NP-MRD: Showing NP-Card for (3as,4s,5r,6r,10r,11ar)-5-(acetyloxy)-6-hydroxy-6,10-dimethyl-3-methylidene-2,7-dioxo-3ah,4h,5h,10h,11h,11ah-cyclodeca[b]furan-4-yl (2e)-2-methylbut-2-enoate (NP0206260)

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Record Information

Version

2.0

Created at

2022-09-05 02:26:44 UTC

Updated at

2022-09-05 02:26:44 UTC

NP-MRD ID

NP0206260

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3as,4s,5r,6r,10r,11ar)-5-(acetyloxy)-6-hydroxy-6,10-dimethyl-3-methylidene-2,7-dioxo-3ah,4h,5h,10h,11h,11ah-cyclodeca[b]furan-4-yl (2e)-2-methylbut-2-enoate

Description

Calein C belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety. (3as,4s,5r,6r,10r,11ar)-5-(acetyloxy)-6-hydroxy-6,10-dimethyl-3-methylidene-2,7-dioxo-3ah,4h,5h,10h,11h,11ah-cyclodeca[b]furan-4-yl (2e)-2-methylbut-2-enoate is found in Brickellia cavanillesii. (3as,4s,5r,6r,10r,11ar)-5-(acetyloxy)-6-hydroxy-6,10-dimethyl-3-methylidene-2,7-dioxo-3ah,4h,5h,10h,11h,11ah-cyclodeca[b]furan-4-yl (2e)-2-methylbut-2-enoate was first documented in 2017 (PMID: 28216594). Based on a literature review a small amount of articles have been published on Calein C (PMID: 32630070) (PMID: 30399497) (PMID: 30405412) (PMID: 30399466).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052204262D          

 30 31  0  0  1  0            999 V2000
    1.8304   -1.8899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3460   -1.2458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1279   -0.4501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3561   -0.1588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8173    0.0031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4614   -0.5125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2755   -0.3788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5668    0.3930    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0440    1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3809    0.5267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9037   -0.1115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6124   -0.8834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1352   -1.5216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7983   -1.0170    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0713   -1.7956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5078   -1.4380    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5070   -1.7889    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0298   -2.4271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7384   -3.1990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2612   -3.8372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9243   -3.3326    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6929   -1.9226    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4015   -2.6944    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5874   -2.8281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0647   -2.1899    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2961   -3.5999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8189   -4.2381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4820   -3.7336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1907   -4.5054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1701   -1.2843    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  2  0  0  0  0
  3  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  6  0  0  0
 14 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 17 22  1  0  0  0  0
 22 23  1  1  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 28 29  1  0  0  0  0
 22 30  1  0  0  0  0
 30  2  1  1  0  0  0
  6 30  1  0  0  0  0
M  END

     RDKit          3D

 58 59  0  0  0  0  0  0  0  0999 V2000
    0.9920   -1.1973    2.4739 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0322   -1.7057    1.7878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7851   -2.8758    2.2045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4354   -3.7196    3.0731 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9597   -2.8438    1.4691 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0135   -1.5112    0.8982 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1227   -1.4544   -0.0474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8061   -1.4726   -1.4883 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3338   -2.7941   -2.1279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3782   -0.4100   -2.3217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9699    0.8229   -2.4777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8407    1.4044   -1.8336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7838    1.6018   -2.5677 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6507    1.8498   -0.4395 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9559    1.9971    0.3364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2459    3.2570   -0.5011 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6155    1.1384    0.3798 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4194    2.0163    0.8035 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6098    2.3557    2.1011 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7150    3.2875    2.5137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1696    1.8650    2.9512 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0952   -0.1523   -0.1407 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3397   -0.1729    0.0532 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2303   -0.1340   -1.0018 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7972   -0.0782   -2.1909 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6557   -0.1588   -0.7087 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1069   -0.2239    0.6914 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5716   -0.1246   -1.6648 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9941   -0.1533   -1.2800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6076   -1.3756    0.4612 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6208   -0.3536    2.2613 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2422   -1.6769    3.4445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1375   -0.8833    1.8305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8885   -0.6382    0.1249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7861   -2.3661    0.1489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7145   -1.6148   -1.6319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7027   -3.6224   -1.7735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2455   -2.6181   -3.2188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4020   -2.8853   -1.8913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3097   -0.6646   -2.9089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5582    1.4765   -3.2213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1384    2.9824    0.7501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8034    1.7164   -0.3301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9168    1.2798    1.1814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2773    3.1674   -0.7681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1346    0.8673    1.3499 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5867    3.0242    1.8866 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4466    4.3254    2.2957 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8763    3.1334    3.5847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1651   -0.1033   -1.2426 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6252    0.5714    1.3202 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8032   -1.2219    1.0849 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1836   -0.1186    0.8189 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2137   -0.0768   -2.6886 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2420   -1.0701   -0.7080 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3071    0.7664   -0.7272 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6144   -0.1869   -2.1991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2762   -2.2476   -0.1791 H   0  0  0  0  0  0  0  0  0  0  0  0
 29 28  1  0
 28 26  2  0
 26 27  1  0
 26 24  1  0
 24 25  2  0
 24 23  1  0
 23 22  1  0
 22 30  1  0
 30  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 14 16  1  6
 14 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
  6  5  1  0
  5  3  1  0
  3  4  2  0
  3  2  1  0
  2  1  2  3
 17 22  1  0
  2 30  1  0
 29 55  1  0
 29 56  1  0
 29 57  1  0
 28 54  1  0
 27 51  1  0
 27 52  1  0
 27 53  1  0
 22 50  1  6
 30 58  1  6
  6 33  1  1
  7 34  1  0
  7 35  1  0
  8 36  1  1
  9 37  1  0
  9 38  1  0
  9 39  1  0
 10 40  1  0
 11 41  1  0
 15 42  1  0
 15 43  1  0
 15 44  1  0
 16 45  1  0
 17 46  1  1
 20 47  1  0
 20 48  1  0
 20 49  1  0
  1 31  1  0
  1 32  1  0
M  END


