NP-MRD: Showing NP-Card for (3ar,4s,6ar,8s,9ar,9br)-4-hydroxy-3,6,9-trimethylidene-8-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-octahydroazuleno[4,5-b]furan-2-one (NP0309841)

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Record Information

Version

2.0

Created at

2022-09-11 04:42:45 UTC

Updated at

2022-09-11 04:42:45 UTC

NP-MRD ID

NP0309841

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3ar,4s,6ar,8s,9ar,9br)-4-hydroxy-3,6,9-trimethylidene-8-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-octahydroazuleno[4,5-b]furan-2-one

Description

Crepiside E belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative. (3ar,4s,6ar,8s,9ar,9br)-4-hydroxy-3,6,9-trimethylidene-8-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-octahydroazuleno[4,5-b]furan-2-one is found in Elephantopus scaber, Lapsana communis and Youngia japonica. (3ar,4s,6ar,8s,9ar,9br)-4-hydroxy-3,6,9-trimethylidene-8-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-octahydroazuleno[4,5-b]furan-2-one was first documented in 2018 (PMID: 29935428). Based on a literature review a small amount of articles have been published on Crepiside E (PMID: 30847632) (PMID: 35621325).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112206422D          

 30 33  0  0  1  0            999 V2000
    1.8651    1.7897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5101    1.2753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2534    1.6333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9967    1.2753    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6417    1.7897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1803    0.4710    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9527    0.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6412    0.6356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9157   -0.6430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5607   -1.1574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1204   -0.8625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6659   -0.1740    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8409   -0.1740    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3864   -0.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6763   -1.6349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5912   -0.6430    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9461   -1.1574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1782   -0.8560    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4668   -1.3704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2348   -1.0690    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8798   -1.5834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7569   -2.3992    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3578   -0.2532    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1257    0.0482    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7128    0.2612    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8357    1.0770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0552   -0.0402    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7002    0.4741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5541    0.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3265    0.4710    0.0000 C   0  0  1  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  6  0  0  0
  4  6  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 12 11  1  6  0  0  0
  6 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  1  0  0  0
 18 17  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 25 26  1  6  0  0  0
 25 27  1  0  0  0  0
 18 27  1  0  0  0  0
 27 28  1  1  0  0  0
 16 29  1  0  0  0  0
 30 29  1  1  0  0  0
  2 30  1  0  0  0  0
 13 30  1  0  0  0  0
M  END

     RDKit          3D

 58 61  0  0  0  0  0  0  0  0999 V2000
    2.6581   -2.7007   -0.7959 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7787   -1.7814    0.1404 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1407   -1.6219    0.7043 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9160   -0.6631   -0.1946 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2623   -0.6776    0.0879 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3060    0.6979    0.0121 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0645    1.7070   -0.7467 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3501    2.0010   -0.7962 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0765    2.4462   -1.5433 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2440    3.2691   -2.4765 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7924    2.0828   -1.0864 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9233    0.7651   -0.5971 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8556    0.5047    0.4117 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5419    1.1083    0.0910 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2987    2.3888   -0.0882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4410    0.0055    0.0126 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4684    0.2414   -0.8852 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6840    0.0836   -0.1795 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3149   -1.0139   -0.7569 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4916   -1.2425   -0.0455 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0314   -2.6354   -0.2927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1977   -2.7778    0.4502 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4769   -0.1810   -0.4897 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.6962   -0.4254    0.1657 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9594    1.1655   -0.1397 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.5439    2.1239   -1.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4854    1.3369   -0.2127 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1024    2.1048    0.9124 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4371   -1.1548   -0.4073 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5815   -1.0022    0.5450 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5121   -3.2848   -1.1121 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7195   -2.9217   -1.2932 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1142   -1.1256    1.7175 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6647   -2.5733    0.8496 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6912   -0.9737   -1.2475 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3722   -0.8159    1.0610 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2105    0.9572    1.0899 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7511    2.7897   -1.4148 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0509    1.4587   -0.2101 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8341    0.0284   -1.4231 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1448    0.8722    1.4286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7210    2.7043   -0.3198 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0433    3.1719   -0.0210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8231   -0.2384    1.0331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5023   -0.1818    0.8824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2668   -1.0631    1.0154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2942   -3.3548    0.0910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2086   -2.8097   -1.3603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0724   -2.4041    1.3585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6044   -0.2956   -1.5833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1315    0.4471    0.2960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3702    1.4295    0.8785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2895    3.0066   -0.5886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1568    1.9483   -1.0975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9752    1.4487    1.6443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0846   -2.1297   -0.3251 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8269   -0.9708   -1.4382 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2307   -1.2746    1.5575 H   0  0  0  0  0  0  0  0  0  0  0  0
 22 21  1  0
 21 20  1  0
 20 19  1  0
 19 18  1  0
 18 17  1  0
 17 16  1  0
 16 29  1  0
 29 30  1  0
 30 13  1  0
 13 12  1  0
 12 11  1  0
 11  9  1  0
  9 10  2  0
  9  7  1  0
  7  8  2  3
  7  6  1  0
  6  4  1  0
  4  5  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  3
 13 14  1  0
 14 15  2  3
 18 27  1  0
 27 28  1  0
 27 25  1  0
 25 26  1  0
 25 23  1  0
 23 24  1  0
 23 20  1  0
 14 16  1  0
  2 30  1  0
  6 12  1  0
 22 49  1  0
 21 47  1  0
 21 48  1  0
 20 46  1  1
 18 45  1  1
 16 44  1  1
 29 56  1  0
 29 57  1  0
 30 58  1  1
 13 41  1  1
 12 40  1  6
  8 38  1  0
  8 39  1  0
  6 37  1  1
  4 35  1  6
  5 36  1  0
  3 33  1  0
  3 34  1  0
  1 31  1  0
  1 32  1  0
 15 42  1  0
 15 43  1  0
 27 54  1  6
 28 55  1  0
 25 52  1  1
 26 53  1  0
 23 50  1  6
 24 51  1  0
M  END


