NP-MRD: Showing NP-Card for 3beta-acetoxy-8beta,14alpha-dihydroxy-13,15-abiatene-16,12-olide (NP0027241)

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Record Information

Version

1.0

Created at

2021-06-19 18:55:23 UTC

Updated at

2021-06-29 23:53:15 UTC

NP-MRD ID

NP0027241

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3beta-acetoxy-8beta,14alpha-dihydroxy-13,15-abiatene-16,12-olide

Provided By

JEOL Database JEOL Logo

Description

3beta-acetoxy-8beta,14alpha-dihydroxy-13,15-abiatene-16,12-olide is found in Suregada multiflora. It was first documented in 2004 (Choudhary, M. I., et al.).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192120553D          

 60 63  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306192120553D          

 60 63  0  0  0  0            999 V2000
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   -0.4208   -0.3454    3.9579 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9862   -0.8962    3.9055 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7851    2.9874    2.3286 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2978    3.4918    3.9524 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2571    1.7618    3.5559 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1442    1.6945    4.5978 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8132    3.5033    2.8813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5941    2.4758    3.0441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0789    2.9597    0.6915 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5656    2.3864    0.8774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9412    1.4466    0.3595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8551   -0.2744    0.7438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7581    0.9334    1.9912 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9442   -0.1088    1.3996 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0457   -2.4175    1.9423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5157   -1.9010    1.3570 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1614   -1.9466   -0.1028 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8184   -3.0010   -0.4131 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4068   -0.7583   -1.9046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5070   -2.4535   -2.4125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4868   -2.2669   -1.4428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8166   -1.5444   -5.8913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5072   -1.9400   -5.5228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2009   -2.6824   -4.5942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3020    0.9186   -1.6465 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5341    1.5661   -2.6052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3528    2.4270   -1.3972 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5611    0.8407   -0.7477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8065   -1.3204    3.6454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2699   -0.3955    5.0438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2038    0.3971    3.8105 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6760   -1.9455    3.9464 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1777   -0.5832    4.9390 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9386   -0.8526    3.3659 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 18  2  0  0  0  0
 18 20  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 13 15  1  0  0  0  0
 13 14  1  6  0  0  0
  8 25  1  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
 18 19  1  0  0  0  0
 25 13  1  0  0  0  0
 20 21  2  0  0  0  0
 26 10  1  0  0  0  0
  5  4  1  0  0  0  0
  8  7  1  0  0  0  0
 26 27  1  1  0  0  0
 25 24  1  0  0  0  0
 25 54  1  1  0  0  0
 15 17  1  0  0  0  0
 26 28  1  0  0  0  0
 23 24  1  0  0  0  0
 15 16  1  0  0  0  0
 23 17  1  0  0  0  0
 23 51  1  1  0  0  0
  8 10  1  0  0  0  0
  8  9  1  6  0  0  0
 10 40  1  6  0  0  0
  6  5  1  0  0  0  0
  4  2  1  0  0  0  0
  6  7  1  0  0  0  0
  2  1  1  0  0  0  0
  5 26  1  0  0  0  0
  2  3  2  0  0  0  0
  6 33  1  0  0  0  0
  6 34  1  0  0  0  0
  5 32  1  1  0  0  0
  7 35  1  0  0  0  0
  7 36  1  0  0  0  0
 11 41  1  0  0  0  0
 11 42  1  0  0  0  0
 12 43  1  0  0  0  0
 12 44  1  0  0  0  0
 24 52  1  0  0  0  0
 24 53  1  0  0  0  0
 15 46  1  6  0  0  0
 14 45  1  0  0  0  0
 19 48  1  0  0  0  0
 19 49  1  0  0  0  0
 19 50  1  0  0  0  0
 27 55  1  0  0  0  0
 27 56  1  0  0  0  0
 27 57  1  0  0  0  0
 28 58  1  0  0  0  0
 28 59  1  0  0  0  0
 28 60  1  0  0  0  0
 16 47  1  0  0  0  0
  9 37  1  0  0  0  0
  9 38  1  0  0  0  0
  9 39  1  0  0  0  0
  1 29  1  0  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0027241

