NP-MRD: Showing NP-Card for (2s)-1-[(5r,6r)-5-ethenyl-5-methyl-6-(3-oxoprop-1-en-2-yl)cyclohex-1-en-1-yl]propan-2-yl 6-nitro-2h-phenanthro[3,4-d][1,3]dioxole-5-carboxylate (NP0198661)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-04 17:08:55 UTC

Updated at

2022-09-04 17:08:55 UTC

NP-MRD ID

NP0198661

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-1-[(5r,6r)-5-ethenyl-5-methyl-6-(3-oxoprop-1-en-2-yl)cyclohex-1-en-1-yl]propan-2-yl 6-nitro-2h-phenanthro[3,4-d][1,3]dioxole-5-carboxylate

Description

Aristophyllide C belongs to the class of organic compounds known as aristolochic acids and derivatives. These are organic heterocyclic compounds with a structure characterized by a nitrophenanthro[3,4-d][1,3]dioxole ring system substituted at position 5, 6, and 8 by a carboxyl group (or a derivative thereof), a nitro group, and a methoxy group, respectively. (2s)-1-[(5r,6r)-5-ethenyl-5-methyl-6-(3-oxoprop-1-en-2-yl)cyclohex-1-en-1-yl]propan-2-yl 6-nitro-2h-phenanthro[3,4-d][1,3]dioxole-5-carboxylate is found in Aristolochia heterophylla. Based on a literature review very few articles have been published on Aristophyllide C.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042219082D          

 39 43  0  0  1  0            999 V2000
    6.4330   -6.8529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6149   -6.7468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2977   -5.9852    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1028   -5.8051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6028   -6.4299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8702   -6.0504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8326   -5.2262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5275   -4.7816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4899   -3.9574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7574   -3.5779    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0625   -4.0226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7198   -2.7538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9873   -2.3743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2923   -2.8189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9497   -1.5502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6446   -1.1055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6070   -0.2814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8745    0.0981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1795   -0.3465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2171   -1.1707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5222   -1.6153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5598   -2.4394    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    0.8649   -2.8841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9294   -3.1770    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    0.7897   -1.2358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7521   -0.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0195   -0.0321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0181    0.7920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6769    1.2366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4094    0.8571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4470    0.0330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0090    0.9121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8247    1.0356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1943    0.2980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2601   -5.1611    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9550   -4.7165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6875   -5.0960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9174   -3.8923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6123   -3.4477    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  1  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  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 15 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 21 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 26 31  1  0  0  0  0
 19 31  1  0  0  0  0
 18 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 17 34  1  0  0  0  0
  8 35  1  0  0  0  0
  3 35  1  0  0  0  0
 35 36  1  1  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
 38 39  2  0  0  0  0
M  CHG  2  22   1  24  -1
M  END

