NP-MRD: Showing NP-Card for (2r,3r,3ar,4s,7s,7ar)-3-(acetyloxy)-7,7a-dimethyl-4'-methylidene-2'-oxo-hexahydro-1h-spiro[indene-2,3'-oxolan]-4-yl (2z)-3-(methylsulfanyl)prop-2-enoate (NP0327556)

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Record Information

Version

1.0

Created at

2022-09-12 10:14:17 UTC

Updated at

2022-09-12 10:14:17 UTC

NP-MRD ID

NP0327556

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3r,3ar,4s,7s,7ar)-3-(acetyloxy)-7,7a-dimethyl-4'-methylidene-2'-oxo-hexahydro-1h-spiro[indene-2,3'-oxolan]-4-yl (2z)-3-(methylsulfanyl)prop-2-enoate

Description

Bakkenolide D belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. (2r,3r,3ar,4s,7s,7ar)-3-(acetyloxy)-7,7a-dimethyl-4'-methylidene-2'-oxo-hexahydro-1h-spiro[indene-2,3'-oxolan]-4-yl (2z)-3-(methylsulfanyl)prop-2-enoate is found in Petasites japonicus. It was first documented in 2011 (PMID: 20625987). Based on a literature review a small amount of articles have been published on Bakkenolide D (PMID: 32532086) (PMID: 23723093).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122212142D          

 28 30  0  0  1  0            999 V2000
    2.9285    1.8646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1834    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9680    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9680    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1834   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9285   -1.0396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6985    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2136   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5152   -0.8205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2136    1.0799    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4685    1.8646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9165    2.4777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1095    2.3061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1714    3.2623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  7  5  1  1  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 15 23  1  0  0  0  0
 23  9  1  6  0  0  0
 23 24  1  0  0  0  0
  7 24  1  0  0  0  0
 24 25  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
M  END

     RDKit          3D

 56 58  0  0  0  0  0  0  0  0999 V2000
    1.3570   -1.4649    2.5362 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6725   -0.3564    2.5091 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0862    0.9524    3.0839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1478    1.4509    3.5870 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2081    0.8171    2.9688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4012    0.9942    3.2467 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6737   -0.1032    1.9248 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5030   -1.3244    1.7359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8921   -1.3470    0.3037 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3160   -0.7714    0.1975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0070   -2.7270   -0.2933 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6784   -2.5810   -1.6432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6956   -3.4107   -0.4617 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4338   -2.5676   -0.8795 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2360   -1.1209   -1.0557 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4036   -0.4515   -0.5443 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2584    0.2893   -1.3363 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9637    0.3589   -2.5774 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4337    0.9668   -0.8358 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2391    1.6692   -1.6066 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9011    1.8215   -3.3728 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.9665    3.0840   -4.1143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9438   -0.4791   -0.4289 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5783    0.5881    0.5809 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5517    1.6051    0.4436 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2549    2.9058    0.1331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3467    3.9068    0.0086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0466    3.1948   -0.0352 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9697   -2.3705    2.0988 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3349   -1.5042    2.9996 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8304    0.8515    3.8879 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4524    1.6132    2.2538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4133   -1.1925    2.3949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0517   -2.2675    2.1004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0318   -1.5982    0.4039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5104    0.0058    0.9468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4453   -0.3604   -0.8406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7074   -3.2931    0.3547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7750   -2.4516   -1.5517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5277   -3.5283   -2.1998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2600   -1.7041   -2.1949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4513   -3.8594    0.5482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8247   -4.3106   -1.1151 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3368   -2.7679   -0.2204 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8019   -2.9901   -1.8714 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2572   -0.8699   -2.1616 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6663    0.8973    0.2121 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1199    2.1785   -1.2387 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5856    3.3711   -5.0978 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8850    3.9965   -3.4603 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0348    2.7348   -4.1282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5542    0.0021   -1.2636 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4506    0.9834    0.4058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1420    4.5166   -0.8985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3374    3.4193   -0.0877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4000    4.5985    0.8639 H   0  0  0  0  0  0  0  0  0  0  0  0
 22 21  1  0
 21 20  1  0
 20 19  2  0
 19 17  1  0
 17 18  2  0
 17 16  1  0
 16 15  1  0
 15 14  1  0
 14 13  1  0
 13 11  1  0
 11 12  1  0
 11  9  1  0
  9 10  1  1
  9  8  1  0
  8  7  1  0
  7 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  2  0
 24 23  1  0
  7  2  1  1
  2  1  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
 23 15  1  0
 23  9  1  0
  5  7  1  0
 22 49  1  0
 22 50  1  0
 22 51  1  0
 20 48  1  0
 19 47  1  0
 15 46  1  6
 14 44  1  0
 14 45  1  0
 13 42  1  0
 13 43  1  0
 11 38  1  1
 12 39  1  0
 12 40  1  0
 12 41  1  0
 10 35  1  0
 10 36  1  0
 10 37  1  0
  8 33  1  0
  8 34  1  0
 24 53  1  6
 27 54  1  0
 27 55  1  0
 27 56  1  0
 23 52  1  6
  1 29  1  0
  1 30  1  0
  3 31  1  0
  3 32  1  0
M  END


