NP-MRD: Showing NP-Card for 11-Dihydro-12-norneoquassin (NP0085212)

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Record Information

Version

2.0

Created at

2022-04-29 05:47:49 UTC

Updated at

2022-04-29 05:47:49 UTC

NP-MRD ID

NP0085212

Secondary Accession Numbers

None

Natural Product Identification

Common Name

11-Dihydro-12-norneoquassin

Description

(1S,2S,6S,7S,9R,11S,13S,14R,16S,17S)-11,16-dihydroxy-4-methoxy-2,6,14,17-tetramethyl-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]Heptadec-4-ene-3,15-dione belongs to the class of organic compounds known as quassinoids. These are a group of compounds chemically degraded from triterpenes. According to their basic skeleton, quassinoids are categorized into five distinct groups, C-18, C-19, C-20, C-22 and C-25 types. The C-20 quassinoids can be further classified into two types, tetracyclic and the pentacyclic. The tetracyclic variety does not have oxygenation at C-20, while the pentacyclic quassinoids possess additional oxygenation at C-20 that allows for the formation of an additional ring. 11-Dihydro-12-norneoquassin is found in Quassia amara . Based on a literature review very few articles have been published on (1S,2S,6S,7S,9R,11S,13S,14R,16S,17S)-11,16-dihydroxy-4-methoxy-2,6,14,17-tetramethyl-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]Heptadec-4-ene-3,15-dione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292207472D          

 31 34  0  0  1  0            999 V2000
    4.2868    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2704    0.7145    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  6  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  1  1  0  0  0
  7 16  1  6  0  0  0
  7 17  1  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
  3 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 14 23  1  0  0  0  0
 23 24  2  0  0  0  0
  5 25  1  1  0  0  0
  5 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  0  0  0  0
 28 29  2  0  0  0  0
  2 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
M  END

     RDKit          3D

 57 60  0  0  0  0  0  0  0  0999 V2000
    4.8098    2.0060    2.0392 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6208    1.2522    2.2640 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0335    0.5948    1.1996 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5256   -0.5941    0.8394 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8555   -1.2475   -0.3053 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2600   -2.6948   -0.4634 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3865   -1.0514   -0.1529 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5294   -2.0079   -0.9002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9047   -1.7469   -0.4431 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8318   -1.7854    0.9707 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0807   -1.7681    1.5322 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7817   -2.8876    1.0683 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8359   -0.5051    1.2270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7288   -0.1495   -0.2164 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2883    1.2012   -0.5440 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2004    1.7479    0.5142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2037    2.1945   -0.7650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4420    3.1748   -1.4440 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8376    2.0544   -0.1984 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9179    2.6639    1.0785 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3953    0.6105   -0.1060 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0507    0.3986   -0.4310 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4333    0.8069   -1.8316 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9043    1.1875    0.4892 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6533    2.3936    0.6634 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3281   -0.3315   -0.7906 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4420   -0.2016   -2.2630 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1791    2.4785    2.9524 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5288    2.8038    1.3085 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5623    1.3708    1.5526 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3509   -1.0044    1.3751 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1971   -0.7199   -1.2219 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1301   -3.2798    0.4542 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3309   -2.7209   -0.7479 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6561   -3.0999   -1.3073 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1552   -1.1996    0.9445 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7698   -3.0344   -0.5229 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6485   -2.0288   -1.9756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6043   -2.5087   -0.7880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9759   -1.8756    2.6208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3569   -3.2863    1.7565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6015    0.3171    1.9253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9244   -0.7431    1.4207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3636   -0.8964   -0.7804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8895    1.1751   -1.4986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6109    2.2652    1.3000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9150    1.0224    0.9142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8215    2.5625    0.0396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1577    2.6761   -0.7805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8344    1.9250    1.7313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4820    0.3537    0.9954 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7609    1.5557   -2.2774 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5731   -0.0846   -2.5024 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4537    1.2962   -1.8457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4292   -0.6734   -2.5574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4804    0.8097   -2.6660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6936   -0.7710   -2.8500 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0
  8  7  1  0
  7  5  1  0
  5  6  1  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
  2  1  1  0
  3 24  1  0
 24 25  2  0
 24 22  1  0
 22 23  1  6
 22 21  1  0
 21 19  1  0
 19 20  1  0
 19 17  1  0
 17 18  2  0
 17 15  1  0
 15 16  1  0
 15 14  1  0
 14 13  1  0
 13 11  1  0
 11 12  1  0
 11 10  1  0
 14 26  1  0
 26 27  1  6
 10  9  1  0
 26  9  1  0
 22  7  1  0
 26 21  1  0
  9 39  1  6
  8 37  1  0
  8 38  1  0
  7 36  1  1
  5 32  1  6
  6 33  1  0
  6 34  1  0
  6 35  1  0
  4 31  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
 23 52  1  0
 23 53  1  0
 23 54  1  0
 21 51  1  1
 19 49  1  6
 20 50  1  0
 15 45  1  6
 16 46  1  0
 16 47  1  0
 16 48  1  0
 14 44  1  6
 13 42  1  0
 13 43  1  0
 11 40  1  1
 12 41  1  0
 27 55  1  0
 27 56  1  0
 27 57  1  0
M  END


