NP-MRD: Showing NP-Card for [4R-(4R*,6S*,7R*,10R*)]-4,6-bis(Acetyloxy)-3-[(acetyloxy)methyl]-5,6,7,8,9,10-hexahydro-7-hydroxy-6,10-dimethyl-7,10-epoxycyclodeca[b]furan-2(4H)-one (NP0058705)

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Record Information

Version

2.0

Created at

2022-04-28 04:02:24 UTC

Updated at

2022-04-28 04:02:24 UTC

NP-MRD ID

NP0058705

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[4R-(4R*,6S*,7R*,10R*)]-4,6-bis(Acetyloxy)-3-[(acetyloxy)methyl]-5,6,7,8,9,10-hexahydro-7-hydroxy-6,10-dimethyl-7,10-epoxycyclodeca[b]furan-2(4H)-one

Description

[(1S,8S,10R,11R)-8,10-bis(acetyloxy)-11-hydroxy-1,10-dimethyl-5-oxo-4,14-dioxatricyclo[9.2.1.0³,⁷]Tetradeca-2,6-dien-6-yl]methyl acetate belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups. [4R-(4R*,6S*,7R*,10R*)]-4,6-bis(Acetyloxy)-3-[(acetyloxy)methyl]-5,6,7,8,9,10-hexahydro-7-hydroxy-6,10-dimethyl-7,10-epoxycyclodeca[b]furan-2(4H)-one is found in Stokesia laevis. Based on a literature review very few articles have been published on [(1S,8S,10R,11R)-8,10-bis(acetyloxy)-11-hydroxy-1,10-dimethyl-5-oxo-4,14-dioxatricyclo[9.2.1.0³,⁷]Tetradeca-2,6-dien-6-yl]methyl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282206022D          

 31 33  0  0  1  0            999 V2000
    1.2820   -0.3044    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1022   -0.3924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8176    0.0184    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1549    0.7714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9752    0.6833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3124    1.4362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1198    1.6059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7006    1.9896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9852    1.5787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3733    2.1321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5530    2.2202    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8376    1.8093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5004    1.0564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6701    0.2490    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3580    1.1243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0453   -0.1619    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3833    3.0276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3861   -0.0321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2111   -0.0340    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6220   -0.7494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4470   -0.7512    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2079   -1.4629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4295   -0.5350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2562   -1.3415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8680   -1.8950    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4710   -1.5947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2974   -1.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6562   -0.8420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8090   -1.6528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1833   -2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5875   -1.9258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  1 14  1  0  0  0  0
 14 15  1  0  0  0  0
 11 15  1  0  0  0  0
 14 16  1  6  0  0  0
 11 17  1  6  0  0  0
  5 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
  3 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
  1 27  1  6  0  0  0
  1 28  1  1  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
M  END