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]1([H])C2=C(C(=O)O[C@]2([H])C([H])([H])[C@]2([H])[C@@]1(O[H])C([H])([H])C([H])([H])[C@]1([H])C(C([H])([H])[H])(C([H])([H])[H])[C@@]([H])(OC(=O)C([H])([H])[H])C([H])([H])C([H])([H])[C@@]21C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C22H32O6/c1-11-17-13(28-19(11)25)10-15-21(5)8-7-16(27-12(2)23)20(3,4)14(21)6-9-22(15,26)18(17)24/h13-16,18,24,26H,6-10H2,1-5H3/t13-,14-,15+,16+,18+,21-,22+/m1/s1

> <INCHI_KEY>
LBVMRCGYVDNZED-YFEQSTBNSA-N

> <FORMULA>
C22H32O6

> <MOLECULAR_WEIGHT>
392.492

> <EXACT_MASS>
392.21988875

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
42.39651624311733

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,5S,7S,10S,11S,16R)-10,11-dihydroxy-2,6,6,13-tetramethyl-14-oxo-15-oxatetracyclo[8.7.0.0^{2,7}.0^{12,16}]heptadec-12-en-5-yl acetate

> <ALOGPS_LOGP>
2.14

> <JCHEM_LOGP>
2.0355448093333317

> <ALOGPS_LOGS>
-3.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.480123116671873

