NP-MRD: Showing NP-Card for 2-deoxo-8-O-acetyl pumilin (NP0029498)

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Record Information

Version

2.0

Created at

2021-06-19 21:06:28 UTC

Updated at

2021-06-29 23:56:53 UTC

NP-MRD ID

NP0029498

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-deoxo-8-O-acetyl pumilin

Provided By

JEOL Database JEOL Logo

Description

2-deoxo-8-O-acetyl pumilin is found in Balsamorhiza macrophylla and Balsamorhiza sagittata. 2-deoxo-8-O-acetyl pumilin was first documented in 2000 (Mohamed, A. E. H., et al.). Based on a literature review very few articles have been published on (3aR)-3-Methylene-4beta-acetoxy-5alpha-[[(Z)-2-methyl-2-butenoyl]oxy]-6,9-dimethyl-9abeta-hydroxy-2,3,3abeta,4,5,7,9a,9balpha-octahydroazuleno[4,5-b]furan-2-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192123063D          

 55 57  0  0  0  0            999 V2000
    2.9589   -0.9100    1.2880 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4419    0.3073    1.0857 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.0552    0.7925    0.7708 C   0  0  1  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652306192123063D          

 55 57  0  0  0  0            999 V2000
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   -1.2693   -2.9372    2.7493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9216   -4.3510    1.7449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6540    1.0706    0.7841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6803   -1.3261   -1.5281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4194   -2.5836   -1.5144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1026   -3.0033   -1.1872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3458   -3.5368    1.0591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6508   -2.1031    3.1923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4270   -2.1606    3.3022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4694   -3.6504    3.2875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3468    0.8718   -2.1035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0475   -0.1623   -2.7543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2480    1.4820   -3.3339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2933    2.8802   -3.5279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6671    3.7782   -2.8029 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4353    5.3485   -2.8725 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7511    6.2022   -0.8499 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4271    5.3891    0.6818 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7675    4.8491   -0.3563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9471    4.0364    0.5731 H   0  0  0  0  0  0  0  0  0  0  0  0
 28  6  1  0  0  0  0
 21 22  1  0  0  0  0
 25 26  2  0  0  0  0
  2  1  2  3  0  0  0
 21 13  1  0  0  0  0
  3  4  2  0  0  0  0
 26 28  1  0  0  0  0
 26 27  1  0  0  0  0
 13  8  1  0  0  0  0
 28 29  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  7  6  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 23 24  1  0  0  0  0
 15 17  1  0  0  0  0
 28 23  1  0  0  0  0
 15 16  2  0  0  0  0
 17 19  2  0  0  0  0
 24 25  1  0  0  0  0
 23 21  2  0  0  0  0
 19 20  1  0  0  0  0
  6  5  1  0  0  0  0
 17 18  1  0  0  0  0
  5  3  1  0  0  0  0
  9 10  1  0  0  0  0
  3  2  1  0  0  0  0
 10 11  1  0  0  0  0
  7  2  1  0  0  0  0
 10 12  2  0  0  0  0
 24 49  1  0  0  0  0
 24 50  1  0  0  0  0
 25 51  1  0  0  0  0
 13 38  1  1  0  0  0
  8 34  1  6  0  0  0
  7 33  1  1  0  0  0
  6 32  1  6  0  0  0
 22 46  1  0  0  0  0
 22 47  1  0  0  0  0
 22 48  1  0  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
 27 52  1  0  0  0  0
 27 53  1  0  0  0  0
 27 54  1  0  0  0  0
 29 55  1  0  0  0  0
 19 42  1  0  0  0  0
 20 43  1  0  0  0  0
 20 44  1  0  0  0  0
 20 45  1  0  0  0  0
 18 39  1  0  0  0  0
 18 40  1  0  0  0  0
 18 41  1  0  0  0  0
 11 35  1  0  0  0  0
 11 36  1  0  0  0  0
 11 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0029498

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]12C(=C([H])C([H])([H])C1=C(C([H])([H])[H])[C@@]([H])(OC(=O)C(=C(\[H])C([H])([H])[H])\C([H])([H])[H])[C@]([H])(OC(=O)C([H])([H])[H])[C@@]1([H])C(=C([H])[H])C(=O)O[C@]21[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C22H26O7/c1-7-10(2)20(24)28-17-12(4)15-9-8-11(3)22(15,26)19-16(13(5)21(25)29-19)18(17)27-14(6)23/h7-8,16-19,26H,5,9H2,1-4,6H3/b10-7-/t16-,17-,18-,19+,22-/m1/s1