     RDKit          3D

 57 59  0  0  0  0  0  0  0  0999 V2000
    5.5763    2.0759    1.9042 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9694    1.3582    0.7747 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3772    1.5975   -0.4007 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9627    0.4189    0.9024 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4109   -0.2476   -0.2354 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3628   -1.1808    0.2531 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0549   -1.2062   -0.0449 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4628   -2.2902    0.6595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7882   -2.7165    0.6922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9443   -2.1294    1.4143 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1782   -2.9939    2.6819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1980   -2.1203    0.5882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5432   -0.6797    0.4313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5073    0.0349    1.2233 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0610    0.9834    2.0715 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7372   -0.8595    1.8959 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5236    0.8122    0.3104 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4338    1.2198    1.2655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3236    1.8991   -0.1122 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9376    2.8979   -0.9808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8852    4.0090   -1.3578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7815    2.8429   -1.4367 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0544   -0.0709   -0.8020 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4012   -0.2457   -0.9727 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5764   -0.6797   -2.3390 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1473    0.0822   -3.3187 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3270   -0.3837   -4.7239 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5584    1.2431   -3.0724 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4910   -2.9253    1.4032 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6435   -2.2481    1.1540 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7804   -2.5482    1.6638 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9143    3.0763    1.5419 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8342    2.1815    2.7104 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4572    1.5216    2.3290 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2386   -0.8519   -0.7024 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0573    0.4472   -0.9893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0497   -3.6377    0.1373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2405   -3.0592    2.9203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6552   -2.5478    3.5497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7005   -3.9988    2.5305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1331   -2.7014   -0.3533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9998   -2.6502    1.1909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5382   -0.4989    0.8867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6217   -0.3466   -0.6209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7957    1.4851    1.6616 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3692    1.8075    0.7975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0791    0.3241    1.8002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9028    1.8764    2.0291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6395    4.8376   -0.6313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7449    4.3221   -2.3977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9047    3.6840   -1.1131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3901    0.4774   -1.7462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5601   -1.0300   -0.8931 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8662    0.7470   -0.9202 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8408   -1.3590   -4.8187 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7844    0.3274   -5.3740 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3882   -0.3831   -5.0173 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7 24  1  0
 24 23  1  0
 23 17  1  0
 17 18  1  0
 17 19  1  6
 19 20  1  0
 20 21  1  0
 20 22  2  0
 17 14  1  0
 14 15  1  1
 14 13  1  0
 13 12  1  0
 12 10  1  0
 10 11  1  1
 10 16  1  0
 10  9  1  0
  9  8  2  0
  8 29  1  0
 29 30  1  0
 30 31  2  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  2  0
 30  6  1  0
  8  7  1  0
 16 14  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  5 35  1  0
  5 36  1  0
 24 54  1  6
 23 52  1  0
 23 53  1  0
 18 46  1  0
 18 47  1  0
 18 48  1  0
 21 49  1  0
 21 50  1  0
 21 51  1  0
 15 45  1  0
 13 43  1  0
 13 44  1  0
 12 41  1  0
 12 42  1  0
 11 38  1  0
 11 39  1  0
 11 40  1  0
  9 37  1  0
 27 55  1  0
 27 56  1  0
 27 57  1  0
M  END


  Mrv1652304282206022D          

 31 33  0  0  1  0            999 V2000
    1.2820   -0.3044    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1022   -0.3924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8176    0.0184    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1549    0.7714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9752    0.6833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3124    1.4362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1198    1.6059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7006    1.9896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9852    1.5787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3733    2.1321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5530    2.2202    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8376    1.8093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5004    1.0564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6701    0.2490    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3580    1.1243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0453   -0.1619    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3833    3.0276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3861   -0.0321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2111   -0.0340    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6220   -0.7494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4470   -0.7512    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2079   -1.4629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4295   -0.5350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2562   -1.3415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8680   -1.8950    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4710   -1.5947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2974   -1.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6562   -0.8420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8090   -1.6528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1833   -2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5875   -1.9258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  1 14  1  0  0  0  0
 14 15  1  0  0  0  0
 11 15  1  0  0  0  0
 14 16  1  6  0  0  0
 11 17  1  6  0  0  0
  5 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
  3 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
  1 27  1  6  0  0  0
  1 28  1  1  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0058705

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OCC1=C2[C@H](C[C@@](C)(OC(C)=O)[C@@]3(O)CC[C@](C)(O3)\C=C2\OC1=O)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C21H26O10/c1-11(22)27-10-14-17-15(29-18(14)25)8-19(4)6-7-21(26,31-19)20(5,30-13(3)24)9-16(17)28-12(2)23/h8,16,26H,6-7,9-10H2,1-5H3/b15-8+/t16-,19-,20+,21+/m0/s1