  Mrv1652309112206422D          

 30 33  0  0  1  0            999 V2000
    1.8651    1.7897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5101    1.2753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2534    1.6333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9967    1.2753    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6417    1.7897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1803    0.4710    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9527    0.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6412    0.6356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9157   -0.6430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5607   -1.1574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1204   -0.8625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6659   -0.1740    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8409   -0.1740    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3864   -0.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6763   -1.6349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5912   -0.6430    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9461   -1.1574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1782   -0.8560    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4668   -1.3704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2348   -1.0690    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8798   -1.5834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7569   -2.3992    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3578   -0.2532    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1257    0.0482    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7128    0.2612    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8357    1.0770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0552   -0.0402    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7002    0.4741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5541    0.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3265    0.4710    0.0000 C   0  0  1  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  6  0  0  0
  4  6  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 12 11  1  6  0  0  0
  6 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  1  0  0  0
 18 17  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 25 26  1  6  0  0  0
 25 27  1  0  0  0  0
 18 27  1  0  0  0  0
 27 28  1  1  0  0  0
 16 29  1  0  0  0  0
 30 29  1  1  0  0  0
  2 30  1  0  0  0  0
 13 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0309841

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H](O[C@H]2C[C@@H]3[C@@H]([C@H]4OC(=O)C(=C)[C@@H]4[C@@H](O)CC3=C)C2=C)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C21H28O9/c1-7-4-11(23)15-9(3)20(27)30-19(15)14-8(2)12(5-10(7)14)28-21-18(26)17(25)16(24)13(6-22)29-21/h10-19,21-26H,1-6H2/t10-,11-,12-,13+,14-,15+,16+,17-,18+,19+,21+/m0/s1

> <INCHI_KEY>
XNFZJASXPNFCQW-BHFRCIHZSA-N

> <FORMULA>
C21H28O9

> <MOLECULAR_WEIGHT>
424.446

> <EXACT_MASS>
424.173332482

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
42.662713107964585

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3aR,4S,6aR,8S,9aR,9bR)-4-hydroxy-3,6,9-trimethylidene-8-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dodecahydroazuleno[4,5-b]furan-2-one

> <JCHEM_LOGP>
-1.2715532953333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.18814502842616

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.208733952914569

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9243330447916067

> <JCHEM_POLAR_SURFACE_AREA>
145.91000000000003

> <JCHEM_REFRACTIVITY>
101.4709

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3aR,4S,6aR,8S,9aR,9bR)-4-hydroxy-3,6,9-trimethylidene-8-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-octahydroazuleno[4,5-b]furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       3.482   3.341   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.686   2.381   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.073   3.049   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.461   2.381   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       8.665   3.341   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       7.803   0.879   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.245   0.338   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.530   1.186   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.176  -1.200   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      10.380  -2.161   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       7.691  -1.610   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       6.843  -0.325   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.303  -0.325   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.455  -1.610   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.996  -3.052   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.970  -1.200   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.766  -2.161   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.333  -1.598   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -0.871  -2.558   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -2.305  -1.995   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.509  -2.956   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -3.279  -4.478   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -2.534  -0.473   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -3.968   0.090   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -1.330   0.488   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -1.560   2.010   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       0.103  -0.075   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       1.307   0.885   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       2.901   0.338   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.343   0.879   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   30                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   12                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11    6   13                                                  
CONECT   13   12   14   30                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   29                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   27                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   23                                                  
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23   20   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   18   28                                                  
CONECT   28   27                                                            
CONECT   29   16   30                                                       
CONECT   30   29    2   13                                                  
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₈O₉

Average Mass

424.4460 Da

Monoisotopic Mass

424.17333 Da

IUPAC Name

(3aR,4S,6aR,8S,9aR,9bR)-4-hydroxy-3,6,9-trimethylidene-8-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dodecahydroazuleno[4,5-b]furan-2-one

Traditional Name

(3aR,4S,6aR,8S,9aR,9bR)-4-hydroxy-3,6,9-trimethylidene-8-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-octahydroazuleno[4,5-b]furan-2-one

