NP-MRD: Showing NP-Card for (3s)-3-hydroxy-2,2,5,7-tetramethyl-6-(2-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}ethyl)-3h-inden-1-one (NP0259353)

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Record Information

Version

2.0

Created at

2022-09-08 01:12:04 UTC

Updated at

2022-09-08 01:12:05 UTC

NP-MRD ID

NP0259353

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3s)-3-hydroxy-2,2,5,7-tetramethyl-6-(2-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}ethyl)-3h-inden-1-one

Description

Pteroside D belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond. (3s)-3-hydroxy-2,2,5,7-tetramethyl-6-(2-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}ethyl)-3h-inden-1-one is found in Pteridium aquilinum. (3s)-3-hydroxy-2,2,5,7-tetramethyl-6-(2-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}ethyl)-3h-inden-1-one was first documented in 2012 (PMID: 22792795). Based on a literature review a small amount of articles have been published on Pteroside D.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082203122D          

 29 31  0  0  1  0            999 V2000
    2.7845    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9279    1.9354    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6424    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3569    1.9354    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.0714    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7858    1.9354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3569    1.1104    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.0714    0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6424    0.6979    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6424   -0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9279    1.1104    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2135    0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984    2.9750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2415    2.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2415    0.9709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    0.8555    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3984    0.0709    0.0000 O   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
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  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
 12 11  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 12 21  1  0  0  0  0
 21 22  1  1  0  0  0
  5 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 25 28  1  0  0  0  0
  4 28  1  0  0  0  0
 28 29  1  6  0  0  0
M  END

     RDKit          3D

 59 61  0  0  0  0  0  0  0  0999 V2000
   -1.2799   -2.7083   -2.2514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8783   -1.5691   -1.5403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2802   -1.5433   -1.5052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9412   -0.5055   -0.8630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2046    0.4927   -0.2645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8218    0.4441   -0.3132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0670    1.5377    0.3493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1410   -0.5748   -0.9438 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3393   -0.6163   -0.9693 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8851   -1.5931    0.0452 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2450   -1.6867    0.0914 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9228   -0.5231    0.4119 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7106   -0.1958   -0.6584 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6610    0.7573   -0.3975 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3667    1.2169   -1.6472 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3094    2.1761   -1.2805 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6215    0.1666    0.6106 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.7892    0.8812    0.7253 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8323    0.1335    1.9263 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5954   -0.3031    2.9734 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6725   -0.8017    1.6958 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7612   -0.5397    2.7475 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1514    1.4521    0.3399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8831    2.6313    0.6500 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4438    0.6976    0.4802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4202   -0.1231    1.7618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6207    1.6107    0.5077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4087   -0.2409   -0.6805 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.9384    0.2952   -1.8461 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5196   -3.6429   -1.6737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2226   -2.6028   -2.4926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8209   -2.8023   -3.2409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8600   -2.3211   -1.9702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7137    1.9521    1.1748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1497    1.1913    0.8684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8313    2.3447   -0.3679 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7300    0.3785   -0.7654 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7591   -0.9257   -1.9502 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4402   -1.3967    1.0681 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4898   -2.5933   -0.2222 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2084    0.3310    0.5841 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1408    1.6214    0.0877 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9475    0.3326   -2.0320 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6739    1.6237   -2.3995 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7969    2.5204   -2.0708 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7860   -0.9140    0.3545 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5404    0.2970    0.4399 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4235    1.1590    2.0419 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1791    0.4339    3.2659 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0111   -1.8361    1.7213 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2820   -0.3952    3.5741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6734   -0.9209    1.7073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2859    0.5367    2.6440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4077   -0.6016    1.8707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3723    2.6856    0.3933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2943    1.2975   -0.3369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2097    1.4283    1.4237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8968   -1.2200   -0.4410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3820    1.0704   -2.0952 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  2  0
  5 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  1  0
 25 27  1  0
 25 28  1  0
 28 29  1  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
  8  2  1  0
 21 12  1  0
 28  4  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  3 33  1  0
 26 52  1  0
 26 53  1  0
 26 54  1  0
 27 55  1  0
 27 56  1  0
 27 57  1  0
 28 58  1  1
 29 59  1  0
  7 34  1  0
  7 35  1  0
  7 36  1  0
  9 37  1  0
  9 38  1  0
 10 39  1  0
 10 40  1  0
 12 41  1  1
 14 42  1  1
 15 43  1  0
 15 44  1  0
 16 45  1  0
 17 46  1  6
 18 47  1  0
 19 48  1  1
 20 49  1  0
 21 50  1  6
 22 51  1  0
M  END


  Mrv1652309082203122D          

 29 31  0  0  1  0            999 V2000
    2.7845    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9279    1.9354    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6424    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3569    1.9354    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.0714    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7858    1.9354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3569    1.1104    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.0714    0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6424    0.6979    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6424   -0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9279    1.1104    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2135    0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984    2.9750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2415    2.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2415    0.9709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    0.8555    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3984    0.0709    0.0000 O   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
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  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
 12 11  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 12 21  1  0  0  0  0
 21 22  1  1  0  0  0
  5 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 25 28  1  0  0  0  0
  4 28  1  0  0  0  0
 28 29  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0259353

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC2=C(C(=O)C(C)(C)[C@H]2O)C(C)=C1CCO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C21H30O8/c1-9-7-12-14(19(27)21(3,4)18(12)26)10(2)11(9)5-6-28-20-17(25)16(24)15(23)13(8-22)29-20/h7,13,15-18,20,22-26H,5-6,8H2,1-4H3/t13-,15-,16+,17-,18+,20-/m1/s1

