NP-MRD: Showing NP-Card for (2's,3'as,4's)-4'-hydroxy-2'-(hydroxymethyl)-2',4',6'-trimethyl-7'-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3'a,7'a-dihydro-1'h-spiro[cyclopropane-1,5'-inden]-3'-one (NP0286367)

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Record Information

Version

2.0

Created at

2022-09-09 14:54:39 UTC

Updated at

2022-09-09 14:54:39 UTC

NP-MRD ID

NP0286367

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2's,3'as,4's)-4'-hydroxy-2'-(hydroxymethyl)-2',4',6'-trimethyl-7'-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3'a,7'a-dihydro-1'h-spiro[cyclopropane-1,5'-inden]-3'-one

Description

Caudatoside 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. (2's,3'as,4's)-4'-hydroxy-2'-(hydroxymethyl)-2',4',6'-trimethyl-7'-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3'a,7'a-dihydro-1'h-spiro[cyclopropane-1,5'-inden]-3'-one is found in Pteridium aquilinum and Pteridium caudatum. (2's,3'as,4's)-4'-hydroxy-2'-(hydroxymethyl)-2',4',6'-trimethyl-7'-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3'a,7'a-dihydro-1'h-spiro[cyclopropane-1,5'-inden]-3'-one was first documented in 2013 (PMID: 23232919). Based on a literature review a small amount of articles have been published on Caudatoside (PMID: 32550580) (PMID: 34649082) (PMID: 31931331) (PMID: 35043811).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092216542D          

 30 33  0  0  1  0            999 V2000
    1.9347    1.2652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5169    0.6807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3142    0.8926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5293    1.6891    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9471    2.2736    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1498    2.0617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5676    2.6462    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7702    2.4342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1880    3.0187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7827    3.4426    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2005    4.0272    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5800    3.6546    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7951    4.4511    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1622    3.0701    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9595    3.2820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8964    0.3081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7203    0.3497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0145   -0.4211    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7503   -0.0480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4624   -1.1139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2864   -1.0724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3723   -0.9391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4138   -1.7630    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6813   -0.4884    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8840   -0.7003    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2312   -1.4487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2072   -1.1722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3018   -0.1158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7173   -0.6980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5053    0.0993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
  5 14  1  0  0  0  0
 14 15  1  1  0  0  0
  3 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  1  0  0  0
 20 21  1  0  0  0  0
 18 22  1  0  0  0  0
 22 23  2  0  0  0  0
 24 22  1  6  0  0  0
 16 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  6  0  0  0
 25 28  1  0  0  0  0
  2 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 28 30  1  0  0  0  0
M  END

     RDKit          3D

 62 65  0  0  0  0  0  0  0  0999 V2000
    0.4528   -2.8252   -1.6506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5029   -1.9954   -0.8364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1978   -0.7140   -0.7024 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9268   -0.1299   -1.2629 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2215   -0.2325   -0.7646 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3358    0.2801    0.5425 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6795    0.2742    0.9063 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8575    0.3618    2.4072 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2997    1.5231    2.9118 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3625    1.4662    0.2884 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6450    1.1666   -0.1620 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5507    1.8883   -0.9148 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3982    2.5332   -0.4638 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1187    0.6334   -1.6316 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1970   -0.1337   -2.0545 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0731    0.1945    0.0810 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2623    1.5460   -0.5197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5920    1.9741    0.1248 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2481    2.7054    1.3781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3608    2.8550   -0.8222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5705    3.9763   -1.0895 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3043    0.7024    0.4114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3623    0.6171    0.9822 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4920   -0.3713   -0.1185 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5016   -1.6634    0.6148 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8935   -2.1369    0.8816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8180   -1.4699    1.8289 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7083   -2.6305   -0.2376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6996   -4.0511    0.1590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5265   -3.5706   -1.0316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0721   -3.5807   -2.2494 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0306   -2.1946   -2.3575 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1769   -3.3509   -1.0128 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5879   -1.2779   -0.7052 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1914   -0.6671    0.5894 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9320    0.3379    2.6248 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3562   -0.5258    2.8897 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0234    2.1758    3.0721 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4576    2.2658    1.0376 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8278    1.6813   -0.9893 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1172    2.5026   -1.6232 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5437    2.9777    0.4166 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5780    0.9783   -2.5602 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8237   -1.0420   -2.2750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8119    0.2123    1.1536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4579    2.2587   -0.3032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4528    1.4142   -1.6042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2408    3.1701    1.3253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2267    1.9655    2.2160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0422    3.4266    1.6113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2799    3.1811   -0.3018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5923    2.3381   -1.7634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9892    4.8173   -0.8272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5790   -0.5270   -1.2138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9662   -3.1945    1.1275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5364   -1.8192    0.0368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2622   -1.5760    1.7845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1376   -2.1070    2.5306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8304   -4.7107   -0.0344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2685   -4.3205    1.0616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6374   -3.5898   -0.9197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1951   -3.9929   -1.9922 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  7 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
  3 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  1
 18 20  1  0
 20 21  1  0
 18 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  1  1
 25 28  1  0
 28 29  1  0
 29 30  1  0
 28  2  1  0
 30 28  1  0
 14  5  1  0
 24 16  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  5 34  1  1
  7 35  1  6
  8 36  1  0
  8 37  1  0
  9 38  1  0
 10 39  1  1
 11 40  1  0
 12 41  1  6
 13 42  1  0
 14 43  1  6
 15 44  1  0
 16 45  1  1
 17 46  1  0
 17 47  1  0
 19 48  1  0
 19 49  1  0
 19 50  1  0
 20 51  1  0
 20 52  1  0
 21 53  1  0
 24 54  1  6
 26 55  1  0
 26 56  1  0
 26 57  1  0
 27 58  1  0
 29 59  1  0
 29 60  1  0
 30 61  1  0
 30 62  1  0
M  END


  Mrv1652309092216542D          

 30 33  0  0  1  0            999 V2000
    1.9347    1.2652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5169    0.6807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3142    0.8926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5293    1.6891    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9471    2.2736    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1498    2.0617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5676    2.6462    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7702    2.4342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1880    3.0187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7827    3.4426    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2005    4.0272    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5800    3.6546    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7951    4.4511    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1622    3.0701    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9595    3.2820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8964    0.3081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7203    0.3497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0145   -0.4211    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7503   -0.0480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4624   -1.1139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2864   -1.0724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3723   -0.9391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4138   -1.7630    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6813   -0.4884    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8840   -0.7003    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2312   -1.4487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2072   -1.1722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3018   -0.1158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7173   -0.6980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5053    0.0993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
  5 14  1  0  0  0  0
 14 15  1  1  0  0  0
  3 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  1  0  0  0
 20 21  1  0  0  0  0
 18 22  1  0  0  0  0
 22 23  2  0  0  0  0
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 16 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  6  0  0  0
 25 28  1  0  0  0  0
  2 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 28 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0286367

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C2C[C@@](C)(CO)C(=O)[C@@H]2[C@](C)(O)C11CC1

> <INCHI_IDENTIFIER>
InChI=1S/C21H32O9/c1-9-16(30-18-15(26)14(25)13(24)11(7-22)29-18)10-6-19(2,8-23)17(27)12(10)20(3,28)21(9)4-5-21/h10-15,18,22-26,28H,4-8H2,1-3H3/t10?,11-,12-,13-,14+,15-,18+,19+,20+/m1/s1

> <INCHI_KEY>
NIERWTDCCGPRCQ-ZFVALMAISA-N

> <FORMULA>
C21H32O9

> <MOLECULAR_WEIGHT>
428.478

> <EXACT_MASS>
428.20463261

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
43.71929928485767

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2'S,3'aS,4'S)-4'-hydroxy-2'-(hydroxymethyl)-2',4',6'-trimethyl-7'-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1',2',3',3'a,4',7'a-hexahydrospiro[cyclopropane-1,5'-indene]-3'-one

> <JCHEM_LOGP>
-1.722210573666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.14253384109438

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.194225970667869

> <JCHEM_PKA_STRONGEST_BASIC>
-2.815145911661255

> <JCHEM_POLAR_SURFACE_AREA>
156.91

> <JCHEM_REFRACTIVITY>
104.02189999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2'S,3'aS,4'S)-4'-hydroxy-2'-(hydroxymethyl)-2',4',6'-trimethyl-7'-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3'a,7'a-dihydro-1'H-spiro[cyclopropane-1,5'-indene]-3'-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0       3.611   2.362   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.698   1.271   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.186   1.666   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       6.588   3.153   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       5.501   4.244   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       4.013   3.848   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       2.926   4.940   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.438   4.544   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.351   5.635   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       3.328   6.426   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.241   7.517   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.816   6.822   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.217   8.309   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.903   5.731   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       7.391   6.126   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       7.273   0.575   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.811   0.653   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.360  -0.786   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.734  -0.090   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.197  -2.079   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      11.735  -2.002   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       8.162  -1.753   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       8.239  -3.291   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       6.872  -0.912   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.383  -1.307   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.031  -2.704   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       4.120  -2.188   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       4.297  -0.216   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.206  -1.303   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.810   0.185   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   28                                                  
CONECT    3    2    4   16                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   14                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    7   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    5   15                                                  
CONECT   15   14                                                            
CONECT   16    3   17   24                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20   22                                             
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20                                                            
CONECT   22   18   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   16   25                                                  
CONECT   25   24   26   27   28                                             
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   25    2   29   30                                             
CONECT   29   28   30                                                       
CONECT   30   29   28                                                       
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₃₂O₉

Average Mass

428.4780 Da

Monoisotopic Mass

428.20463 Da

IUPAC Name

(2'S,3'aS,4'S)-4'-hydroxy-2'-(hydroxymethyl)-2',4',6'-trimethyl-7'-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1',2',3',3'a,4',7'a-hexahydrospiro[cyclopropane-1,5'-indene]-3'-one

Traditional Name

(2'S,3'aS,4'S)-4'-hydroxy-2'-(hydroxymethyl)-2',4',6'-trimethyl-7'-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3'a,7'a-dihydro-1'H-spiro[cyclopropane-1,5'-indene]-3'-one

CAS Registry Number

Not Available

SMILES

CC1=C(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C2C[C@@](C)(CO)C(=O)[C@@H]2[C@](C)(O)C11CC1

InChI Identifier

InChI=1S/C21H32O9/c1-9-16(30-18-15(26)14(25)13(24)11(7-22)29-18)10-6-19(2,8-23)17(27)12(10)20(3,28)21(9)4-5-21/h10-15,18,22-26,28H,4-8H2,1-3H3/t10?,11-,12-,13-,14+,15-,18+,19+,20+/m1/s1

InChI Key

NIERWTDCCGPRCQ-ZFVALMAISA-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
Pteridium aquilinum	LOTUS Database	35616633
Pteridium caudatum	LOTUS Database	35616633

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
Illudine sesquiterpenoid
Sesquiterpenoid
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Monosaccharide
Oxane
Tertiary alcohol
Secondary alcohol
Ketone
Polyol
Oxacycle
Acetal
Organoheterocyclic compound
Primary alcohol
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Aldehyde
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	-1.7	ChemAxon
pKa (Strongest Acidic)	12.19	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	156.91 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	104.02 m³·mol⁻¹	ChemAxon
Polarizability	43.72 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

C00045735

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

102065498

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

de Oliveira LGS, Boabaid FM, Kisielius V, Rasmussen LH, Buroni F, Lucas M, Schild CO, Lopez F, Machado M, Riet-Correa F: Hemorrhagic diathesis in cattle due to consumption of Adiantopsis chlorophylla (Swartz) Fee (Pteridaceae). Toxicon X. 2020 Jan 23;5:100024. doi: 10.1016/j.toxcx.2020.100024. eCollection 2020 Mar. [PubMed:32550580 ]
Mrkajic NS, Hama JR, Strobel BW, Hansen HCB, Rasmussen LH, Pedersen AK, Christensen SCB, Hedegaard MJ: Removal of phytotoxins in filter sand used for drinking water treatment. Water Res. 2021 Oct 15;205:117610. doi: 10.1016/j.watres.2021.117610. Epub 2021 Aug 27. [PubMed:34649082 ]
Kisielius V, Lindqvist DN, Thygesen MB, Rodamer M, Hansen HCB, Rasmussen LH: Fast LC-MS quantification of ptesculentoside, caudatoside, ptaquiloside and corresponding pterosins in bracken ferns. J Chromatogr B Analyt Technol Biomed Life Sci. 2020 Feb 1;1138:121966. doi: 10.1016/j.jchromb.2019.121966. Epub 2020 Jan 3. [PubMed:31931331 ]
Kisielius V, Drejer M, Dornhoff JK, Mrkajic NS, Lindqvist DN, Hansen HCB, Rasmussen LH: Occurrence and stability of ptesculentoside, caudatoside and ptaquiloside in surface waters. Environ Sci Process Impacts. 2022 Feb 23;24(2):277-289. doi: 10.1039/d1em00364j. [PubMed:35043811 ]
Sharma R, Bhat TK, Sharma OP: The environmental and human effects of ptaquiloside-induced enzootic bovine hematuria: a tumorous disease of cattle. Rev Environ Contam Toxicol. 2013;224:53-95. doi: 10.1007/978-1-4614-5882-1_3. [PubMed:23232919 ]
LOTUS database [Link]

Showing NP-Card for (2's,3'as,4's)-4'-hydroxy-2'-(hydroxymethyl)-2',4',6'-trimethyl-7'-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3'a,7'a-dihydro-1'h-spiro[cyclopropane-1,5'-inden]-3'-one (NP0286367)

MOL for NP0286367 ((2's,3'as,4's)-4'-hydroxy-2'-(hydroxymethyl)-2',4',6'-trimethyl-7'-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3'a,7'a-dihydro-1'h-spiro[cyclopropane-1,5'-inden]-3'-one)

3D MOL for NP0286367 ((2's,3'as,4's)-4'-hydroxy-2'-(hydroxymethyl)-2',4',6'-trimethyl-7'-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3'a,7'a-dihydro-1'h-spiro[cyclopropane-1,5'-inden]-3'-one)

3D SDF for NP0286367 ((2's,3'as,4's)-4'-hydroxy-2'-(hydroxymethyl)-2',4',6'-trimethyl-7'-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3'a,7'a-dihydro-1'h-spiro[cyclopropane-1,5'-inden]-3'-one)

3D-SDF for NP0286367 ((2's,3'as,4's)-4'-hydroxy-2'-(hydroxymethyl)-2',4',6'-trimethyl-7'-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3'a,7'a-dihydro-1'h-spiro[cyclopropane-1,5'-inden]-3'-one)

PDB for NP0286367 ((2's,3'as,4's)-4'-hydroxy-2'-(hydroxymethyl)-2',4',6'-trimethyl-7'-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3'a,7'a-dihydro-1'h-spiro[cyclopropane-1,5'-inden]-3'-one)

3D PDB for NP0286367 ((2's,3'as,4's)-4'-hydroxy-2'-(hydroxymethyl)-2',4',6'-trimethyl-7'-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3'a,7'a-dihydro-1'h-spiro[cyclopropane-1,5'-inden]-3'-one)

SMILES for NP0286367 ((2's,3'as,4's)-4'-hydroxy-2'-(hydroxymethyl)-2',4',6'-trimethyl-7'-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3'a,7'a-dihydro-1'h-spiro[cyclopropane-1,5'-inden]-3'-one)

INCHI for NP0286367 ((2's,3'as,4's)-4'-hydroxy-2'-(hydroxymethyl)-2',4',6'-trimethyl-7'-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3'a,7'a-dihydro-1'h-spiro[cyclopropane-1,5'-inden]-3'-one)

Structure for NP0286367 ((2's,3'as,4's)-4'-hydroxy-2'-(hydroxymethyl)-2',4',6'-trimethyl-7'-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3'a,7'a-dihydro-1'h-spiro[cyclopropane-1,5'-inden]-3'-one)

3D Structure for NP0286367 ((2's,3'as,4's)-4'-hydroxy-2'-(hydroxymethyl)-2',4',6'-trimethyl-7'-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3'a,7'a-dihydro-1'h-spiro[cyclopropane-1,5'-inden]-3'-one)