NP-MRD: Showing NP-Card for Nigakihemiacetal A (NP0052204)

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Record Information

Version

2.0

Created at

2022-04-27 23:20:49 UTC

Updated at

2022-04-27 23:20:49 UTC

NP-MRD ID

NP0052204

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Nigakihemiacetal A

Description

(1S,2S,6R,7S,9R,11S,13R,14S,15R,16S,17R)-11,14,16-trihydroxy-4,15-dimethoxy-2,6,14,17-tetramethyl-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]Heptadec-4-en-3-one 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. Nigakihemiacetal A is found in Picrasma quassioides and Trypanosoma brucei. Based on a literature review very few articles have been published on (1S,2S,6R,7S,9R,11S,13R,14S,15R,16S,17R)-11,14,16-trihydroxy-4,15-dimethoxy-2,6,14,17-tetramethyl-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]Heptadec-4-en-3-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282201202D          

 29 32  0  0  1  0            999 V2000
    4.2868    0.8250    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
    3.5724   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  1  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 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   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
    1.4289    0.8250    0.0000 C   0  0  1  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 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1100    2.0913    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2773    2.7621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 C   0  0  0  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
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    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  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  2  0  0  0  0
  8  5  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  4 11  1  6  0  0  0
 10 12  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 15 14  1  1  0  0  0
  9 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
  8 18  1  0  0  0  0
 18 19  1  1  0  0  0
 17 20  1  6  0  0  0
 20 21  1  0  0  0  0
 16 22  1  6  0  0  0
 16 23  1  1  0  0  0
 13 24  1  6  0  0  0
  9 25  1  6  0  0  0
  5 26  1  6  0  0  0
  3 27  1  6  0  0  0
  1 28  1  0  0  0  0
 28 29  1  0  0  0  0
M  END

     RDKit          3D

 63 66  0  0  0  0  0  0  0  0999 V2000
    3.5686    2.1379    2.7908 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9153    2.0919    1.4212 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3469    1.1358    0.5518 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9688   -0.0324    0.5420 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3760   -1.0572   -0.3742 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0896   -0.9916   -1.6992 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9037   -0.9666   -0.4266 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2417   -2.0480   -1.1780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2208   -2.0512   -0.7627 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2363   -2.5635    0.5264 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5576   -2.9208    0.7888 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1991   -3.4330   -0.3444 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2434   -1.5702    1.0662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2495   -0.8341   -0.2281 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9693    0.4883   -0.1282 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2300    0.2533    0.6784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4042    0.9943   -1.3427 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0957    1.3957    0.6374 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6823    2.6210    0.9841 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7170    2.8094    2.3625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7328    1.6625   -0.0338 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1171    2.3519    1.0553 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0595    0.3601   -0.2893 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3479    0.4152   -0.8078 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4556    0.6431   -2.3027 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1844    1.4712   -0.2347 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9241    2.6719   -0.4082 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8932   -0.7137   -0.9024 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1992   -0.5778   -2.3740 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8394    1.1605    3.2404 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5224    2.4326    2.9632 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2173    2.9040    3.2577 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8304   -0.3092    1.1061 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6682   -2.0394    0.0691 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1273   -1.4042   -1.5169 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6173   -1.7405   -2.3866 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1757    0.0050   -2.1257 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5533   -1.1002    0.6511 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6605   -3.0212   -0.7785 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3831   -2.1044   -2.2506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7403   -2.7793   -1.4166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6614   -3.5986    1.6528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7863   -4.3185   -0.5403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6736   -1.1149    1.8724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3031   -1.7410    1.3490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8894   -1.4624   -0.9215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8935   -0.4941    0.1951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8071    1.2233    0.6101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0701    0.0781    1.7389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2872    1.9704   -1.3833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8391    0.8994    1.6031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3017    2.0157    2.8653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1928    3.7624    2.6385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6837    2.7201    2.8054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8294    2.3053   -0.9062 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2014    1.6839    1.7085 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0761   -0.0267    0.7830 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5782    1.1509   -2.7414 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2804    1.3900   -2.5607 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8155   -0.2390   -2.8669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0466   -1.3206   -2.5573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4187   -0.9972   -3.0411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6377    0.3662   -2.6837 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 19  1  0
 19 18  1  0
 18 21  1  0
 21 22  1  0
 21 23  1  0
 23 28  1  0
 28 29  1  6
 28  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 26  1  0
 26 27  2  0
 26 24  1  0
 24 25  1  6
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  6
 15 18  1  0
 24 23  1  0
 14 28  1  0
 24  7  1  0
 20 52  1  0
 20 53  1  0
 20 54  1  0
 18 51  1  1
 21 55  1  6
 22 56  1  0
 23 57  1  1
 29 61  1  0
 29 62  1  0
 29 63  1  0
  9 41  1  6
  8 39  1  0
  8 40  1  0
  7 38  1  1
  5 34  1  1
  6 35  1  0
  6 36  1  0
  6 37  1  0
  4 33  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
 25 58  1  0
 25 59  1  0
 25 60  1  0
 11 42  1  1
 12 43  1  0
 13 44  1  0
 13 45  1  0
 14 46  1  6
 16 47  1  0
 16 48  1  0
 16 49  1  0
 17 50  1  0
M  END


