NP-MRD: Showing NP-Card for (-)-Adalinine (NP0069532)

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Record Information

Version

2.0

Created at

2022-04-28 14:53:39 UTC

Updated at

2022-04-28 14:53:39 UTC

NP-MRD ID

NP0069532

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Adalinine

Description

(-)-Adalinine belongs to the class of organic compounds known as alkaloids and derivatives. These are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus. (-)-Adalinine is found in Adalia bipunctata, Adalia decempunctata and Fritillaria yuminensis L.. (-)-Adalinine was first documented in 2016 (PMID: 26730565). Based on a literature review a small amount of articles have been published on (-)-Adalinine.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 39  0  0  0  0  0  0  0  0999 V2000
    4.2599   -0.9840   -0.4262 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3119   -1.2903    0.6844 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0961   -0.3418    0.6671 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3559   -0.4716   -0.6205 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1746    0.3837   -0.8140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9683    0.2735    0.1030 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6257   -1.0608    0.1862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1743   -1.6098   -1.0506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9036   -2.9224   -0.9834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0919   -1.0987   -2.1232 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0287    1.2790   -0.3814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5431    2.6917   -0.3341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0614    3.1128    1.0086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3428    2.0261    1.7492 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5049    2.3674    2.5980 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6287    0.6619    1.4825 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0507    0.0153   -0.8661 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1762   -1.7447   -1.2144 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3129   -0.9639   -0.0678 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9331   -2.3198    0.5644 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8181   -1.2103    1.6697 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4762    0.6590    0.8777 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4483   -0.7610    1.4884 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1810   -1.5536   -0.8335 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0980   -0.1756   -1.4252 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5244    1.4455   -0.7999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1918    0.2300   -1.8576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5105   -0.9214    0.8860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9963   -1.8064    0.7460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9505   -2.7656   -0.6233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9786   -3.3977   -1.9623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3897   -3.6036   -0.2768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9479    1.1751    0.2324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2587    1.0335   -1.4339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4310    3.3325   -0.5776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8232    2.9085   -1.1540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3778    3.9961    0.9515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8912    3.4286    1.6811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6064   -0.0172    2.2499 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  6  5  1  6
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
  6 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16  6  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  7 28  1  0
  7 29  1  0
  9 30  1  0
  9 31  1  0
  9 32  1  0
 11 33  1  0
 11 34  1  0
 12 35  1  0
 12 36  1  0
 13 37  1  0
 13 38  1  0
 16 39  1  0
M  END


  Mrv1652304282216532D          

 16 16  0  0  1  0            999 V2000
   -0.4372    4.6891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.9894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3873    3.2610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2118    3.2322    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6490    3.9319    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2617    4.6603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6989    5.3599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2118    2.4072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4973    1.9947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2171    2.4072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9316    1.9947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6461    2.4072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8958    2.7709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8382    1.9479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0967    1.5862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5222    1.4866    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
  6  7  2  0  0  0  0
  4  8  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  4 13  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0069532

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCC[C@]1(CC(C)=O)CCCC(=O)N1

> <INCHI_IDENTIFIER>
InChI=1S/C13H23NO2/c1-3-4-5-8-13(10-11(2)15)9-6-7-12(16)14-13/h3-10H2,1-2H3,(H,14,16)/t13-/m1/s1

> <INCHI_KEY>
CNUUHKVLRVPYKE-CYBMUJFWSA-N

> <FORMULA>
C13H23NO2

> <MOLECULAR_WEIGHT>
225.332

> <EXACT_MASS>
225.172878985

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
26.19589980887533

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(6R)-6-(2-oxopropyl)-6-pentylpiperidin-2-one

> <ALOGPS_LOGP>
2.28

> <JCHEM_LOGP>
2.106153062333333

> <ALOGPS_LOGS>
-2.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.226377164711156

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.709477362310995

> <JCHEM_PKA_STRONGEST_BASIC>
-1.2108087828809855

> <JCHEM_POLAR_SURFACE_AREA>
46.17

> <JCHEM_REFRACTIVITY>
63.8294

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.81e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(6R)-6-(2-oxopropyl)-6-pentylpiperidin-2-one

> <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      -0.816   8.753   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   7.447   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.723   6.087   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.262   6.033   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      -3.078   7.339   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      -2.355   8.699   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -3.171  10.005   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -2.262   4.493   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.928   3.723   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.405   4.493   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.739   3.723   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.073   4.493   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.539   5.172   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.431   3.636   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -2.047   2.961   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -4.708   2.775   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    8   13                                             
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    4    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13    4   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₃H₂₃NO₂

Average Mass

225.3320 Da

Monoisotopic Mass

225.17288 Da

IUPAC Name

(6R)-6-(2-oxopropyl)-6-pentylpiperidin-2-one

Traditional Name

(6R)-6-(2-oxopropyl)-6-pentylpiperidin-2-one

CAS Registry Number

Not Available

SMILES

CCCCC[C@]1(CC(C)=O)CCCC(=O)N1

InChI Identifier

InChI=1S/C13H23NO2/c1-3-4-5-8-13(10-11(2)15)9-6-7-12(16)14-13/h3-10H2,1-2H3,(H,14,16)/t13-/m1/s1

InChI Key

CNUUHKVLRVPYKE-CYBMUJFWSA-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
Adalia bipunctata	-	KNApSAcK
Adalia decempunctata	-	KNApSAcK
Fritillaria yuminensis L.	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkaloids and derivatives. These are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Not Available

Sub Class

Not Available

Direct Parent

Alkaloids and derivatives

Alternative Parents

Substituents

Alkaloid or derivatives
Delta-lactam
Piperidinone
Piperidine
Secondary carboxylic acid amide
Lactam
Ketone
Carboxamide group
Azacycle
Organoheterocyclic compound
Carboxylic acid derivative
Hydrocarbon derivative
Organic nitrogen compound
Carbonyl group
Organooxygen compound
Organonitrogen compound
Organic oxide
Organic oxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	2.28	ALOGPS
logP	2.11	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	14.71	ChemAxon
pKa (Strongest Basic)	-1.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.17 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	63.83 m³·mol⁻¹	ChemAxon
Polarizability	26.2 Å³	ChemAxon
Number of Rings	1	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

C00027808

Chemspider ID

9313924

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11138811

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Annadi K, Wee AG: An Alkylidene Carbene C-H Activation Approach toward the Enantioselective Syntheses of Spirolactams: Application to the Synthesis of (-)-Adalinine. J Org Chem. 2016 Feb 5;81(3):1021-38. doi: 10.1021/acs.joc.5b02582. Epub 2016 Jan 14. [PubMed:26730565 ]

Showing NP-Card for (-)-Adalinine (NP0069532)

MOL for NP0069532 ((-)-Adalinine)

3D MOL for NP0069532 ((-)-Adalinine)

3D SDF for NP0069532 ((-)-Adalinine)

3D-SDF for NP0069532 ((-)-Adalinine)

PDB for NP0069532 ((-)-Adalinine)

3D PDB for NP0069532 ((-)-Adalinine)

SMILES for NP0069532 ((-)-Adalinine)

INCHI for NP0069532 ((-)-Adalinine)

Structure for NP0069532 ((-)-Adalinine)

3D Structure for NP0069532 ((-)-Adalinine)