NP-MRD: Showing NP-Card for 2-[(4,5-dihydroxy-6-{5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]oxy}-2-{[(3,4,5-trihydroxyoxan-2-yl)oxy]methyl}oxan-3-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol (NP0186194)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-04 01:56:18 UTC

Updated at

2022-09-04 01:56:18 UTC

NP-MRD ID

NP0186194

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-[(4,5-dihydroxy-6-{5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]oxy}-2-{[(3,4,5-trihydroxyoxan-2-yl)oxy]methyl}oxan-3-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

Description

Artemoin B belongs to the class of organic compounds known as annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain. An artemoin in which the two hydroxy groups on the C-30 side-chain are located at positions 17 and 18. Artemoin B is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Artemoin B has been detected, but not quantified in, fruits. 2-[(4,5-dihydroxy-6-{5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]oxy}-2-{[(3,4,5-trihydroxyoxan-2-yl)oxy]methyl}oxan-3-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol is found in Smilax officinalis and Smilax sieboldii. This could make artemoin b a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061305062D          

 61 69  0  0  0  0            999 V2000
    2.5224   -0.8848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4270    0.1094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2004   -0.3672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6545   -0.2661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4876   -2.5309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6640   -2.4830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6277   -1.7905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8476   -0.4631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3768   -0.3192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0240   -0.4151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5532   -0.2713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4417   -1.9243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7645   -1.8896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8834   -2.2778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0765   -2.9145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8594   -0.3805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5154   -6.1692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8754   -4.1013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3365   -1.0186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5514   -0.7062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9409   -1.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2179   -1.2003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2937   -1.7458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7470   -1.0565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4701   -1.6978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8857   -6.9064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1505   -1.8990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6231   -3.6038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3287   -3.4120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2843   -1.0849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7093   -6.9544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9934   -4.3410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5401   -5.0303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6056   -2.7707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1626   -6.2651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7165   -4.9824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2354   -2.0334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1523   -3.4599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7924   -5.5278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4118   -1.9855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3462   -4.2451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5707   -1.1044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0998   -0.9606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9646   -1.2861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9001   -2.9624    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4324   -7.5957    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0796   -7.6916    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8170   -4.3889    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.9104   -5.7675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4293   -2.8186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9862   -6.3130    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2632   -5.6717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6887   -1.3441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9688   -5.4799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2457   -4.8385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6734   -0.5142    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0415   -1.2482    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7995   -3.5558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9584   -2.6748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5226   -4.1972    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3349   -2.0234    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
 10  8  1  0  0  0  0
 11  9  1  0  0  0  0
 12  7  1  0  0  0  0
 19  1  1  0  0  0  0
 19  7  1  0  0  0  0
 19 16  1  0  0  0  0
 20  2  1  0  0  0  0
 21  5  1  0  0  0  0
 21 13  1  0  0  0  0
 22  8  1  0  0  0  0
 22 13  1  0  0  0  0
 23  6  1  0  0  0  0
 24  9  1  0  0  0  0
 24 23  1  0  0  0  0
 25 14  1  0  0  0  0
 25 23  1  0  0  0  0
 26 17  1  0  0  0  0
 27 14  1  0  0  0  0
 28 15  1  0  0  0  0
 29 18  1  0  0  0  0
 30 20  1  0  0  0  0
 30 27  1  0  0  0  0
 31 26  1  0  0  0  0
 32 28  1  0  0  0  0
 33 32  1  0  0  0  0
 35 31  1  0  0  0  0
 36 33  1  0  0  0  0
 37 34  1  0  0  0  0
 38 29  1  0  0  0  0
 38 34  1  0  0  0  0
 39 35  1  0  0  0  0
 40 37  1  0  0  0  0
 41 36  1  0  0  0  0
 42  3  1  0  0  0  0
 42 10  1  0  0  0  0
 42 21  1  0  0  0  0
 42 24  1  0  0  0  0
 43  4  1  0  0  0  0
 43 11  1  0  0  0  0
 43 25  1  0  0  0  0
 43 30  1  0  0  0  0
 44 12  1  0  0  0  0
 44 20  1  0  0  0  0
 45 15  1  0  0  0  0
 46 26  1  0  0  0  0
 47 31  1  0  0  0  0
 48 32  1  0  0  0  0
 49 33  1  0  0  0  0
 50 34  1  0  0  0  0
 51 35  1  0  0  0  0
 52 36  1  0  0  0  0
 53 37  1  0  0  0  0
 54 17  1  0  0  0  0
 54 39  1  0  0  0  0
 55 18  1  0  0  0  0
 55 39  1  0  0  0  0
 56 16  1  0  0  0  0
 56 44  1  0  0  0  0
 57 22  1  0  0  0  0
 57 40  1  0  0  0  0
 58 28  1  0  0  0  0
 58 41  1  0  0  0  0
 59 29  1  0  0  0  0
 59 40  1  0  0  0  0
 60 38  1  0  0  0  0
 60 41  1  0  0  0  0
 61 27  1  0  0  0  0
 61 44  1  0  0  0  0
M  END