> <INCHI_KEY>
WHXLWWIXANDURR-QWNQIIKESA-N

> <FORMULA>
C22H26O7

> <MOLECULAR_WEIGHT>
402.443

> <EXACT_MASS>
402.167853177

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
42.20154037847148

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3aR,4R,5R,9aR,9bS)-4-(acetyloxy)-9a-hydroxy-6,9-dimethyl-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,7H,9aH,9bH-azuleno[4,5-b]furan-5-yl (2Z)-2-methylbut-2-enoate

> <ALOGPS_LOGP>
2.08

> <JCHEM_LOGP>
2.536103635

> <ALOGPS_LOGS>
-3.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.69398512467011

> <JCHEM_PKA_STRONGEST_BASIC>
-3.8074509064692927

> <JCHEM_POLAR_SURFACE_AREA>
99.13000000000001

> <JCHEM_REFRACTIVITY>
104.75240000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.42e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3aR,4R,5R,9aR,9bS)-4-(acetyloxy)-9a-hydroxy-6,9-dimethyl-3-methylidene-2-oxo-3aH,4H,5H,7H,9bH-azuleno[4,5-b]furan-5-yl (2Z)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 55 57  0  0  0  0  0  0  0  0999 V2000
    2.9589   -0.9100    1.2880 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4419    0.3073    1.0857 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3137    1.5092    1.0837 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4375    1.6000    1.5376 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6125    2.5025    0.4757 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4534    1.9309   -0.1666 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0552    0.7925    0.7708 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0233   -0.2122    0.2280 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1651   -1.2090    1.2755 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3383   -2.4988    0.8778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5358   -3.3813    2.0718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3079   -2.8969   -0.2773 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3613    0.4434   -0.0658 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3434   -0.6088   -0.2373 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2175   -0.8187    0.7773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2787   -0.1781    1.8131 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0972   -1.9764    0.4340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3365   -2.2369   -1.0268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6855   -2.7327    1.3828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5443   -2.6406    2.8698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3862    1.3081   -1.3285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3050    0.8549   -2.4402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6528    2.4387   -1.4375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6636    3.3781   -2.6261 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2602    4.4843   -2.2456 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8184    4.2796   -1.0438 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7414    5.2256   -0.3535 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3464    2.9823   -0.4181 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3559    3.2909    0.7777 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0212   -1.0361    1.4879 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3613   -1.8112    1.2678 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8030    1.5447   -1.1376 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6724    1.1942    1.7212 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4160   -0.6907   -0.6786 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4180   -3.5251    2.5845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2693   -2.9372    2.7493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9216   -4.3510    1.7449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6540    1.0706    0.7841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6803   -1.3261   -1.5281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4194   -2.5836   -1.5144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1026   -3.0033   -1.1872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3458   -3.5368    1.0591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6508   -2.1031    3.1923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4270   -2.1606    3.3022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4694   -3.6504    3.2875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3468    0.8718   -2.1035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0475   -0.1623   -2.7543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2480    1.4820   -3.3339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2933    2.8802   -3.5279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6671    3.7782   -2.8029 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4353    5.3485   -2.8725 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7511    6.2022   -0.8499 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4271    5.3891    0.6818 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7675    4.8491   -0.3563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9471    4.0364    0.5731 H   0  0  0  0  0  0  0  0  0  0  0  0
 28  6  1  0
 21 22  1  0
 25 26  2  0
  2  1  2  3
 21 13  1  0
  3  4  2  0
 26 28  1  0
 26 27  1  0
 13  8  1  0
 28 29  1  1
  7  8  1  0
  8  9  1  0
  7  6  1  0
 13 14  1  0
 14 15  1  0
 23 24  1  0
 15 17  1  0
 28 23  1  0
 15 16  2  0
 17 19  2  0
 24 25  1  0
 23 21  2  0
 19 20  1  0
  6  5  1  0
 17 18  1  0
  5  3  1  0
  9 10  1  0
  3  2  1  0
 10 11  1  0
  7  2  1  0
 10 12  2  0
 24 49  1  0
 24 50  1  0
 25 51  1  0
 13 38  1  1
  8 34  1  6
  7 33  1  1
  6 32  1  6
 22 46  1  0
 22 47  1  0
 22 48  1  0
  1 30  1  0
  1 31  1  0
 27 52  1  0
 27 53  1  0
 27 54  1  0
 29 55  1  0
 19 42  1  0
 20 43  1  0
 20 44  1  0
 20 45  1  0
 18 39  1  0
 18 40  1  0
 18 41  1  0
 11 35  1  0
 11 36  1  0
 11 37  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0       2.959  -0.910   1.288  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.442   0.307   1.086  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.314   1.509   1.084  0.00  0.00           C+0
HETATM    4  O   UNK     0       4.438   1.600   1.538  0.00  0.00           O+0
HETATM    5  O   UNK     0       2.612   2.502   0.476  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.453   1.931  -0.167  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.055   0.793   0.771  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.023  -0.212   0.228  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.165  -1.209   1.276  0.00  0.00           O+0
HETATM   10  C   UNK     0      -0.338  -2.499   0.878  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.536  -3.381   2.072  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.308  -2.897  -0.277  0.00  0.00           O+0
HETATM   13  C   UNK     0      -1.361   0.443  -0.066  0.00  0.00           C+0
HETATM   14  O   UNK     0      -2.343  -0.609  -0.237  0.00  0.00           O+0
HETATM   15  C   UNK     0      -3.217  -0.819   0.777  0.00  0.00           C+0