  Mrv1652309052204262D          

 30 31  0  0  1  0            999 V2000
    1.8304   -1.8899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3460   -1.2458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1279   -0.4501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3561   -0.1588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8173    0.0031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4614   -0.5125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2755   -0.3788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5668    0.3930    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0440    1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3809    0.5267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9037   -0.1115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6124   -0.8834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1352   -1.5216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7983   -1.0170    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0713   -1.7956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5078   -1.4380    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5070   -1.7889    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0298   -2.4271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7384   -3.1990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2612   -3.8372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9243   -3.3326    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6929   -1.9226    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4015   -2.6944    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5874   -2.8281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0647   -2.1899    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2961   -3.5999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8189   -4.2381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4820   -3.7336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1907   -4.5054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1701   -1.2843    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  2  0  0  0  0
  3  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  6  0  0  0
 14 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 17 22  1  0  0  0  0
 22 23  1  1  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 28 29  1  0  0  0  0
 22 30  1  0  0  0  0
 30  2  1  1  0  0  0
  6 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0206260

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C(/C)C(=O)O[C@H]1[C@@H]2[C@@H](C[C@@H](C)\C=C/C(=O)[C@](C)(O)[C@@H]1OC(C)=O)OC(=O)C2=C

> <INCHI_IDENTIFIER>
InChI=1S/C22H28O8/c1-7-12(3)20(25)30-18-17-13(4)21(26)29-15(17)10-11(2)8-9-16(24)22(6,27)19(18)28-14(5)23/h7-9,11,15,17-19,27H,4,10H2,1-3,5-6H3/b9-8-,12-7+/t11-,15+,17-,18-,19+,22-/m0/s1

> <INCHI_KEY>
DXPFQBFCOCKNEU-RMCHFIGYSA-N

> <FORMULA>
C22H28O8

> <MOLECULAR_WEIGHT>
420.458

> <EXACT_MASS>
420.178417862

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
41.95088859909508

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3aS,4S,5R,6R,10R,11aR)-5-(acetyloxy)-6-hydroxy-6,10-dimethyl-3-methylidene-2,7-dioxo-2H,3H,3aH,4H,5H,6H,7H,10H,11H,11aH-cyclodeca[b]furan-4-yl (2E)-2-methylbut-2-enoate

> <JCHEM_LOGP>
3.110516940666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.18777321572882