  Mrv1652309122212142D          

 28 30  0  0  1  0            999 V2000
    2.9285    1.8646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1834    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9680    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9680    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1834   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9285   -1.0396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6985    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2136   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5152   -0.8205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2136    1.0799    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4685    1.8646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9165    2.4777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1095    2.3061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1714    3.2623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  7  5  1  1  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 15 23  1  0  0  0  0
 23  9  1  6  0  0  0
 23 24  1  0  0  0  0
  7 24  1  0  0  0  0
 24 25  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0327556

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CS\C=C/C(=O)O[C@H]1CC[C@H](C)[C@@]2(C)C[C@]3([C@H](OC(C)=O)[C@@H]12)C(=C)COC3=O

> <INCHI_IDENTIFIER>
InChI=1S/C21H28O6S/c1-12-6-7-15(27-16(23)8-9-28-5)17-18(26-14(3)22)21(11-20(12,17)4)13(2)10-25-19(21)24/h8-9,12,15,17-18H,2,6-7,10-11H2,1,3-5H3/b9-8-/t12-,15-,17+,18+,20+,21+/m0/s1

> <INCHI_KEY>
LWHLMCCRIWZBQO-PDSBHGERSA-N

> <FORMULA>
C21H28O6S

> <MOLECULAR_WEIGHT>
408.51

> <EXACT_MASS>
408.160659796

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
41.88814409175175

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2R,3aR,4S,7S,7aR)-1-(acetyloxy)-3a,4-dimethyl-4'-methylidene-2'-oxo-octahydrospiro[indene-2,3'-oxolane]-7-yl (2Z)-3-(methylsulfanyl)prop-2-enoate

> <JCHEM_LOGP>
2.9630240479999994

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.513341891013879

> <JCHEM_POLAR_SURFACE_AREA>
78.9

> <JCHEM_REFRACTIVITY>
105.28519999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R,3aR,4S,7S,7aR)-3-(acetyloxy)-7,7a-dimethyl-4'-methylidene-2'-oxo-hexahydro-1H-spiro[indene-2,3'-oxolane]-4-yl (2Z)-3-(methylsulfanyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0       5.466   3.481   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.942   2.016   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.407   1.540   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       7.407   0.000   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       5.942  -0.476   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       5.466  -1.941   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       5.037   0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.132  -0.476   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.828  -1.532   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM   21  S   UNK     0      -2.667   6.160   0.000  0.00  0.00           S+0
HETATM   22  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.132   2.016   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       4.608   3.481   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       3.577   4.625   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.071   4.305   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       4.053   6.090   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    2    8   24                                             
CONECT    8    7    9                                                       
CONECT    9    8   10   11   23                                             
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   23                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23   15    9   24                                                  
CONECT   24   23    7   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   60    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₈O₆S

Average Mass

408.5100 Da

Monoisotopic Mass

408.16066 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CS\C=C/C(=O)O[C@H]1CC[C@H](C)[C@@]2(C)C[C@]3([C@H](OC(C)=O)[C@@H]12)C(=C)COC3=O

InChI Identifier

InChI=1S/C21H28O6S/c1-12-6-7-15(27-16(23)8-9-28-5)17-18(26-14(3)22)21(11-20(12,17)4)13(2)10-25-19(21)24/h8-9,12,15,17-18H,2,6-7,10-11H2,1,3-5H3/b9-8-/t12-,15-,17+,18+,20+,21+/m0/s1

InChI Key

LWHLMCCRIWZBQO-PDSBHGERSA-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
Petasites japonicus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene lactones

Alternative Parents

Substituents

Terpene lactone
Sesquiterpenoid
Tricarboxylic acid or derivatives
Gamma butyrolactone
Vinylogous thioester
Acrylic acid or derivatives
Tetrahydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Lactone
Thioenolether
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Sulfenyl compound
Hydrocarbon derivative
Organic oxide
Organosulfur compound
Organooxygen compound
Carbonyl group
Organic oxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00021355

