NP-MRD: Showing NP-Card for Raucaffricine (NP0140366)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-06-29 21:28:16 UTC

Updated at

2022-06-29 21:28:16 UTC

NP-MRD ID

NP0140366

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Raucaffricine

Description

Raucaffricine belongs to the class of organic compounds known as ajmaline-sarpagine alkaloids. These are organic compounds containing either of the ajmalan, sarpagan skeleton, or derivative thereof. The Sarpagine (Akuammidine) group, based on the sarpagan nucleus, arises from bond formation between C-16 and C-5 of the corynantheine precursor. Ajmaline alkaloids are based on a 17,19-secoyohimban skeleton (oxayohimban) which is invariably present as an ether. Raucaffricine is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Raucaffricine was first documented in 2015 (PMID: 25140865). Based on a literature review a small amount of articles have been published on raucaffricine (PMID: 32825216) (PMID: 32314186) (PMID: 30583480) (PMID: 26827882).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652306292223282D          

 37 43  0  0  1  0            999 V2000
   -0.2699    1.6643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4772    0.8658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1106    0.2870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9791    0.1877    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9515    1.0223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5871    0.4291    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4498    0.5739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0204    1.2285    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6572    0.6743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4211    0.9859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0729    0.4801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9608   -0.3372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1969   -0.6488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5451   -0.1430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6786   -0.2627    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1182   -1.0762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3140   -1.1684    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7535   -0.4514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6022   -0.9752    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9651   -1.7161    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7882   -1.7723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2484   -1.0876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1510   -2.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0676   -0.3823    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2173   -0.5325    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2709   -1.1975    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0609   -1.9528    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4273   -2.6179    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0955   -3.3732    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7246   -3.4635    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2128   -2.7985    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8810   -2.0431    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0328   -2.8887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3647   -3.6441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0564   -4.2188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837   -4.0382    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2473   -2.5276    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  4  3  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
  7 15  1  0  0  0  0
 15 16  1  6  0  0  0
 17 16  1  6  0  0  0
 17 18  1  0  0  0  0
  4 18  1  0  0  0  0
 18 19  1  0  0  0  0
 15 19  1  0  0  0  0
 19 20  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 17 24  1  0  0  0  0
  6 24  1  0  0  0  0
 24 25  1  0  0  0  0
  3 25  1  0  0  0  0
 25 26  1  6  0  0  0
 27 26  1  6  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 27 32  1  0  0  0  0
 31 33  1  6  0  0  0
 33 34  1  0  0  0  0
 30 35  1  1  0  0  0
 29 36  1  6  0  0  0
 28 37  1  1  0  0  0
M  END

