NP-MRD: Showing NP-Card for (3s,3ar,4s,6s,7r,7as)-6-ethenyl-4-hydroxy-3,6-dimethyl-7-[(1e)-1-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}prop-1-en-2-yl]-hexahydro-1-benzofuran-2-one (NP0176183)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-03 13:48:12 UTC

Updated at

2022-09-03 13:48:12 UTC

NP-MRD ID

NP0176183

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3s,3ar,4s,6s,7r,7as)-6-ethenyl-4-hydroxy-3,6-dimethyl-7-[(1e)-1-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}prop-1-en-2-yl]-hexahydro-1-benzofuran-2-one

Description

(3S,3aR,4S,6S,7R,7aS)-6-ethenyl-4-hydroxy-3,6-dimethyl-7-[(1E)-1-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}prop-1-en-2-yl]-octahydro-1-benzofuran-2-one belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated. (3s,3ar,4s,6s,7r,7as)-6-ethenyl-4-hydroxy-3,6-dimethyl-7-[(1e)-1-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}prop-1-en-2-yl]-hexahydro-1-benzofuran-2-one is found in Cichorium endivia. Based on a literature review very few articles have been published on (3S,3aR,4S,6S,7R,7aS)-6-ethenyl-4-hydroxy-3,6-dimethyl-7-[(1E)-1-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}prop-1-en-2-yl]-octahydro-1-benzofuran-2-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032215482D          

 30 32  0  0  1  0            999 V2000
    4.4469    1.0169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1648    1.7922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6345    2.7107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6378   -0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8838    0.0709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    4.4104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    4.8229    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0668    5.6479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    6.0604    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7812    6.8854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    7.2979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    5.6479    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2102    6.0604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    4.8229    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2102    4.4104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    4.4104    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7812    3.5854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  1  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 14 13  1  1  0  0  0
  8 14  1  0  0  0  0
 14 15  1  0  0  0  0
  3 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 18 19  1  0  0  0  0
 20 19  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  6  0  0  0
 23 24  1  0  0  0  0
 22 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 20 29  1  0  0  0  0
 29 30  1  1  0  0  0
M  END

     RDKit          3D

 62 64  0  0  0  0  0  0  0  0999 V2000
   -2.9374   -3.3975   -1.0896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6191   -2.1324   -1.2731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1143   -1.3392   -0.0937 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0152   -2.1381    0.5286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2841   -1.2857    0.8753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4823   -0.6033    0.2622 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0738   -1.4545   -0.6732 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1193    0.6754   -0.4449 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.8731    1.7950    0.2892 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.1021    2.9297   -0.6538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8855    2.1448    1.3332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1380    2.8656    2.3255 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6500    1.5723    1.0695 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7055    1.0922   -0.2555 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6793    0.0261   -0.5509 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4058    0.4677    0.0132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1437    0.6331    1.4707 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6026    0.7476   -0.7961 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8390    1.1730   -0.3085 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9429    0.3305   -0.1858 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9997    1.1016    0.3351 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0922    0.2860    0.6357 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1928    1.1912    1.1384 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2938    0.4208    1.4472 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4892   -0.5200   -0.5624 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9989   -1.8204   -0.3740 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7614    0.0367   -1.7804 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9248    1.4121   -1.8317 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2826   -0.2277   -1.5502 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0980   -1.6206   -1.5049 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2978   -3.9697   -1.9248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8423   -3.8721   -0.1113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7113   -1.6602   -2.2360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9427   -3.1614    0.1057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1635   -2.2842    1.6289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0473   -1.6451    0.3073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5867   -2.3571    1.0335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0246   -0.8914    1.8553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2287   -0.4658    1.0705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3971   -0.9398   -1.4564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4638    0.7063   -1.4933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8032    1.3751    0.7137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2431    2.5526   -1.7042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9696    3.5368   -0.3719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1947    3.5879   -0.6088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5062    1.9514   -0.9274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5870   -0.0051   -1.6558 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7789    0.0596    1.7808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9701    0.3210    2.1058 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0904    1.6956    1.7332 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5215    0.6616   -1.8721 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7718   -0.4846    0.5591 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7644   -0.3526    1.5009 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3693    1.9506    0.3714 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8179    1.6785    2.0605 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0921    0.7631    0.9902 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5882   -0.5321   -0.7280 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5476   -2.3402    0.2454 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0672   -0.4695   -2.7112 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0888    1.8836   -2.1004 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6635    0.1936   -2.3517 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5288   -1.8484   -0.7312 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  9  1  0
  9  8  1  0
  8 14  1  0
 14 13  1  0
 13 11  1  0
 11 12  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 22 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
 15  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  3  2  1  6
  2  1  2  3
 11  9  1  0
 29 20  1  0
  6  8  1  0
 10 43  1  0
 10 44  1  0
 10 45  1  0
  9 42  1  1
  8 41  1  6
 14 46  1  6
 15 47  1  6
 17 48  1  0
 17 49  1  0
 17 50  1  0
 18 51  1  0
 20 52  1  1
 22 53  1  1
 23 54  1  0
 23 55  1  0
 24 56  1  0
 25 57  1  6
 26 58  1  0
 27 59  1  6
 28 60  1  0
 29 61  1  6
 30 62  1  0
  4 34  1  0
  4 35  1  0
  4 36  1  0
  5 37  1  0
  5 38  1  0
  6 39  1  1
  7 40  1  0
  2 33  1  0
  1 31  1  0
  1 32  1  0
M  END