     RDKit          3D

 68 72  0  0  0  0  0  0  0  0999 V2000
   -5.7036    2.6874   -0.7680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9503    1.6904   -0.2856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5197    0.3030   -0.4430 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.6476    0.1922    0.4904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8185    0.1264   -1.8964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5588    0.4117   -2.6917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3684    0.5860   -1.8380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1938    0.0197   -0.6028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9136    0.3670   -0.0085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9630   -0.7856    0.0746 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2835   -1.9901    0.8267 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2970   -0.2761    0.5838 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4036   -0.2586   -0.2321 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3024   -0.6963   -1.4043 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6814    0.2586    0.2179 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6417    1.5686    0.7244 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7526    2.3045    0.9323 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9954    1.7494    0.6283 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0786    0.4717    0.1336 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8861   -0.3009   -0.0665 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9925   -1.5637   -0.5587 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9379   -2.4799   -0.6514 N   0  0  0  0  0  4  0  0  0  0  0  0
    2.1263   -2.6360    0.2667 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8881   -3.3785   -1.6775 O   0  0  0  0  0  1  0  0  0  0  0  0
    5.2367   -2.1034   -0.8846 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3641   -1.3560   -0.6948 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6105   -1.8991   -1.0194 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7853   -1.2028   -0.8511 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6972    0.0666   -0.3449 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4709    0.6501   -0.0061 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3259   -0.0736   -0.1882 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8994    2.7340    0.9410 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2728    4.0102    1.0326 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9472    3.6109    1.4234 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3447   -0.7218   -0.1440 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.5562   -1.1559    1.2191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9454   -0.9209    2.3302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6757   -2.1358    1.3599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9799   -2.6454    2.4524 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6504    2.5232   -1.2397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3446    3.7002   -0.6793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0236    1.9135    0.1683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4567   -0.5004    0.2499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1683    1.2134    0.4555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2777    0.1626    1.5359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0663   -0.9408   -2.0723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6830    0.7219   -2.2334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7569    1.3253   -3.2795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3450   -0.3841   -3.4401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5639    1.2329   -2.2594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9925    0.9202    0.9620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3498    1.1363   -0.6328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7501   -1.1283   -1.0045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3048   -1.8322    1.9463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2351   -2.4979    0.5475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5162   -2.8090    0.7205 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6772    1.9932    0.9538 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3294   -3.1029   -1.2861 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6764   -2.9106   -1.4214 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7576   -1.6484   -1.1128 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5905    0.6601   -0.1914 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4498    1.6396    0.3842 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2919    4.4457    0.0210 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7375    4.6196    1.8169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5476   -1.5582   -0.8302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3286   -1.3951    3.2556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0822   -0.3110    2.5215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2381   -2.4170    0.5020 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 10  1  0
 10  9  1  0
  9  8  1  0
  8  7  2  0
  7  6  1  0
  6  5  1  0
  5  3  1  0
  3  4  1  0
  3  2  1  6
  2  1  2  3
  3 35  1  0
 35 36  1  0
 36 37  2  3
 36 38  1  0
 38 39  2  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 20  1  0
 20 21  2  0
 21 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 19  2  0
 19 18  1  0
 18 32  1  0
 32 33  1  0
 33 34  1  0
 34 17  1  0
 17 16  1  0
 21 22  1  0
 22 24  1  0
 22 23  2  0
 35  8  1  0
 16 15  2  0
 19 20  1  0
 17 18  2  0
 31 26  1  0
 11 54  1  0
 11 55  1  0
 11 56  1  0
 10 53  1  6
  9 51  1  0
  9 52  1  0
  7 50  1  0
  6 48  1  0
  6 49  1  0
  5 46  1  0
  5 47  1  0
  4 43  1  0
  4 44  1  0
  4 45  1  0
  2 42  1  0
  1 40  1  0
  1 41  1  0
 35 65  1  6
 37 66  1  0
 37 67  1  0
 38 68  1  0
 25 58  1  0
 27 59  1  0
 28 60  1  0
 29 61  1  0
 30 62  1  0
 33 63  1  0
 33 64  1  0
 16 57  1  0
M  CHG  2  22   1  24  -1
M  END


  Mrv1652309042219082D          

 39 43  0  0  1  0            999 V2000
    6.4330   -6.8529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6149   -6.7468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2977   -5.9852    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1028   -5.8051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6028   -6.4299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8702   -6.0504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8326   -5.2262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5275   -4.7816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4899   -3.9574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7574   -3.5779    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0625   -4.0226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7198   -2.7538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9873   -2.3743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2923   -2.8189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9497   -1.5502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6446   -1.1055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6070   -0.2814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8745    0.0981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1795   -0.3465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2171   -1.1707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5222   -1.6153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5598   -2.4394    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    0.8649   -2.8841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9294   -3.1770    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    0.7897   -1.2358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7521   -0.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0195   -0.0321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0181    0.7920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6769    1.2366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4094    0.8571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4470    0.0330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0090    0.9121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8247    1.0356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1943    0.2980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2601   -5.1611    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9550   -4.7165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6875   -5.0960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9174   -3.8923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6123   -3.4477    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  1  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  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 15 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 21 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 26 31  1  0  0  0  0
 19 31  1  0  0  0  0
 18 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 17 34  1  0  0  0  0
  8 35  1  0  0  0  0
  3 35  1  0  0  0  0
 35 36  1  1  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
 38 39  2  0  0  0  0
M  CHG  2  22   1  24  -1
M  END
> <DATABASE_ID>
NP0198661

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H](CC1=CCC[C@](C)(C=C)[C@@H]1C(=C)C=O)OC(=O)C1=C2C(=CC3=CC=CC=C3C2=C2OCOC2=C1)[N+]([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C31H29NO7/c1-5-31(4)12-8-10-21(28(31)18(2)16-33)13-19(3)39-30(34)23-15-25-29(38-17-37-25)27-22-11-7-6-9-20(22)14-24(26(23)27)32(35)36/h5-7,9-11,14-16,19,28H,1-2,8,12-13,17H2,3-4H3/t19-,28+,31-/m0/s1