     RDKit          3D

133141  0  0  0  0  0  0  0  0999 V2000
    8.9238    1.6590    1.9299 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2740    0.7196    0.9103 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9750    1.3147    0.5095 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.0707    1.4339   -1.0058 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7534    0.8603   -1.5561 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8871    0.9857   -0.3756 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5981    0.2455   -0.3636 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7897    0.4826   -1.6401 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3070    0.3519   -1.3497 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0930   -0.5401   -0.1356 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2954   -1.0714   -0.1557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1503   -0.5364    0.9736 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4794   -0.6133    0.4965 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2493   -1.4760    1.2367 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3242   -0.9064    1.8514 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5002   -0.8759    1.0999 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.4134    0.1034   -0.0377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1879    1.4085    0.3353 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2046    1.9424    1.1070 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.6342    2.3164    2.3489 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9315    3.4993    2.1636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8844    4.7015    2.2136 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.0608    5.0460    3.5555 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1799    4.1992    1.5957 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.9120    5.2076    0.9973 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7622    3.2183    0.5072 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.9158    2.9541   -0.2447 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9699   -2.2224    0.6753 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.3706   -2.2190   -0.6443 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6603   -2.6897   -0.8502 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.5439   -3.8553   -1.5849 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6825   -3.7473   -2.9341 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.4928   -3.0731   -3.6023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6893   -2.9894   -4.9800 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9866   -3.1698   -3.4138 C   0  0  1  0  0  0  0  0  0  0  0  0
   -9.8822   -4.2216   -3.5964 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5800   -2.2430   -2.3857 C   0  0  2  0  0  0  0  0  0  0  0  0
  -10.2586   -1.1628   -2.9765 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5286   -1.6589   -1.4605 C   0  0  1  0  0  0  0  0  0  0  0  0
   -9.2116   -0.9803   -0.4517 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8866   -3.2549    0.9366 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7461   -3.3684    2.3196 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6045   -2.6829    0.3928 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6291   -3.6766    0.4609 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8523    0.9004    1.2435 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5713    1.1302    1.5936 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5543    0.0933    1.1254 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7409   -0.9919    2.1672 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8588    0.8108    0.8375 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7218    1.0380    2.0202 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0915    0.5000    1.9928 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7870    0.4000    0.7072 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2599   -0.9924    0.3875 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1641    0.7195   -1.4113 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0784    0.7216   -0.3541 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.0303   -0.4450   -0.4470 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3916   -0.1339    0.1358 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0108    1.0891   -0.4929 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.0816    0.7094   -1.4906 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9135    1.8303   -1.2182 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7899    1.9174   -0.4027 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6924    1.0936    2.4913 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4275    2.5035    1.4229 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1658    1.9832    2.6749 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2116   -0.2697    1.3932 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7546    2.3018    0.9710 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1408    2.5192   -1.2548 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4412    1.5066   -2.3882 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8962   -0.2001   -1.8532 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7189    2.0407   -0.1268 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6777   -0.8289   -0.2250 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0339    1.4800   -2.0148 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0680   -0.2716   -2.4029 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8419   -0.1669   -2.2105 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8145    1.3260   -1.2377 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7733   -1.4314   -0.3386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3209   -2.1839   -0.0474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7742   -0.8555   -1.1304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0633   -1.1924    1.8423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5789   -1.8892    2.0484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2716   -0.4844    1.8158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4447    0.1025   -0.5034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7513   -0.2410   -0.8519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0309    1.2467    1.2676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1526    3.6511    2.9463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4705    3.4592    1.1538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5097    5.5417    1.6148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8146    4.5598    3.9513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7439    3.6854    2.3993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6873    4.8027    0.5727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0269    3.7478   -0.1319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7229    2.7644   -1.1863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8543   -2.6030    1.2691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0690   -2.9426    0.1722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6451   -4.8067   -3.3302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2555   -2.0925   -3.1417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5667   -3.6870   -3.4710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6592   -2.0295   -5.2500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7853   -2.6541   -4.3789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4501   -5.0963   -3.5427 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3334   -2.7856   -1.7757 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1687   -1.1793   -3.9621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9825   -0.8580   -2.0379 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1116   -1.3589   -0.2904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1595   -4.2276    0.5359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5106   -3.8623    2.7386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6562   -2.3619   -0.6485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9476   -4.4979    0.8750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0527    1.5287    0.3225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5137    1.3464    2.0137 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9336    2.1233    1.2090 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6097    1.2565    2.7106 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8181   -1.2577    2.1635 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4407   -0.6889    3.1773 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2103   -1.9304    1.8882 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5435    1.8400    0.4733 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1910    0.5926    2.9149 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7886    2.1308    2.3115 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7357    1.0917    2.7037 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0836   -0.5295    2.4602 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1923   -1.0250   -0.2013 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5348   -1.6371   -0.1020 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4897   -1.4716    1.3844 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6257   -1.3364    0.0288 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2063   -0.6068   -1.5504 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.3514   -0.0923    1.2285 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.0460   -1.0011   -0.1263 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.4977    1.7380    0.2786 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.9295    1.1995   -2.4806 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.1222   -0.3809   -1.6927 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.1023    0.9934   -1.1550 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7224    1.2798   -2.1595 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.1961    2.8674   -1.4902 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  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
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 45  1  0
 45 46  1  0
 46 47  1  0
 47 48  1  1
 47 49  1  0
 49 50  1  0
 50 51  1  0
 51 52  1  0
 52 53  1  6
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 16 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 32 35  1  0
 35 36  1  0
 35 37  1  0
 37 38  1  0
 37 39  1  0
 39 40  1  0
 28 41  1  0
 41 42  1  0
 41 43  1  0
 43 44  1  0
  4 54  1  0
 55 54  1  6
 55 56  1  0
 56 57  1  0
 57 58  1  0
 58 59  1  0
 58 60  1  0
 60 61  1  0
 55  2  1  0
 61 55  1  0
 52  3  1  0
 43 14  1  0
 52  6  1  0
 26 19  1  0
 39 30  1  0
 49  7  1  0
 47 10  1  0
  1 62  1  0
  1 63  1  0
  1 64  1  0
  2 65  1  1
  3 66  1  1
  4 67  1  1
  5 68  1  0
  5 69  1  0
  6 70  1  1
  7 71  1  1
  8 72  1  0
  8 73  1  0
  9 74  1  0
  9 75  1  0
 10 76  1  6
 11 77  1  0
 11 78  1  0
 12 79  1  1
 45109  1  0
 45110  1  0
 46111  1  0
 46112  1  0
 48113  1  0
 48114  1  0
 48115  1  0
 49116  1  6
 50117  1  0
 50118  1  0
 51119  1  0
 51120  1  0
 53121  1  0
 53122  1  0
 53123  1  0
 14 80  1  1
 16 81  1  1
 17 82  1  0
 17 83  1  0
 19 84  1  1
 21 85  1  0
 21 86  1  0
 22 87  1  6
 23 88  1  0
 24 89  1  1
 25 90  1  0
 26 91  1  6
 27 92  1  0
 28 93  1  1
 30 94  1  1
 32 95  1  6
 33 96  1  0
 33 97  1  0
 34 98  1  0
 35 99  1  6
 36100  1  0
 37101  1  1
 38102  1  0
 39103  1  6
 40104  1  0
 41105  1  6
 42106  1  0
 43107  1  6
 44108  1  0
 56124  1  0
 56125  1  0
 57126  1  0
 57127  1  0
 58128  1  1
 59129  1  0
 59130  1  0
 59131  1  0
 60132  1  0
 60133  1  0
M  END


