NP-MRD: Showing NP-Card for nigakilactone c (NP0292923)

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Record Information

Version

2.0

Created at

2022-09-10 00:40:51 UTC

Updated at

2022-09-10 00:40:51 UTC

NP-MRD ID

NP0292923

Secondary Accession Numbers

None

Natural Product Identification

Common Name

nigakilactone c

Description

Nigakilactone C, also known as quassin, 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. nigakilactone c is found in Picrasma quassioides. Based on a literature review very few articles have been published on Nigakilactone C.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102202402D          

 31 34  0  0  1  0            999 V2000
    6.4302   -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
    5.0013   -0.4125    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
    4.2868   -1.6500    0.0000 C   0  0  1  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
    3.5724   -1.2375    0.0000 C   0  0  2  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  0  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
    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
    2.1434    1.2375    0.0000 C   0  0  2  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
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  1  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
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 O   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
    3.5724   -0.4125    0.0000 C   0  0  2  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
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  1  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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  5  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 14 13  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 25 20  1  6  0  0  0
 25 26  1  0  0  0  0
  7 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
  3 28  1  0  0  0  0
 28 29  2  0  0  0  0
 25 30  1  0  0  0  0
 14 30  1  0  0  0  0
  9 30  1  0  0  0  0
 30 31  1  6  0  0  0
M  END

     RDKit          3D

 65 68  0  0  0  0  0  0  0  0999 V2000
    3.7109    1.6190    3.3828 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7550    0.6420    2.9890 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7047    0.2971    1.6597 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4167   -0.7732    1.2746 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3644   -1.1596   -0.1901 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7499   -2.6379   -0.2221 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9145   -1.0809   -0.5597 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5136   -1.7173   -1.8292 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1640   -1.4303   -2.3445 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5640   -2.6441   -2.3788 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2323   -3.0643   -1.2613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1140   -4.2323   -0.8195 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1098   -2.0798   -0.5874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0889   -0.8555   -1.4683 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9725    0.2323   -0.9947 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1213   -0.4546   -0.2213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3674    1.2772   -0.1657 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4573    2.5010   -0.8215 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2720    3.4173   -0.2153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9731    1.0397    0.3577 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1541    0.4814    1.6499 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9011    1.0693    2.8535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1580    0.2875    4.0917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4655    2.2380    2.8427 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1350    0.0961   -0.4155 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3308    0.3489   -0.4535 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8508    1.0787   -1.6749 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9225    1.0435    0.6886 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7657    2.2604    0.8324 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6646   -0.3585   -1.7476 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8671    0.7728   -2.7507 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6588    1.8166    4.4794 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5385    2.5983    2.8909 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7499    1.3073    3.0820 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0150   -1.3662    1.9184 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0422   -0.5459   -0.7792 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6472   -3.0838   -1.2074 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0668   -3.1693    0.4735 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8208   -2.7664    0.0852 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3879   -1.6164    0.2964 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2604   -1.4174   -2.5995 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6879   -2.8293   -1.7152 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2407   -1.1762   -3.4613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1695   -2.4625   -0.6503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9210   -1.9206    0.4636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4589   -1.1946   -2.4640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5102    0.6824   -1.8743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6958   -0.9643    0.6638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6831   -1.1251   -0.8700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7379    0.4060    0.1530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0478    1.4273    0.7364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3351    4.3810   -0.7429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3195    3.0252   -0.1561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9349    3.6060    0.8415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4967    2.0471    0.5481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0301   -0.4074    3.9606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3072    0.9527    4.9651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3018   -0.3785    4.3539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2231   -0.8878    0.1881 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7210    2.1626   -1.6505 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6283    0.5761   -2.6301 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9837    0.9611   -1.6086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9294    0.9556   -3.0037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4494    1.7318   -2.4293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4431    0.4608   -3.7587 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 18  1  0
 18 17  1  0
 17 15  1  0
 15 16  1  0
 15 14  1  0
 14 13  1  0
 13 11  1  0
 11 12  2  0
 11 10  1  0
 10  9  1  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 28  1  0
 28 29  2  0
 28 26  1  0
 26 27  1  6
 26 25  1  0
 25 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  2  0
 25 30  1  0
 30 31  1  6
 20 17  1  0
 30 14  1  0
 30  9  1  0
 26  7  1  0
 19 52  1  0
 19 53  1  0
 19 54  1  0
 17 51  1  1
 15 47  1  6
 16 48  1  0
 16 49  1  0
 16 50  1  0
 14 46  1  6
 13 44  1  0
 13 45  1  0
  9 43  1  6
  8 41  1  0
  8 42  1  0
  7 40  1  1
  5 36  1  6
  6 37  1  0
  6 38  1  0
  6 39  1  0
  4 35  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
 27 60  1  0
 27 61  1  0
 27 62  1  0
 25 59  1  1
 20 55  1  1
 23 56  1  0
 23 57  1  0
 23 58  1  0
 31 63  1  0
 31 64  1  0
 31 65  1  0
M  END