> <INCHI_KEY>
IIBMSRRBRIHDMP-GOVLGDJKSA-N

> <FORMULA>
C31H29NO7

> <MOLECULAR_WEIGHT>
527.573

> <EXACT_MASS>
527.194402278

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
54.710857306726666

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-1-[(5R,6R)-5-ethenyl-5-methyl-6-(3-oxoprop-1-en-2-yl)cyclohex-1-en-1-yl]propan-2-yl 9-nitro-14,16-dioxatetracyclo[8.7.0.0^{2,7}.0^{13,17}]heptadeca-1(17),2,4,6,8,10,12-heptaene-11-carboxylate

> <JCHEM_LOGP>
6.4424719853333325

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.470618332981418

> <JCHEM_POLAR_SURFACE_AREA>
104.97

> <JCHEM_REFRACTIVITY>
146.6992

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-1-[(5R,6R)-5-ethenyl-5-methyl-6-(3-oxoprop-1-en-2-yl)cyclohex-1-en-1-yl]propan-2-yl 9-nitro-14,16-dioxatetracyclo[8.7.0.0^{2,7}.0^{13,17}]heptadeca-1(17),2,4,6,8,10,12-heptaene-11-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      12.008 -12.792   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.481 -12.594   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.889 -11.172   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.392 -10.836   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.592 -12.002   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.224 -11.294   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.154  -9.756   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.451  -8.926   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.381  -7.387   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.014  -6.679   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.717  -7.509   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       6.944  -5.140   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       5.576  -4.432   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       4.279  -5.262   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       5.506  -2.894   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.803  -2.064   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.733  -0.525   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.366   0.183   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.068  -0.647   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.139  -2.185   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.841  -3.015   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0       2.912  -4.554   0.000  0.00  0.00           N+1
HETATM   23  O   UNK     0       1.614  -5.384   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       3.602  -5.930   0.000  0.00  0.00           O-1
HETATM   25  C   UNK     0       1.474  -2.307   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.404  -0.768   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.036  -0.060   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.034   1.478   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.263   2.308   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.631   1.600   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.701   0.062   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       5.617   1.703   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       7.139   1.933   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       7.829   0.556   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       9.819  -9.634   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      11.116  -8.804   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      12.483  -9.512   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      11.046  -7.266   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      12.343  -6.436   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5   35                                             
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   35                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   34                                                  
CONECT   18   17   19   32                                                  
CONECT   19   18   20   31                                                  
CONECT   20   19   15   21                                                  
CONECT   21   20   22   25                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   21   26                                                       
CONECT   26   25   27   31                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   26   19                                                  
CONECT   32   18   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   17                                                       
CONECT   35    8    3   36                                                  
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39                                                       
CONECT   39   38                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   86    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₁H₂₉NO₇

Average Mass

527.5730 Da

Monoisotopic Mass

527.19440 Da

IUPAC Name

(2S)-1-[(5R,6R)-5-ethenyl-5-methyl-6-(3-oxoprop-1-en-2-yl)cyclohex-1-en-1-yl]propan-2-yl 9-nitro-14,16-dioxatetracyclo[8.7.0.0^{2,7}.0^{13,17}]heptadeca-1(17),2,4,6,8,10,12-heptaene-11-carboxylate

Traditional Name

(2S)-1-[(5R,6R)-5-ethenyl-5-methyl-6-(3-oxoprop-1-en-2-yl)cyclohex-1-en-1-yl]propan-2-yl 9-nitro-14,16-dioxatetracyclo[8.7.0.0^{2,7}.0^{13,17}]heptadeca-1(17),2,4,6,8,10,12-heptaene-11-carboxylate

CAS Registry Number

Not Available

SMILES

C[C@@H](CC1=CCC[C@](C)(C=C)[C@@H]1C(=C)C=O)OC(=O)C1=C2C(=CC3=CC=CC=C3C2=C2OCOC2=C1)[N+]([O-])=O

InChI Identifier

InChI=1S/C31H29NO7/c1-5-31(4)12-8-10-21(28(31)18(2)16-33)13-19(3)39-30(34)23-15-25-29(38-17-37-25)27-22-11-7-6-9-20(22)14-24(26(23)27)32(35)36/h5-7,9-11,14-16,19,28H,1-2,8,12-13,17H2,3-4H3/t19-,28+,31-/m0/s1

InChI Key

IIBMSRRBRIHDMP-GOVLGDJKSA-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
Aristolochia heterophylla	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aristolochic acids and derivatives. These are organic heterocyclic compounds with a structure characterized by a nitrophenanthro[3,4-d][1,3]dioxole ring system substituted at position 5, 6, and 8 by a carboxyl group (or a derivative thereof), a nitro group, and a methoxy group, respectively.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenanthrenes and derivatives

