NP-MRD: Showing NP-Card for (-)-Paraherquamide (NP0061600)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-28 06:21:43 UTC

Updated at

2022-04-28 06:21:43 UTC

NP-MRD ID

NP0061600

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Paraherquamide

Description

Paraherquamide belongs to the class of organic compounds known as azaspirodecane derivatives. These are organic compounds containing a spirodecane moiety with at least one nitrogen atom. (-)-Paraherquamide is found in Penicillium charlesii, Penicillium charlesii ATCC 20841, Penicillium dierckxii, Penicillium paraherquei and Penicillium simplicissimum. Based on a literature review very few articles have been published on Paraherquamide.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282208212D          

 36 42  0  0  1  0            999 V2000
   10.1058    0.7046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7101   -0.0193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8974   -0.1613    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2797    0.3855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3221    1.2094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9927    1.6900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7865    1.4653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9933    2.2639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5542    1.7674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6298    1.6581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8950    1.2829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8526    0.4590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5449    0.0103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3321   -0.7868    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5083   -0.8307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0596   -1.5230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2119   -0.0608    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5362   -0.5576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7907   -0.1472    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0164    0.7357    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8721    0.7071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9516    1.5283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6039    1.0879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3914    1.4157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5286    1.0717    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3066    0.1836    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9393   -0.4988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4508    0.1557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0962    0.9161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7536    1.4401    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2800    2.1157    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0613    2.2056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2682    0.8208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0030    1.1959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0457    0.1005    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3121   -0.2768    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  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  4 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 17 15  1  6  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 19 18  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 17 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 20 24  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  1  0  0  0  0
 19 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 25 30  1  0  0  0  0
 30 31  1  1  0  0  0
 30 32  1  6  0  0  0
 25 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 19 35  1  0  0  0  0
 35 36  1  0  0  0  0
M  END

     RDKit          3D

 71 77  0  0  0  0  0  0  0  0999 V2000
    3.5500   -0.3269    2.6956 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3307   -0.0871    1.3163 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3396    0.3196    0.4019 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5014    0.6847    0.7197 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8769    0.2730   -1.0376 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6887    1.1699   -1.2960 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9006    1.1429   -0.0449 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4627    1.4512   -0.1045 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1825    1.4059   -1.4460 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1667    2.8801    0.4007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1651    0.5310    0.9264 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8767   -0.4288    1.3987 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0712   -0.2098    0.6073 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3445   -1.3337   -0.3604 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3732   -1.0865   -1.3039 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5562   -1.8601   -1.1751 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5770   -1.0274   -1.9537 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9765    0.3858   -2.0042 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0185    1.4213   -1.6502 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4866    0.6752   -3.2541 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5867    1.3148    2.1436 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1400    1.9911    2.9035 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9864    1.1280    2.2531 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4788    0.2768    1.2295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4010   -0.0903    0.4520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6769   -0.9370   -0.5941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9324   -1.4111   -0.8834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9831   -1.0360   -0.1040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7664   -0.1977    0.9478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7146    0.2855    1.8429 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0606    0.0557    1.9044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8054   -0.5974    1.0276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5327   -1.2712   -0.2321 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.3346   -2.5728   -0.3623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0416   -0.3743   -1.3613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2077   -1.5763   -0.4899 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2963    0.6092    3.2702 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9866   -1.1863    3.1092 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6544   -0.4891    2.8480 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0150    2.2054   -1.5524 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1650    0.8062   -2.2018 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3717    1.9599    0.5878 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1469    0.6583   -2.1480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0208    2.4003   -1.9635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2934    1.3850   -1.2936 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2198    3.5869   -0.4479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7861    2.9275    0.9269 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0249    3.1264    1.0621 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4712   -1.4570    1.2565 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1206   -0.3105    2.4889 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4466   -1.6871   -0.8916 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6687   -2.2008    0.2699 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4560   -2.8630   -1.6579 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8368   -1.9467   -0.1147 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5561   -1.0275   -1.4694 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6065   -1.3933   -3.0008 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4171    1.8692   -2.5916 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5099    2.2079   -1.0531 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8953    0.9862   -1.1321 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9020   -0.0437   -3.6020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6425    1.5381    2.9773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8892   -1.2950   -1.2733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1132   -2.0769   -1.7158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5795    0.4474    2.7596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8670   -0.6375    1.3207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8663   -3.2701    0.3734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3919   -2.3834   -0.1565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1254   -2.9664   -1.3712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9259   -0.8724   -2.3383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5235    0.5946   -1.3885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1241   -0.1698   -1.2346 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  5  3  1  0
  5  6  1  1
  6  7  1  0
  7  8  1  0
  8  9  1  6
  8 10  1  0
  8 11  1  0
 11 12  1  1
 13 12  1  1
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  6
 11 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  1  1
 33 35  1  0
 33 36  1  0
 13  2  1  0
 29 24  1  0
 15  5  1  0
 36 28  1  0
 18  5  1  0
 13  7  1  0
 25 11  1  0
  1 37  1  0
  1 38  1  0
  1 39  1  0
  6 40  1  0
  6 41  1  0
  7 42  1  1
  9 43  1  0
  9 44  1  0
  9 45  1  0
 10 46  1  0
 10 47  1  0
 10 48  1  0
 12 49  1  0
 12 50  1  0
 14 51  1  0
 14 52  1  0
 16 53  1  0
 16 54  1  0
 17 55  1  0
 17 56  1  0
 19 57  1  0
 19 58  1  0
 19 59  1  0
 20 60  1  0
 23 61  1  0
 26 62  1  0
 27 63  1  0
 31 64  1  0
 32 65  1  0
 34 66  1  0
 34 67  1  0
 34 68  1  0
 35 69  1  0
 35 70  1  0
 35 71  1  0
M  END