  Mrv0541 05061305062D          

 61 69  0  0  0  0            999 V2000
    2.5224   -0.8848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4270    0.1094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2004   -0.3672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6545   -0.2661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4876   -2.5309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6640   -2.4830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6277   -1.7905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8476   -0.4631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3768   -0.3192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0240   -0.4151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5532   -0.2713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4417   -1.9243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7645   -1.8896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8834   -2.2778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0765   -2.9145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8594   -0.3805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5154   -6.1692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8754   -4.1013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3365   -1.0186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5514   -0.7062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9409   -1.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2179   -1.2003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2937   -1.7458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7470   -1.0565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4701   -1.6978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8857   -6.9064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1505   -1.8990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6231   -3.6038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3287   -3.4120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2843   -1.0849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7093   -6.9544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9934   -4.3410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5401   -5.0303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6056   -2.7707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1626   -6.2651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7165   -4.9824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2354   -2.0334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1523   -3.4599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7924   -5.5278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4118   -1.9855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3462   -4.2451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5707   -1.1044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0998   -0.9606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9646   -1.2861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9001   -2.9624    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4324   -7.5957    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0796   -7.6916    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8170   -4.3889    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.9104   -5.7675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4293   -2.8186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9862   -6.3130    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2632   -5.6717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6887   -1.3441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9688   -5.4799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2457   -4.8385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6734   -0.5142    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0415   -1.2482    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7995   -3.5558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9584   -2.6748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5226   -4.1972    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3349   -2.0234    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
 10  8  1  0  0  0  0
 11  9  1  0  0  0  0
 12  7  1  0  0  0  0
 19  1  1  0  0  0  0
 19  7  1  0  0  0  0
 19 16  1  0  0  0  0
 20  2  1  0  0  0  0
 21  5  1  0  0  0  0
 21 13  1  0  0  0  0
 22  8  1  0  0  0  0
 22 13  1  0  0  0  0
 23  6  1  0  0  0  0
 24  9  1  0  0  0  0
 24 23  1  0  0  0  0
 25 14  1  0  0  0  0
 25 23  1  0  0  0  0
 26 17  1  0  0  0  0
 27 14  1  0  0  0  0
 28 15  1  0  0  0  0
 29 18  1  0  0  0  0
 30 20  1  0  0  0  0
 30 27  1  0  0  0  0
 31 26  1  0  0  0  0
 32 28  1  0  0  0  0
 33 32  1  0  0  0  0
 35 31  1  0  0  0  0
 36 33  1  0  0  0  0
 37 34  1  0  0  0  0
 38 29  1  0  0  0  0
 38 34  1  0  0  0  0
 39 35  1  0  0  0  0
 40 37  1  0  0  0  0
 41 36  1  0  0  0  0
 42  3  1  0  0  0  0
 42 10  1  0  0  0  0
 42 21  1  0  0  0  0
 42 24  1  0  0  0  0
 43  4  1  0  0  0  0
 43 11  1  0  0  0  0
 43 25  1  0  0  0  0
 43 30  1  0  0  0  0
 44 12  1  0  0  0  0
 44 20  1  0  0  0  0
 45 15  1  0  0  0  0
 46 26  1  0  0  0  0
 47 31  1  0  0  0  0
 48 32  1  0  0  0  0
 49 33  1  0  0  0  0
 50 34  1  0  0  0  0
 51 35  1  0  0  0  0
 52 36  1  0  0  0  0
 53 37  1  0  0  0  0
 54 17  1  0  0  0  0
 54 39  1  0  0  0  0
 55 18  1  0  0  0  0
 55 39  1  0  0  0  0
 56 16  1  0  0  0  0
 56 44  1  0  0  0  0
 57 22  1  0  0  0  0
 57 40  1  0  0  0  0
 58 28  1  0  0  0  0
 58 41  1  0  0  0  0
 59 29  1  0  0  0  0
 59 40  1  0  0  0  0
 60 38  1  0  0  0  0
 60 41  1  0  0  0  0
 61 27  1  0  0  0  0
 61 44  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0186194