     RDKit          3D

 69 75  0  0  0  0  0  0  0  0999 V2000
   -0.0331    0.6566    4.2478 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7921    0.8031    3.0117 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3294    0.5551    1.8294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0655    0.1016    1.5866 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8333   -1.2730    0.9348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3312   -0.9410   -0.4490 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5374   -0.9952   -1.3400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9613   -1.9429   -2.0720 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1464   -1.5360   -2.7483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9123   -2.2806   -3.6529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0246   -1.6908   -4.2141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3239   -0.3971   -3.8538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5646    0.3150   -2.9683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4564   -0.2452   -2.3967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4570    0.1667   -1.4508 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5279    1.2803   -1.8477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7258    1.3641   -0.5685 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6545    1.0479    0.5577 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9025    0.4812   -0.0788 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9279    1.3192    0.1616 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0354    1.0418    0.9116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1514    1.9940    1.1569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9970   -0.1218    1.3718 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3128    0.3486   -0.5591 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1290    0.6959    0.5910 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3348    0.0766    0.6293 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4496    0.8678    0.5690 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0836    0.6139   -0.6106 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9356   -0.4235   -0.7214 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1076   -1.6356   -1.1985 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5524   -1.2987   -2.4342 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6846   -0.8860    0.4749 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9357   -0.2830    0.6099 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9048   -0.6519    1.7394 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8518   -1.5646    1.7342 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4164    0.7881    1.6799 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5629    1.5255    1.2805 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6548    0.4808    5.0971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6331    1.5486    4.4402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6820   -0.2426    4.2019 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8252    1.1386    3.1544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6955    0.0550    2.4607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7261   -1.9010    0.9484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0208   -1.8134    1.4640 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3395   -1.7673   -0.7809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6446   -3.2994   -3.9125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6137   -2.2749   -4.9153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2011    0.0415   -4.3086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8548    1.3216   -2.7303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9965    2.1976   -2.1530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8430    0.9211   -2.6427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2259    2.3421   -0.4735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8578    2.0003    1.1030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1025   -0.5010    0.4427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6269    1.8422    2.1488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8565    1.9979    0.3257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7182    3.0348    1.2001 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2940    1.7958    0.5255 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0774    1.9346    0.5018 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6436   -0.2930   -1.6167 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8193   -2.4579   -1.2784 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3013   -1.8563   -0.4886 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2652   -2.1427   -2.8519 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8965   -1.9885    0.4525 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2241   -0.4467    1.5456 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5296   -0.8043    2.6507 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0814   -2.4252    2.1146 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1519    1.2099    2.6399 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3817    2.4759    1.2059 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6 24  1  0
 24 17  1  0
 17 16  1  0
 16 15  1  0
 15 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 19 18  1  0
 15  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 29 32  1  0
 32 33  1  0
 32 34  1  0
 34 35  1  0
 34 36  1  0
 36 37  1  0
 25  3  1  0
 36 27  1  0
 18  4  1  0
 14  9  1  0
  7  6  1  0
 18 17  1  0
 15 14  1  6
  1 38  1  0
  1 39  1  0
  1 40  1  0
  2 41  1  0
  4 42  1  1
  5 43  1  0
  5 44  1  0
  6 45  1  6
 17 52  1  1
 16 50  1  0
 16 51  1  0
 19 54  1  1
 22 55  1  0
 22 56  1  0
 22 57  1  0
 18 53  1  1
 10 46  1  0
 11 47  1  0
 12 48  1  0
 13 49  1  0
 25 58  1  6
 27 59  1  6
 29 60  1  6
 30 61  1  0
 30 62  1  0
 31 63  1  0
 32 64  1  6
 33 65  1  0
 34 66  1  1
 35 67  1  0
 36 68  1  1
 37 69  1  0
M  END


  Mrv1652306292223282D          

 37 43  0  0  1  0            999 V2000
   -0.2699    1.6643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4772    0.8658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1106    0.2870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9791    0.1877    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9515    1.0223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5871    0.4291    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4498    0.5739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0204    1.2285    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6572    0.6743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4211    0.9859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0729    0.4801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9608   -0.3372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1969   -0.6488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5451   -0.1430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6786   -0.2627    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1182   -1.0762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3140   -1.1684    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7535   -0.4514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6022   -0.9752    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9651   -1.7161    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7882   -1.7723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2484   -1.0876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1510   -2.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0676   -0.3823    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2173   -0.5325    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2709   -1.1975    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0609   -1.9528    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4273   -2.6179    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0955   -3.3732    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7246   -3.4635    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2128   -2.7985    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8810   -2.0431    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0328   -2.8887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3647   -3.6441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0564   -4.2188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837   -4.0382    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2473   -2.5276    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  4  3  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
  7 15  1  0  0  0  0
 15 16  1  6  0  0  0
 17 16  1  6  0  0  0
 17 18  1  0  0  0  0
  4 18  1  0  0  0  0
 18 19  1  0  0  0  0
 15 19  1  0  0  0  0
 19 20  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 17 24  1  0  0  0  0
  6 24  1  0  0  0  0
 24 25  1  0  0  0  0
  3 25  1  0  0  0  0
 25 26  1  6  0  0  0
 27 26  1  6  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 27 32  1  0  0  0  0
 31 33  1  6  0  0  0
 33 34  1  0  0  0  0
 30 35  1  1  0  0  0
 29 36  1  6  0  0  0
 28 37  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0140366

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C1/[C@@H]2C[C@@H]3N([C@H]4C[C@]5([C@H](OC(C)=O)C24)C3=NC2=CC=CC=C52)[C@@H]1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C27H32N2O8/c1-3-12-13-8-16-23-27(14-6-4-5-7-15(14)28-23)9-17(19(13)24(27)35-11(2)31)29(16)25(12)37-26-22(34)21(33)20(32)18(10-30)36-26/h3-7,13,16-22,24-26,30,32-34H,8-10H2,1-2H3/b12-3+/t13-,16-,17-,18+,19?,20+,21-,22+,24+,25+,26-,27+/m0/s1