  Mrv1652304282208212D          

 36 42  0  0  1  0            999 V2000
   10.1058    0.7046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7101   -0.0193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8974   -0.1613    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2797    0.3855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3221    1.2094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9927    1.6900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7865    1.4653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9933    2.2639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5542    1.7674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6298    1.6581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8950    1.2829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8526    0.4590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5449    0.0103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3321   -0.7868    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5083   -0.8307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0596   -1.5230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2119   -0.0608    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5362   -0.5576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7907   -0.1472    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0164    0.7357    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8721    0.7071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9516    1.5283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6039    1.0879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3914    1.4157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5286    1.0717    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3066    0.1836    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9393   -0.4988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4508    0.1557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0962    0.9161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7536    1.4401    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2800    2.1157    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0613    2.2056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2682    0.8208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0030    1.1959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0457    0.1005    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3121   -0.2768    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  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  4 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 17 15  1  6  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 19 18  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 17 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 20 24  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  1  0  0  0  0
 19 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 25 30  1  0  0  0  0
 30 31  1  1  0  0  0
 30 32  1  6  0  0  0
 25 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 19 35  1  0  0  0  0
 35 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0061600

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C(=O)[C@]23C[C@H]4C(C)(C)[C@@]5(C[C@]14CN2CC[C@@]3(C)O)C(=O)NC1=C5C=CC2=C1OC=CC(C)(C)O2

> <INCHI_IDENTIFIER>
InChI=1S/C28H35N3O5/c1-23(2)10-12-35-20-17(36-23)8-7-16-19(20)29-21(32)27(16)14-26-15-31-11-9-25(5,34)28(31,22(33)30(26)6)13-18(26)24(27,3)4/h7-8,10,12,18,34H,9,11,13-15H2,1-6H3,(H,29,32)/t18-,25+,26+,27+,28-/m0/s1

> <INCHI_KEY>
UVZZDDLIOJPDKX-ITKQZBBDSA-N

> <FORMULA>
C28H35N3O5

> <MOLECULAR_WEIGHT>
493.604

> <EXACT_MASS>
493.257671239

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
53.73599657343633

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1'R,3'S,7'S,8R,12'R)-12'-hydroxy-4,4,4',4',12',14'-hexamethyl-9,10-dihydro-4H-9',14'-diazaspiro[[1,4]dioxepino[2,3-g]indole-8,5'-tetracyclo[5.5.2.0^{1,9}.0^{3,7}]tetradecane]-9,13'-dione

> <ALOGPS_LOGP>
3.02

> <JCHEM_LOGP>
1.6051481673333308

> <ALOGPS_LOGS>
-3.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.966635928118091

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.58996172825735

> <JCHEM_PKA_STRONGEST_BASIC>
8.210739015308341

> <JCHEM_POLAR_SURFACE_AREA>
91.33999999999999

> <JCHEM_REFRACTIVITY>
134.91059999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.03e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1'R,3'S,7'S,8R,12'R)-12'-hydroxy-4,4,4',4',12',14'-hexamethyl-10H-9',14'-diazaspiro[[1,4]dioxepino[2,3-g]indole-8,5'-tetracyclo[5.5.2.0^{1,9}.0^{3,7}]tetradecane]-9,13'-dione

> <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      18.864   1.315   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      18.125  -0.036   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      16.608  -0.301   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      15.455   0.720   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      15.535   2.258   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      16.786   3.155   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      18.268   2.735   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      18.654   4.226   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      19.701   3.299   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.242   3.095   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.871   2.395   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.792   0.857   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.084   0.019   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0      13.687  -1.469   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0      12.149  -1.551   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      11.311  -2.843   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      11.596  -0.113   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.334  -1.041   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.943  -0.275   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.364   1.373   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.961   1.320   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.110   2.853   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.327   2.031   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.197   2.643   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.587   2.000   0.000  0.00  0.00           C+0
HETATM   26  N   UNK     0       6.172   0.343   0.000  0.00  0.00           N+0
HETATM   27  C   UNK     0       7.353  -0.931   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.575   0.291   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.913   1.710   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.140   2.688   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       4.256   3.949   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       5.714   4.117   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       7.967   1.532   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       9.339   2.232   0.000  0.00  0.00           O+0
HETATM   35  N   UNK     0       7.552   0.188   0.000  0.00  0.00           N+0
HETATM   36  C   UNK     0       6.183  -0.517   0.000  0.00  0.00           C+0
CONECT    1    2    7                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   13                                                  
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    1    8    9                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    5   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12    4   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   12   18   21                                             
CONECT   18   17   19                                                       
CONECT   19   18   20   27   35                                             
CONECT   20   19   21   24                                                  
CONECT   21   20   17   22   23                                             
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   20   25                                                       
CONECT   25   24   26   30   33                                             
CONECT   26   25   27   28                                                  
CONECT   27   26   19                                                       
CONECT   28   26   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   25   31   32                                             
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   25   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   19   36                                                  
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   84    0
END

