NP-MRD: Showing NP-Card for 19-hydroxy-10-[(5-hydroxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl)oxy]-4,5,9,9,13,19,20-heptamethyl-21-oxahexacyclo[18.2.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracosa-15,17-dien-22-one (NP0235422)

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Record Information

Version

2.0

Created at

2022-09-06 18:02:12 UTC

Updated at

2022-09-06 18:02:12 UTC

NP-MRD ID

NP0235422

Secondary Accession Numbers

None

Natural Product Identification

Common Name

19-hydroxy-10-[(5-hydroxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl)oxy]-4,5,9,9,13,19,20-heptamethyl-21-oxahexacyclo[18.2.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracosa-15,17-dien-22-one

Description

Kudinoside D belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. 19-hydroxy-10-[(5-hydroxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl)oxy]-4,5,9,9,13,19,20-heptamethyl-21-oxahexacyclo[18.2.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracosa-15,17-dien-22-one is found in Ilex kaushue. 19-hydroxy-10-[(5-hydroxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl)oxy]-4,5,9,9,13,19,20-heptamethyl-21-oxahexacyclo[18.2.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracosa-15,17-dien-22-one was first documented in 2012 (PMID: 22593006). Based on a literature review a significant number of articles have been published on Kudinoside D (PMID: 35054508) (PMID: 31965859) (PMID: 29170122) (PMID: 27074384) (PMID: 25305433).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062220022D          

 64 72  0  0  0  0            999 V2000
   13.0871    2.8814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7143    2.1455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8906    2.1003    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5178    1.3643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6940    1.3192    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3212    0.5832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4975    0.5381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0465    1.2289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2227    1.1838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8500    0.4478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0262    0.4026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5752    1.0935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2024    0.3575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9480    1.8294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4970    2.5203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6732    2.4751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3005    1.7391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8495    2.4300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7514    1.0483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3787    0.3123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5549    0.2672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1039    0.9580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2345    0.9168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6564    1.5813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9693    1.9155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1472    1.0061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8317    0.2173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5711   -0.5655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1742    0.7346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.2807    2.0825    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6808    0.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3384   -0.2606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6710   -0.5874    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2493    2.2461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0759    2.4415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.3809    2.5134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7718    1.8746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7554    2.6994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4464    2.3494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1247   -0.1979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5757   -0.8887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3994   -0.8436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8504   -1.5344    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7722   -0.1076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5960   -0.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0470   -0.7533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6742   -1.4893    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1252   -2.1801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7524   -2.9161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9286   -2.9612    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9489   -2.1349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3999   -2.8258    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3217   -1.3990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1455   -1.3538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8707   -0.7081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2435    0.0278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9688    0.6735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0998   -0.1410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7925    0.7187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5634    0.4249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1653    1.4546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9891    1.4998    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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  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
 17 19  1  0  0  0  0
 12 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
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 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
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 37 38  1  0  0  0  0
 14 39  1  0  0  0  0
  9 39  1  0  0  0  0
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  7 42  1  0  0  0  0
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  6 46  1  0  0  0  0
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  4 59  1  0  0  0  0
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 61 62  1  0  0  0  0
 61 63  1  0  0  0  0
  2 63  1  0  0  0  0
 63 64  1  0  0  0  0
M  END

     RDKit          3D

136144  0  0  0  0  0  0  0  0999 V2000
   -6.7649    0.9716    4.6313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0259   -0.2525    4.0954 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0397    0.1867    3.2380 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.1115   -2.4169    0.8570 C   0  0  2  0  0  0  0  0  0  0  0  0
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    0.0423   -1.5388    0.6079 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2045   -0.0413    0.7119 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7754    0.6822   -0.4104 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0994   -0.0851   -1.6928 C   0  0  2  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309062220022D          

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M  END
> <DATABASE_ID>
NP0235422