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.220289643018246

> <JCHEM_PKA_STRONGEST_BASIC>
-4.014645015696737

> <JCHEM_POLAR_SURFACE_AREA>
116.20000000000002

> <JCHEM_REFRACTIVITY>
107.3975

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3aS,4S,5R,6R,10R,11aR)-5-(acetyloxy)-6-hydroxy-6,10-dimethyl-3-methylidene-2,7-dioxo-3aH,4H,5H,10H,11H,11aH-cyclodeca[b]furan-4-yl (2E)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       3.417  -3.528   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.379  -2.326   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.972  -0.840   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.531  -0.296   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       5.259   0.006   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       6.461  -0.957   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.981  -0.707   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.525   0.734   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.549   1.925   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.044   0.983   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.020  -0.208   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.476  -1.649   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      11.452  -2.840   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       8.957  -1.898   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.466  -3.352   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      10.281  -2.684   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       8.413  -3.339   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       9.389  -4.531   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       8.845  -5.971   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.821  -7.163   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       7.325  -6.221   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       6.893  -3.589   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.350  -5.030   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       4.830  -5.279   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       3.854  -4.088   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       4.286  -6.720   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.262  -7.911   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.766  -6.969   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.223  -8.410   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.917  -2.397   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   30                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   30                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16   17                                             
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   14   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   17   23   30                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28                                                            
CONECT   30   22    2    6                                                  
MASTER        0    0    0    0    0    0    0    0   30    0   62    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₈O₈

Average Mass

420.4580 Da

Monoisotopic Mass

420.17842 Da

IUPAC Name

(3aS,4S,5R,6R,10R,11aR)-5-(acetyloxy)-6-hydroxy-6,10-dimethyl-3-methylidene-2,7-dioxo-2H,3H,3aH,4H,5H,6H,7H,10H,11H,11aH-cyclodeca[b]furan-4-yl (2E)-2-methylbut-2-enoate

Traditional Name

(3aS,4S,5R,6R,10R,11aR)-5-(acetyloxy)-6-hydroxy-6,10-dimethyl-3-methylidene-2,7-dioxo-3aH,4H,5H,10H,11H,11aH-cyclodeca[b]furan-4-yl (2E)-2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

C\C=C(/C)C(=O)O[C@H]1[C@@H]2[C@@H](C[C@@H](C)\C=C/C(=O)[C@](C)(O)[C@@H]1OC(C)=O)OC(=O)C2=C

InChI Identifier

InChI=1S/C22H28O8/c1-7-12(3)20(25)30-18-17-13(4)21(26)29-15(17)10-11(2)8-9-16(24)22(6,27)19(18)28-14(5)23/h7-9,11,15,17-19,27H,4,10H2,1-3,5-6H3/b9-8-,12-7+/t11-,15+,17-,18-,19+,22-/m0/s1

InChI Key

DXPFQBFCOCKNEU-RMCHFIGYSA-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
Brickellia cavanillesii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Germacranolides and derivatives

Alternative Parents

Substituents

Germacranolide
Germacrane sesquiterpenoid
Sesquiterpenoid
Tricarboxylic acid or derivatives
Fatty acid ester
Fatty acyl
Acyloin
Gamma butyrolactone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Tertiary alcohol
Carboxylic acid ester
Cyclic ketone
Ketone
Lactone
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
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	3.11	ChemAxon
pKa (Strongest Acidic)	12.22	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	116.2 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	107.4 m³·mol⁻¹	ChemAxon
Polarizability	41.95 Å³	ChemAxon
Number of Rings	2	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

C00012308

Chemspider ID

28506490

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

66551442

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Caldas LA, Rodrigues MT, Batista ANL, Batista JM Jr, Lago JHG, Ferreira MJP, Rubio IGS, Sartorelli P: Sesquiterpene Lactones from Calea pinnatifida: Absolute Configuration and Structural Requirements for Antitumor Activity. Molecules. 2020 Jun 30;25(13):3005. doi: 10.3390/molecules25133005. [PubMed:32630070 ]
Gogineni V, Nael MA, Leon F, Nunez MJ, Cutler SJ: Computationally aided stereochemical assignment of undescribed bisabolenes from Calea urticifolia. Phytochemistry. 2019 Jan;157:145-150. doi: 10.1016/j.phytochem.2018.10.022. Epub 2018 Nov 3. [PubMed:30399497 ]
Caldas LA, Horvath RO, Ferreira-Silva GA, Ferreira MJP, Ionta M, Sartorelli P: Calein C, a Sesquiterpene Lactone Isolated From Calea Pinnatifida (Asteraceae), Inhibits Mitotic Progression and Induces Apoptosis in MCF-7 Cells. Front Pharmacol. 2018 Oct 18;9:1191. doi: 10.3389/fphar.2018.01191. eCollection 2018. [PubMed:30405412 ]
Caldas LA, Yoshinaga ML, Ferreira MJP, Lago JHG, de Souza AB, Laurenti MD, Passero LFD, Sartorelli P: Antileishmanial activity and ultrastructural changes of sesquiterpene lactones isolated from Calea pinnatifida (Asteraceae). Bioorg Chem. 2019 Mar;83:348-353. doi: 10.1016/j.bioorg.2018.10.059. Epub 2018 Oct 30. [PubMed:30399466 ]
Escandon-Rivera S, Perez-Vasquez A, Navarrete A, Hernandez M, Linares E, Bye R, Mata R: Anti-Hyperglycemic Activity of Major Compounds from Calea ternifolia. Molecules. 2017 Feb 14;22(2):289. doi: 10.3390/molecules22020289. [PubMed:28216594 ]
LOTUS database [Link]

