NP-MRD: Showing NP-Card for 3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 5,9-dimethyl-14-methylidene-13-{[3,4,5-trihydroxy-6-({[3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylate (NP0230580)

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Record Information

Version

2.0

Created at

2022-09-06 11:04:26 UTC

Updated at

2022-09-06 11:04:27 UTC

NP-MRD ID

NP0230580

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 5,9-dimethyl-14-methylidene-13-{[3,4,5-trihydroxy-6-({[3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylate

Description

3,4,5-Trihydroxy-6-(hydroxymethyl)oxan-2-yl 5,9-dimethyl-14-methylidene-13-{[3,4,5-trihydroxy-6-({[3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]Hexadecane-5-carboxylate belongs to the class of organic compounds known as steviol glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically linked to a steviol (a diterpenoid based on a 13-Hydroxykaur-16-en-18-oic acid) moiety. 3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 5,9-dimethyl-14-methylidene-13-{[3,4,5-trihydroxy-6-({[3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylate is found in Rubus chingii. 3,4,5-Trihydroxy-6-(hydroxymethyl)oxan-2-yl 5,9-dimethyl-14-methylidene-13-{[3,4,5-trihydroxy-6-({[3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]Hexadecane-5-carboxylate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241507472D          

 56 62  0  0  0  0            999 V2000
    3.4675   -1.1600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7079   -0.3708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2660   -0.9783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0712   -0.7987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3183   -0.0116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7601    0.5959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4554    1.0401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9549    0.4163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4013    1.0406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5923    0.8721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2888    0.0848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4780    0.4659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8565   -0.1421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0431   -0.0038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2392   -0.9158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8005   -1.5738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6457   -1.4133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8891   -0.5680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8145   -0.4488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5504   -1.3699    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5993   -2.1934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3369   -2.5629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3858   -3.3865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1234   -3.7559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1723   -4.5795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9099   -4.9489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5987   -4.4949    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9588   -5.7725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6964   -6.1420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7453   -6.9655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4829   -7.3350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5318   -8.1585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8430   -8.6126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8919   -9.4362    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1054   -8.2432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0565   -7.4196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6970   -3.8405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7459   -4.6641    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0406   -3.4711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7294   -3.9252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0895   -2.6475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8271   -2.2781    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4434    1.3577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9448    2.0129    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6254    1.4643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3087    2.2261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4906    2.3328    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1739    3.0945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3558    3.2012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0391    3.9630    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6753    3.7497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3586    4.5115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4933    3.6431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9947    4.2983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8100    2.8813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6281    2.7747    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
  6  8  1  0  0  0  0
  2  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
 13 14  2  0  0  0  0
 13 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
  2 18  1  0  0  0  0
 11 18  1  0  0  0  0
 15 19  1  0  0  0  0
 11 19  1  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 28 26  1  4  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 35 36  2  0  0  0  0
 30 36  1  0  0  0  0
 23 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
 39 40  1  0  0  0  0
 39 41  1  0  0  0  0
 21 41  1  0  0  0  0
 41 42  1  0  0  0  0
  6 43  1  0  0  0  0
 43 44  2  0  0  0  0
 43 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
 48 51  1  0  0  0  0
 51 52  1  0  0  0  0
 51 53  1  0  0  0  0
 53 54  1  0  0  0  0
 53 55  1  0  0  0  0
 46 55  1  0  0  0  0
 55 56  1  0  0  0  0
M  END

     RDKit          3D

112118  0  0  0  0  0  0  0  0999 V2000
    1.3532   -2.5488   -1.6283 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8244   -2.0645   -0.5384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5505   -2.4743   -0.0909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0568   -1.2530    0.5658 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2773   -1.4410    1.3990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5754   -1.1511    0.7593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6791    0.0499   -0.1104 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4545    0.1590   -0.9939 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6172   -0.8806   -2.1095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4904    1.4895   -1.7093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4308    2.6730   -0.8355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2495    2.4987    0.3670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0788    1.3014    0.5574 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2918    1.1626    2.0768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4799    1.6892    0.1236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7550    2.8165   -0.3468 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4800    0.7671    0.2542 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8370    0.9518   -0.0917 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.6584    0.9102    1.0376 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8878    1.4477    0.6632 C   0  0  2  0  0  0  0  0  0  0  0  0
  -10.7858    1.6105    1.8905 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1613    2.4703    2.8123 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6203    0.5219   -0.2885 C   0  0  2  0  0  0  0  0  0  0  0  0
  -11.6902   -0.1116    0.3421 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6621   -0.5423   -0.7307 C   0  0  2  0  0  0  0  0  0  0  0  0
   -9.4444   -1.3998    0.3571 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3144    0.0022   -1.1594 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.3955   -1.0446   -1.2492 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1774   -0.0144   -0.2522 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0428    0.2662   -1.0940 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2671    0.2738   -0.1675 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2812   -1.1035    0.4782 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3821   -1.3785    1.1867 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6082   -1.5072    0.6297 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4145   -0.5076    1.1860 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7848   -0.8285    1.1647 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.5661    0.4393    1.3124 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9088    0.4324    1.2944 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9806    0.0762    1.9767 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6832   -0.4764    3.1413 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3907    0.1750    1.6957 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1597    0.5907    0.7844 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0354    1.2047   -0.4964 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8591    1.5187   -1.1251 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7958    2.1255   -2.3864 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9383    2.4403   -3.0657 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8630    3.0403   -4.3129 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1272    2.1400   -2.4662 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1900    1.5482   -1.2359 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1383   -1.8578    2.1593 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.2245   -2.5977    1.6561 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9907   -2.8708    2.2020 C   0  0  1  0  0  0  0  0  0  0  0  0
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    4.9831   -3.2322   -0.1947 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.3175   -2.3442   -2.0614 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.1473   -2.9131   -0.8692 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.2814   -2.5442    1.6724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3539   -1.1597    1.5608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8445   -2.0686    0.1475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5159   -0.1881   -0.8451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6565   -1.1662   -2.5543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2152   -1.7483   -1.7614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2231   -0.4442   -2.9536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5102    1.5093   -2.2065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7957    1.5131   -2.5748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3920    3.0430   -0.6356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8692    3.5318   -1.4473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5585    2.5980    1.2683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8976    3.4298    0.4961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3704    1.0363    2.6332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1386    0.5306    2.3330 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.1554   -1.1965   -2.1940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1589    0.8307    0.5078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0260    1.2969   -1.4865 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1742   -0.4055   -1.9323 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1533004241507472D          