HETATM   16  O   UNK     0      -3.279  -0.178   1.813  0.00  0.00           O+0
HETATM   17  C   UNK     0      -4.097  -1.976   0.434  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.337  -2.237  -1.027  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.686  -2.733   1.383  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.544  -2.641   2.870  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.386   1.308  -1.329  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.305   0.855  -2.440  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.653   2.439  -1.438  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.664   3.378  -2.626  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.260   4.484  -2.246  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.818   4.280  -1.044  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.741   5.226  -0.354  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.346   2.982  -0.418  0.00  0.00           C+0
HETATM   29  O   UNK     0      -0.356   3.291   0.778  0.00  0.00           O+0
HETATM   30  H   UNK     0       4.021  -1.036   1.488  0.00  0.00           H+0
HETATM   31  H   UNK     0       2.361  -1.811   1.268  0.00  0.00           H+0
HETATM   32  H   UNK     0       1.803   1.545  -1.138  0.00  0.00           H+0
HETATM   33  H   UNK     0       0.672   1.194   1.721  0.00  0.00           H+0
HETATM   34  H   UNK     0       0.416  -0.691  -0.679  0.00  0.00           H+0
HETATM   35  H   UNK     0       0.418  -3.525   2.584  0.00  0.00           H+0
HETATM   36  H   UNK     0      -1.269  -2.937   2.749  0.00  0.00           H+0
HETATM   37  H   UNK     0      -0.922  -4.351   1.745  0.00  0.00           H+0
HETATM   38  H   UNK     0      -1.654   1.071   0.784  0.00  0.00           H+0
HETATM   39  H   UNK     0      -4.680  -1.326  -1.528  0.00  0.00           H+0
HETATM   40  H   UNK     0      -3.419  -2.584  -1.514  0.00  0.00           H+0
HETATM   41  H   UNK     0      -5.103  -3.003  -1.187  0.00  0.00           H+0
HETATM   42  H   UNK     0      -5.346  -3.537   1.059  0.00  0.00           H+0
HETATM   43  H   UNK     0      -3.651  -2.103   3.192  0.00  0.00           H+0
HETATM   44  H   UNK     0      -5.427  -2.161   3.302  0.00  0.00           H+0
HETATM   45  H   UNK     0      -4.469  -3.650   3.288  0.00  0.00           H+0
HETATM   46  H   UNK     0      -3.347   0.872  -2.103  0.00  0.00           H+0
HETATM   47  H   UNK     0      -2.047  -0.162  -2.754  0.00  0.00           H+0
HETATM   48  H   UNK     0      -2.248   1.482  -3.334  0.00  0.00           H+0
HETATM   49  H   UNK     0      -0.293   2.880  -3.528  0.00  0.00           H+0
HETATM   50  H   UNK     0      -1.667   3.778  -2.803  0.00  0.00           H+0
HETATM   51  H   UNK     0       0.435   5.348  -2.873  0.00  0.00           H+0
HETATM   52  H   UNK     0       1.751   6.202  -0.850  0.00  0.00           H+0
HETATM   53  H   UNK     0       1.427   5.389   0.682  0.00  0.00           H+0
HETATM   54  H   UNK     0       2.768   4.849  -0.356  0.00  0.00           H+0
HETATM   55  H   UNK     0      -0.947   4.036   0.573  0.00  0.00           H+0
CONECT    1    2   30   31                                                  
CONECT    2    1    3    7                                                  
CONECT    3    4    5    2                                                  
CONECT    4    3                                                            
CONECT    5    6    3                                                       
CONECT    6   28    7    5   32                                             
CONECT    7    8    6    2   33                                             
CONECT    8   13    7    9   34                                             
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10   35   36   37                                             
CONECT   12   10                                                            
CONECT   13   21    8   14   38                                             
CONECT   14   13   15                                                       
CONECT   15   14   17   16                                                  
CONECT   16   15                                                            
CONECT   17   15   19   18                                                  
CONECT   18   17   39   40   41                                             
CONECT   19   17   20   42                                                  
CONECT   20   19   43   44   45                                             
CONECT   21   22   13   23                                                  
CONECT   22   21   46   47   48                                             
CONECT   23   24   28   21                                                  
CONECT   24   23   25   49   50                                             
CONECT   25   26   24   51                                                  
CONECT   26   25   28   27                                                  
CONECT   27   26   52   53   54                                             
CONECT   28    6   26   29   23                                             
CONECT   29   28   55                                                       
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    6                                                            
CONECT   33    7                                                            
CONECT   34    8                                                            
CONECT   35   11                                                            
CONECT   36   11                                                            
CONECT   37   11                                                            
CONECT   38   13                                                            
CONECT   39   18                                                            
CONECT   40   18                                                            
CONECT   41   18                                                            
CONECT   42   19                                                            
CONECT   43   20                                                            
CONECT   44   20                                                            
CONECT   45   20                                                            
CONECT   46   22                                                            
CONECT   47   22                                                            
CONECT   48   22                                                            
CONECT   49   24                                                            
CONECT   50   24                                                            
CONECT   51   25                                                            
CONECT   52   27                                                            
CONECT   53   27                                                            
CONECT   54   27                                                            
CONECT   55   29                                                            
MASTER        0    0    0    0    0    0    0    0   55    0  114    0
END