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@@H](O[C@H]2C[C@@H]3[C@@H]([C@H]4OC(=O)C(=C)[C@@H]4[C@@H](O)CC3=C)C2=C)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C21H28O9/c1-7-4-11(23)15-9(3)20(27)30-19(15)14-8(2)12(5-10(7)14)28-21-18(26)17(25)16(24)13(6-22)29-21/h10-19,21-26H,1-6H2/t10-,11-,12-,13+,14-,15+,16+,17-,18+,19+,21+/m0/s1

InChI Key

XNFZJASXPNFCQW-BHFRCIHZSA-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
Elephantopus scaber	LOTUS Database	35616633
Lapsana communis L.	LOTUS Database	35616633
Youngia japonica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Guaianolides and derivatives

Alternative Parents

Substituents

Guaianolide-skeleton
Terpene glycoside
Guaiane sesquiterpenoid
Sesquiterpenoid
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Gamma butyrolactone
Monosaccharide
Oxane
Tetrahydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Cyclic alcohol
Carboxylic acid ester
Secondary alcohol
Lactone
Monocarboxylic acid or derivatives
Acetal
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Polyol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Primary alcohol
Carbonyl group
Alcohol
Organooxygen 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
logP	-1.3	ChemAxon
pKa (Strongest Acidic)	12.21	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	145.91 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	101.47 m³·mol⁻¹	ChemAxon
Polarizability	42.66 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00020507

Chemspider ID

8020954

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9845240

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kumar MS, R A, Bhaskaran S, D DR, Nair AS, R SP: Molecular docking and dynamic studies of crepiside E beta glucopyranoside as an inhibitor of snake venom PLA2. J Mol Model. 2019 Mar 8;25(4):88. doi: 10.1007/s00894-019-3954-2. [PubMed:30847632 ]
Milutinovic VM, Matic IZ, Stanojkovic TP, Sokovic MD, Ciric AD, Usjak LJ, Niketic MS, Petrovic SD: Antimicrobial and Cytotoxic Activities of Selected Hieracium L. s. str. (Asteraceae) Extracts and Isolated Sesquiterpene Lactones. Chem Biodivers. 2022 Jul;19(7):e202200326. doi: 10.1002/cbdv.202200326. Epub 2022 Jun 8. [PubMed:35621325 ]
Milutinovic V, Niketic M, Krunic A, Nikolic D, Petkovic M, Usjak L, Petrovic S: Sesquiterpene lactones from the methanol extracts of twenty-eight Hieracium species from the Balkan Peninsula and their chemosystematic significance. Phytochemistry. 2018 Oct;154:19-30. doi: 10.1016/j.phytochem.2018.06.008. Epub 2018 Jun 20. [PubMed:29935428 ]
LOTUS database [Link]

Showing NP-Card for (3ar,4s,6ar,8s,9ar,9br)-4-hydroxy-3,6,9-trimethylidene-8-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-octahydroazuleno[4,5-b]furan-2-one (NP0309841)

MOL for NP0309841 ((3ar,4s,6ar,8s,9ar,9br)-4-hydroxy-3,6,9-trimethylidene-8-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-octahydroazuleno[4,5-b]furan-2-one)

3D MOL for NP0309841 ((3ar,4s,6ar,8s,9ar,9br)-4-hydroxy-3,6,9-trimethylidene-8-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-octahydroazuleno[4,5-b]furan-2-one)

3D SDF for NP0309841 ((3ar,4s,6ar,8s,9ar,9br)-4-hydroxy-3,6,9-trimethylidene-8-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-octahydroazuleno[4,5-b]furan-2-one)

3D-SDF for NP0309841 ((3ar,4s,6ar,8s,9ar,9br)-4-hydroxy-3,6,9-trimethylidene-8-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-octahydroazuleno[4,5-b]furan-2-one)

PDB for NP0309841 ((3ar,4s,6ar,8s,9ar,9br)-4-hydroxy-3,6,9-trimethylidene-8-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-octahydroazuleno[4,5-b]furan-2-one)

3D PDB for NP0309841 ((3ar,4s,6ar,8s,9ar,9br)-4-hydroxy-3,6,9-trimethylidene-8-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-octahydroazuleno[4,5-b]furan-2-one)

SMILES for NP0309841 ((3ar,4s,6ar,8s,9ar,9br)-4-hydroxy-3,6,9-trimethylidene-8-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-octahydroazuleno[4,5-b]furan-2-one)

INCHI for NP0309841 ((3ar,4s,6ar,8s,9ar,9br)-4-hydroxy-3,6,9-trimethylidene-8-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-octahydroazuleno[4,5-b]furan-2-one)

Structure for NP0309841 ((3ar,4s,6ar,8s,9ar,9br)-4-hydroxy-3,6,9-trimethylidene-8-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-octahydroazuleno[4,5-b]furan-2-one)

3D Structure for NP0309841 ((3ar,4s,6ar,8s,9ar,9br)-4-hydroxy-3,6,9-trimethylidene-8-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-octahydroazuleno[4,5-b]furan-2-one)