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 46 55  1  0  0  0  0
 55 56  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0230580

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC12CCCC(C)(C1CCC13CC(=C)C(C1)(CCC23)OC1OC(COC(=O)C=CC2=CC=C(O)C=C2)C(O)C(O)C1O)C(=O)OC1OC(CO)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C41H56O15/c1-21-17-40-15-11-26-38(2,13-4-14-39(26,3)37(51)55-35-33(49)31(47)29(45)24(18-42)53-35)27(40)12-16-41(21,20-40)56-36-34(50)32(48)30(46)25(54-36)19-52-28(44)10-7-22-5-8-23(43)9-6-22/h5-10,24-27,29-36,42-43,45-50H,1,4,11-20H2,2-3H3

> <INCHI_KEY>
NGJFUJVMLWRHKV-UHFFFAOYSA-N

> <FORMULA>
C41H56O15

> <MOLECULAR_WEIGHT>
788.884

> <EXACT_MASS>
788.361921103

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
112

> <JCHEM_AVERAGE_POLARIZABILITY>
82.16619702326011

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 5,9-dimethyl-14-methylidene-13-{[3,4,5-trihydroxy-6-({[3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylate

> <ALOGPS_LOGP>
0.75

> <JCHEM_LOGP>
2.3399526566666657

> <ALOGPS_LOGS>
-4.00

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.90353569615176

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.397285424644533

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981093680169468

> <JCHEM_POLAR_SURFACE_AREA>
242.12999999999997

> <JCHEM_REFRACTIVITY>
195.28480000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.92e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 5,9-dimethyl-14-methylidene-13-{[3,4,5-trihydroxy-6-({[3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       6.473  -2.165   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.921  -0.692   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.963  -1.826   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.466  -1.491   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.927  -0.022   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.886   1.112   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.183   1.942   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.383   0.777   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.349   1.942   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.839   1.628   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.272   0.158   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.759   0.870   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.599  -0.265   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.081  -0.007   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.313  -1.709   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.361  -2.938   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.939  -2.638   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.393  -1.060   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.387  -0.838   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.027  -2.557   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.119  -4.094   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.496  -4.784   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       2.587  -6.321   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.964  -7.011   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       4.055  -8.548   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       5.432  -9.238   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       6.718  -8.390   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       5.523 -10.775   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.900 -11.465   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.991 -13.002   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.368 -13.692   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       8.459 -15.229   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       7.174 -16.077   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       7.265 -17.614   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       5.797 -15.387   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       5.705 -13.850   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       1.301  -7.169   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       1.392  -8.706   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      -0.076  -6.479   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      -1.362  -7.327   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      -0.167  -4.942   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      -1.544  -4.252   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0       8.294   2.534   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0       9.230   3.757   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0       6.767   2.733   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0       6.176   4.155   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0       4.649   4.354   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0       4.058   5.776   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       2.531   5.976   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0       1.940   7.398   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0       4.994   6.999   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0       4.403   8.421   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0       6.521   6.800   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0       7.457   8.023   0.000  0.00  0.00           O+0
HETATM   55  C   UNK     0       7.112   5.378   0.000  0.00  0.00           C+0
HETATM   56  O   UNK     0       8.639   5.179   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    8   18                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8   43                                             
CONECT    7    6                                                            
CONECT    8    6    2    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   18   19                                             
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   19   20                                             
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17    2   11                                                  
CONECT   19   15   11                                                       
CONECT   20   15   21                                                       
CONECT   21   20   22   41                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   37                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   36                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36                                                       
CONECT   36   35   30                                                       
CONECT   37   23   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   21   42                                                  
CONECT   42   41                                                            
CONECT   43    6   44   45                                                  
CONECT   44   43                                                            
CONECT   45   43   46                                                       
CONECT   46   45   47   55                                                  
CONECT   47   46   48                                                       
CONECT   48   47   49   51                                                  
CONECT   49   48   50                                                       
CONECT   50   49                                                            
CONECT   51   48   52   53                                                  
CONECT   52   51                                                            
CONECT   53   51   54   55                                                  
CONECT   54   53                                                            
CONECT   55   53   46   56                                                  
CONECT   56   55                                                            
MASTER        0    0    0    0    0    0    0    0   56    0  124    0
END