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.087275051126651

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4394547698884788

> <JCHEM_POLAR_SURFACE_AREA>
93.06000000000002

> <JCHEM_REFRACTIVITY>
101.60049999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.96e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,5S,7S,10S,11S,16R)-10,11-dihydroxy-2,6,6,13-tetramethyl-14-oxo-15-oxatetracyclo[8.7.0.0^{2,7}.0^{12,16}]heptadec-12-en-5-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 60 63  0  0  0  0  0  0  0  0999 V2000
    4.7630    2.7221    3.3886 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3446    2.6531    3.8648 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8743    3.3652    4.7397 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6737    1.6895    3.1763 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2810    1.4934    3.5269 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4474    2.4835    2.7092 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5329    2.2087    1.2048 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0916    0.7688    0.7971 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4367    0.7001    0.9789 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8898   -0.2519    1.6904 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5555   -1.6967    1.2815 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0628   -1.9691   -0.1297 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5588   -0.9900   -1.2052 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5488   -1.0321   -2.2735 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7496   -1.5247   -1.8817 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7695   -1.8339   -0.9472 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964   -0.5241   -2.8366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5827   -0.6234   -4.1350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5220   -1.7577   -5.0819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9616    0.7278   -4.5731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3070    1.0302   -5.7007 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8558    1.5881   -3.5222 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4740    0.8576   -2.3562 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1758    1.4161   -1.7777 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5102    0.5077   -0.7173 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9014    0.0052    3.2453 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4208   -0.3454    3.9579 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9862   -0.8962    3.9055 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7851    2.9874    2.3286 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2978    3.4918    3.9524 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2571    1.7618    3.5559 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1442    1.6945    4.5978 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8132    3.5033    2.8813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5941    2.4758    3.0441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0789    2.9597    0.6915 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5656    2.3864    0.8774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9412    1.4466    0.3595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8551   -0.2744    0.7438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7581    0.9334    1.9912 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9442   -0.1088    1.3996 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0457   -2.4175    1.9423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5157   -1.9010    1.3570 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1614   -1.9466   -0.1028 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8184   -3.0010   -0.4131 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4068   -0.7583   -1.9046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5070   -2.4535   -2.4125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4868   -2.2669   -1.4428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8166   -1.5444   -5.8913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5072   -1.9400   -5.5228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2009   -2.6824   -4.5942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3020    0.9186   -1.6465 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5341    1.5661   -2.6052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3528    2.4270   -1.3972 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5611    0.8407   -0.7477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8065   -1.3204    3.6454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2699   -0.3955    5.0438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2038    0.3971    3.8105 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6760   -1.9455    3.9464 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1777   -0.5832    4.9390 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9386   -0.8526    3.3659 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 18  2  0
 18 20  1  0
 20 22  1  0
 22 23  1  0
 13 15  1  0
 13 14  1  6
  8 25  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 18 19  1  0
 25 13  1  0
 20 21  2  0
 26 10  1  0
  5  4  1  0
  8  7  1  0
 26 27  1  1
 25 24  1  0
 25 54  1  1
 15 17  1  0
 26 28  1  0
 23 24  1  0
 15 16  1  0
 23 17  1  0
 23 51  1  1
  8 10  1  0
  8  9  1  6
 10 40  1  6
  6  5  1  0
  4  2  1  0
  6  7  1  0
  2  1  1  0
  5 26  1  0
  2  3  2  0
  6 33  1  0
  6 34  1  0
  5 32  1  1
  7 35  1  0
  7 36  1  0
 11 41  1  0
 11 42  1  0
 12 43  1  0
 12 44  1  0
 24 52  1  0
 24 53  1  0
 15 46  1  6
 14 45  1  0
 19 48  1  0
 19 49  1  0
 19 50  1  0
 27 55  1  0
 27 56  1  0
 27 57  1  0
 28 58  1  0
 28 59  1  0
 28 60  1  0
 16 47  1  0
  9 37  1  0
  9 38  1  0
  9 39  1  0
  1 29  1  0
  1 30  1  0
  1 31  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       4.763   2.722   3.389  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.345   2.653   3.865  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.874   3.365   4.740  0.00  0.00           O+0
HETATM    4  O   UNK     0       2.674   1.690   3.176  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.281   1.493   3.527  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.447   2.483   2.709  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.533   2.209   1.205  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.092   0.769   0.797  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.437   0.700   0.979  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.890  -0.252   1.690  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.556  -1.697   1.282  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.063  -1.969  -0.130  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.559  -0.990  -1.205  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.549  -1.032  -2.273  0.00  0.00           O+0
HETATM   15  C   UNK     0      -0.750  -1.525  -1.882  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.770  -1.834  -0.947  0.00  0.00           O+0
HETATM   17  C   UNK     0      -1.296  -0.524  -2.837  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.583  -0.623  -4.135  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.522  -1.758  -5.082  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.962   0.728  -4.573  0.00  0.00           C+0