Showing NP-Card for (3as,4s,5r,6r,10r,11ar)-5-(acetyloxy)-6-hydroxy-6,10-dimethyl-3-methylidene-2,7-dioxo-3ah,4h,5h,10h,11h,11ah-cyclodeca[b]furan-4-yl (2e)-2-methylbut-2-enoate (NP0206260)

MOL for NP0206260 ((3as,4s,5r,6r,10r,11ar)-5-(acetyloxy)-6-hydroxy-6,10-dimethyl-3-methylidene-2,7-dioxo-3ah,4h,5h,10h,11h,11ah-cyclodeca[b]furan-4-yl (2e)-2-methylbut-2-enoate)

3D MOL for NP0206260 ((3as,4s,5r,6r,10r,11ar)-5-(acetyloxy)-6-hydroxy-6,10-dimethyl-3-methylidene-2,7-dioxo-3ah,4h,5h,10h,11h,11ah-cyclodeca[b]furan-4-yl (2e)-2-methylbut-2-enoate)

3D SDF for NP0206260 ((3as,4s,5r,6r,10r,11ar)-5-(acetyloxy)-6-hydroxy-6,10-dimethyl-3-methylidene-2,7-dioxo-3ah,4h,5h,10h,11h,11ah-cyclodeca[b]furan-4-yl (2e)-2-methylbut-2-enoate)

3D-SDF for NP0206260 ((3as,4s,5r,6r,10r,11ar)-5-(acetyloxy)-6-hydroxy-6,10-dimethyl-3-methylidene-2,7-dioxo-3ah,4h,5h,10h,11h,11ah-cyclodeca[b]furan-4-yl (2e)-2-methylbut-2-enoate)

PDB for NP0206260 ((3as,4s,5r,6r,10r,11ar)-5-(acetyloxy)-6-hydroxy-6,10-dimethyl-3-methylidene-2,7-dioxo-3ah,4h,5h,10h,11h,11ah-cyclodeca[b]furan-4-yl (2e)-2-methylbut-2-enoate)

3D PDB for NP0206260 ((3as,4s,5r,6r,10r,11ar)-5-(acetyloxy)-6-hydroxy-6,10-dimethyl-3-methylidene-2,7-dioxo-3ah,4h,5h,10h,11h,11ah-cyclodeca[b]furan-4-yl (2e)-2-methylbut-2-enoate)

SMILES for NP0206260 ((3as,4s,5r,6r,10r,11ar)-5-(acetyloxy)-6-hydroxy-6,10-dimethyl-3-methylidene-2,7-dioxo-3ah,4h,5h,10h,11h,11ah-cyclodeca[b]furan-4-yl (2e)-2-methylbut-2-enoate)

INCHI for NP0206260 ((3as,4s,5r,6r,10r,11ar)-5-(acetyloxy)-6-hydroxy-6,10-dimethyl-3-methylidene-2,7-dioxo-3ah,4h,5h,10h,11h,11ah-cyclodeca[b]furan-4-yl (2e)-2-methylbut-2-enoate)

Structure for NP0206260 ((3as,4s,5r,6r,10r,11ar)-5-(acetyloxy)-6-hydroxy-6,10-dimethyl-3-methylidene-2,7-dioxo-3ah,4h,5h,10h,11h,11ah-cyclodeca[b]furan-4-yl (2e)-2-methylbut-2-enoate)

3D Structure for NP0206260 ((3as,4s,5r,6r,10r,11ar)-5-(acetyloxy)-6-hydroxy-6,10-dimethyl-3-methylidene-2,7-dioxo-3ah,4h,5h,10h,11h,11ah-cyclodeca[b]furan-4-yl (2e)-2-methylbut-2-enoate)