NP-MRD: Showing NP-Card for Perakine (NP0140593)

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Record Information

Version

2.0

Created at

2022-06-29 21:42:11 UTC

Updated at

2022-06-29 21:42:11 UTC

NP-MRD ID

NP0140593

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Perakine

Description

Perakine 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. Perakine was first documented in 2014 (PMID: 24887700). Based on a literature review a small amount of articles have been published on Perakine (PMID: 32198108) (PMID: 31459996) (PMID: 31045374) (PMID: 28654178).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652306292223422D          

 26 31  0  0  1  0            999 V2000
   -0.2789   -0.7445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2093   -0.0795    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1027    0.7400    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9711    0.6407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9435    1.4753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5792    0.8821    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0597    0.0707    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3060   -0.7154    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7456    0.0016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5942   -0.5222    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6707    0.1903    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1103   -0.6232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4418    1.0269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0125    1.6815    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6493    1.1273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4132    1.4389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0650    0.9331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9529    0.1158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1890   -0.1958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5372    0.3100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9571   -1.2631    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7802   -1.3193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2404   -0.6346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1431   -2.0602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4852    1.3188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2804    1.0991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  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
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
  8 12  1  6  0  0  0
 11 13  1  0  0  0  0
  6 13  1  1  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 11 20  1  0  0  0  0
 15 20  1  0  0  0  0
 10 21  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
  3 25  1  6  0  0  0
 25 26  2  0  0  0  0
M  END

     RDKit          3D

 48 53  0  0  0  0  0  0  0  0999 V2000
    2.8170   -3.0642   -2.3042 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9732   -2.4441   -1.2564 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8789   -3.0036   -0.1445 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2740   -1.2644   -1.4417 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4908   -0.7327   -0.3997 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9535   -0.5884   -0.7591 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2723    0.8973   -0.7509 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1034    1.5647   -0.8832 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9005    0.6515    0.0095 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4212    0.8688    1.3987 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4383    1.1868    2.0922 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6396    1.2250    1.3322 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9581    1.5179    1.6715 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9448    1.4779    0.7115 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6422    1.1502   -0.5862 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3161    0.8560   -0.9255 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3269    0.8940    0.0270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0396    0.6748    1.6315 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4392   -0.7604    1.6852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8747   -1.2061    0.2977 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2338   -0.5338    0.0586 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3038   -1.3765    0.5957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2739   -0.8725    1.1120 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1646    0.8298    0.6848 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1153    1.7721   -0.0041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7816    1.3071    0.5515 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6197   -3.6410   -1.8003 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2474   -3.7812   -2.9256 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3369   -2.2966   -2.9209 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5450   -1.3854    0.5028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2265   -1.0719   -1.7152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9583    1.1906   -1.5384 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4464    1.5824   -1.9217 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0281    2.5694   -0.4246 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1747    1.7741    2.7017 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9676    1.7069    0.9833 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4361    1.1265   -1.3184 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1402    0.6060   -1.9586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3239    1.1817    2.5581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3549   -0.8332    2.3375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6910   -1.4312    2.1265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9284   -2.2931    0.1961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3490   -0.3719   -1.0505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2284   -2.4462    0.5319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4218    0.8252    1.7618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1304    1.3637    0.0839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1106    2.7560    0.4888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8919    1.8420   -1.1022 H   0  0  0  0  0  0  0  0  0  0  0  0
 25 24  1  0
 24 21  1  0
 21 22  1  0
 22 23  2  0
 21 20  1  0
 20 19  1  0
 19 18  1  0
 18 26  1  0
 26  7  1  0
  7  8  1  0
  8  9  1  0
  9  5  1  0
  5  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  2  0
  5  6  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 26 24  1  0
  6  7  1  0
 17 12  1  0
  6 20  1  0
 10 18  1  0
  9 17  1  1
 25 46  1  0
 25 47  1  0
 25 48  1  0
 24 45  1  1
 21 43  1  6
 22 44  1  0
 20 42  1  1
 19 40  1  0
 19 41  1  0
 18 39  1  1
  7 32  1  6
  8 33  1  0
  8 34  1  0
  5 30  1  1
  1 27  1  0
  1 28  1  0
  1 29  1  0
  6 31  1  6
 13 35  1  0
 14 36  1  0
 15 37  1  0
 16 38  1  0
M  END