HETATM   21  O   UNK     0      -2.307   1.030  -5.701  0.00  0.00           O+0
HETATM   22  O   UNK     0      -1.856   1.588  -3.522  0.00  0.00           O+0
HETATM   23  C   UNK     0      -1.474   0.858  -2.356  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.176   1.416  -1.778  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.510   0.508  -0.717  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.901   0.005   3.245  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.421  -0.345   3.958  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.986  -0.896   3.906  0.00  0.00           C+0
HETATM   29  H   UNK     0       4.785   2.987   2.329  0.00  0.00           H+0
HETATM   30  H   UNK     0       5.298   3.492   3.952  0.00  0.00           H+0
HETATM   31  H   UNK     0       5.257   1.762   3.556  0.00  0.00           H+0
HETATM   32  H   UNK     0       1.144   1.694   4.598  0.00  0.00           H+0
HETATM   33  H   UNK     0       0.813   3.503   2.881  0.00  0.00           H+0
HETATM   34  H   UNK     0      -0.594   2.476   3.044  0.00  0.00           H+0
HETATM   35  H   UNK     0      -0.079   2.960   0.692  0.00  0.00           H+0
HETATM   36  H   UNK     0       1.566   2.386   0.877  0.00  0.00           H+0
HETATM   37  H   UNK     0      -1.941   1.447   0.360  0.00  0.00           H+0
HETATM   38  H   UNK     0      -1.855  -0.274   0.744  0.00  0.00           H+0
HETATM   39  H   UNK     0      -1.758   0.933   1.991  0.00  0.00           H+0
HETATM   40  H   UNK     0       1.944  -0.109   1.400  0.00  0.00           H+0
HETATM   41  H   UNK     0       1.046  -2.418   1.942  0.00  0.00           H+0
HETATM   42  H   UNK     0      -0.516  -1.901   1.357  0.00  0.00           H+0
HETATM   43  H   UNK     0       2.161  -1.947  -0.103  0.00  0.00           H+0
HETATM   44  H   UNK     0       0.818  -3.001  -0.413  0.00  0.00           H+0
HETATM   45  H   UNK     0       2.407  -0.758  -1.905  0.00  0.00           H+0
HETATM   46  H   UNK     0      -0.507  -2.454  -2.413  0.00  0.00           H+0
HETATM   47  H   UNK     0      -2.487  -2.267  -1.443  0.00  0.00           H+0
HETATM   48  H   UNK     0      -0.817  -1.544  -5.891  0.00  0.00           H+0
HETATM   49  H   UNK     0      -2.507  -1.940  -5.523  0.00  0.00           H+0
HETATM   50  H   UNK     0      -1.201  -2.682  -4.594  0.00  0.00           H+0
HETATM   51  H   UNK     0      -2.302   0.919  -1.647  0.00  0.00           H+0
HETATM   52  H   UNK     0       0.534   1.566  -2.605  0.00  0.00           H+0
HETATM   53  H   UNK     0      -0.353   2.427  -1.397  0.00  0.00           H+0
HETATM   54  H   UNK     0       1.561   0.841  -0.748  0.00  0.00           H+0
HETATM   55  H   UNK     0      -0.807  -1.320   3.645  0.00  0.00           H+0
HETATM   56  H   UNK     0      -0.270  -0.396   5.044  0.00  0.00           H+0
HETATM   57  H   UNK     0      -1.204   0.397   3.811  0.00  0.00           H+0
HETATM   58  H   UNK     0       1.676  -1.946   3.946  0.00  0.00           H+0
HETATM   59  H   UNK     0       2.178  -0.583   4.939  0.00  0.00           H+0
HETATM   60  H   UNK     0       2.939  -0.853   3.366  0.00  0.00           H+0
CONECT    1    2   29   30   31                                             
CONECT    2    4    1    3                                                  
CONECT    3    2                                                            
CONECT    4    5    2                                                       
CONECT    5    4    6   26   32                                             
CONECT    6    5    7   33   34                                             
CONECT    7    8    6   35   36                                             
CONECT    8   25    7   10    9                                             
CONECT    9    8   37   38   39                                             
CONECT   10   11   26    8   40                                             
CONECT   11   10   12   41   42                                             
CONECT   12   11   13   43   44                                             
CONECT   13   15   14   12   25                                             
CONECT   14   13   45                                                       
CONECT   15   13   17   16   46                                             
CONECT   16   15   47                                                       
CONECT   17   18   15   23                                                  
CONECT   18   17   20   19                                                  
CONECT   19   18   48   49   50                                             
CONECT   20   18   22   21                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24   17   51                                             
CONECT   24   25   23   52   53                                             
CONECT   25    8   13   24   54                                             
CONECT   26   10   27   28    5                                             
CONECT   27   26   55   56   57                                             
CONECT   28   26   58   59   60                                             
CONECT   29    1                                                            
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    5                                                            
CONECT   33    6                                                            
CONECT   34    6                                                            
CONECT   35    7                                                            
CONECT   36    7                                                            
CONECT   37    9                                                            
CONECT   38    9                                                            
CONECT   39    9                                                            
CONECT   40   10                                                            
CONECT   41   11                                                            
CONECT   42   11                                                            
CONECT   43   12                                                            
CONECT   44   12                                                            
CONECT   45   14                                                            
CONECT   46   15                                                            
CONECT   47   16                                                            
CONECT   48   19                                                            
CONECT   49   19                                                            
CONECT   50   19                                                            
CONECT   51   23                                                            
CONECT   52   24                                                            
CONECT   53   24                                                            
CONECT   54   25                                                            
CONECT   55   27                                                            
CONECT   56   27                                                            
CONECT   57   27                                                            
CONECT   58   28                                                            
CONECT   59   28                                                            
CONECT   60   28                                                            
MASTER        0    0    0    0    0    0    0    0   60    0  126    0
END

RDKit          3D

60 63  0  0  0  0  0  0  0  0999 V2000
    4.7630    2.7221    3.3886 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3446    2.6531    3.8648 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8743    3.3652    4.7397 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6737    1.6895    3.1763 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2810    1.4934    3.5269 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4474    2.4835    2.7092 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5329    2.2087    1.2048 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0916    0.7688    0.7971 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4367    0.7001    0.9789 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8898   -0.2519    1.6904 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5555   -1.6967    1.2815 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0628   -1.9691   -0.1297 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5588   -0.9900   -1.2052 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5488   -1.0321   -2.2735 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7496   -1.5247   -1.8817 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7695   -1.8339   -0.9472 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964   -0.5241   -2.8366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5827   -0.6234   -4.1350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5220   -1.7577   -5.0819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9616    0.7278   -4.5731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3070    1.0302   -5.7007 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8558    1.5881   -3.5222 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4740    0.8576   -2.3562 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1758    1.4161   -1.7777 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5102    0.5077   -0.7173 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9014    0.0052    3.2453 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4208   -0.3454    3.9579 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9862   -0.8962    3.9055 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7851    2.9874    2.3286 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2978    3.4918    3.9524 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2571    1.7618    3.5559 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1442    1.6945    4.5978 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8132    3.5033    2.8813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5941    2.4758    3.0441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0789    2.9597    0.6915 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5656    2.3864    0.8774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9412    1.4466    0.3595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8551   -0.2744    0.7438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7581    0.9334    1.9912 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9442   -0.1088    1.3996 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0457   -2.4175    1.9423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5157   -1.9010    1.3570 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1614   -1.9466   -0.1028 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8184   -3.0010   -0.4131 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4068   -0.7583   -1.9046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5070   -2.4535   -2.4125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4868   -2.2669   -1.4428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8166   -1.5444   -5.8913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5072   -1.9400   -5.5228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2009   -2.6824   -4.5942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3020    0.9186   -1.6465 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5341    1.5661   -2.6052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3528    2.4270   -1.3972 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5611    0.8407   -0.7477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8065   -1.3204    3.6454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2699   -0.3955    5.0438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2038    0.3971    3.8105 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6760   -1.9455    3.9464 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1777   -0.5832    4.9390 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9386   -0.8526    3.3659 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 18  2  0
 18 20  1  0
 20 22  1  0
 22 23  1  0
 13 15  1  0
 13 14  1  6
  8 25  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 18 19  1  0
 25 13  1  0
 20 21  2  0
 26 10  1  0
  5  4  1  0
  8  7  1  0
 26 27  1  1
 25 24  1  0
 25 54  1  1
 15 17  1  0
 26 28  1  0
 23 24  1  0
 15 16  1  0
 23 17  1  0
 23 51  1  1
  8 10  1  0
  8  9  1  6
 10 40  1  6
  6  5  1  0
  4  2  1  0
  6  7  1  0
  2  1  1  0
  5 26  1  0
  2  3  2  0
  6 33  1  0
  6 34  1  0
  5 32  1  1
  7 35  1  0
  7 36  1  0
 11 41  1  0
 11 42  1  0
 12 43  1  0
 12 44  1  0
 24 52  1  0
 24 53  1  0
 15 46  1  6
 14 45  1  0
 19 48  1  0
 19 49  1  0
 19 50  1  0
 27 55  1  0
 27 56  1  0
 27 57  1  0
 28 58  1  0
 28 59  1  0
 28 60  1  0
 16 47  1  0
  9 37  1  0
  9 38  1  0
  9 39  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Not Available