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1C2C(CC3C4CCC5CC(CCC5(C)C4CCC23C)OC2OC(COC3OCC(O)C(O)C3O)C(OC3OC(CO)C(O)C(O)C3O)C(O)C2O)OC11CCC(C)CO1

> <INCHI_IDENTIFIER>
InChI=1S/C44H72O17/c1-19-7-12-44(56-16-19)20(2)30-27(61-44)14-25-23-6-5-21-13-22(8-10-42(21,3)24(23)9-11-43(25,30)4)57-40-37(53)34(50)38(60-41-36(52)33(49)32(48)28(15-45)58-41)29(59-40)18-55-39-35(51)31(47)26(46)17-54-39/h19-41,45-53H,5-18H2,1-4H3

> <INCHI_KEY>
ZUIQPSIQYROGAZ-UHFFFAOYSA-N

> <FORMULA>
C44H72O17

> <MOLECULAR_WEIGHT>
873.0323

> <EXACT_MASS>
872.476950878

> <JCHEM_ACCEPTOR_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
95.13883524649262

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(4,5-dihydroxy-6-{5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]oxy}-2-{[(3,4,5-trihydroxyoxan-2-yl)oxy]methyl}oxan-3-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

> <ALOGPS_LOGP>
0.39

> <JCHEM_LOGP>
0.6507129403333375

> <ALOGPS_LOGS>
-3.47

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
9

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.21613452522514

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.76691670927846

> <JCHEM_PKA_STRONGEST_BASIC>
-3.526580404084765

> <JCHEM_POLAR_SURFACE_AREA>
255.9099999999999

> <JCHEM_REFRACTIVITY>
210.69330000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.97e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(4,5-dihydroxy-6-{5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]oxy}-2-{[(3,4,5-trihydroxyoxan-2-yl)oxy]methyl}oxan-3-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       4.708  -1.652   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.130   0.204   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      17.174  -0.685   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.422  -0.497   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      17.710  -4.724   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      16.173  -4.635   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.772  -3.342   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      20.249  -0.864   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      15.637  -0.596   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      18.711  -0.775   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.099  -0.506   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.291  -3.592   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      20.094  -3.527   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.849  -4.252   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      30.009  -5.440   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.204  -0.710   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      19.629 -11.516   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      22.167  -7.656   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.228  -1.901   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.363  -1.318   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      18.556  -3.438   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      20.940  -2.241   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      15.482  -3.259   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      16.328  -1.972   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      13.944  -3.169   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      20.320 -12.892   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      11.481  -3.545   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      29.163  -6.727   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      23.014  -6.369   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      11.731  -2.025   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      21.857 -12.982   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      29.854  -8.103   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      29.008  -9.390   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      25.397  -5.172   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      22.704 -11.695   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      27.471  -9.300   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      24.706  -3.796   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      24.551  -6.458   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      22.012 -10.319   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      23.169  -3.706   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      26.780  -7.924   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      17.865  -2.062   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      13.253  -1.793   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       9.267  -2.401   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0      31.547  -5.530   0.000  0.00  0.00           O+0
HETATM   46  O   UNK     0      19.474 -14.179   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0      22.549 -14.358   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0      31.392  -8.193   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0      29.699 -10.766   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0      26.935  -5.261   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0      24.241 -11.784   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0      26.625 -10.587   0.000  0.00  0.00           O+0
HETATM   53  O   UNK     0      25.552  -2.509   0.000  0.00  0.00           O+0
