NP-MRD: Showing NP-Card for Ajmalan-17-one (NP0140328)

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Record Information

Version

2.0

Created at

2022-06-29 21:24:42 UTC

Updated at

2022-06-29 21:24:42 UTC

NP-MRD ID

NP0140328

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Ajmalan-17-one

Description

Ajmalan-17-one 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. Based on a literature review very few articles have been published on Ajmalan-17-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 46 51  0  0  0  0  0  0  0  0999 V2000
    5.1395   -0.4286   -1.0388 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5386   -0.1691    0.3137 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2622    0.1301    0.4344 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5937    0.4002    1.7360 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1702    0.1300    1.4917 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1383   -1.1741    0.8136 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3159   -1.5805    0.8037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8260   -0.6822   -0.3023 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1698   -0.9162   -1.3549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0568   -1.0182   -2.5284 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4664   -0.9950   -0.6686 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3306    0.2323   -0.7456 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5380    1.5085   -0.4221 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5534    1.1519    0.7058 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7081    0.7850    0.0515 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9361    1.0257    0.7096 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1784    1.8950    1.8144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8918    0.2186    0.0424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2787    0.3508   -0.0432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9244    1.4033    0.6036 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0197   -0.5529   -0.7637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3764   -1.5839   -1.3957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0049   -1.7100   -1.3075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2200   -0.8344   -0.6004 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6321   -1.2625   -1.5536 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2224   -0.6039   -0.8703 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0804    0.5181   -1.6303 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1224   -0.2170    1.2305 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9719   -0.3117    2.4730 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7322    1.4685    2.0537 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7989   -1.8718    1.3143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3809   -2.6136    0.4488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8256   -1.4093    1.7651 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0355   -1.8352   -1.0666 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8530    0.3689   -1.6859 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2375    2.2696   -0.0439 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0020    1.8673   -1.3065 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3911    2.0311    1.3600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7923    1.3120   -0.9503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1771    2.3837    1.8037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0472    1.3631    2.8017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4465    2.7484    1.8753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9098    1.4757    0.5279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1103   -0.4417   -0.8261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9890   -2.2815   -1.9574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5644   -2.5446   -1.8293 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  7  1  0
  7  8  1  0
  8 15  1  0
 15 14  1  0
 14 13  1  0
 13 12  1  0
 12 11  1  0
 11  9  1  0
  9 10  2  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 24  2  0
 24 23  1  0
 23 22  2  0
 22 21  1  0
 21 19  2  0
 19 20  1  0
 12  3  1  0
 19 18  1  0
 14  5  1  0
 11  6  1  0
  8  9  1  6
 24  8  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  4 29  1  0
  4 30  1  0
  6 31  1  1
  7 32  1  0
  7 33  1  0
 15 39  1  6
 14 38  1  1
 13 36  1  0
 13 37  1  0
 12 35  1  6
 11 34  1  6
 17 40  1  0
 17 41  1  0
 17 42  1  0
 23 46  1  0
 22 45  1  0
 21 44  1  0
 20 43  1  0
M  END


  Mrv1652306292223242D          

 24 29  0  0  0  0            999 V2000
   -0.2779   -1.2924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4852   -0.4938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1027    0.0850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2093    0.9045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0597    0.7543    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5792   -0.0571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9435   -0.6503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9711    0.1843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7456    0.8234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3060    1.5404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1103    1.4482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6707    0.6347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4418   -0.2019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0125   -0.8565    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6493   -0.3023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5372    0.5150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1890    1.0208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9529    0.7092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0650   -0.1081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4132   -0.6139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5253   -1.4312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9557   -1.6795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5942    1.3472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9571    2.0881    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
  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
  7  8  1  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  6 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
 12 16  1  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
 15 20  1  0  0  0  0
 20 21  1  0  0  0  0
 14 22  1  0  0  0  0
 12 23  1  0  0  0  0
  9 23  1  0  0  0  0
 23 24  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0140328

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C1\CN2C3CC45C(C2CC1C3C4=O)N(C)C1=C5C=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C20H22N2O2/c1-3-10-9-22-13-7-11(10)16-14(22)8-20(19(16)24)12-5-4-6-15(23)17(12)21(2)18(13)20/h3-6,11,13-14,16,18,23H,7-9H2,1-2H3/b10-3-

> <INCHI_KEY>
VVLPFXAEVKKWTK-KMKOMSMNSA-N

> <FORMULA>
C20H22N2O2

> <MOLECULAR_WEIGHT>
322.408

> <EXACT_MASS>
322.168127956

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
35.39264312012426

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(13E)-13-ethylidene-6-hydroxy-8-methyl-8,15-diazahexacyclo[14.2.1.0^{1,9}.0^{2,7}.0^{10,15}.0^{12,17}]nonadeca-2(7),3,5-trien-18-one

> <ALOGPS_LOGP>
2.22

> <JCHEM_LOGP>
2.5540832793333332

> <ALOGPS_LOGS>
-2.13

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.486304126655124

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.08457360896973

> <JCHEM_PKA_STRONGEST_BASIC>
6.52487206598791

> <JCHEM_POLAR_SURFACE_AREA>
43.78

> <JCHEM_REFRACTIVITY>
93.46

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.37e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(13E)-13-ethylidene-6-hydroxy-8-methyl-8,15-diazahexacyclo[14.2.1.0^{1,9}.0^{2,7}.0^{10,15}.0^{12,17}]nonadeca-2(7),3,5-trien-18-one

> <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      -0.519  -2.412   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.906  -0.922   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.192   0.159   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.391   1.688   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       1.978   1.408   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       2.948  -0.107   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.761  -1.214   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.813   0.344   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.258   1.537   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.438   2.875   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.939   2.703   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.985   1.185   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.558  -0.377   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       5.623  -1.599   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       6.812  -0.564   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.603   0.961   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.819   1.905   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.245   1.324   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.455  -0.202   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.238  -1.146   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       8.447  -2.672   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       5.517  -3.135   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.843   2.515   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       5.520   3.898   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7   13                                                  
CONECT    7    6    8                                                       
CONECT    8    7    3    9                                                  
CONECT    9    8   10   23                                                  
CONECT   10    9    5   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   16   23                                             
CONECT   13   12    6   14                                                  
CONECT   14   13   15   22                                                  
CONECT   15   14   16   20                                                  
CONECT   16   15   12   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   15   21                                                  
CONECT   21   20                                                            
CONECT   22   14                                                            
CONECT   23   12    9   24                                                  
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   58    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₂N₂O₂

Average Mass

322.4080 Da

Monoisotopic Mass

322.16813 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C\C=C1\CN2C3CC45C(C2CC1C3C4=O)N(C)C1=C5C=CC=C1O

InChI Identifier

InChI=1S/C20H22N2O2/c1-3-10-9-22-13-7-11(10)16-14(22)8-20(19(16)24)12-5-4-6-15(23)17(12)21(2)18(13)20/h3-6,11,13-14,16,18,23H,7-9H2,1-2H3/b10-3-

InChI Key

VVLPFXAEVKKWTK-KMKOMSMNSA-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
Beta-carboline
Pyridoindole
Quinolizidine
Indole or derivatives
Quinuclidine
Tertiary aliphatic/aromatic amine
Dialkylarylamine
Aralkylamine
Azepane
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Piperidine
Tertiary aliphatic amine
Tertiary amine
Ketone
Organoheterocyclic compound
Azacycle
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Carbonyl group
Organic oxide
Organic nitrogen compound
Amine
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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78367982

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101136495

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Ajmalan-17-one (NP0140328)

MOL for NP0140328 (Ajmalan-17-one)

3D MOL for NP0140328 (Ajmalan-17-one)

3D SDF for NP0140328 (Ajmalan-17-one)

3D-SDF for NP0140328 (Ajmalan-17-one)

PDB for NP0140328 (Ajmalan-17-one)

3D PDB for NP0140328 (Ajmalan-17-one)

SMILES for NP0140328 (Ajmalan-17-one)

INCHI for NP0140328 (Ajmalan-17-one)

Structure for NP0140328 (Ajmalan-17-one)

3D Structure for NP0140328 (Ajmalan-17-one)