  Mrv1652304292207472D          

 31 34  0  0  1  0            999 V2000
    4.2868    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2704    0.7145    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  6  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  1  1  0  0  0
  7 16  1  6  0  0  0
  7 17  1  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
  3 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 14 23  1  0  0  0  0
 23 24  2  0  0  0  0
  5 25  1  1  0  0  0
  5 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  0  0  0  0
 28 29  2  0  0  0  0
  2 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0085212

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12C[C@@]3([H])[C@H](C)C=C(OC)C(=O)[C@]3(C)[C@@]3([H])[C@H](O)C(=O)[C@H](C)[C@]([H])(C[C@@H](O)O1)[C@]23C

> <INCHI_IDENTIFIER>
InChI=1S/C21H30O6/c1-9-6-13(26-5)19(25)21(4)11(9)7-14-20(3)12(8-15(22)27-14)10(2)16(23)17(24)18(20)21/h6,9-12,14-15,17-18,22,24H,7-8H2,1-5H3/t9-,10-,11+,12+,14-,15+,17-,18+,20-,21+/m1/s1

> <INCHI_KEY>
ZXEXAUWPQPJYJZ-NUTZWRRFSA-N

> <FORMULA>
C21H30O6

> <MOLECULAR_WEIGHT>
378.465

> <EXACT_MASS>
378.204238686

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
40.291443924014956

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,6S,7S,9R,11S,13S,14R,16S,17S)-11,16-dihydroxy-4-methoxy-2,6,14,17-tetramethyl-10-oxatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadec-4-ene-3,15-dione