View in JSmol

Synonyms

Value	Source
3,4,5-Trihydroxy-6-(hydroxymethyl)oxan-2-yl 5,9-dimethyl-14-methylidene-13-{[3,4,5-trihydroxy-6-({[3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}tetracyclo[11.2.1.0,.0,]hexadecane-5-carboxylic acid	Generator
3,4,5-Trihydroxy-6-(hydroxymethyl)oxan-2-yl 5,9-dimethyl-14-methylidene-13-{[3,4,5-trihydroxy-6-({[3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid	Generator

Chemical Formula

C₄₁H₅₆O₁₅

Average Mass

788.8840 Da

Monoisotopic Mass

788.36192 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

CC12CCCC(C)(C1CCC13CC(=C)C(C1)(CCC23)OC1OC(COC(=O)C=CC2=CC=C(O)C=C2)C(O)C(O)C1O)C(=O)OC1OC(CO)C(O)C(O)C1O

InChI Identifier

InChI=1S/C41H56O15/c1-21-17-40-15-11-26-38(2,13-4-14-39(26,3)37(51)55-35-33(49)31(47)29(45)24(18-42)53-35)27(40)12-16-41(21,20-40)56-36-34(50)32(48)30(46)25(54-36)19-52-28(44)10-7-22-5-8-23(43)9-6-22/h5-10,24-27,29-36,42-43,45-50H,1,4,11-20H2,2-3H3

InChI Key

NGJFUJVMLWRHKV-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
Rubus chingii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as steviol glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically linked to a steviol (a diterpenoid based on a 13-Hydroxykaur-16-en-18-oic acid) moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Steviol glycosides

Alternative Parents

Substituents

Steviol glycoside
Kaurane diterpenoid
Diterpenoid
Fatty acyl glycoside of mono- or disaccharide
Fatty acyl glycoside
Coumaric acid ester
Hydroxycinnamic acid or derivatives
Cinnamic acid or derivatives
Coumaric acid or derivatives
Cinnamic acid ester
O-glycosyl compound
Glycosyl compound
Styrene
1-hydroxy-2-unsubstituted benzenoid
Phenol
Fatty acid ester
Fatty acyl
Monosaccharide
Oxane
Dicarboxylic acid or derivatives
Benzenoid
Monocyclic benzene moiety
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Secondary alcohol
Carboxylic acid ester
Acetal
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Polyol
Primary alcohol
Alcohol
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	0.75	ALOGPS
logP	2.34	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	9.4	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	242.13 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	195.28 m³·mol⁻¹	ChemAxon
Polarizability	82.17 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 5,9-dimethyl-14-methylidene-13-{[3,4,5-trihydroxy-6-({[3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylate (NP0230580)

MOL for NP0230580 (3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 5,9-dimethyl-14-methylidene-13-{[3,4,5-trihydroxy-6-({[3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylate)

3D MOL for NP0230580 (3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 5,9-dimethyl-14-methylidene-13-{[3,4,5-trihydroxy-6-({[3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylate)

3D SDF for NP0230580 (3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 5,9-dimethyl-14-methylidene-13-{[3,4,5-trihydroxy-6-({[3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylate)

3D-SDF for NP0230580 (3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 5,9-dimethyl-14-methylidene-13-{[3,4,5-trihydroxy-6-({[3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylate)

PDB for NP0230580 (3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 5,9-dimethyl-14-methylidene-13-{[3,4,5-trihydroxy-6-({[3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylate)

3D PDB for NP0230580 (3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 5,9-dimethyl-14-methylidene-13-{[3,4,5-trihydroxy-6-({[3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylate)

SMILES for NP0230580 (3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 5,9-dimethyl-14-methylidene-13-{[3,4,5-trihydroxy-6-({[3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylate)

INCHI for NP0230580 (3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 5,9-dimethyl-14-methylidene-13-{[3,4,5-trihydroxy-6-({[3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylate)

Structure for NP0230580 (3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 5,9-dimethyl-14-methylidene-13-{[3,4,5-trihydroxy-6-({[3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylate)

3D Structure for NP0230580 (3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 5,9-dimethyl-14-methylidene-13-{[3,4,5-trihydroxy-6-({[3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylate)