NP-MRD: Showing NP-Card for (-)-Anaferine (NP0051113)

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Record Information

Version

2.0

Created at

2022-04-27 22:32:27 UTC

Updated at

2022-04-27 22:32:27 UTC

NP-MRD ID

NP0051113

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Anaferine

Description

(-)-Anaferine belongs to the class of organic compounds known as piperidines. Piperidines are compounds containing a piperidine ring, which is a saturated aliphatic six-member ring with one nitrogen atom and five carbon atoms (-)-anaferine is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. (-)-Anaferine is found in Averrhoa bilimbi and Withania somnifera . (-)-Anaferine was first documented in 2020 (PMID: 32120931). Based on a literature review a small amount of articles have been published on (-)-anaferine.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 40 41  0  0  0  0  0  0  0  0999 V2000
   -0.1672    1.1701   -1.0569 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0330    1.0691    0.1366 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3793    1.2404    0.7240 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1257   -0.0691    0.7521 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2812   -0.5938   -0.6223 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4086    0.1942   -1.3017 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6694   -0.1981   -0.5701 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5201   -0.3709    0.8937 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3323    0.1213    1.4804 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1024    0.7660    1.0269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4073    0.6211    0.2710 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2484   -0.4975   -0.7061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4560   -1.3690   -0.8481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6807   -0.4581   -0.7121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7004    0.0197    0.7054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4539    0.4498    1.2195 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2421    1.6290    1.7699 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9320    2.0172    0.1329 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4906   -0.7880    1.3340 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3612   -0.5439   -1.2097 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6770   -1.6475   -0.5856 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2765    1.2777   -1.1950 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5181   -0.1260   -2.3602 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9707   -1.1991   -0.9995 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4862    0.4907   -0.8655 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3909    0.1563    1.3868 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6483   -1.4444    1.2205 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4175    1.0445    1.9531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2116    1.5084    1.8562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8799   -0.2077    1.5542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5645    1.6001   -0.2665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3541   -1.1240   -0.4913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0494   -0.0480   -1.7179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4904   -2.0656    0.0173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4538   -1.8696   -1.8222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6405    0.3594   -1.4466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5734   -1.1067   -0.8707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4990    0.7977    0.8391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0587   -0.8491    1.3318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1691    0.0433    2.1295 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  2 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
  9  4  1  0
 16 11  1  0
  3 17  1  0
  3 18  1  0
  4 19  1  1
  5 20  1  0
  5 21  1  0
  6 22  1  0
  6 23  1  0
  7 24  1  0
  7 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  6
 12 32  1  0
 12 33  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  0
 15 39  1  0
 16 40  1  0
M  END


  Mrv1652304282200322D          

 16 17  0  0  1  0            999 V2000
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  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
  1  6  1  0  0  0  0
  4  7  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 11 10  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 11 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051113

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O=C(C[C@H]1CCCCN1)C[C@H]1CCCCN1

> <INCHI_IDENTIFIER>
InChI=1S/C13H24N2O/c16-13(9-11-5-1-3-7-14-11)10-12-6-2-4-8-15-12/h11-12,14-15H,1-10H2/t11-,12-/m1/s1

> <INCHI_KEY>
JFMCQBGTUJUOAB-VXGBXAGGSA-N

> <FORMULA>
C13H24N2O

> <MOLECULAR_WEIGHT>
224.348

> <EXACT_MASS>
224.188863401

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
26.82016074863039

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,3-bis[(2R)-piperidin-2-yl]propan-2-one

> <ALOGPS_LOGP>
1.26

> <JCHEM_LOGP>
1.4174727863333327

> <ALOGPS_LOGS>
-2.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.53425632211807

> <JCHEM_PKA_STRONGEST_BASIC>
10.164709033161097

> <JCHEM_POLAR_SURFACE_AREA>
41.13

> <JCHEM_REFRACTIVITY>
65.4866

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.76e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(-)-anaferine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       4.001  -5.390   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       8.002   1.540   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   11                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₃H₂₄N₂O

Average Mass

224.3480 Da

Monoisotopic Mass

224.18886 Da

IUPAC Name

1,3-bis[(2R)-piperidin-2-yl]propan-2-one

Traditional Name

(-)-anaferine

CAS Registry Number

Not Available

SMILES

O=C(C[C@H]1CCCCN1)C[C@H]1CCCCN1

InChI Identifier

InChI=1S/C13H24N2O/c16-13(9-11-5-1-3-7-14-11)10-12-6-2-4-8-15-12/h11-12,14-15H,1-10H2/t11-,12-/m1/s1

InChI Key

JFMCQBGTUJUOAB-VXGBXAGGSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Averrhoa bilimbi	Plant	KNApSAcK
Withania somnifera	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as piperidines. Piperidines are compounds containing a piperidine ring, which is a saturated aliphatic six-member ring with one nitrogen atom and five carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Piperidines

Sub Class

Not Available

Direct Parent

Piperidines

Alternative Parents

Substituents

Beta-aminoketone
Piperidine
Ketone
Secondary aliphatic amine
Secondary amine
Azacycle
Amine
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

ketone (CHEBI:75 )
piperidine alkaloid (CHEBI:75 )
Piperidine alkaloids (C11358 )

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	1.26	ALOGPS
logP	1.42	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	17.53	ChemAxon
pKa (Strongest Basic)	10.16	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	41.13 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	65.49 m³·mol⁻¹	ChemAxon
Polarizability	26.82 Å³	ChemAxon
Number of Rings	2	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

C00002016

Chemspider ID

391415

KEGG Compound ID

C11358

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

443143

PDB ID

Not Available

ChEBI ID

Good Scents ID

Not Available

References

General References

Bonandi E, Tedesco G, Perdicchia D, Passarella D: Total Synthesis of (-)-Anaferine: A Further Ramification in a Diversity-Oriented Approach. Molecules. 2020 Feb 27;25(5). pii: molecules25051057. doi: 10.3390/molecules25051057. [PubMed:32120931 ]

Showing NP-Card for (-)-Anaferine (NP0051113)

MOL for NP0051113 ((-)-Anaferine)

3D MOL for NP0051113 ((-)-Anaferine)

3D SDF for NP0051113 ((-)-Anaferine)

3D-SDF for NP0051113 ((-)-Anaferine)

PDB for NP0051113 ((-)-Anaferine)

3D PDB for NP0051113 ((-)-Anaferine)

SMILES for NP0051113 ((-)-Anaferine)

INCHI for NP0051113 ((-)-Anaferine)

Structure for NP0051113 ((-)-Anaferine)

3D Structure for NP0051113 ((-)-Anaferine)