RDKit          3D

55 57  0  0  0  0  0  0  0  0999 V2000
    2.9589   -0.9100    1.2880 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4419    0.3073    1.0857 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3137    1.5092    1.0837 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4375    1.6000    1.5376 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6125    2.5025    0.4757 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4534    1.9309   -0.1666 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0552    0.7925    0.7708 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0233   -0.2122    0.2280 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1651   -1.2090    1.2755 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3383   -2.4988    0.8778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5358   -3.3813    2.0718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3079   -2.8969   -0.2773 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3613    0.4434   -0.0658 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3434   -0.6088   -0.2373 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2175   -0.8187    0.7773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2787   -0.1781    1.8131 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0972   -1.9764    0.4340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3365   -2.2369   -1.0268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6855   -2.7327    1.3828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5443   -2.6406    2.8698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3862    1.3081   -1.3285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3050    0.8549   -2.4402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6528    2.4387   -1.4375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6636    3.3781   -2.6261 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2602    4.4843   -2.2456 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8184    4.2796   -1.0438 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7414    5.2256   -0.3535 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3464    2.9823   -0.4181 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3559    3.2909    0.7777 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0212   -1.0361    1.4879 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3613   -1.8112    1.2678 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8030    1.5447   -1.1376 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6724    1.1942    1.7212 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4160   -0.6907   -0.6786 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4180   -3.5251    2.5845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2693   -2.9372    2.7493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9216   -4.3510    1.7449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6540    1.0706    0.7841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6803   -1.3261   -1.5281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4194   -2.5836   -1.5144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1026   -3.0033   -1.1872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3458   -3.5368    1.0591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6508   -2.1031    3.1923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4270   -2.1606    3.3022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4694   -3.6504    3.2875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3468    0.8718   -2.1035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0475   -0.1623   -2.7543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2480    1.4820   -3.3339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2933    2.8802   -3.5279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6671    3.7782   -2.8029 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4353    5.3485   -2.8725 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7511    6.2022   -0.8499 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4271    5.3891    0.6818 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7675    4.8491   -0.3563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9471    4.0364    0.5731 H   0  0  0  0  0  0  0  0  0  0  0  0
 28  6  1  0
 21 22  1  0
 25 26  2  0
  2  1  2  3
 21 13  1  0
  3  4  2  0
 26 28  1  0
 26 27  1  0
 13  8  1  0
 28 29  1  1
  7  8  1  0
  8  9  1  0
  7  6  1  0
 13 14  1  0
 14 15  1  0
 23 24  1  0
 15 17  1  0
 28 23  1  0
 15 16  2  0
 17 19  2  0
 24 25  1  0
 23 21  2  0
 19 20  1  0
  6  5  1  0
 17 18  1  0
  5  3  1  0
  9 10  1  0
  3  2  1  0
 10 11  1  0
  7  2  1  0
 10 12  2  0
 24 49  1  0
 24 50  1  0
 25 51  1  0
 13 38  1  1
  8 34  1  6
  7 33  1  1
  6 32  1  6
 22 46  1  0
 22 47  1  0
 22 48  1  0
  1 30  1  0
  1 31  1  0
 27 52  1  0
 27 53  1  0
 27 54  1  0
 29 55  1  0
 19 42  1  0
 20 43  1  0
 20 44  1  0
 20 45  1  0
 18 39  1  0
 18 40  1  0
 18 41  1  0
 11 35  1  0
 11 36  1  0
 11 37  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Value	Source
(3AR)-3-methylene-4b-acetoxy-5a-[[(Z)-2-methyl-2-butenoyl]oxy]-6,9-dimethyl-9abeta-hydroxy-2,3,3abeta,4,5,7,9a,9balpha-octahydroazuleno[4,5-b]furan-2-one	Generator
(3AR)-3-methylene-4β-acetoxy-5α-[[(Z)-2-methyl-2-butenoyl]oxy]-6,9-dimethyl-9abeta-hydroxy-2,3,3abeta,4,5,7,9a,9balpha-octahydroazuleno[4,5-b]furan-2-one	Generator

