NP-MRD: Showing NP-Card for hierapolitanin C (NP0030235)

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Record Information

Version

2.0

Created at

2021-06-19 21:38:33 UTC

Updated at

2021-06-29 23:58:05 UTC

NP-MRD ID

NP0030235

Secondary Accession Numbers

None

Natural Product Identification

Common Name

hierapolitanin C

Provided By

JEOL Database JEOL Logo

Description

Hierapolitanin C belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone. hierapolitanin C is found in Centaurea hierapolitana and Youngia japonica (L.) DC.. hierapolitanin C was first documented in 2007 (Karamenderes, C., et al.). Based on a literature review very few articles have been published on Hierapolitanin C.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192123383D          

 61 63  0  0  0  0            999 V2000
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   -1.9366    1.3208    3.7782 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.1605    0.1704    3.1486 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5608   -0.8324    4.1529 C   0  0  1  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652306192123383D          

 61 63  0  0  0  0            999 V2000
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    4.3582    1.1369   -2.9661 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6991   -0.0272    0.4238 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1218    1.2361    0.2358 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6686   -0.4377    1.4783 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0681    0.7095    2.2023 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9844    1.3990    5.6850 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.3160    3.1855    2.7977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8723   -0.4103    2.5437 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1199   -0.3326    4.8503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3626   -1.2698    4.7613 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6270   -2.6310    4.1991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5355   -2.5622    2.8851 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1101    0.0288    3.9098 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8659   -1.5596    4.0071 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2648   -0.4651    2.6845 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3710   -3.3604    2.3703 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0270   -3.2305    1.2474 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7584   -1.8877    0.9787 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0930   -3.1560   -0.0115 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3408   -1.6884   -0.8875 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8721    0.1040   -2.5671 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8081   -0.9453   -4.4405 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5820   -2.9103   -5.9640 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8648   -3.7552   -5.0628 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5627   -3.4091   -3.1753 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4985   -1.8886   -5.6290 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8666   -0.3665   -7.2529 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6336    0.9715   -4.9485 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9088    1.2370   -5.2597 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6752   -0.8043   -3.4975 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5906    0.9354   -2.0371 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8644    1.4880   -0.5126 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7552    2.0684    0.8269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1170   -0.9717    0.9192 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6370    1.3309    2.7685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5277    1.3667    1.4524 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 12  1  0  0  0  0
  9 28  1  0  0  0  0
 20 17  1  0  0  0  0
 17 16  1  0  0  0  0
 16 15  1  0  0  0  0
  9  8  1  0  0  0  0
 28 29  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
 20 21  1  0  0  0  0
 26 27  2  3  0  0  0
  6 29  1  0  0  0  0
 22 23  1  0  0  0  0
 24 25  1  0  0  0  0
  9 10  1  1  0  0  0
 28 59  1  6  0  0  0
 18 19  1  0  0  0  0
 12 13  1  0  0  0  0
 15 24  1  0  0  0  0
  6  2  1  0  0  0  0
 24 22  1  0  0  0  0
  2  3  1  0  0  0  0
 13 26  1  0  0  0  0
  2  1  2  3  0  0  0
 26 28  1  0  0  0  0
  3  4  2  0  0  0  0
 22 20  1  0  0  0  0
  3  5  1  0  0  0  0
 13 14  1  0  0  0  0
  9 11  1  0  0  0  0
  6 33  1  6  0  0  0
 15 14  1  0  0  0  0
 17 18  1  0  0  0  0
 15 46  1  1  0  0  0
 20 51  1  6  0  0  0
 21 52  1  0  0  0  0
 22 53  1  1  0  0  0
 23 54  1  0  0  0  0
 24 55  1  6  0  0  0
 25 56  1  0  0  0  0
 18 48  1  0  0  0  0
 18 49  1  0  0  0  0
 17 47  1  1  0  0  0
 19 50  1  0  0  0  0
 12 43  1  0  0  0  0
 12 44  1  0  0  0  0
 11 41  1  0  0  0  0
 11 42  1  0  0  0  0
  7 34  1  0  0  0  0
  7 35  1  0  0  0  0
  8 36  1  0  0  0  0
  8 37  1  0  0  0  0
 27 57  1  0  0  0  0
 27 58  1  0  0  0  0
 29 60  1  0  0  0  0
 29 61  1  0  0  0  0
 10 38  1  0  0  0  0
 10 39  1  0  0  0  0
 10 40  1  0  0  0  0
 13 45  1  6  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
  5 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0030235