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1OC(OC2C(OC3CCC4(C)C(CCC5(C)C4C=CC4=C6C(C)(O)C7(C)CCC6(CCC54C)C(=O)O7)C3(C)C)OCC(O)C2OC2OC(CO)C(O)C(O)C2O)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C47H72O17/c1-21-28(50)30(52)32(54)37(59-21)63-35-34(62-38-33(55)31(53)29(51)24(19-48)60-38)23(49)20-58-39(35)61-27-12-13-42(4)25(41(27,2)3)11-14-44(6)26(42)10-9-22-36-46(8,57)45(7)16-18-47(36,40(56)64-45)17-15-43(22,44)5/h9-10,21,23-35,37-39,48-55,57H,11-20H2,1-8H3

> <INCHI_KEY>
ROLIIKCIEQNTMT-UHFFFAOYSA-N

> <FORMULA>
C47H72O17

> <MOLECULAR_WEIGHT>
909.076

> <EXACT_MASS>
908.476950858

> <JCHEM_ACCEPTOR_COUNT>
16

> <JCHEM_ATOM_COUNT>
136

> <JCHEM_AVERAGE_POLARIZABILITY>
97.08610657029624

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
19-hydroxy-10-[(5-hydroxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl)oxy]-4,5,9,9,13,19,20-heptamethyl-21-oxahexacyclo[18.2.2.0^{1,18}.0^{4,17}.0^{5,14}.0^{8,13}]tetracosa-15,17-dien-22-one

> <JCHEM_LOGP>
0.8868354946666684

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
9

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.368066268563307

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.881535498038756

> <JCHEM_PKA_STRONGEST_BASIC>
-3.533745949652732

> <JCHEM_POLAR_SURFACE_AREA>
263.74999999999994

> <JCHEM_REFRACTIVITY>
223.84570000000014

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
19-hydroxy-10-[(5-hydroxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl)oxy]-4,5,9,9,13,19,20-heptamethyl-21-oxahexacyclo[18.2.2.0^{1,18}.0^{4,17}.0^{5,14}.0^{8,13}]tetracosa-15,17-dien-22-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      24.429   5.379   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      23.733   4.005   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      22.196   3.921   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      21.500   2.547   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      19.962   2.463   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      19.266   1.089   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      17.729   1.004   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      16.887   2.294   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      15.349   2.210   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.653   0.836   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.116   0.752   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.274   2.041   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.578   0.667   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.970   3.415   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.128   4.704   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.590   4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.894   3.246   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.052   4.536   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.736   1.957   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.040   0.583   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.502   0.499   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.661   1.788   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.038   1.711   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.959   2.952   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.676   3.576   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.008   1.878   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.419   0.406   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.933  -1.056   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       2.192   1.371   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       3.189   2.570   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       2.391   3.887   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       5.004   0.443   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.232  -0.486   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       4.986  -1.097   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       6.065   4.193   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       7.608   4.558   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       8.357   3.162   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       8.178   4.692   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      14.507   3.499   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      14.477   5.039   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      15.767   4.386   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      17.033  -0.369   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      17.875  -1.659   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      19.412  -1.575   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0      20.254  -2.864   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0      20.108  -0.201   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0      21.646  -0.117   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0      22.488  -1.406   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0      21.792  -2.780   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0      22.634  -4.069   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      21.938  -5.443   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0      20.400  -5.528   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0      24.171  -3.985   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0      25.013  -5.275   0.000  0.00  0.00           O+0
HETATM   55  C   UNK     0      24.867  -2.611   0.000  0.00  0.00           C+0
HETATM   56  O   UNK     0      26.405  -2.527   0.000  0.00  0.00           O+0
HETATM   57  C   UNK     0      24.025  -1.322   0.000  0.00  0.00           C+0
HETATM   58  O   UNK     0      24.721   0.052   0.000  0.00  0.00           O+0
HETATM   59  C   UNK     0      22.342   1.257   0.000  0.00  0.00           C+0
HETATM   60  O   UNK     0      22.586  -0.263   0.000  0.00  0.00           O+0
HETATM   61  C   UNK     0      23.879   1.342   0.000  0.00  0.00           C+0
HETATM   62  O   UNK     0      25.318   0.793   0.000  0.00  0.00           O+0
HETATM   63  C   UNK     0      24.575   2.715   0.000  0.00  0.00           C+0
HETATM   64  O   UNK     0      26.113   2.800   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   63                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   59                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   46                                                  
CONECT    7    6    8   42                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   39                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14   19                                             
CONECT   13   12                                                            
CONECT   14   12   15   39                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19   37                                             
CONECT   18   17                                                            
CONECT   19   17   12   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   37                                                  
CONECT   23   22   24   32                                                  
CONECT   24   23   25   30   35                                             
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29   32                                             
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   24   31                                                  
CONECT   31   30                                                            
CONECT   32   27   23   33   34                                             
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35   24   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   22   17   38                                             
CONECT   38   37                                                            
CONECT   39   14    9   40   41                                             
CONECT   40   39                                                            
CONECT   41   39                                                            
CONECT   42    7   43                                                       
CONECT   43   42   44                                                       
CONECT   44   43   45   46                                                  
CONECT   45   44                                                            
CONECT   46   44    6   47                                                  
CONECT   47   46   48                                                       
CONECT   48   47   49   57                                                  
CONECT   49   48   50                                                       
CONECT   50   49   51   53                                                  
CONECT   51   50   52                                                       
CONECT   52   51                                                            
CONECT   53   50   54   55                                                  
CONECT   54   53                                                            
CONECT   55   53   56   57                                                  
CONECT   56   55                                                            
CONECT   57   55   48   58                                                  
CONECT   58   57                                                            
CONECT   59    4   60   61                                                  
CONECT   60   59                                                            
CONECT   61   59   62   63                                                  
CONECT   62   61                                                            
CONECT   63   61    2   64                                                  
CONECT   64   63                                                            
MASTER        0    0    0    0    0    0    0    0   64    0  144    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₇H₇₂O₁₇