> <INCHI_KEY>
OSJPGOJPRNTSHP-ICYIRATMSA-N

> <FORMULA>
C27H32N2O8

> <MOLECULAR_WEIGHT>
512.559

> <EXACT_MASS>
512.215865998

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
53.16753647905862

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,10S,12R,13E,14R,16S,18R)-13-ethylidene-14-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-8,15-diazahexacyclo[14.2.1.0^{1,9}.0^{2,7}.0^{10,15}.0^{12,17}]nonadeca-2,4,6,8-tetraen-18-yl acetate

> <ALOGPS_LOGP>
0.83

> <JCHEM_LOGP>
0.6370797499999992

> <ALOGPS_LOGS>
-2.97

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.199085672378665

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.207969032030846

> <JCHEM_PKA_STRONGEST_BASIC>
5.03543420596711

> <JCHEM_POLAR_SURFACE_AREA>
141.28

> <JCHEM_REFRACTIVITY>
130.67710000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.54e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,10S,12R,13E,14R,16S,18R)-13-ethylidene-14-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-8,15-diazahexacyclo[14.2.1.0^{1,9}.0^{2,7}.0^{10,15}.0^{12,17}]nonadeca-2,4,6,8-tetraen-18-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-JUN-22         0                                  
HETATM    1  C   UNK     0      -0.504   3.107   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.891   1.616   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.207   0.536   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.828   0.350   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.776   1.908   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.963   0.801   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.573   1.071   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       5.638   2.293   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       6.827   1.259   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.253   1.840   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.469   0.896   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.260  -0.629   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.834  -1.211   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.618  -0.267   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.000  -0.490   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.954  -2.009   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.453  -2.181   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.273  -0.843   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.857  -1.820   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       5.535  -3.203   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       7.071  -3.308   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       7.930  -2.030   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       7.749  -4.691   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0       1.993  -0.714   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0       0.406  -0.994   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -0.506  -2.235   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       0.114  -3.645   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.798  -4.887   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -0.178  -6.297   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.353  -6.465   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.264  -5.224   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       1.644  -3.814   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       3.795  -5.392   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       4.414  -6.802   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       1.972  -7.875   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      -1.090  -7.538   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      -2.328  -4.718   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   25                                                  
CONECT    4    3    5   18                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   24                                                  
CONECT    7    6    8   15                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    9   15                                                  
CONECT   15   14    7   16   19                                             
CONECT   16   15   17                                                       
CONECT   17   16   18   24                                                  
CONECT   18   17    4   19                                                  
CONECT   19   18   15   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   17    6   25                                                  
CONECT   25   24    3   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   32                                                  
CONECT   28   27   29   37                                                  
CONECT   29   28   30   36                                                  
CONECT   30   29   31   35                                                  
CONECT   31   30   32   33                                                  
CONECT   32   31   27                                                       
CONECT   33   31   34                                                       
CONECT   34   33                                                            
CONECT   35   30                                                            
CONECT   36   29                                                            
CONECT   37   28                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   86    0
END

View in JSmol

Synonyms

Value	Source
Vomilenine beta-D-glucoside	Kegg
Vomilenine b-D-glucoside	Generator
Vomilenine β-D-glucoside	Generator

Chemical Formula

C₂₇H₃₂N₂O₈

Average Mass

512.5590 Da

Monoisotopic Mass

512.21587 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C\C=C1/[C@@H]2C[C@@H]3N([C@H]4C[C@]5([C@H](OC(C)=O)C24)C3=NC2=CC=CC=C52)[C@@H]1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C27H32N2O8/c1-3-12-13-8-16-23-27(14-6-4-5-7-15(14)28-23)9-17(19(13)24(27)35-11(2)31)29(16)25(12)37-26-22(34)21(33)20(32)18(10-30)36-26/h3-7,13,16-22,24-26,30,32-34H,8-10H2,1-2H3/b12-3+/t13-,16-,17-,18+,19?,20+,21-,22+,24+,25+,26-,27+/m0/s1