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C(=C([H])[H])[C@]1([H])C([H])([H])C([H])([H])[C@@]2(C([H])([H])[H])C([H])([H])C([H])([H])[C@]([H])(O[C@]3([H])O[C@]([H])(C([H])([H])O[H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@@]3([H])O[H])C(=C([H])[H])[C@]2([H])C1([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C21H32O8/c1-10(19(26)27)12-4-6-21(3)7-5-14(11(2)13(21)8-12)28-20-18(25)17(24)16(23)15(9-22)29-20/h12-18,20,22-25H,1-2,4-9H2,3H3,(H,26,27)/t12-,13+,14+,15-,16-,17+,18-,20-,21+/m1/s1

> <INCHI_KEY>
XGBLAAVKNYADBQ-XBYPWPIDSA-N

> <FORMULA>
C21H32O8

> <MOLECULAR_WEIGHT>
412.479

> <EXACT_MASS>
412.20971799

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
43.84384487346737

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(2R,4aS,7S,8aR)-4a-methyl-8-methylidene-7-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-decahydronaphthalen-2-yl]prop-2-enoic acid

> <ALOGPS_LOGP>
0.44

> <JCHEM_LOGP>
0.7672889483333329

> <ALOGPS_LOGS>
-2.19

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.210096447910574

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.585459833989866

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981083684387478

> <JCHEM_POLAR_SURFACE_AREA>
136.68

> <JCHEM_REFRACTIVITY>
102.02590000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.66e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(2R,4aS,7S,8aR)-4a-methyl-8-methylidene-7-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-octahydronaphthalen-2-yl]prop-2-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 61 63  0  0  0  0  0  0  0  0999 V2000
   -1.7436    1.7971    5.0221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9366    1.3208    3.7782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9987    1.9086    2.9131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2709    1.5436    1.7827 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6705    2.9218    3.4853 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1605    0.1704    3.1486 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5608   -0.8324    4.1529 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1933   -1.9615    3.4456 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2965   -1.4535    2.4832 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4439   -0.8240    3.3124 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8587   -2.6672    1.6916 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8144   -2.2648    0.5654 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1973   -1.2262   -0.3786 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2075   -0.8679   -1.3249 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6791   -0.6375   -2.6351 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1915   -1.8554   -3.2017 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6431   -1.6541   -4.5212 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0772   -2.9976   -4.9928 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1192   -3.4714   -4.0425 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7167   -1.1321   -5.4846 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1632   -0.8468   -6.7697 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3492    0.1404   -4.9163 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4413    0.5375   -5.7609 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8384   -0.0944   -3.4904 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3582    1.1369   -2.9661 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6991   -0.0272    0.4238 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1218    1.2361    0.2358 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6686   -0.4377    1.4783 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0681    0.7095    2.2023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9844    1.3990    5.6850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3351    2.6145    5.4256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3160    3.1855    2.7977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8723   -0.4103    2.5437 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1199   -0.3326    4.8503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3626   -1.2698    4.7613 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6270   -2.6310    4.1991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5355   -2.5622    2.8851 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1101    0.0288    3.9098 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8659   -1.5596    4.0071 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2648   -0.4651    2.6845 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3710   -3.3604    2.3703 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0270   -3.2305    1.2474 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7584   -1.8877    0.9787 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0930   -3.1560   -0.0115 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3408   -1.6884   -0.8875 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8721    0.1040   -2.5671 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8081   -0.9453   -4.4405 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5820   -2.9103   -5.9640 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8648   -3.7552   -5.0628 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5627   -3.4091   -3.1753 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4985   -1.8886   -5.6290 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8666   -0.3665   -7.2529 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6336    0.9715   -4.9485 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9088    1.2370   -5.2597 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6752   -0.8043   -3.4975 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5906    0.9354   -2.0371 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8644    1.4880   -0.5126 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7552    2.0684    0.8269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1170   -0.9717    0.9192 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6370    1.3309    2.7685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5277    1.3667    1.4524 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 12  1  0
  9 28  1  0
 20 17  1  0
 17 16  1  0
 16 15  1  0
  9  8  1  0
 28 29  1  0
  6  7  1  0
  7  8  1  0
 20 21  1  0
 26 27  2  3
  6 29  1  0
 22 23  1  0
 24 25  1  0
  9 10  1  1
 28 59  1  6
 18 19  1  0
 12 13  1  0
 15 24  1  0
  6  2  1  0
 24 22  1  0
  2  3  1  0
 13 26  1  0
  2  1  2  3
 26 28  1  0
  3  4  2  0
 22 20  1  0
  3  5  1  0
 13 14  1  0
  9 11  1  0
  6 33  1  6
 15 14  1  0
 17 18  1  0
 15 46  1  1
 20 51  1  6
 21 52  1  0
 22 53  1  1
 23 54  1  0
 24 55  1  6
 25 56  1  0
 18 48  1  0
 18 49  1  0
 17 47  1  1
 19 50  1  0
 12 43  1  0
 12 44  1  0
 11 41  1  0
 11 42  1  0
  7 34  1  0
  7 35  1  0
  8 36  1  0
  8 37  1  0
 27 57  1  0
 27 58  1  0
 29 60  1  0
 29 61  1  0
 10 38  1  0
 10 39  1  0
 10 40  1  0
 13 45  1  6
  1 30  1  0
  1 31  1  0
  5 32  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      -1.744   1.797   5.022  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.937   1.321   3.778  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.999   1.909   2.913  0.00  0.00           C+0
HETATM    4  O   UNK     0      -3.271   1.544   1.783  0.00  0.00           O+0
HETATM    5  O   UNK     0      -3.671   2.922   3.485  0.00  0.00           O+0
HETATM    6  C   UNK     0      -1.161   0.170   3.149  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.561  -0.832   4.153  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.193  -1.962   3.446  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.297  -1.454   2.483  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.444  -0.824   3.312  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.859  -2.667   1.692  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.814  -2.265   0.565  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.197  -1.226  -0.379  0.00  0.00           C+0
HETATM   14  O   UNK     0       3.208  -0.868  -1.325  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.679  -0.638  -2.635  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.192  -1.855  -3.202  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.643  -1.654  -4.521  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.077  -2.998  -4.993  0.00  0.00           C+0
HETATM   19  O   UNK     0       0.119  -3.471  -4.043  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.717  -1.132  -5.485  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.163  -0.847  -6.770  0.00  0.00           O+0
HETATM   22  C   UNK     0       3.349   0.140  -4.916  0.00  0.00           C+0
HETATM   23  O   UNK     0       4.441   0.538  -5.761  0.00  0.00           O+0
HETATM   24  C   UNK     0       3.838  -0.094  -3.490  0.00  0.00           C+0
HETATM   25  O   UNK     0       4.358   1.137  -2.966  0.00  0.00           O+0
HETATM   26  C   UNK     0       1.699  -0.027   0.424  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.122   1.236   0.236  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.669  -0.438   1.478  0.00  0.00           C+0
HETATM   29  C   UNK     0      -0.068   0.710   2.202  0.00  0.00           C+0
HETATM   30  H   UNK     0      -0.984   1.399   5.685  0.00  0.00           H+0
HETATM   31  H   UNK     0      -2.335   2.615   5.426  0.00  0.00           H+0
HETATM   32  H   UNK     0      -4.316   3.186   2.798  0.00  0.00           H+0
HETATM   33  H   UNK     0      -1.872  -0.410   2.544  0.00  0.00           H+0
HETATM   34  H   UNK     0       0.120  -0.333   4.850  0.00  0.00           H+0
HETATM   35  H   UNK     0      -1.363  -1.270   4.761  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.627  -2.631   4.199  0.00  0.00           H+0
HETATM   37  H   UNK     0      -0.536  -2.562   2.885  0.00  0.00           H+0
HETATM   38  H   UNK     0       2.110   0.029   3.910  0.00  0.00           H+0
HETATM   39  H   UNK     0       2.866  -1.560   4.007  0.00  0.00           H+0
HETATM   40  H   UNK     0       3.265  -0.465   2.684  0.00  0.00           H+0
HETATM   41  H   UNK     0       2.371  -3.360   2.370  0.00  0.00           H+0
HETATM   42  H   UNK     0       1.027  -3.231   1.247  0.00  0.00           H+0
HETATM   43  H   UNK     0       3.758  -1.888   0.979  0.00  0.00           H+0
HETATM   44  H   UNK     0       3.093  -3.156  -0.012  0.00  0.00           H+0
HETATM   45  H   UNK     0       1.341  -1.688  -0.888  0.00  0.00           H+0
HETATM   46  H   UNK     0       1.872   0.104  -2.567  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.808  -0.945  -4.441  0.00  0.00           H+0
HETATM   48  H   UNK     0       0.582  -2.910  -5.964  0.00  0.00           H+0
HETATM   49  H   UNK     0       1.865  -3.755  -5.063  0.00  0.00           H+0