> <INCHI_KEY>
SLFXSRCDJNCMKH-ZIIUARHZSA-N

> <FORMULA>
C21H26O10

> <MOLECULAR_WEIGHT>
438.429

> <EXACT_MASS>
438.152597037

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
43.21548537136469

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(1S,8S,10R,11R)-8,10-bis(acetyloxy)-11-hydroxy-1,10-dimethyl-5-oxo-4,14-dioxatricyclo[9.2.1.0^{3,7}]tetradeca-2,6-dien-6-yl]methyl acetate

> <ALOGPS_LOGP>
0.70

> <JCHEM_LOGP>
-0.10747620966666732

> <ALOGPS_LOGS>
-3.35

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.94372869561911

> <JCHEM_PKA_STRONGEST_BASIC>
-4.419768146835518

> <JCHEM_POLAR_SURFACE_AREA>
134.66000000000003

> <JCHEM_REFRACTIVITY>
104.11710000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.94e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(1S,8S,10R,11R)-8,10-bis(acetyloxy)-11-hydroxy-1,10-dimethyl-5-oxo-4,14-dioxatricyclo[9.2.1.0^{3,7}]tetradeca-2,6-dien-6-yl]methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       2.393  -0.568   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.924  -0.733   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.260   0.034   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.889   1.440   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.420   1.275   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.050   2.681   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       9.557   2.998   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       6.908   3.714   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       5.572   2.947   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.430   3.980   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.899   4.144   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.564   3.377   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.934   1.972   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.251   0.465   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.535   2.099   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -0.085  -0.302   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.582   5.651   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.187  -0.060   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       9.727  -0.063   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      10.494  -1.399   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      12.034  -1.402   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       9.721  -2.731   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.402  -0.999   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       6.078  -2.504   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       7.220  -3.537   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       4.612  -2.977   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.422  -2.108   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       1.225  -1.572   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       1.510  -3.085   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       0.342  -4.089   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       2.963  -3.595   0.000  0.00  0.00           C+0
CONECT    1    2   14   27   28                                             
CONECT    2    1    3                                                       
CONECT    3    2    4   23                                                  
CONECT    4    3    5    9                                                  
CONECT    5    4    6   18                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8    4   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   15   17                                             
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    1   15   16                                             
CONECT   15   14   11                                                       
CONECT   16   14                                                            
CONECT   17   11                                                            
CONECT   18    5   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23    3   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27    1                                                            
CONECT   28    1   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   66    0
END

View in JSmol

Synonyms

Value	Source
[(1S,8S,10R,11R)-8,10-Bis(acetyloxy)-11-hydroxy-1,10-dimethyl-5-oxo-4,14-dioxatricyclo[9.2.1.0,]tetradeca-2,6-dien-6-yl]methyl acetic acid	Generator

Chemical Formula

C₂₁H₂₆O₁₀

Average Mass

438.4290 Da

Monoisotopic Mass

438.15260 Da

IUPAC Name

[(1S,8S,10R,11R)-8,10-bis(acetyloxy)-11-hydroxy-1,10-dimethyl-5-oxo-4,14-dioxatricyclo[9.2.1.0^{3,7}]tetradeca-2,6-dien-6-yl]methyl acetate

Traditional Name

[(1S,8S,10R,11R)-8,10-bis(acetyloxy)-11-hydroxy-1,10-dimethyl-5-oxo-4,14-dioxatricyclo[9.2.1.0^{3,7}]tetradeca-2,6-dien-6-yl]methyl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OCC1=C2[C@H](C[C@@](C)(OC(C)=O)[C@@]3(O)CC[C@](C)(O3)\C=C2\OC1=O)OC(C)=O

InChI Identifier

InChI=1S/C21H26O10/c1-11(22)27-10-14-17-15(29-18(14)25)8-19(4)6-7-21(26,31-19)20(5,30-13(3)24)9-16(17)28-12(2)23/h8,16,26H,6-7,9-10H2,1-5H3/b15-8+/t16-,19-,20+,21+/m0/s1