Average Mass

909.0760 Da

Monoisotopic Mass

908.47695 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC1OC(OC2C(OC3CCC4(C)C(CCC5(C)C4C=CC4=C6C(C)(O)C7(C)CCC6(CCC54C)C(=O)O7)C3(C)C)OCC(O)C2OC2OC(CO)C(O)C(O)C2O)C(O)C(O)C1O

InChI Identifier

InChI=1S/C47H72O17/c1-21-28(50)30(52)32(54)37(59-21)63-35-34(62-38-33(55)31(53)29(51)24(19-48)60-38)23(49)20-58-39(35)61-27-12-13-42(4)25(41(27,2)3)11-14-44(6)26(42)10-9-22-36-46(8,57)45(7)16-18-47(36,40(56)64-45)17-15-43(22,44)5/h9-10,21,23-35,37-39,48-55,57H,11-20H2,1-8H3

InChI Key

ROLIIKCIEQNTMT-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
Ilex kaushue	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthopyrans

Sub Class

Not Available

Direct Parent

Naphthopyrans

Alternative Parents

Substituents

Naphthopyran
Disaccharide
Glycosyl compound
O-glycosyl compound
Naphthalene
Delta valerolactone
Delta_valerolactone
Pyran
Oxane
Cyclic alcohol
Tertiary alcohol
Secondary alcohol
Lactone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Oxacycle
Acetal
Carboxylic acid derivative
Polyol
Primary alcohol
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00037296

