NP-MRD: Showing NP-Card for Ajmalimine (NP0139544)

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Record Information

Version

2.0

Created at

2022-06-29 19:59:18 UTC

Updated at

2022-06-29 19:59:18 UTC

NP-MRD ID

NP0139544

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Ajmalimine

Description

Ajmalimine 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. Ajmalimine was first documented in 1987 (PMID: 17269023). Based on a literature review very few articles have been published on Ajmalimine (PMID: 11374979).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652306292221592D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306292221592D          

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  4  5  1  0  0  0  0
  6  5  1  6  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  1  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  1  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
 15 20  1  0  0  0  0
 12 20  1  0  0  0  0
 14 21  1  0  0  0  0
 12 22  1  0  0  0  0
  9 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 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
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 29 34  1  0  0  0  0
 34 35  1  0  0  0  0
 28 36  1  0  0  0  0
 36 37  1  0  0  0  0
  4 38  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0139544

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@@H]1[C@@H](O)N2[C@H]3CC45C(OC(=O)C6=CC(OC)=C(OC)C(OC)=C6)C3C1C[C@H]2[C@@H]4N(C)C1=CC=CC=C51

> <INCHI_IDENTIFIER>
InChI=1S/C30H36N2O6/c1-6-16-17-13-20-26-30(18-9-7-8-10-19(18)31(26)2)14-21(32(20)28(16)33)24(17)27(30)38-29(34)15-11-22(35-3)25(37-5)23(12-15)36-4/h7-12,16-17,20-21,24,26-28,33H,6,13-14H2,1-5H3/t16-,17?,20-,21-,24?,26-,27?,28+,30?/m0/s1

> <INCHI_KEY>
JCRQPLRRHXVYJF-DBROWAFRSA-N

> <FORMULA>
C30H36N2O6

> <MOLECULAR_WEIGHT>
520.626

> <EXACT_MASS>
520.257336887

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
56.39063491691437

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(9R,10S,13S,14R,16S)-13-ethyl-14-hydroxy-8-methyl-8,15-diazahexacyclo[14.2.1.0^{1,9}.0^{2,7}.0^{10,15}.0^{12,17}]nonadeca-2,4,6-trien-18-yl 3,4,5-trimethoxybenzoate

> <ALOGPS_LOGP>
3.60

> <JCHEM_LOGP>
3.873093838666669

> <ALOGPS_LOGS>
-3.74

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.325569331971789

> <JCHEM_PKA_STRONGEST_BASIC>
7.240585140320955

> <JCHEM_POLAR_SURFACE_AREA>
80.70000000000002

> <JCHEM_REFRACTIVITY>
141.77739999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.49e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(9R,10S,13S,14R,16S)-13-ethyl-14-hydroxy-8-methyl-8,15-diazahexacyclo[14.2.1.0^{1,9}.0^{2,7}.0^{10,15}.0^{12,17}]nonadeca-2,4,6-trien-18-yl 3,4,5-trimethoxybenzoate

> <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      -2.390  -0.512   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       8.238  -1.146   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.455  -0.202   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       7.819   1.905   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.603   0.961   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.517  -3.135   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.843   2.515   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       5.520   3.898   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       4.661   5.176   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       3.124   5.071   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       5.338   6.559   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.479   7.837   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.157   9.220   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.693   9.325   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.552   8.047   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.875   6.664   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       9.089   8.152   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       9.948   6.874   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       7.370  10.708   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       6.511  11.986   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       4.298  10.498   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       4.975  11.881   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -0.521   2.930   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5   38                                                  
CONECT    5    4    6   10                                                  
CONECT    6    5    7   13                                                  
CONECT    7    6    8                                                       
CONECT    8    7    3    9                                                  
CONECT    9    8   10   22                                                  
CONECT   10    9    5   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   20   22                                             
CONECT   13   12    6   14                                                  
CONECT   14   13   15   21                                                  
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   15   12                                                  
CONECT   21   14                                                            
CONECT   22   12    9   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   31                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   36                                                  
CONECT   29   28   30   34                                                  
CONECT   30   29   31   32                                                  
CONECT   31   30   26                                                       
CONECT   32   30   33                                                       
CONECT   33   32                                                            
CONECT   34   29   35                                                       
CONECT   35   34                                                            
CONECT   36   28   37                                                       
CONECT   37   36                                                            
CONECT   38    4                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   88    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₃₆N₂O₆

Average Mass

520.6260 Da

Monoisotopic Mass

520.25734 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC[C@@H]1[C@@H](O)N2[C@H]3CC45C(OC(=O)C6=CC(OC)=C(OC)C(OC)=C6)C3C1C[C@H]2[C@@H]4N(C)C1=CC=CC=C51

InChI Identifier

InChI=1S/C30H36N2O6/c1-6-16-17-13-20-26-30(18-9-7-8-10-19(18)31(26)2)14-21(32(20)28(16)33)24(17)27(30)38-29(34)15-11-22(35-3)25(37-5)23(12-15)36-4/h7-12,16-17,20-21,24,26-28,33H,6,13-14H2,1-5H3/t16-,17?,20-,21-,24?,26-,27?,28+,30?/m0/s1

InChI Key

JCRQPLRRHXVYJF-DBROWAFRSA-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
Pyridoindole
Beta-carboline
Gallic acid or derivatives
M-methoxybenzoic acid or derivatives
P-methoxybenzoic acid or derivatives
Quinolizidine
Benzoate ester
Indole or derivatives
Benzoic acid or derivatives
Benzoyl
Methoxybenzene
Tertiary aliphatic/aromatic amine
Quinuclidine
Phenoxy compound
Anisole
Phenol ether
Dialkylarylamine
Azepane
Alkyl aryl ether
Aralkylamine
Monocyclic benzene moiety
Benzenoid
Piperidine
Hemiaminal
Amino acid or derivatives
Tertiary amine
Carboxylic acid ester
Alkanolamine
Organoheterocyclic compound
Azacycle
Carboxylic acid derivative
Ether
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Amine
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00024288

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

42621393

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Hanhinen P, Lounasmaa M: Revision of the structure of ajmalimine. J Nat Prod. 2001 May;64(5):686-7. doi: 10.1021/np000618m. [PubMed:11374979 ]
Siddiqui S, Ahmad SS, Haider SI: A New Alkaloid Ajmalimine from the Roots of Rauwolfia serpentina. Planta Med. 1987 Jun;53(3):288-9. doi: 10.1055/s-2006-962708. [PubMed:17269023 ]

Showing NP-Card for Ajmalimine (NP0139544)

MOL for NP0139544 (Ajmalimine)

3D MOL for NP0139544 (Ajmalimine)

3D SDF for NP0139544 (Ajmalimine)

3D-SDF for NP0139544 (Ajmalimine)

PDB for NP0139544 (Ajmalimine)

3D PDB for NP0139544 (Ajmalimine)

SMILES for NP0139544 (Ajmalimine)

INCHI for NP0139544 (Ajmalimine)

Structure for NP0139544 (Ajmalimine)

3D Structure for NP0139544 (Ajmalimine)