InChI Key

SLFXSRCDJNCMKH-ZIIUARHZSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Stokesia laevis	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tetracarboxylic acids and derivatives

Direct Parent

Tetracarboxylic acids and derivatives

Alternative Parents

Substituents

Tetracarboxylic acid or derivatives
2-furanone
Dihydrofuran
Enol ester
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Lactone
Hemiacetal
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Carbonyl group
Organic oxide
Organooxygen compound
Organic oxygen 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	0.7	ALOGPS
logP	-0.11	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	10.94	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	134.66 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	104.12 m³·mol⁻¹	ChemAxon
Polarizability	43.22 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

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

163044262

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for [4R-(4R*,6S*,7R*,10R*)]-4,6-bis(Acetyloxy)-3-[(acetyloxy)methyl]-5,6,7,8,9,10-hexahydro-7-hydroxy-6,10-dimethyl-7,10-epoxycyclodeca[b]furan-2(4H)-one (NP0058705)

MOL for NP0058705 ([4R-(4R*,6S*,7R*,10R*)]-4,6-bis(Acetyloxy)-3-[(acetyloxy)methyl]-5,6,7,8,9,10-hexahydro-7-hydroxy-6,10-dimethyl-7,10-epoxycyclodeca[b]furan-2(4H)-one)

3D MOL for NP0058705 ([4R-(4R*,6S*,7R*,10R*)]-4,6-bis(Acetyloxy)-3-[(acetyloxy)methyl]-5,6,7,8,9,10-hexahydro-7-hydroxy-6,10-dimethyl-7,10-epoxycyclodeca[b]furan-2(4H)-one)

3D SDF for NP0058705 ([4R-(4R*,6S*,7R*,10R*)]-4,6-bis(Acetyloxy)-3-[(acetyloxy)methyl]-5,6,7,8,9,10-hexahydro-7-hydroxy-6,10-dimethyl-7,10-epoxycyclodeca[b]furan-2(4H)-one)

3D-SDF for NP0058705 ([4R-(4R*,6S*,7R*,10R*)]-4,6-bis(Acetyloxy)-3-[(acetyloxy)methyl]-5,6,7,8,9,10-hexahydro-7-hydroxy-6,10-dimethyl-7,10-epoxycyclodeca[b]furan-2(4H)-one)

PDB for NP0058705 ([4R-(4R*,6S*,7R*,10R*)]-4,6-bis(Acetyloxy)-3-[(acetyloxy)methyl]-5,6,7,8,9,10-hexahydro-7-hydroxy-6,10-dimethyl-7,10-epoxycyclodeca[b]furan-2(4H)-one)

3D PDB for NP0058705 ([4R-(4R*,6S*,7R*,10R*)]-4,6-bis(Acetyloxy)-3-[(acetyloxy)methyl]-5,6,7,8,9,10-hexahydro-7-hydroxy-6,10-dimethyl-7,10-epoxycyclodeca[b]furan-2(4H)-one)

SMILES for NP0058705 ([4R-(4R*,6S*,7R*,10R*)]-4,6-bis(Acetyloxy)-3-[(acetyloxy)methyl]-5,6,7,8,9,10-hexahydro-7-hydroxy-6,10-dimethyl-7,10-epoxycyclodeca[b]furan-2(4H)-one)

INCHI for NP0058705 ([4R-(4R*,6S*,7R*,10R*)]-4,6-bis(Acetyloxy)-3-[(acetyloxy)methyl]-5,6,7,8,9,10-hexahydro-7-hydroxy-6,10-dimethyl-7,10-epoxycyclodeca[b]furan-2(4H)-one)

Structure for NP0058705 ([4R-(4R*,6S*,7R*,10R*)]-4,6-bis(Acetyloxy)-3-[(acetyloxy)methyl]-5,6,7,8,9,10-hexahydro-7-hydroxy-6,10-dimethyl-7,10-epoxycyclodeca[b]furan-2(4H)-one)