Chemspider ID

34965596

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12299954

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Woo HS, Shin KC, Kim JY, Kim YS, Ban YJ, Oh YJ, Cho HJ, Oh DK, Kim DW: Bakkenolides and Caffeoylquinic Acids from the Aerial Portion of Petasites japonicus and Their Bacterial Neuraminidase Inhibition Ability. Biomolecules. 2020 Jun 10;10(6):888. doi: 10.3390/biom10060888. [PubMed:32532086 ]
Dai D, Pei L, Tang L, Chen F, Chen X: LC-MS/MS determination of bakkenolide D in rats plasma and its application in pharmacokinetic studies. Biomed Chromatogr. 2013 Sep;27(9):1200-7. doi: 10.1002/bmc.2927. Epub 2013 May 30. [PubMed:23723093 ]
Zhang FJ, Wang Q, Wang Y, Guo ML: Anti-allergic effects of total bakkenolides from Petasites tricholobus in ovalbumin-sensitized rats. Phytother Res. 2011 Jan;25(1):116-21. doi: 10.1002/ptr.3237. [PubMed:20625987 ]
LOTUS database [Link]

Showing NP-Card for (2r,3r,3ar,4s,7s,7ar)-3-(acetyloxy)-7,7a-dimethyl-4'-methylidene-2'-oxo-hexahydro-1h-spiro[indene-2,3'-oxolan]-4-yl (2z)-3-(methylsulfanyl)prop-2-enoate (NP0327556)

MOL for NP0327556 ((2r,3r,3ar,4s,7s,7ar)-3-(acetyloxy)-7,7a-dimethyl-4'-methylidene-2'-oxo-hexahydro-1h-spiro[indene-2,3'-oxolan]-4-yl (2z)-3-(methylsulfanyl)prop-2-enoate)

3D MOL for NP0327556 ((2r,3r,3ar,4s,7s,7ar)-3-(acetyloxy)-7,7a-dimethyl-4'-methylidene-2'-oxo-hexahydro-1h-spiro[indene-2,3'-oxolan]-4-yl (2z)-3-(methylsulfanyl)prop-2-enoate)

3D SDF for NP0327556 ((2r,3r,3ar,4s,7s,7ar)-3-(acetyloxy)-7,7a-dimethyl-4'-methylidene-2'-oxo-hexahydro-1h-spiro[indene-2,3'-oxolan]-4-yl (2z)-3-(methylsulfanyl)prop-2-enoate)

3D-SDF for NP0327556 ((2r,3r,3ar,4s,7s,7ar)-3-(acetyloxy)-7,7a-dimethyl-4'-methylidene-2'-oxo-hexahydro-1h-spiro[indene-2,3'-oxolan]-4-yl (2z)-3-(methylsulfanyl)prop-2-enoate)

PDB for NP0327556 ((2r,3r,3ar,4s,7s,7ar)-3-(acetyloxy)-7,7a-dimethyl-4'-methylidene-2'-oxo-hexahydro-1h-spiro[indene-2,3'-oxolan]-4-yl (2z)-3-(methylsulfanyl)prop-2-enoate)

3D PDB for NP0327556 ((2r,3r,3ar,4s,7s,7ar)-3-(acetyloxy)-7,7a-dimethyl-4'-methylidene-2'-oxo-hexahydro-1h-spiro[indene-2,3'-oxolan]-4-yl (2z)-3-(methylsulfanyl)prop-2-enoate)

SMILES for NP0327556 ((2r,3r,3ar,4s,7s,7ar)-3-(acetyloxy)-7,7a-dimethyl-4'-methylidene-2'-oxo-hexahydro-1h-spiro[indene-2,3'-oxolan]-4-yl (2z)-3-(methylsulfanyl)prop-2-enoate)

INCHI for NP0327556 ((2r,3r,3ar,4s,7s,7ar)-3-(acetyloxy)-7,7a-dimethyl-4'-methylidene-2'-oxo-hexahydro-1h-spiro[indene-2,3'-oxolan]-4-yl (2z)-3-(methylsulfanyl)prop-2-enoate)

Structure for NP0327556 ((2r,3r,3ar,4s,7s,7ar)-3-(acetyloxy)-7,7a-dimethyl-4'-methylidene-2'-oxo-hexahydro-1h-spiro[indene-2,3'-oxolan]-4-yl (2z)-3-(methylsulfanyl)prop-2-enoate)

3D Structure for NP0327556 ((2r,3r,3ar,4s,7s,7ar)-3-(acetyloxy)-7,7a-dimethyl-4'-methylidene-2'-oxo-hexahydro-1h-spiro[indene-2,3'-oxolan]-4-yl (2z)-3-(methylsulfanyl)prop-2-enoate)