  Mrv1652309102202402D          

 31 34  0  0  1  0            999 V2000
    6.4302   -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
    5.0013   -0.4125    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
    4.2868   -1.6500    0.0000 C   0  0  1  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
    3.5724   -1.2375    0.0000 C   0  0  2  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  0  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
    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
    2.1434    1.2375    0.0000 C   0  0  2  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
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  1  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
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 O   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
    3.5724   -0.4125    0.0000 C   0  0  2  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
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  1  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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  5  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 14 13  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 25 20  1  6  0  0  0
 25 26  1  0  0  0  0
  7 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
  3 28  1  0  0  0  0
 28 29  2  0  0  0  0
 25 30  1  0  0  0  0
 14 30  1  0  0  0  0
  9 30  1  0  0  0  0
 30 31  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0292923

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@H]1[C@H](C)[C@@H]2CC(=O)O[C@@H]3C[C@H]4[C@H](C)C=C(OC)C(=O)[C@]4(C)[C@@H]([C@@H]1OC(C)=O)[C@]23C

> <INCHI_IDENTIFIER>
InChI=1S/C24H34O7/c1-11-8-16(28-6)22(27)24(5)14(11)9-17-23(4)15(10-18(26)31-17)12(2)19(29-7)20(21(23)24)30-13(3)25/h8,11-12,14-15,17,19-21H,9-10H2,1-7H3/t11-,12-,14+,15+,17-,19+,20-,21+,23-,24+/m1/s1

> <INCHI_KEY>
JFFUKRBVELYCPJ-FIKFPIMESA-N

> <FORMULA>
C24H34O7

> <MOLECULAR_WEIGHT>
434.529

> <EXACT_MASS>
434.230453435

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
45.93040938066512

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,6S,7S,9R,13S,14R,15S,16S,17S)-4,15-dimethoxy-2,6,14,17-tetramethyl-3,11-dioxo-10-oxatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadec-4-en-16-yl acetate

> <JCHEM_LOGP>
2.3886967929999967

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.071208423197784

> <JCHEM_POLAR_SURFACE_AREA>
88.13

> <JCHEM_REFRACTIVITY>
112.77049999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,6S,7S,9R,13S,14R,15S,16S,17S)-4,15-dimethoxy-2,6,14,17-tetramethyl-3,11-dioxo-10-oxatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadec-4-en-16-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      10.669   0.000   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       6.668   2.310   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       8.002   4.620   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.668   0.770   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       8.002   1.540   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.335  -1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   28                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   26                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   30                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   30                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20   17   21   25                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   20   26   30                                                  
CONECT   26   25    7   27   28                                             
CONECT   27   26                                                            
CONECT   28   26    3   29                                                  
CONECT   29   28                                                            
CONECT   30   25   14    9   31                                             
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

View in JSmol

Synonyms

Value	Source
Quassin	Kegg

Chemical Formula

C₂₄H₃₄O₇

Average Mass

434.5290 Da

Monoisotopic Mass

434.23045 Da

IUPAC Name

(1S,2S,6S,7S,9R,13S,14R,15S,16S,17S)-4,15-dimethoxy-2,6,14,17-tetramethyl-3,11-dioxo-10-oxatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadec-4-en-16-yl acetate

Traditional Name

(1S,2S,6S,7S,9R,13S,14R,15S,16S,17S)-4,15-dimethoxy-2,6,14,17-tetramethyl-3,11-dioxo-10-oxatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadec-4-en-16-yl acetate

CAS Registry Number

Not Available

SMILES

CO[C@H]1[C@H](C)[C@@H]2CC(=O)O[C@@H]3C[C@H]4[C@H](C)C=C(OC)C(=O)[C@]4(C)[C@@H]([C@@H]1OC(C)=O)[C@]23C

InChI Identifier

InChI=1S/C24H34O7/c1-11-8-16(28-6)22(27)24(5)14(11)9-17-23(4)15(10-18(26)31-17)12(2)19(29-7)20(21(23)24)30-13(3)25/h8,11-12,14-15,17,19-21H,9-10H2,1-7H3/t11-,12-,14+,15+,17-,19+,20-,21+,23-,24+/m1/s1

InChI Key

JFFUKRBVELYCPJ-FIKFPIMESA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Picrasma quassioides	LOTUS Database	35616633

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
C-20 quassinoid skeleton
Quassinoid
Naphthopyran
Naphthalene
Delta valerolactone
Delta_valerolactone
Cyclohexenone
Dicarboxylic acid or derivatives
Oxane
Pyran
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Ether
Dialkyl ether
Carboxylic acid derivative
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

triterpenoid (CHEBI:80871 )
Dammarenes (C17029 )

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	2.39	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	88.13 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	112.77 m³·mol⁻¹	ChemAxon
Polarizability	45.93 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

Not Available

Chemspider ID

161314

KEGG Compound ID

C17029

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

185556

PDB ID

Not Available

ChEBI ID

80871

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for nigakilactone c (NP0292923)

MOL for NP0292923 (nigakilactone c)

3D MOL for NP0292923 (nigakilactone c)

3D SDF for NP0292923 (nigakilactone c)

3D-SDF for NP0292923 (nigakilactone c)

PDB for NP0292923 (nigakilactone c)

3D PDB for NP0292923 (nigakilactone c)

SMILES for NP0292923 (nigakilactone c)

INCHI for NP0292923 (nigakilactone c)

Structure for NP0292923 (nigakilactone c)

3D Structure for NP0292923 (nigakilactone c)