InChI Key

OSJPGOJPRNTSHP-ICYIRATMSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ajmaline-sarpagine alkaloids. These are organic compounds containing either of the ajmalan, sarpagan skeleton, or derivative thereof. The Sarpagine (Akuammidine) group, based on the sarpagan nucleus, arises from bond formation between C-16 and C-5 of the corynantheine precursor. Ajmaline alkaloids are based on a 17,19-secoyohimban skeleton (oxayohimban) which is invariably present as an ether.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Ajmaline-sarpagine alkaloids

Sub Class

Not Available

Direct Parent

Ajmaline-sarpagine alkaloids

Alternative Parents

Substituents

Sarpagine-skeleton
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Quinolizidine
3-alkylindole
Indole or derivatives
Quinuclidine
Azepane
Monosaccharide
Oxane
Piperidine
Benzenoid
Secondary alcohol
Carboxylic acid ester
Ketimine
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Organoheterocyclic compound
Carboxylic acid derivative
Azacycle
Monocarboxylic acid or derivatives
Acetal
Oxacycle
Polyol
Hydrocarbon derivative
Imine
Organic oxide
Primary alcohol
Carbonyl group
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
Alcohol
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

beta-D-glucoside (CHEBI:17400 )
Indole alkaloids (C02074 )

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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00024300

Chemspider ID

4444126

KEGG Compound ID

C02074

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5280486

PDB ID

Not Available

ChEBI ID

17400

Good Scents ID

Not Available

References

General References

Tlhapi DB, Ramaite IDI, Anokwuru CP, van Ree T, Hoppe HC: In Vitro Studies on Antioxidant and Anti-Parasitic Activities of Compounds Isolated from Rauvolfia caffra Sond. Molecules. 2020 Aug 20;25(17):3781. doi: 10.3390/molecules25173781. [PubMed:32825216 ]
Yang Y, Hou M, Zhang T, Sun Y, Zhang Y, Huang S, Xu X, Yuan H: A beta-glucosidase gene from Stevia rebaudiana may be involved in the steviol glycosides catabolic pathway. Mol Biol Rep. 2020 May;47(5):3577-3584. doi: 10.1007/s11033-020-05450-2. Epub 2020 Apr 20. [PubMed:32314186 ]
Tlhapi DB, Ramaite IDI, Van Ree T, Anokwuru CP, Orazio TS, Hoppe HC: Isolation, Chemical Profile and Antimalarial Activities of Bioactive Compounds from Rauvolfia caffra Sond. Molecules. 2018 Dec 21;24(1):39. doi: 10.3390/molecules24010039. [PubMed:30583480 ]
Wu F, Kercmar P, Zhang C, Stockigt J: Sarpagan-Ajmalan-Type Indoles: Biosynthesis, Structural Biology, and Chemo-Enzymatic Significance. Alkaloids Chem Biol. 2016;76:1-61. doi: 10.1016/bs.alkal.2015.10.001. Epub 2015 Nov 28. [PubMed:26827882 ]
Xia L, Lin H, Staniek A, Panjikar S, Ruppert M, Hilgers P, Williardt J, Rajendran C, Wang M, Warzecha H, Jager V, Stockigt J: Ligand structures of synthetic deoxa-pyranosylamines with raucaffricine and strictosidine glucosidases provide structural insights into their binding and inhibitory behaviours. J Enzyme Inhib Med Chem. 2015 Jun;30(3):472-8. doi: 10.3109/14756366.2014.949252. Epub 2014 Aug 20. [PubMed:25140865 ]

Showing NP-Card for Raucaffricine (NP0140366)

MOL for NP0140366 (Raucaffricine)

3D MOL for NP0140366 (Raucaffricine)

3D SDF for NP0140366 (Raucaffricine)

3D-SDF for NP0140366 (Raucaffricine)

PDB for NP0140366 (Raucaffricine)

3D PDB for NP0140366 (Raucaffricine)

SMILES for NP0140366 (Raucaffricine)

INCHI for NP0140366 (Raucaffricine)

Structure for NP0140366 (Raucaffricine)

3D Structure for NP0140366 (Raucaffricine)