  Mrv1652304282201202D          

 29 32  0  0  1  0            999 V2000
    4.2868    0.8250    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
    3.5724   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  1  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 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   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
    1.4289    0.8250    0.0000 C   0  0  1  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 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1100    2.0913    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2773    2.7621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 C   0  0  0  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
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    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  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  2  0  0  0  0
  8  5  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  4 11  1  6  0  0  0
 10 12  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 15 14  1  1  0  0  0
  9 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
  8 18  1  0  0  0  0
 18 19  1  1  0  0  0
 17 20  1  6  0  0  0
 20 21  1  0  0  0  0
 16 22  1  6  0  0  0
 16 23  1  1  0  0  0
 13 24  1  6  0  0  0
  9 25  1  6  0  0  0
  5 26  1  6  0  0  0
  3 27  1  6  0  0  0
  1 28  1  0  0  0  0
 28 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0052204

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@@H]1[C@@H](O)[C@H]2[C@@]3(C)[C@@H](C[C@H]4[C@@H](C)C=C(OC)C(=O)[C@]24C)O[C@H](O)C[C@H]3[C@]1(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C22H34O7/c1-10-7-12(27-5)18(25)20(2)11(10)8-14-21(3)13(9-15(23)29-14)22(4,26)19(28-6)16(24)17(20)21/h7,10-11,13-17,19,23-24,26H,8-9H2,1-6H3/t10-,11-,13+,14+,15-,16-,17+,19+,20-,21+,22-/m0/s1

> <INCHI_KEY>
POGHHDUAPIJTLG-DQDHTNEXSA-N

> <FORMULA>
C22H34O7

> <MOLECULAR_WEIGHT>
410.507

> <EXACT_MASS>
410.230453435

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
43.90475453971536

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
0.75

> <JCHEM_LOGP>
0.6540955359999976

> <ALOGPS_LOGS>
-2.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.496948722508161

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.412207585837933

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3204625199582916

> <JCHEM_POLAR_SURFACE_AREA>
105.45000000000002

> <JCHEM_REFRACTIVITY>
106.45579999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.72e+00 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+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       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   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  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       5.335   4.620   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -0.205   3.904   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       0.518   5.156   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.667   3.080   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.335   3.080   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
CONECT    1    2    6   28                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   27                                                  
CONECT    4    3    5   11                                                  
CONECT    5    4    6    8   26                                             
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    5    9   18                                                  
CONECT    9    8   10   15   25                                             
CONECT   10    9   11   12                                                  
CONECT   11   10    4                                                       
CONECT   12   10   13                                                       
CONECT   13   12   14   24                                                  
CONECT   14   13   15                                                       
CONECT   15   14    9   16                                                  
CONECT   16   15   17   22   23                                             
CONECT   17   16   18   20                                                  
CONECT   18   17    8   19                                                  
CONECT   19   18                                                            
CONECT   20   17   21                                                       
CONECT   21   20                                                            
CONECT   22   16                                                            
CONECT   23   16                                                            
CONECT   24   13                                                            
CONECT   25    9                                                            
CONECT   26    5                                                            
CONECT   27    3                                                            
CONECT   28    1   29                                                       
CONECT   29   28                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₃₄O₇

Average Mass

410.5070 Da

Monoisotopic Mass

410.23045 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CO[C@@H]1[C@@H](O)[C@H]2[C@@]3(C)[C@@H](C[C@H]4[C@@H](C)C=C(OC)C(=O)[C@]24C)O[C@H](O)C[C@H]3[C@]1(C)O

InChI Identifier

InChI=1S/C22H34O7/c1-10-7-12(27-5)18(25)20(2)11(10)8-14-21(3)13(9-15(23)29-14)22(4,26)19(28-6)16(24)17(20)21/h7,10-11,13-17,19,23-24,26H,8-9H2,1-6H3/t10-,11-,13+,14+,15-,16-,17+,19+,20-,21+,22-/m0/s1

InChI Key

POGHHDUAPIJTLG-DQDHTNEXSA-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
Picrasma quassioides	Plant	KNApSAcK
Trypanosoma brucei	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
Quassinoid
Naphthopyran
Naphthalene
Cyclohexenone
Pyran
Oxane
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Ketone
Hemiacetal
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Dialkyl ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	0.75	ALOGPS
logP	0.65	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	12.41	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	105.45 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	106.46 m³·mol⁻¹	ChemAxon
Polarizability	43.9 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

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

162974633

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Nigakihemiacetal A (NP0052204)

MOL for NP0052204 (Nigakihemiacetal A)

3D MOL for NP0052204 (Nigakihemiacetal A)

3D SDF for NP0052204 (Nigakihemiacetal A)

3D-SDF for NP0052204 (Nigakihemiacetal A)

PDB for NP0052204 (Nigakihemiacetal A)

3D PDB for NP0052204 (Nigakihemiacetal A)

SMILES for NP0052204 (Nigakihemiacetal A)

INCHI for NP0052204 (Nigakihemiacetal A)

Structure for NP0052204 (Nigakihemiacetal A)

3D Structure for NP0052204 (Nigakihemiacetal A)