> <ALOGPS_LOGP>
1.50

> <JCHEM_LOGP>
1.6816670073333337

> <ALOGPS_LOGS>
-2.65

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.190112117076154

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.3681883998505

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6292509098811605

> <JCHEM_POLAR_SURFACE_AREA>
93.06000000000002

> <JCHEM_REFRACTIVITY>
99.45899999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.51e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,6S,7S,9R,11S,13S,14R,16S,17S)-11,16-dihydroxy-4-methoxy-2,6,14,17-tetramethyl-10-oxatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadec-4-ene-3,15-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  O   UNK     0       8.002   1.540   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668   0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   13  H   UNK     0       4.001   0.770   0.000  0.00  0.00           H+0
HETATM   14  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   16  H   UNK     0       2.667  -1.540   0.000  0.00  0.00           H+0
HETATM   17  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.335  -1.540   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   20  H   UNK     0       6.105   1.334   0.000  0.00  0.00           H+0
HETATM   21  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.668   2.310   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   25  H   UNK     0       6.668  -3.850   0.000  0.00  0.00           H+0
HETATM   26  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      10.669  -0.000   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   29                                                  
CONECT    3    2    4    5   19                                             
CONECT    4    3                                                            
CONECT    5    3    6   25   26                                             
CONECT    6    5    7                                                       
CONECT    7    6    8   16   17                                             
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   14   17                                             
CONECT   13   12                                                            
CONECT   14   12   15   23                                                  
CONECT   15   14                                                            
CONECT   16    7                                                            
CONECT   17    7   12   18   19                                             
CONECT   18   17                                                            
CONECT   19   17    3   20   21                                             
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   14   24                                                  
CONECT   24   23                                                            
CONECT   25    5                                                            
CONECT   26    5   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28    2   30                                                  
CONECT   30   29   31                                                       
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₃₀O₆

Average Mass

378.4650 Da

Monoisotopic Mass

378.20424 Da

IUPAC Name

(1S,2S,6S,7S,9R,11S,13S,14R,16S,17S)-11,16-dihydroxy-4-methoxy-2,6,14,17-tetramethyl-10-oxatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadec-4-ene-3,15-dione

Traditional Name

(1S,2S,6S,7S,9R,11S,13S,14R,16S,17S)-11,16-dihydroxy-4-methoxy-2,6,14,17-tetramethyl-10-oxatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadec-4-ene-3,15-dione

CAS Registry Number

Not Available

SMILES

[H][C@]12C[C@@]3([H])[C@H](C)C=C(OC)C(=O)[C@]3(C)[C@@]3([H])[C@H](O)C(=O)[C@H](C)[C@]([H])(C[C@@H](O)O1)[C@]23C

InChI Identifier

InChI=1S/C21H30O6/c1-9-6-13(26-5)19(25)21(4)11(9)7-14-20(3)12(8-15(22)27-14)10(2)16(23)17(24)18(20)21/h6,9-12,14-15,17-18,22,24H,7-8H2,1-5H3/t9-,10-,11+,12+,14-,15+,17-,18+,20-,21+/m1/s1

InChI Key

ZXEXAUWPQPJYJZ-NUTZWRRFSA-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
Quassia amara	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as quassinoids. These are a group of compounds chemically degraded from triterpenes. According to their basic skeleton, quassinoids are categorized into five distinct groups, C-18, C-19, C-20, C-22 and C-25 types. The C-20 quassinoids can be further classified into two types, tetracyclic and the pentacyclic. The tetracyclic variety does not have oxygenation at C-20, while the pentacyclic quassinoids possess additional oxygenation at C-20 that allows for the formation of an additional ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Quassinoids

Alternative Parents

Substituents

Polycyclic triterpenoid
Triterpenoid
Quassinoid
Naphthopyran
Naphthalene
Cyclohexenone
Oxane
Pyran
Cyclic alcohol
Hemiacetal
Ketone
Cyclic ketone
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organic oxygen compound
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	1.5	ALOGPS
logP	1.68	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	12.37	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	99.46 m³·mol⁻¹	ChemAxon
Polarizability	40.29 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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00054987

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

163068582

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 11-Dihydro-12-norneoquassin (NP0085212)

MOL for NP0085212 (11-Dihydro-12-norneoquassin)

3D MOL for NP0085212 (11-Dihydro-12-norneoquassin)

3D SDF for NP0085212 (11-Dihydro-12-norneoquassin)

3D-SDF for NP0085212 (11-Dihydro-12-norneoquassin)

PDB for NP0085212 (11-Dihydro-12-norneoquassin)

3D PDB for NP0085212 (11-Dihydro-12-norneoquassin)

SMILES for NP0085212 (11-Dihydro-12-norneoquassin)

INCHI for NP0085212 (11-Dihydro-12-norneoquassin)

Structure for NP0085212 (11-Dihydro-12-norneoquassin)

3D Structure for NP0085212 (11-Dihydro-12-norneoquassin)