Chemical Formula

C₂₂H₃₂O₆

Average Mass

392.4920 Da

Monoisotopic Mass

392.21989 Da

IUPAC Name

(1S,2R,5S,7S,10S,11S,16R)-10,11-dihydroxy-2,6,6,13-tetramethyl-14-oxo-15-oxatetracyclo[8.7.0.0^{2,7}.0^{12,16}]heptadec-12-en-5-yl acetate

Traditional Name

(1S,2R,5S,7S,10S,11S,16R)-10,11-dihydroxy-2,6,6,13-tetramethyl-14-oxo-15-oxatetracyclo[8.7.0.0^{2,7}.0^{12,16}]heptadec-12-en-5-yl acetate

CAS Registry Number

Not Available

SMILES

[H]O[C@@]1([H])C2=C(C(=O)O[C@]2([H])C([H])([H])[C@]2([H])[C@@]1(O[H])C([H])([H])C([H])([H])[C@]1([H])C(C([H])([H])[H])(C([H])([H])[H])[C@@]([H])(OC(=O)C([H])([H])[H])C([H])([H])C([H])([H])[C@@]21C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C22H32O6/c1-11-17-13(28-19(11)25)10-15-21(5)8-7-16(27-12(2)23)20(3,4)14(21)6-9-22(15,26)18(17)24/h13-16,18,24,26H,6-10H2,1-5H3/t13-,14-,15+,16+,18+,21-,22+/m1/s1

InChI Key

LBVMRCGYVDNZED-YFEQSTBNSA-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
Suregada multiflora	JEOL database	Choudhary, M. I., et al, Tetrahedron 60, 7933 (2004)

Chemical Taxonomy

Classification

Not classified

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	2.14	ALOGPS
logP	2.04	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	12.09	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	101.6 m³·mol⁻¹	ChemAxon
Polarizability	42.4 Å³	ChemAxon
Number of Rings	4	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

Not Available

References

General References

Choudhary, M. I., et al. (2004). Choudhary, M. I., et al, Tetrahedron 60, 7933 (2004). Tetrahedron.

Showing NP-Card for 3beta-acetoxy-8beta,14alpha-dihydroxy-13,15-abiatene-16,12-olide (NP0027241)

MOL for NP0027241 (3beta-acetoxy-8beta,14alpha-dihydroxy-13,15-abiatene-16,12-olide)

3D MOL for NP0027241 (3beta-acetoxy-8beta,14alpha-dihydroxy-13,15-abiatene-16,12-olide)

3D SDF for NP0027241 (3beta-acetoxy-8beta,14alpha-dihydroxy-13,15-abiatene-16,12-olide)

3D-SDF for NP0027241 (3beta-acetoxy-8beta,14alpha-dihydroxy-13,15-abiatene-16,12-olide)

PDB for NP0027241 (3beta-acetoxy-8beta,14alpha-dihydroxy-13,15-abiatene-16,12-olide)

3D PDB for NP0027241 (3beta-acetoxy-8beta,14alpha-dihydroxy-13,15-abiatene-16,12-olide)

SMILES for NP0027241 (3beta-acetoxy-8beta,14alpha-dihydroxy-13,15-abiatene-16,12-olide)

INCHI for NP0027241 (3beta-acetoxy-8beta,14alpha-dihydroxy-13,15-abiatene-16,12-olide)

Structure for NP0027241 (3beta-acetoxy-8beta,14alpha-dihydroxy-13,15-abiatene-16,12-olide)

3D Structure for NP0027241 (3beta-acetoxy-8beta,14alpha-dihydroxy-13,15-abiatene-16,12-olide)