  Mrv1652309032215482D          

 30 32  0  0  1  0            999 V2000
    4.4469    1.0169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1648    1.7922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6345    2.7107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6378   -0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8838    0.0709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    4.4104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    4.8229    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0668    5.6479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    6.0604    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7812    6.8854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    7.2979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    5.6479    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2102    6.0604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    4.8229    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2102    4.4104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    4.4104    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7812    3.5854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  1  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 14 13  1  1  0  0  0
  8 14  1  0  0  0  0
 14 15  1  0  0  0  0
  3 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 18 19  1  0  0  0  0
 20 19  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  6  0  0  0
 23 24  1  0  0  0  0
 22 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 20 29  1  0  0  0  0
 29 30  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0176183

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1[C@H]2[C@@H](OC1=O)[C@@H](\C(C)=C\O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)[C@@](C)(C[C@@H]2O)C=C

> <INCHI_IDENTIFIER>
InChI=1S/C21H32O9/c1-5-21(4)6-11(23)13-10(3)19(27)30-18(13)14(21)9(2)8-28-20-17(26)16(25)15(24)12(7-22)29-20/h5,8,10-18,20,22-26H,1,6-7H2,2-4H3/b9-8+/t10-,11-,12+,13+,14+,15+,16-,17+,18+,20+,21+/m0/s1

> <INCHI_KEY>
PNUZTGLWURTQTO-XJCQEDGZSA-N

> <FORMULA>
C21H32O9

> <MOLECULAR_WEIGHT>
428.478

> <EXACT_MASS>
428.20463261

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
44.24171402818212

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S,3aR,4S,6S,7R,7aS)-6-ethenyl-4-hydroxy-3,6-dimethyl-7-[(1E)-1-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}prop-1-en-2-yl]-octahydro-1-benzofuran-2-one

> <ALOGPS_LOGP>
-0.21

> <JCHEM_LOGP>
-0.7826967669999999

> <ALOGPS_LOGS>
-1.92

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.187080358631967

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.200123943726515

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8824751447891837

> <JCHEM_POLAR_SURFACE_AREA>
145.91000000000003

> <JCHEM_REFRACTIVITY>
104.12500000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.17e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S,3aR,4S,6S,7R,7aS)-6-ethenyl-4-hydroxy-3,6-dimethyl-7-[(1E)-1-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}prop-1-en-2-yl]-hexahydro-1-benzofuran-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       8.301   1.898   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.774   3.345   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.784   5.060   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.924  -0.237   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.126   1.597   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.650   0.132   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.320   2.843   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       2.126   4.089   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.924   5.923   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.590   6.693   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.258   6.693   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       6.258   8.233   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       7.591   9.003   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       7.591  10.543   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       8.925  11.313   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.925  12.853   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       7.591  13.623   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      10.259  10.543   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      11.592  11.313   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      10.259   9.003   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      11.592   8.233   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       8.925   8.233   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       8.925   6.693   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5   15                                             
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   14                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13    8   15                                                  
CONECT   15   14    3   16                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   29                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   25                                                  
CONECT   23   22   24                                                       
CONECT   24   23                                                            
CONECT   25   22   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   20   30                                                  
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₃₂O₉