3D Structure for NP0058705 ([4R-(4R*,6S*,7R*,10R*)]-4,6-bis(Acetyloxy)-3-[(acetyloxy)methyl]-5,6,7,8,9,10-hexahydro-7-hydroxy-6,10-dimethyl-7,10-epoxycyclodeca[b]furan-2(4H)-one)

Showing NP-Card for [4R-(4R,6S,7R,10R)]-4,6-bis(Acetyloxy)-3-[(acetyloxy)methyl]-5,6,7,8,9,10-hexahydro-7-hydroxy-6,10-dimethyl-7,10-epoxycyclodeca[b]furan-2(4H)-one (NP0058705)

MOL for NP0058705 ([4R-(4R,6S,7R,10R)]-4,6-bis(Acetyloxy)-3-[(acetyloxy)methyl]-5,6,7,8,9,10-hexahydro-7-hydroxy-6,10-dimethyl-7,10-epoxycyclodeca[b]furan-2(4H)-one)

3D MOL for NP0058705 ([4R-(4R,6S,7R,10R)]-4,6-bis(Acetyloxy)-3-[(acetyloxy)methyl]-5,6,7,8,9,10-hexahydro-7-hydroxy-6,10-dimethyl-7,10-epoxycyclodeca[b]furan-2(4H)-one)

3D SDF for NP0058705 ([4R-(4R,6S,7R,10R)]-4,6-bis(Acetyloxy)-3-[(acetyloxy)methyl]-5,6,7,8,9,10-hexahydro-7-hydroxy-6,10-dimethyl-7,10-epoxycyclodeca[b]furan-2(4H)-one)

3D-SDF for NP0058705 ([4R-(4R,6S,7R,10R)]-4,6-bis(Acetyloxy)-3-[(acetyloxy)methyl]-5,6,7,8,9,10-hexahydro-7-hydroxy-6,10-dimethyl-7,10-epoxycyclodeca[b]furan-2(4H)-one)

PDB for NP0058705 ([4R-(4R,6S,7R,10R)]-4,6-bis(Acetyloxy)-3-[(acetyloxy)methyl]-5,6,7,8,9,10-hexahydro-7-hydroxy-6,10-dimethyl-7,10-epoxycyclodeca[b]furan-2(4H)-one)

3D PDB for NP0058705 ([4R-(4R,6S,7R,10R)]-4,6-bis(Acetyloxy)-3-[(acetyloxy)methyl]-5,6,7,8,9,10-hexahydro-7-hydroxy-6,10-dimethyl-7,10-epoxycyclodeca[b]furan-2(4H)-one)

SMILES for NP0058705 ([4R-(4R,6S,7R,10R)]-4,6-bis(Acetyloxy)-3-[(acetyloxy)methyl]-5,6,7,8,9,10-hexahydro-7-hydroxy-6,10-dimethyl-7,10-epoxycyclodeca[b]furan-2(4H)-one)

INCHI for NP0058705 ([4R-(4R,6S,7R,10R)]-4,6-bis(Acetyloxy)-3-[(acetyloxy)methyl]-5,6,7,8,9,10-hexahydro-7-hydroxy-6,10-dimethyl-7,10-epoxycyclodeca[b]furan-2(4H)-one)

Structure for NP0058705 ([4R-(4R,6S,7R,10R)]-4,6-bis(Acetyloxy)-3-[(acetyloxy)methyl]-5,6,7,8,9,10-hexahydro-7-hydroxy-6,10-dimethyl-7,10-epoxycyclodeca[b]furan-2(4H)-one)

3D Structure for NP0058705 ([4R-(4R,6S,7R,10R)]-4,6-bis(Acetyloxy)-3-[(acetyloxy)methyl]-5,6,7,8,9,10-hexahydro-7-hydroxy-6,10-dimethyl-7,10-epoxycyclodeca[b]furan-2(4H)-one)