> <INCHI_KEY>
TUGWHBZURNWRDG-LNZAMEHWSA-N

> <FORMULA>
C21H30O8

> <MOLECULAR_WEIGHT>
410.463

> <EXACT_MASS>
410.194067926

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
43.6991511943566

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S)-3-hydroxy-2,2,5,7-tetramethyl-6-(2-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}ethyl)-2,3-dihydro-1H-inden-1-one

> <JCHEM_LOGP>
0.6379715473333338

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.099084927919009

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.197763233735191

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810834118809577

> <JCHEM_POLAR_SURFACE_AREA>
136.68

> <JCHEM_REFRACTIVITY>
104.22930000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3S)-3-hydroxy-2,2,5,7-tetramethyl-6-(2-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}ethyl)-3H-inden-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0       5.198   1.303   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.864   2.073   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.530   1.303   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.197   2.073   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.197   3.613   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.530   4.383   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.530   5.923   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.864   3.613   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.198   4.383   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.531   3.613   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       7.865   4.383   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       9.199   3.613   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      10.533   4.383   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      11.866   3.613   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.200   4.383   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      14.534   3.613   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      11.866   2.073   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      13.200   1.303   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      10.533   1.303   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      10.533  -0.237   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       9.199   2.073   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       7.865   1.303   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -0.268   4.089   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -0.744   5.553   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -1.173   2.843   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.318   3.873   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.318   1.812   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.268   1.597   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -0.744   0.132   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   28                                                  
CONECT    5    4    6   23                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    2    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   21                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15                                                            
CONECT   17   14   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   12   22                                                  
CONECT   22   21                                                            
CONECT   23    5   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27   28                                             
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   25    4   29                                                  
CONECT   29   28                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   62    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₃₀O₈

Average Mass

410.4630 Da

Monoisotopic Mass

410.19407 Da

IUPAC Name

(3S)-3-hydroxy-2,2,5,7-tetramethyl-6-(2-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}ethyl)-2,3-dihydro-1H-inden-1-one

Traditional Name

(3S)-3-hydroxy-2,2,5,7-tetramethyl-6-(2-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}ethyl)-3H-inden-1-one

CAS Registry Number

Not Available

SMILES

CC1=CC2=C(C(=O)C(C)(C)[C@H]2O)C(C)=C1CCO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C21H30O8/c1-9-7-12-14(19(27)21(3,4)18(12)26)10(2)11(9)5-6-28-20-17(25)16(24)15(23)13(8-22)29-20/h7,13,15-18,20,22-26H,5-6,8H2,1-4H3/t13-,15-,16+,17-,18+,20-/m1/s1

InChI Key

TUGWHBZURNWRDG-LNZAMEHWSA-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

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

O-glycosyl compounds

Alternative Parents

Substituents

Hexose monosaccharide
Indanone
O-glycosyl compound
Indane
Aryl ketone
Aryl alkyl ketone
Benzenoid
Oxane
Monosaccharide
Secondary alcohol
Ketone
Polyol
Organoheterocyclic compound
Oxacycle
Acetal
Primary alcohol
Hydrocarbon derivative
Organic oxide
Alcohol
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	0.64	ChemAxon
pKa (Strongest Acidic)	12.2	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	136.68 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	104.23 m³·mol⁻¹	ChemAxon
Polarizability	43.7 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00021495

Chemspider ID

28425575

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

169738

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Chen Y, Liu S, Wang F: [Sesquiterpenoids of Coniogramme maxima]. Zhongguo Zhong Yao Za Zhi. 2012 Apr;37(7):946-50. [PubMed:22792795 ]
LOTUS database [Link]

Showing NP-Card for (3s)-3-hydroxy-2,2,5,7-tetramethyl-6-(2-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}ethyl)-3h-inden-1-one (NP0259353)

MOL for NP0259353 ((3s)-3-hydroxy-2,2,5,7-tetramethyl-6-(2-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}ethyl)-3h-inden-1-one)

3D MOL for NP0259353 ((3s)-3-hydroxy-2,2,5,7-tetramethyl-6-(2-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}ethyl)-3h-inden-1-one)

3D SDF for NP0259353 ((3s)-3-hydroxy-2,2,5,7-tetramethyl-6-(2-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}ethyl)-3h-inden-1-one)

3D-SDF for NP0259353 ((3s)-3-hydroxy-2,2,5,7-tetramethyl-6-(2-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}ethyl)-3h-inden-1-one)

PDB for NP0259353 ((3s)-3-hydroxy-2,2,5,7-tetramethyl-6-(2-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}ethyl)-3h-inden-1-one)

3D PDB for NP0259353 ((3s)-3-hydroxy-2,2,5,7-tetramethyl-6-(2-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}ethyl)-3h-inden-1-one)

SMILES for NP0259353 ((3s)-3-hydroxy-2,2,5,7-tetramethyl-6-(2-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}ethyl)-3h-inden-1-one)

INCHI for NP0259353 ((3s)-3-hydroxy-2,2,5,7-tetramethyl-6-(2-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}ethyl)-3h-inden-1-one)

Structure for NP0259353 ((3s)-3-hydroxy-2,2,5,7-tetramethyl-6-(2-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}ethyl)-3h-inden-1-one)

3D Structure for NP0259353 ((3s)-3-hydroxy-2,2,5,7-tetramethyl-6-(2-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}ethyl)-3h-inden-1-one)