HETATM   50  H   UNK     0       0.563  -3.409  -3.175  0.00  0.00           H+0
HETATM   51  H   UNK     0       3.498  -1.889  -5.629  0.00  0.00           H+0
HETATM   52  H   UNK     0       2.867  -0.367  -7.253  0.00  0.00           H+0
HETATM   53  H   UNK     0       2.634   0.972  -4.949  0.00  0.00           H+0
HETATM   54  H   UNK     0       4.909   1.237  -5.260  0.00  0.00           H+0
HETATM   55  H   UNK     0       4.675  -0.804  -3.498  0.00  0.00           H+0
HETATM   56  H   UNK     0       4.591   0.935  -2.037  0.00  0.00           H+0
HETATM   57  H   UNK     0       2.864   1.488  -0.513  0.00  0.00           H+0
HETATM   58  H   UNK     0       1.755   2.068   0.827  0.00  0.00           H+0
HETATM   59  H   UNK     0      -0.117  -0.972   0.919  0.00  0.00           H+0
HETATM   60  H   UNK     0       0.637   1.331   2.769  0.00  0.00           H+0
HETATM   61  H   UNK     0      -0.528   1.367   1.452  0.00  0.00           H+0
CONECT    1    2   30   31                                                  
CONECT    2    6    3    1                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3   32                                                       
CONECT    6    7   29    2   33                                             
CONECT    7    6    8   34   35                                             
CONECT    8    9    7   36   37                                             
CONECT    9   28    8   10   11                                             
CONECT   10    9   38   39   40                                             
CONECT   11   12    9   41   42                                             
CONECT   12   11   13   43   44                                             
CONECT   13   12   26   14   45                                             
CONECT   14   13   15                                                       
CONECT   15   16   24   14   46                                             
CONECT   16   17   15                                                       
CONECT   17   20   16   18   47                                             
CONECT   18   19   17   48   49                                             
CONECT   19   18   50                                                       
CONECT   20   17   21   22   51                                             
CONECT   21   20   52                                                       
CONECT   22   23   24   20   53                                             
CONECT   23   22   54                                                       
CONECT   24   25   15   22   55                                             
CONECT   25   24   56                                                       
CONECT   26   27   13   28                                                  
CONECT   27   26   57   58                                                  
CONECT   28    9   29   59   26                                             
CONECT   29   28    6   60   61                                             
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    5                                                            
CONECT   33    6                                                            
CONECT   34    7                                                            
CONECT   35    7                                                            
CONECT   36    8                                                            
CONECT   37    8                                                            
CONECT   38   10                                                            
CONECT   39   10                                                            
CONECT   40   10                                                            
CONECT   41   11                                                            
CONECT   42   11                                                            
CONECT   43   12                                                            
CONECT   44   12                                                            
CONECT   45   13                                                            
CONECT   46   15                                                            
CONECT   47   17                                                            
CONECT   48   18                                                            
CONECT   49   18                                                            
CONECT   50   19                                                            
CONECT   51   20                                                            
CONECT   52   21                                                            
CONECT   53   22                                                            
CONECT   54   23                                                            
CONECT   55   24                                                            
CONECT   56   25                                                            
CONECT   57   27                                                            
CONECT   58   27                                                            
CONECT   59   28                                                            
CONECT   60   29                                                            
CONECT   61   29                                                            
MASTER        0    0    0    0    0    0    0    0   61    0  126    0
END