Chemical Formula

C₂₂H₂₆O₇

Average Mass

402.4430 Da

Monoisotopic Mass

402.16785 Da

IUPAC Name

(3aR,4R,5R,9aR,9bS)-4-(acetyloxy)-9a-hydroxy-6,9-dimethyl-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,7H,9aH,9bH-azuleno[4,5-b]furan-5-yl (2Z)-2-methylbut-2-enoate

Traditional Name

(3aR,4R,5R,9aR,9bS)-4-(acetyloxy)-9a-hydroxy-6,9-dimethyl-3-methylidene-2-oxo-3aH,4H,5H,7H,9bH-azuleno[4,5-b]furan-5-yl (2Z)-2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

[H]O[C@]12C(=C([H])C([H])([H])C1=C(C([H])([H])[H])[C@@]([H])(OC(=O)C(=C(\[H])C([H])([H])[H])\C([H])([H])[H])[C@]([H])(OC(=O)C([H])([H])[H])[C@@]1([H])C(=C([H])[H])C(=O)O[C@]21[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C22H26O7/c1-7-10(2)20(24)28-17-12(4)15-9-8-11(3)22(15,26)19-16(13(5)21(25)29-19)18(17)27-14(6)23/h7-8,16-19,26H,5,9H2,1-4,6H3/b10-7-/t16-,17-,18-,19+,22-/m1/s1

InChI Key

WHXLWWIXANDURR-QWNQIIKESA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, chcl3, 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
Balsamorhiza macrophylla	JEOL database	Mohamed, A. E. H., et al, Chem. Pharm. Bull. 54, 152 (2000)
Balsamorhiza sagittata	JEOL database	Mohamed, A. E. H., et al, Chem. Pharm. Bull. 54, 152 (2000)

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tricarboxylic acids and derivatives

Direct Parent

Tricarboxylic acids and derivatives

Alternative Parents

Substituents

Tricarboxylic acid or derivatives
Fatty acid ester
Gamma butyrolactone
Fatty acyl
Tertiary alcohol
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Lactone
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Hydrocarbon derivative
Alcohol
Organooxygen compound
Organic oxide
Organic oxygen compound
Carbonyl group
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	2.08	ALOGPS
logP	2.54	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	12.69	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	99.13 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	104.75 m³·mol⁻¹	ChemAxon
Polarizability	42.2 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	No	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

9764213

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11589449

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Mohamed, A. E. H., et al. (2000). Mohamed, A. E. H., et al, Chem. Pharm. Bull. 54, 152 (2000). Chem. Pharm. Bull..

Showing NP-Card for 2-deoxo-8-O-acetyl pumilin (NP0029498)

MOL for NP0029498 (2-deoxo-8-O-acetyl pumilin)

3D MOL for NP0029498 (2-deoxo-8-O-acetyl pumilin)

3D SDF for NP0029498 (2-deoxo-8-O-acetyl pumilin)

3D-SDF for NP0029498 (2-deoxo-8-O-acetyl pumilin)

PDB for NP0029498 (2-deoxo-8-O-acetyl pumilin)

3D PDB for NP0029498 (2-deoxo-8-O-acetyl pumilin)

SMILES for NP0029498 (2-deoxo-8-O-acetyl pumilin)

INCHI for NP0029498 (2-deoxo-8-O-acetyl pumilin)

Structure for NP0029498 (2-deoxo-8-O-acetyl pumilin)

3D Structure for NP0029498 (2-deoxo-8-O-acetyl pumilin)