HETATM   54  O   UNK     0      20.475 -10.229   0.000  0.00  0.00           O+0
HETATM   55  O   UNK     0      22.859  -9.032   0.000  0.00  0.00           O+0
HETATM   56  O   UNK     0       8.724  -0.960   0.000  0.00  0.00           O+0
HETATM   57  O   UNK     0      22.477  -2.330   0.000  0.00  0.00           O+0
HETATM   58  O   UNK     0      27.626  -6.637   0.000  0.00  0.00           O+0
HETATM   59  O   UNK     0      22.322  -4.993   0.000  0.00  0.00           O+0
HETATM   60  O   UNK     0      25.242  -7.835   0.000  0.00  0.00           O+0
HETATM   61  O   UNK     0       9.958  -3.777   0.000  0.00  0.00           O+0
CONECT    1   19                                                            
CONECT    2   20                                                            
CONECT    3   42                                                            
CONECT    4   43                                                            
CONECT    5    6   21                                                       
CONECT    6    5   23                                                       
CONECT    7   12   19                                                       
CONECT    8   10   22                                                       
CONECT    9   11   24                                                       
CONECT   10    8   42                                                       
CONECT   11    9   43                                                       
CONECT   12    7   44                                                       
CONECT   13   21   22                                                       
CONECT   14   25   27                                                       
CONECT   15   28   45                                                       
CONECT   16   19   56                                                       
CONECT   17   26   54                                                       
CONECT   18   29   55                                                       
CONECT   19    1    7   16                                                  
CONECT   20    2   30   44                                                  
CONECT   21    5   13   42                                                  
CONECT   22    8   13   57                                                  
CONECT   23    6   24   25                                                  
CONECT   24    9   23   42                                                  
CONECT   25   14   23   43                                                  
CONECT   26   17   31   46                                                  
CONECT   27   14   30   61                                                  
CONECT   28   15   32   58                                                  
CONECT   29   18   38   59                                                  
CONECT   30   20   27   43                                                  
CONECT   31   26   35   47                                                  
CONECT   32   28   33   48                                                  
CONECT   33   32   36   49                                                  
CONECT   34   37   38   50                                                  
CONECT   35   31   39   51                                                  
CONECT   36   33   41   52                                                  
CONECT   37   34   40   53                                                  
CONECT   38   29   34   60                                                  
CONECT   39   35   54   55                                                  
CONECT   40   37   57   59                                                  
CONECT   41   36   58   60                                                  
CONECT   42    3   10   21   24                                             
CONECT   43    4   11   25   30                                             
CONECT   44   12   20   56   61                                             
CONECT   45   15                                                            
CONECT   46   26                                                            
CONECT   47   31                                                            
CONECT   48   32                                                            
CONECT   49   33                                                            
CONECT   50   34                                                            
CONECT   51   35                                                            
CONECT   52   36                                                            
CONECT   53   37                                                            
CONECT   54   17   39                                                       
CONECT   55   18   39                                                       
CONECT   56   16   44                                                       
CONECT   57   22   40                                                       
CONECT   58   28   41                                                       
CONECT   59   29   40                                                       
CONECT   60   38   41                                                       
CONECT   61   27   44                                                       
MASTER        0    0    0    0    0    0    0    0   61    0  138    0
END

View in JSmol

Synonyms

Value	Source
3-(17,18-Dihydroxytriacontyl)-5-methyl-2(5H)-furanone	ChEBI
3-(17,18-Dihydroxytriacontyl)-5-methyl-2,5-dihydrofuran-2-one	ChEBI