  Mrv1652306292223422D          

 26 31  0  0  1  0            999 V2000
   -0.2789   -0.7445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2093   -0.0795    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1027    0.7400    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9711    0.6407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9435    1.4753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5792    0.8821    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0597    0.0707    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3060   -0.7154    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7456    0.0016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5942   -0.5222    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6707    0.1903    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1103   -0.6232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4418    1.0269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0125    1.6815    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6493    1.1273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4132    1.4389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0650    0.9331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9529    0.1158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1890   -0.1958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5372    0.3100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9571   -1.2631    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7802   -1.3193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2404   -0.6346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1431   -2.0602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4852    1.3188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2804    1.0991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  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
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
  8 12  1  6  0  0  0
 11 13  1  0  0  0  0
  6 13  1  1  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 11 20  1  0  0  0  0
 15 20  1  0  0  0  0
 10 21  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
  3 25  1  6  0  0  0
 25 26  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0140593

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1[C@H](C=O)C2C[C@@H]3N1[C@H]1C[C@]4([C@H](OC(C)=O)C21)C3=NC1=CC=CC=C41

> <INCHI_IDENTIFIER>
InChI=1S/C21H22N2O3/c1-10-13(9-24)12-7-16-19-21(14-5-3-4-6-15(14)22-19)8-17(23(10)16)18(12)20(21)26-11(2)25/h3-6,9-10,12-13,16-18,20H,7-8H2,1-2H3/t10-,12?,13-,16-,17-,18?,20+,21+/m0/s1

> <INCHI_KEY>
GDXJMOGWONJRHL-HWUILILVSA-N

> <FORMULA>
C21H22N2O3

> <MOLECULAR_WEIGHT>
350.418

> <EXACT_MASS>
350.163042576

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
37.64009536156601

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,10S,13R,14S,16S,18R)-13-formyl-14-methyl-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>
1.98

> <JCHEM_LOGP>
1.926834343

> <ALOGPS_LOGS>
-3.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.07265576577203

> <JCHEM_PKA_STRONGEST_BASIC>
5.913544103136134

> <JCHEM_POLAR_SURFACE_AREA>
58.97

> <JCHEM_REFRACTIVITY>
96.9676

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.19e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,10S,13R,14S,16S,18R)-13-formyl-14-methyl-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      -0.521  -1.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.391  -0.148   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.192   1.381   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.813   1.196   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.761   2.754   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.948   1.647   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       1.978   0.132   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       2.438  -1.335   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.258   0.003   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.843  -0.975   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.985   0.355   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.939  -1.163   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.558   1.917   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       5.623   3.139   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       6.812   2.104   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.238   2.686   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.455   1.742   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.245   0.216   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.819  -0.365   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.603   0.579   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.520  -2.358   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       7.056  -2.463   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       7.915  -1.185   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       7.734  -3.846   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.906   2.462   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -2.390   2.052   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4   25                                                  
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   13                                                  
CONECT    7    6    2    8                                                  
CONECT    8    7    9   12                                                  
CONECT    9    8    4   10                                                  
CONECT   10    9   11   21                                                  
CONECT   11   10   12   13   20                                             
CONECT   12   11    8                                                       
CONECT   13   11    6   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   11   15                                                  
CONECT   21   10   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25    3   26                                                       
CONECT   26   25                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   62    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₂N₂O₃

Average Mass

350.4180 Da

Monoisotopic Mass

350.16304 Da

IUPAC Name

(1R,10S,13R,14S,16S,18R)-13-formyl-14-methyl-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

Traditional Name

(1R,10S,13R,14S,16S,18R)-13-formyl-14-methyl-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