RDKit          3D

61 63  0  0  0  0  0  0  0  0999 V2000
   -1.7436    1.7971    5.0221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9366    1.3208    3.7782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9987    1.9086    2.9131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2709    1.5436    1.7827 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6705    2.9218    3.4853 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1605    0.1704    3.1486 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5608   -0.8324    4.1529 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1933   -1.9615    3.4456 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2965   -1.4535    2.4832 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4439   -0.8240    3.3124 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8587   -2.6672    1.6916 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8144   -2.2648    0.5654 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1973   -1.2262   -0.3786 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2075   -0.8679   -1.3249 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6791   -0.6375   -2.6351 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1915   -1.8554   -3.2017 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6431   -1.6541   -4.5212 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0772   -2.9976   -4.9928 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1192   -3.4714   -4.0425 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7167   -1.1321   -5.4846 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1632   -0.8468   -6.7697 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3492    0.1404   -4.9163 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4413    0.5375   -5.7609 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8384   -0.0944   -3.4904 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3582    1.1369   -2.9661 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6991   -0.0272    0.4238 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1218    1.2361    0.2358 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6686   -0.4377    1.4783 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0681    0.7095    2.2023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9844    1.3990    5.6850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3351    2.6145    5.4256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3160    3.1855    2.7977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8723   -0.4103    2.5437 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1199   -0.3326    4.8503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3626   -1.2698    4.7613 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6270   -2.6310    4.1991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5355   -2.5622    2.8851 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1101    0.0288    3.9098 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8659   -1.5596    4.0071 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2648   -0.4651    2.6845 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3710   -3.3604    2.3703 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0270   -3.2305    1.2474 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7584   -1.8877    0.9787 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0930   -3.1560   -0.0115 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3408   -1.6884   -0.8875 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8721    0.1040   -2.5671 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8081   -0.9453   -4.4405 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5820   -2.9103   -5.9640 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8648   -3.7552   -5.0628 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5627   -3.4091   -3.1753 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4985   -1.8886   -5.6290 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8666   -0.3665   -7.2529 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6336    0.9715   -4.9485 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9088    1.2370   -5.2597 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6752   -0.8043   -3.4975 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5906    0.9354   -2.0371 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8644    1.4880   -0.5126 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7552    2.0684    0.8269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1170   -0.9717    0.9192 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6370    1.3309    2.7685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5277    1.3667    1.4524 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 12  1  0
  9 28  1  0
 20 17  1  0
 17 16  1  0
 16 15  1  0
  9  8  1  0
 28 29  1  0
  6  7  1  0
  7  8  1  0
 20 21  1  0
 26 27  2  3
  6 29  1  0
 22 23  1  0
 24 25  1  0
  9 10  1  1
 28 59  1  6
 18 19  1  0
 12 13  1  0
 15 24  1  0
  6  2  1  0
 24 22  1  0
  2  3  1  0
 13 26  1  0
  2  1  2  3
 26 28  1  0
  3  4  2  0
 22 20  1  0
  3  5  1  0
 13 14  1  0
  9 11  1  0
  6 33  1  6
 15 14  1  0
 17 18  1  0
 15 46  1  1
 20 51  1  6
 21 52  1  0
 22 53  1  1
 23 54  1  0
 24 55  1  6
 25 56  1  0
 18 48  1  0
 18 49  1  0
 17 47  1  1
 19 50  1  0
 12 43  1  0
 12 44  1  0
 11 41  1  0
 11 42  1  0
  7 34  1  0
  7 35  1  0
  8 36  1  0
  8 37  1  0
 27 57  1  0
 27 58  1  0
 29 60  1  0
 29 61  1  0
 10 38  1  0
 10 39  1  0
 10 40  1  0
 13 45  1  6
  1 30  1  0
  1 31  1  0
  5 32  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₃₂O₈