Chemical Formula

C₄₄H₇₂O₁₇

Average Mass

873.0323 Da

Monoisotopic Mass

872.47695 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

CC1C2C(CC3C4CCC5CC(CCC5(C)C4CCC23C)OC2OC(COC3OCC(O)C(O)C3O)C(OC3OC(CO)C(O)C(O)C3O)C(O)C2O)OC11CCC(C)CO1

InChI Identifier

InChI=1S/C44H72O17/c1-19-7-12-44(56-16-19)20(2)30-27(61-44)14-25-23-6-5-21-13-22(8-10-42(21,3)24(23)9-11-43(25,30)4)57-40-37(53)34(50)38(60-41-36(52)33(49)32(48)28(15-45)58-41)29(59-40)18-55-39-35(51)31(47)26(46)17-54-39/h19-41,45-53H,5-18H2,1-4H3

InChI Key

ZUIQPSIQYROGAZ-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
Smilax officinalis	LOTUS Database	35616633
Smilax sieboldii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty alcohols

Direct Parent

Annonaceous acetogenins

Alternative Parents

Substituents

Annonaceae acetogenin skeleton
Long chain fatty alcohol
2-furanone
Dihydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Lactone
1,2-diol
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Alcohol
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organic oxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	0.39	ALOGPS
logP	0.65	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	11.77	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	17	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	255.91 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	210.69 m³·mol⁻¹	ChemAxon
Polarizability	95.14 Å³	ChemAxon
Number of Rings	9	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

HMDB0033605

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB011693

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

129011027

PDB ID

Not Available

ChEBI ID

134013

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-[(4,5-dihydroxy-6-{5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]oxy}-2-{[(3,4,5-trihydroxyoxan-2-yl)oxy]methyl}oxan-3-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol (NP0186194)

MOL for NP0186194 (2-[(4,5-dihydroxy-6-{5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]oxy}-2-{[(3,4,5-trihydroxyoxan-2-yl)oxy]methyl}oxan-3-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol)

3D MOL for NP0186194 (2-[(4,5-dihydroxy-6-{5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]oxy}-2-{[(3,4,5-trihydroxyoxan-2-yl)oxy]methyl}oxan-3-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol)

3D SDF for NP0186194 (2-[(4,5-dihydroxy-6-{5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]oxy}-2-{[(3,4,5-trihydroxyoxan-2-yl)oxy]methyl}oxan-3-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol)

3D-SDF for NP0186194 (2-[(4,5-dihydroxy-6-{5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]oxy}-2-{[(3,4,5-trihydroxyoxan-2-yl)oxy]methyl}oxan-3-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol)

PDB for NP0186194 (2-[(4,5-dihydroxy-6-{5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]oxy}-2-{[(3,4,5-trihydroxyoxan-2-yl)oxy]methyl}oxan-3-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol)

3D PDB for NP0186194 (2-[(4,5-dihydroxy-6-{5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]oxy}-2-{[(3,4,5-trihydroxyoxan-2-yl)oxy]methyl}oxan-3-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol)

SMILES for NP0186194 (2-[(4,5-dihydroxy-6-{5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]oxy}-2-{[(3,4,5-trihydroxyoxan-2-yl)oxy]methyl}oxan-3-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol)

INCHI for NP0186194 (2-[(4,5-dihydroxy-6-{5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]oxy}-2-{[(3,4,5-trihydroxyoxan-2-yl)oxy]methyl}oxan-3-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol)

Structure for NP0186194 (2-[(4,5-dihydroxy-6-{5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]oxy}-2-{[(3,4,5-trihydroxyoxan-2-yl)oxy]methyl}oxan-3-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol)

3D Structure for NP0186194 (2-[(4,5-dihydroxy-6-{5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]oxy}-2-{[(3,4,5-trihydroxyoxan-2-yl)oxy]methyl}oxan-3-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol)