  -4.207   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.127  -1.540   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.413  -1.540   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -1.183  -0.206   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -2.723  -0.206   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -3.493   1.127   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.723   2.461   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -3.493   3.795   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -1.183   2.461   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -0.413   3.795   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -0.413   1.127   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       1.127   1.127   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.897  -0.206   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.437  -0.206   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.207   1.127   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       3.437   2.461   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       5.747   1.127   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       6.517  -0.206   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.747  -1.540   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.207  -1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   30                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   31                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   32                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   25                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   23                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   16   24                                                  
CONECT   24   23                                                            
CONECT   25   14   26                                                       
CONECT   26   25   27   32                                                  
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29    3   31                                                  
CONECT   31   30    7   32                                                  
CONECT   32   31   11   26                                                  
MASTER        0    0    0    0    0    0    0    0   32    0   72    0
END

View in JSmol

Synonyms

Value	Source
3'-O-Methyl-ellagic acid-4-O-beta-D-xylopyranoside	MeSH

Chemical Formula

C₂₀H₁₆O₁₂

Average Mass

448.3360 Da

Monoisotopic Mass

448.06418 Da

IUPAC Name

7,13-dihydroxy-14-methoxy-6-[(3,4,5-trihydroxyoxan-2-yl)oxy]-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4(16),5,7,11,13-hexaene-3,10-dione

Traditional Name

7,13-dihydroxy-14-methoxy-6-[(3,4,5-trihydroxyoxan-2-yl)oxy]-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4(16),5,7,11,13-hexaene-3,10-dione

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=C2C(=O)OC3=C(O)C(OC4OCC(O)C(O)C4O)=CC4=C3C2=C1OC4=O

InChI Identifier

InChI=1S/C20H16O12/c1-28-15-7(21)2-5-11-10-6(19(27)32-17(11)15)3-9(13(24)16(10)31-18(5)26)30-20-14(25)12(23)8(22)4-29-20/h2-3,8,12,14,20-25H,4H2,1H3

InChI Key

VAXNJGHUQUHOGC-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Aphananthe aspera	LOTUS Database	35616633
Castanopsis fissa	LOTUS Database	35616633
Platycarya strobilacea	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Pregnane steroids

Direct Parent

Gluco/mineralocorticoids, progestogins and derivatives

Alternative Parents

Substituents

Progestogin-skeleton
20-oxosteroid
3-hydroxysteroid
17-hydroxysteroid
Oxosteroid
Hydroxysteroid
Alpha-hydroxy ketone
Cyclic alcohol
Tertiary alcohol
Secondary alcohol
Ketone
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	0.48	ALOGPS
logP	0.17	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	6.17	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	181.44 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	101.27 m³·mol⁻¹	ChemAxon
Polarizability	41.29 Å³	ChemAxon
Number of Rings	5	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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

78384860

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 6,14-dihydroxy-7-methoxy-13-[(3,4,5-trihydroxyoxan-2-yl)oxy]-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4,6,8(16),11,13-hexaene-3,10-dione (NP0282673)

MOL for NP0282673 (6,14-dihydroxy-7-methoxy-13-[(3,4,5-trihydroxyoxan-2-yl)oxy]-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4,6,8(16),11,13-hexaene-3,10-dione)

3D MOL for NP0282673 (6,14-dihydroxy-7-methoxy-13-[(3,4,5-trihydroxyoxan-2-yl)oxy]-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4,6,8(16),11,13-hexaene-3,10-dione)

3D SDF for NP0282673 (6,14-dihydroxy-7-methoxy-13-[(3,4,5-trihydroxyoxan-2-yl)oxy]-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4,6,8(16),11,13-hexaene-3,10-dione)

3D-SDF for NP0282673 (6,14-dihydroxy-7-methoxy-13-[(3,4,5-trihydroxyoxan-2-yl)oxy]-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4,6,8(16),11,13-hexaene-3,10-dione)

PDB for NP0282673 (6,14-dihydroxy-7-methoxy-13-[(3,4,5-trihydroxyoxan-2-yl)oxy]-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4,6,8(16),11,13-hexaene-3,10-dione)

3D PDB for NP0282673 (6,14-dihydroxy-7-methoxy-13-[(3,4,5-trihydroxyoxan-2-yl)oxy]-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4,6,8(16),11,13-hexaene-3,10-dione)

SMILES for NP0282673 (6,14-dihydroxy-7-methoxy-13-[(3,4,5-trihydroxyoxan-2-yl)oxy]-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4,6,8(16),11,13-hexaene-3,10-dione)

INCHI for NP0282673 (6,14-dihydroxy-7-methoxy-13-[(3,4,5-trihydroxyoxan-2-yl)oxy]-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4,6,8(16),11,13-hexaene-3,10-dione)

Structure for NP0282673 (6,14-dihydroxy-7-methoxy-13-[(3,4,5-trihydroxyoxan-2-yl)oxy]-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4,6,8(16),11,13-hexaene-3,10-dione)

3D Structure for NP0282673 (6,14-dihydroxy-7-methoxy-13-[(3,4,5-trihydroxyoxan-2-yl)oxy]-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4,6,8(16),11,13-hexaene-3,10-dione)