Average Mass

428.4780 Da

Monoisotopic Mass

428.20463 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@H]1[C@H]2[C@@H](OC1=O)[C@@H](\C(C)=C\O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)[C@@](C)(C[C@@H]2O)C=C

InChI Identifier

InChI=1S/C21H32O9/c1-5-21(4)6-11(23)13-10(3)19(27)30-18(13)14(21)9(2)8-28-20-17(26)16(25)15(24)12(7-22)29-20/h5,8,10-18,20,22-26H,1,6-7H2,2-4H3/b9-8+/t10-,11-,12+,13+,14+,15+,16-,17+,18+,20+,21+/m0/s1

InChI Key

PNUZTGLWURTQTO-XJCQEDGZSA-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
Cichorium endivia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Diterpene glycosides

Alternative Parents

Substituents

Diterpene glycoside
Diterpenoid
Diterpene lactone
Elemanolide-skeleton
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
Benzofuran
Oxane
Monosaccharide
Gamma butyrolactone
Tetrahydrofuran
Cyclic alcohol
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
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	-0.21	ALOGPS
logS	-1.9	ALOGPS

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

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

162851294

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3s,3ar,4s,6s,7r,7as)-6-ethenyl-4-hydroxy-3,6-dimethyl-7-[(1e)-1-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}prop-1-en-2-yl]-hexahydro-1-benzofuran-2-one (NP0176183)

MOL for NP0176183 ((3s,3ar,4s,6s,7r,7as)-6-ethenyl-4-hydroxy-3,6-dimethyl-7-[(1e)-1-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}prop-1-en-2-yl]-hexahydro-1-benzofuran-2-one)

3D MOL for NP0176183 ((3s,3ar,4s,6s,7r,7as)-6-ethenyl-4-hydroxy-3,6-dimethyl-7-[(1e)-1-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}prop-1-en-2-yl]-hexahydro-1-benzofuran-2-one)

3D SDF for NP0176183 ((3s,3ar,4s,6s,7r,7as)-6-ethenyl-4-hydroxy-3,6-dimethyl-7-[(1e)-1-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}prop-1-en-2-yl]-hexahydro-1-benzofuran-2-one)

3D-SDF for NP0176183 ((3s,3ar,4s,6s,7r,7as)-6-ethenyl-4-hydroxy-3,6-dimethyl-7-[(1e)-1-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}prop-1-en-2-yl]-hexahydro-1-benzofuran-2-one)

PDB for NP0176183 ((3s,3ar,4s,6s,7r,7as)-6-ethenyl-4-hydroxy-3,6-dimethyl-7-[(1e)-1-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}prop-1-en-2-yl]-hexahydro-1-benzofuran-2-one)

3D PDB for NP0176183 ((3s,3ar,4s,6s,7r,7as)-6-ethenyl-4-hydroxy-3,6-dimethyl-7-[(1e)-1-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}prop-1-en-2-yl]-hexahydro-1-benzofuran-2-one)

SMILES for NP0176183 ((3s,3ar,4s,6s,7r,7as)-6-ethenyl-4-hydroxy-3,6-dimethyl-7-[(1e)-1-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}prop-1-en-2-yl]-hexahydro-1-benzofuran-2-one)

INCHI for NP0176183 ((3s,3ar,4s,6s,7r,7as)-6-ethenyl-4-hydroxy-3,6-dimethyl-7-[(1e)-1-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}prop-1-en-2-yl]-hexahydro-1-benzofuran-2-one)

Structure for NP0176183 ((3s,3ar,4s,6s,7r,7as)-6-ethenyl-4-hydroxy-3,6-dimethyl-7-[(1e)-1-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}prop-1-en-2-yl]-hexahydro-1-benzofuran-2-one)

3D Structure for NP0176183 ((3s,3ar,4s,6s,7r,7as)-6-ethenyl-4-hydroxy-3,6-dimethyl-7-[(1e)-1-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}prop-1-en-2-yl]-hexahydro-1-benzofuran-2-one)