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

131849705

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Sakauchi K, Taira W, Otaki JM: Metabolomic Profiles of the Creeping Wood Sorrel Oxalis corniculata in Radioactively Contaminated Fields in Fukushima: Dose-Dependent Changes in Key Metabolites. Life (Basel). 2022 Jan 13;12(1):115. doi: 10.3390/life12010115. [PubMed:35054508 ]
Mai NT, Dung DT, Nga TT, Xuan VT, Doan VV, Tai BH, Nhiem NX, Yen PH, Kiem PV, Seo Y, Namkung W, Park S, Kim SH: Triterpenoid glycosides from the rhizomes of Allium ascalonicum and their anoctamin-1 inhibitory activity. Nat Prod Res. 2021 Nov;35(22):4338-4346. doi: 10.1080/14786419.2020.1713122. Epub 2020 Jan 22. [PubMed:31965859 ]
Che Y, Wang Q, Xiao R, Zhang J, Zhang Y, Gu W, Rao G, Wang C, Kuang H: Kudinoside-D, a triterpenoid saponin derived from Ilex kudingcha suppresses adipogenesis through modulation of the AMPK pathway in 3T3-L1 adipocytes. Fitoterapia. 2018 Mar;125:208-216. doi: 10.1016/j.fitote.2017.11.018. Epub 2017 Nov 21. [PubMed:29170122 ]
Song C, Yu Q, Li X, Jin S, Li S, Zhang Y, Jia S, Chen C, Xiang Y, Jiang H: The Hypolipidemic Effect of Total Saponins from Kuding Tea in High-Fat Diet-Induced Hyperlipidemic Mice and Its Composition Characterized by UPLC-QTOF-MS/MS. J Food Sci. 2016 May;81(5):H1313-9. doi: 10.1111/1750-3841.13299. Epub 2016 Apr 13. [PubMed:27074384 ]
Zhang W, Guo J, Qiu H, Wang C, Chen QQ, Liu B: Quantitation of kudinoside A, kudinoside D and kudinoside F in human plasma using a high performance liquid chromatography-electrospray ionization tandem mass spectrometric method. J Chromatogr B Analyt Technol Biomed Life Sci. 2014 Dec 1;972:1-5. doi: 10.1016/j.jchromb.2014.09.023. Epub 2014 Sep 28. [PubMed:25305433 ]
Li L, Peng Y, Ma G, He C, Feng Y, Lei Q, Xiao P: Quantitative analysis of five kudinosides in the large-leaved Kudingcha and related species from the genus Ilex by UPLC-ELSD. Phytochem Anal. 2012 Nov-Dec;23(6):677-83. doi: 10.1002/pca.2372. Epub 2012 May 17. [PubMed:22593006 ]
LOTUS database [Link]

Showing NP-Card for 19-hydroxy-10-[(5-hydroxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl)oxy]-4,5,9,9,13,19,20-heptamethyl-21-oxahexacyclo[18.2.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracosa-15,17-dien-22-one (NP0235422)

MOL for NP0235422 (19-hydroxy-10-[(5-hydroxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl)oxy]-4,5,9,9,13,19,20-heptamethyl-21-oxahexacyclo[18.2.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracosa-15,17-dien-22-one)

3D MOL for NP0235422 (19-hydroxy-10-[(5-hydroxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl)oxy]-4,5,9,9,13,19,20-heptamethyl-21-oxahexacyclo[18.2.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracosa-15,17-dien-22-one)

3D SDF for NP0235422 (19-hydroxy-10-[(5-hydroxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl)oxy]-4,5,9,9,13,19,20-heptamethyl-21-oxahexacyclo[18.2.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracosa-15,17-dien-22-one)

3D-SDF for NP0235422 (19-hydroxy-10-[(5-hydroxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl)oxy]-4,5,9,9,13,19,20-heptamethyl-21-oxahexacyclo[18.2.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracosa-15,17-dien-22-one)

PDB for NP0235422 (19-hydroxy-10-[(5-hydroxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl)oxy]-4,5,9,9,13,19,20-heptamethyl-21-oxahexacyclo[18.2.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracosa-15,17-dien-22-one)

3D PDB for NP0235422 (19-hydroxy-10-[(5-hydroxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl)oxy]-4,5,9,9,13,19,20-heptamethyl-21-oxahexacyclo[18.2.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracosa-15,17-dien-22-one)

SMILES for NP0235422 (19-hydroxy-10-[(5-hydroxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl)oxy]-4,5,9,9,13,19,20-heptamethyl-21-oxahexacyclo[18.2.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracosa-15,17-dien-22-one)

INCHI for NP0235422 (19-hydroxy-10-[(5-hydroxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl)oxy]-4,5,9,9,13,19,20-heptamethyl-21-oxahexacyclo[18.2.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracosa-15,17-dien-22-one)

Structure for NP0235422 (19-hydroxy-10-[(5-hydroxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl)oxy]-4,5,9,9,13,19,20-heptamethyl-21-oxahexacyclo[18.2.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracosa-15,17-dien-22-one)

3D Structure for NP0235422 (19-hydroxy-10-[(5-hydroxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl)oxy]-4,5,9,9,13,19,20-heptamethyl-21-oxahexacyclo[18.2.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracosa-15,17-dien-22-one)