CAS Registry Number

Not Available

SMILES

C[C@H]1[C@H](C=O)C2C[C@@H]3N1[C@H]1C[C@]4([C@H](OC(C)=O)C21)C3=NC1=CC=CC=C41

InChI Identifier

InChI=1S/C21H22N2O3/c1-10-13(9-24)12-7-16-19-21(14-5-3-4-6-15(14)22-19)8-17(23(10)16)18(12)20(21)26-11(2)25/h3-6,9-10,12-13,16-18,20H,7-8H2,1-2H3/t10-,12?,13-,16-,17-,18?,20+,21+/m0/s1

InChI Key

GDXJMOGWONJRHL-HWUILILVSA-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
Quinolizidine
3-alkylindole
Indole or derivatives
Quinuclidine
Azepane
Aralkylamine
Piperidine
Benzenoid
Amino acid or derivatives
Carboxylic acid ester
Ketimine
Tertiary amine
Tertiary aliphatic amine
Azacycle
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Organoheterocyclic compound
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Amine
Organopnictogen compound
Imine
Aldehyde
Organonitrogen compound
Carbonyl group
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Organic oxide
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	1.98	ALOGPS
logP	1.93	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	17.07	ChemAxon
pKa (Strongest Basic)	5.91	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	58.97 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	96.97 m³·mol⁻¹	ChemAxon
Polarizability	37.64 Å³	ChemAxon
Number of Rings	6	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

C00024279

Chemspider ID

399181

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Perakine

METLIN ID

Not Available

PubChem Compound

453213

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Rosales PF, Bordin GS, Gower AE, Moura S: Indole alkaloids: 2012 until now, highlighting the new chemical structures and biological activities. Fitoterapia. 2020 Jun;143:104558. doi: 10.1016/j.fitote.2020.104558. Epub 2020 Mar 17. [PubMed:32198108 ]
Ngoune B, Pengou M, Nouteza AM, Nanseu-Njiki CP, Ngameni E: Performances of Alkaloid Extract from Rauvolfia macrophylla Stapf toward Corrosion Inhibition of C38 Steel in Acidic Media. ACS Omega. 2019 May 23;4(5):9081-9091. doi: 10.1021/acsomega.9b01076. eCollection 2019 May 31. [PubMed:31459996 ]
Cai S, Shao N, Chen Y, Li A, Pan J, Zhu H, Zou H, Zeng S, Sun L, Zhao J: Enantioselective Reduction of alpha,beta-Unsaturated Ketones and Aryl Ketones by Perakine Reductase. Org Lett. 2019 Jun 21;21(12):4411-4414. doi: 10.1021/acs.orglett.9b00950. Epub 2019 May 2. [PubMed:31045374 ]
Dang TT, Franke J, Tatsis E, O'Connor SE: Dual Catalytic Activity of a Cytochrome P450 Controls Bifurcation at a Metabolic Branch Point of Alkaloid Biosynthesis in Rauwolfia serpentina. Angew Chem Int Ed Engl. 2017 Aug 1;56(32):9440-9444. doi: 10.1002/anie.201705010. Epub 2017 Jul 12. [PubMed:28654178 ]
Zhang L, Hua Z, Song Y, Feng C: Monoterpenoid indole alkaloids from Alstonia rupestris with cytotoxic, antibacterial and antifungal activities. Fitoterapia. 2014 Sep;97:142-7. doi: 10.1016/j.fitote.2014.05.018. Epub 2014 Jun 2. [PubMed:24887700 ]

Showing NP-Card for Perakine (NP0140593)

MOL for NP0140593 (Perakine)

3D MOL for NP0140593 (Perakine)

3D SDF for NP0140593 (Perakine)

3D-SDF for NP0140593 (Perakine)

PDB for NP0140593 (Perakine)

3D PDB for NP0140593 (Perakine)

SMILES for NP0140593 (Perakine)

INCHI for NP0140593 (Perakine)

Structure for NP0140593 (Perakine)

3D Structure for NP0140593 (Perakine)