Average Mass

412.4790 Da

Monoisotopic Mass

412.20972 Da

IUPAC Name

2-[(2R,4aS,7S,8aR)-4a-methyl-8-methylidene-7-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-decahydronaphthalen-2-yl]prop-2-enoic acid

Traditional Name

2-[(2R,4aS,7S,8aR)-4a-methyl-8-methylidene-7-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-octahydronaphthalen-2-yl]prop-2-enoic acid

CAS Registry Number

Not Available

SMILES

[H]OC(=O)C(=C([H])[H])[C@]1([H])C([H])([H])C([H])([H])[C@@]2(C([H])([H])[H])C([H])([H])C([H])([H])[C@]([H])(O[C@]3([H])O[C@]([H])(C([H])([H])O[H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@@]3([H])O[H])C(=C([H])[H])[C@]2([H])C1([H])[H]

InChI Identifier

InChI=1S/C21H32O8/c1-10(19(26)27)12-4-6-21(3)7-5-14(11(2)13(21)8-12)28-20-18(25)17(24)16(23)15(9-22)29-20/h12-18,20,22-25H,1-2,4-9H2,3H3,(H,26,27)/t12-,13+,14+,15-,16-,17+,18-,20-,21+/m1/s1

InChI Key

XGBLAAVKNYADBQ-XBYPWPIDSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, 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
Centaurea hierapolitana	JEOL database	Karamenderes, C., et al, Phytochemistry 68, 609 (2007)
Youngia japonica (L.) DC.	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Terpene glycosides

Alternative Parents

Substituents

Terpene glycoside
Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoid
Fatty acyl glycoside
Fatty acyl glycoside of mono- or disaccharide
Sesquiterpenoid
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Fatty acyl
Monosaccharide
Oxane
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Carboxylic acid
Acetal
Monocarboxylic acid or derivatives
Polyol
Alcohol
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Primary alcohol
Organic oxide
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
logP	0.44	ALOGPS
logP	0.77	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	4.59	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	136.68 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	102.03 m³·mol⁻¹	ChemAxon
Polarizability	43.84 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

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

102595391

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Karamenderes, C., et al. (2007). Karamenderes, C., et al, Phytochemistry 68, 609 (2007). Phytochem..

Showing NP-Card for hierapolitanin C (NP0030235)

MOL for NP0030235 (hierapolitanin C)

3D MOL for NP0030235 (hierapolitanin C)

3D SDF for NP0030235 (hierapolitanin C)

3D-SDF for NP0030235 (hierapolitanin C)

PDB for NP0030235 (hierapolitanin C)

3D PDB for NP0030235 (hierapolitanin C)

SMILES for NP0030235 (hierapolitanin C)

INCHI for NP0030235 (hierapolitanin C)

Structure for NP0030235 (hierapolitanin C)

3D Structure for NP0030235 (hierapolitanin C)