Sub Class

Aristolochic acids and derivatives

Direct Parent

Aristolochic acids and derivatives

Alternative Parents

Substituents

Aristolochic acid or derivatives
1-naphthalenecarboxylic acid or derivatives
1-nitronaphthalene
2-nitronaphthalene
Aromatic monoterpenoid
Monoterpenoid
Naphthalene
Benzodioxole
Nitroaromatic compound
Alpha,beta-unsaturated aldehyde
Enal
Carboxylic acid ester
Organic nitro compound
C-nitro compound
Acetal
Carboxylic acid derivative
Oxacycle
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Allyl-type 1,3-dipolar organic compound
Organic oxoazanium
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Organic salt
Organopnictogen compound
Organic oxide
Carbonyl group
Aldehyde
Organonitrogen compound
Organooxygen compound
Organic cation
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	6.44	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	104.97 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	146.7 m³·mol⁻¹	ChemAxon
Polarizability	54.71 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00027295

Chemspider ID

9015180

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10839881

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s)-1-[(5r,6r)-5-ethenyl-5-methyl-6-(3-oxoprop-1-en-2-yl)cyclohex-1-en-1-yl]propan-2-yl 6-nitro-2h-phenanthro[3,4-d][1,3]dioxole-5-carboxylate (NP0198661)

MOL for NP0198661 ((2s)-1-[(5r,6r)-5-ethenyl-5-methyl-6-(3-oxoprop-1-en-2-yl)cyclohex-1-en-1-yl]propan-2-yl 6-nitro-2h-phenanthro[3,4-d][1,3]dioxole-5-carboxylate)

3D MOL for NP0198661 ((2s)-1-[(5r,6r)-5-ethenyl-5-methyl-6-(3-oxoprop-1-en-2-yl)cyclohex-1-en-1-yl]propan-2-yl 6-nitro-2h-phenanthro[3,4-d][1,3]dioxole-5-carboxylate)

3D SDF for NP0198661 ((2s)-1-[(5r,6r)-5-ethenyl-5-methyl-6-(3-oxoprop-1-en-2-yl)cyclohex-1-en-1-yl]propan-2-yl 6-nitro-2h-phenanthro[3,4-d][1,3]dioxole-5-carboxylate)

3D-SDF for NP0198661 ((2s)-1-[(5r,6r)-5-ethenyl-5-methyl-6-(3-oxoprop-1-en-2-yl)cyclohex-1-en-1-yl]propan-2-yl 6-nitro-2h-phenanthro[3,4-d][1,3]dioxole-5-carboxylate)

PDB for NP0198661 ((2s)-1-[(5r,6r)-5-ethenyl-5-methyl-6-(3-oxoprop-1-en-2-yl)cyclohex-1-en-1-yl]propan-2-yl 6-nitro-2h-phenanthro[3,4-d][1,3]dioxole-5-carboxylate)

3D PDB for NP0198661 ((2s)-1-[(5r,6r)-5-ethenyl-5-methyl-6-(3-oxoprop-1-en-2-yl)cyclohex-1-en-1-yl]propan-2-yl 6-nitro-2h-phenanthro[3,4-d][1,3]dioxole-5-carboxylate)

SMILES for NP0198661 ((2s)-1-[(5r,6r)-5-ethenyl-5-methyl-6-(3-oxoprop-1-en-2-yl)cyclohex-1-en-1-yl]propan-2-yl 6-nitro-2h-phenanthro[3,4-d][1,3]dioxole-5-carboxylate)

INCHI for NP0198661 ((2s)-1-[(5r,6r)-5-ethenyl-5-methyl-6-(3-oxoprop-1-en-2-yl)cyclohex-1-en-1-yl]propan-2-yl 6-nitro-2h-phenanthro[3,4-d][1,3]dioxole-5-carboxylate)

Structure for NP0198661 ((2s)-1-[(5r,6r)-5-ethenyl-5-methyl-6-(3-oxoprop-1-en-2-yl)cyclohex-1-en-1-yl]propan-2-yl 6-nitro-2h-phenanthro[3,4-d][1,3]dioxole-5-carboxylate)

3D Structure for NP0198661 ((2s)-1-[(5r,6r)-5-ethenyl-5-methyl-6-(3-oxoprop-1-en-2-yl)cyclohex-1-en-1-yl]propan-2-yl 6-nitro-2h-phenanthro[3,4-d][1,3]dioxole-5-carboxylate)