View in JSmol

Synonyms

Value	Source
Paraherquamide a	MeSH

Chemical Formula

C₂₈H₃₅N₃O₅

Average Mass

493.6040 Da

Monoisotopic Mass

493.25767 Da

IUPAC Name

(1'R,3'S,7'S,8R,12'R)-12'-hydroxy-4,4,4',4',12',14'-hexamethyl-9,10-dihydro-4H-9',14'-diazaspiro[[1,4]dioxepino[2,3-g]indole-8,5'-tetracyclo[5.5.2.0^{1,9}.0^{3,7}]tetradecane]-9,13'-dione

Traditional Name

(1'R,3'S,7'S,8R,12'R)-12'-hydroxy-4,4,4',4',12',14'-hexamethyl-10H-9',14'-diazaspiro[[1,4]dioxepino[2,3-g]indole-8,5'-tetracyclo[5.5.2.0^{1,9}.0^{3,7}]tetradecane]-9,13'-dione

CAS Registry Number

Not Available

SMILES

CN1C(=O)[C@]23C[C@H]4C(C)(C)[C@@]5(C[C@]14CN2CC[C@@]3(C)O)C(=O)NC1=C5C=CC2=C1OC=CC(C)(C)O2

InChI Identifier

InChI=1S/C28H35N3O5/c1-23(2)10-12-35-20-17(36-23)8-7-16-19(20)29-21(32)27(16)14-26-15-31-11-9-25(5,34)28(31,22(33)30(26)6)13-18(26)24(27,3)4/h7-8,10,12,18,34H,9,11,13-15H2,1-6H3,(H,29,32)/t18-,25+,26+,27+,28-/m0/s1

InChI Key

UVZZDDLIOJPDKX-ITKQZBBDSA-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
Penicillium charlesii	LOTUS Database	35616633
Penicillium charlesii ATCC 20841	Fungi	KNApSAcK
Penicillium dierckxii	LOTUS Database	35616633
Penicillium paraherquei	Fungi	KNApSAcK
Penicillium simplicissimum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as azaspirodecane derivatives. These are organic compounds containing a spirodecane moiety with at least one nitrogen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azaspirodecane derivatives

Sub Class

Not Available

Direct Parent

Azaspirodecane derivatives

Alternative Parents

Substituents

Alpha-amino acid or derivatives
Azaspirodecane
Indole or derivatives
Dihydroindole
Indolizidine
1,4-dioxepine
Alkyl aryl ether
Delta-lactam
Dioxepine
Aralkylamine
N-alkylpiperazine
N-methylpiperazine
Piperidinone
1,4-diazinane
Benzenoid
N-alkylpyrrolidine
Piperazine
Piperidine
Tertiary carboxylic acid amide
Tertiary alcohol
Pyrrolidine
Tertiary aliphatic amine
Tertiary amine
Secondary carboxylic acid amide
Lactam
Amino acid or derivatives
Carboxamide group
Azacycle
Ether
Oxacycle
Carboxylic acid derivative
Amine
Hydrocarbon derivative
Organic nitrogen compound
Carbonyl group
Organic oxide
Alcohol
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	3.02	ALOGPS
logP	1.61	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	11.59	ChemAxon
pKa (Strongest Basic)	8.21	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	91.34 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	134.91 m³·mol⁻¹	ChemAxon
Polarizability	53.74 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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

C00016381

Chemspider ID

138139

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

156934

PDB ID

H8U

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (-)-Paraherquamide (NP0061600)

MOL for NP0061600 ((-)-Paraherquamide)

3D MOL for NP0061600 ((-)-Paraherquamide)

3D SDF for NP0061600 ((-)-Paraherquamide)

3D-SDF for NP0061600 ((-)-Paraherquamide)

PDB for NP0061600 ((-)-Paraherquamide)

3D PDB for NP0061600 ((-)-Paraherquamide)

SMILES for NP0061600 ((-)-Paraherquamide)

INCHI for NP0061600 ((-)-Paraherquamide)

Structure for NP0061600 ((-)-Paraherquamide)

3D Structure for NP0061600 ((-)-Paraherquamide)