NP-MRD: Showing NP-Card for Adenocarpine (NP0051111)

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Record Information

Version

2.0

Created at

2022-04-27 22:32:22 UTC

Updated at

2022-04-27 22:32:22 UTC

NP-MRD ID

NP0051111

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Adenocarpine

Description

Adenocarpine belongs to the class of organic compounds known as cinnamic acids and derivatives. These are organic aromatic compounds containing a benzene and a carboxylic acid group (or a derivative thereof) forming 3-phenylprop-2-enoic acid. Adenocarpine is found in Adenocarpus complicatus, Adenocarpus grandiflorus, Adenocarpus hispanicus, Adenocarpus intermedius, Adenocarpus mannii and Cytisophyllum sessilifolium. Based on a literature review very few articles have been published on Adenocarpine.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 46 48  0  0  0  0  0  0  0  0999 V2000
    1.1792    1.8400    0.9229 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3869    0.7864    0.2556 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7843    0.3952    0.0306 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7783    1.1089    0.5025 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1704    0.7459    0.2953 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1752    1.5622    0.8329 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5160    1.2983    0.6880 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9349    0.1885   -0.0119 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9589   -0.6221   -0.5454 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6067   -0.3545   -0.3983 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2802    0.0682   -0.2209 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0489    0.5193    0.0402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0968   -0.2780   -0.0642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4772    0.2574    0.2247 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0936   -0.5225    1.3633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4230    0.0914    1.7013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8423    1.0495    0.6208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6661    0.3552   -0.7165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2755    0.1102   -0.9662 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9533   -1.7134   -0.4655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5299   -2.1592   -0.2757 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3801   -1.1511   -0.9940 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9865   -0.4899   -0.5302 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5343    2.0105    1.0727 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559    2.4359    1.3842 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2557    1.9581    1.1212 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9777   -0.0418   -0.1407 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2360   -1.5026   -1.1017 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8841   -1.0148   -0.8316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1925    1.5514    0.3332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3670    1.2928    0.5427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2811   -1.5453    1.0003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4162   -0.5757    2.2308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2288   -0.6900    1.7609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4097    0.5743    2.7045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2990    1.9934    0.6756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9234    1.2689    0.7407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1875   -0.6282   -0.6634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0836    1.0188   -1.5024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8687    0.7057   -1.7149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3062   -1.8877   -1.5011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5768   -2.3514    0.2216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2876   -2.0379    0.8122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3445   -3.1646   -0.6482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0860   -0.9203   -1.9893 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3839   -1.5355   -1.1231 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  2 11  1  0
 11 22  1  0
 22 21  1  0
 21 20  1  0
 20 13  1  0
 13 12  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 10  5  1  0
 12 11  1  0
 19 14  1  0
  3 23  1  0
  4 24  1  0
  6 25  1  0
  7 26  1  0
  8 27  1  0
  9 28  1  0
 10 29  1  0
 22 45  1  0
 22 46  1  0
 21 43  1  0
 21 44  1  0
 20 41  1  0
 20 42  1  0
 12 30  1  0
 14 31  1  1
 15 32  1  0
 15 33  1  0
 16 34  1  0
 16 35  1  0
 17 36  1  0
 17 37  1  0
 18 38  1  0
 18 39  1  0
 19 40  1  0
M  END


  Mrv1652304282200322D          

 22 24  0  0  1  0            999 V2000
    2.8579   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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  0  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
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    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  6  0  0  0
  7  8  2  0  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
  7 12  1  0  0  0  0
  9 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 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
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 17 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051111

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O=C(\C=C\C1=CC=CC=C1)N1CCCC(=C1)[C@@H]1CCCCN1

> <INCHI_IDENTIFIER>
InChI=1S/C19H24N2O/c22-19(12-11-16-7-2-1-3-8-16)21-14-6-9-17(15-21)18-10-4-5-13-20-18/h1-3,7-8,11-12,15,18,20H,4-6,9-10,13-14H2/b12-11+/t18-/m0/s1

> <INCHI_KEY>
XNURMNJHFKSULV-DXRVJIQQSA-N

> <FORMULA>
C19H24N2O

> <MOLECULAR_WEIGHT>
296.414

> <EXACT_MASS>
296.188863401

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
35.27715277460372

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-3-phenyl-1-{5-[(2S)-piperidin-2-yl]-1,2,3,4-tetrahydropyridin-1-yl}prop-2-en-1-one

> <ALOGPS_LOGP>
2.82

> <JCHEM_LOGP>
2.8372628679999985

> <ALOGPS_LOGS>
-4.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.63391393304111

> <JCHEM_POLAR_SURFACE_AREA>
32.34

> <JCHEM_REFRACTIVITY>
91.21160000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.27e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
adenocarpine

> <JCHEM_VEBER_RULE>
1

$$$$

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 -12.320   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       4.001 -10.010   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668 -11.550   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       4.001  -5.390   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.667   0.000   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   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   13                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    7                                                       
CONECT   13    9   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   17                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₂₄N₂O

Average Mass

296.4140 Da

Monoisotopic Mass

296.18886 Da

IUPAC Name

(2E)-3-phenyl-1-{5-[(2S)-piperidin-2-yl]-1,2,3,4-tetrahydropyridin-1-yl}prop-2-en-1-one

Traditional Name

adenocarpine

CAS Registry Number

Not Available

SMILES

O=C(\C=C\C1=CC=CC=C1)N1CCCC(=C1)[C@@H]1CCCCN1

InChI Identifier

InChI=1S/C19H24N2O/c22-19(12-11-16-7-2-1-3-8-16)21-14-6-9-17(15-21)18-10-4-5-13-20-18/h1-3,7-8,11-12,15,18,20H,4-6,9-10,13-14H2/b12-11+/t18-/m0/s1

InChI Key

XNURMNJHFKSULV-DXRVJIQQSA-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
Adenocarpus complicatus	Plant	KNApSAcK
Adenocarpus grandiflorus	Plant	KNApSAcK
Adenocarpus hispanicus	Plant	KNApSAcK
Adenocarpus intermedius	Plant	KNApSAcK
Adenocarpus mannii	Plant	KNApSAcK
Cytisophyllum sessilifolium	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cinnamic acids and derivatives. These are organic aromatic compounds containing a benzene and a carboxylic acid group (or a derivative thereof) forming 3-phenylprop-2-enoic acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Not Available

Direct Parent

Cinnamic acids and derivatives

Alternative Parents

Substituents

Cinnamic acid or derivatives
Styrene
Tetrahydropyridine
Monocyclic benzene moiety
Hydropyridine
Piperidine
Benzenoid
Tertiary carboxylic acid amide
Amino acid or derivatives
Carboxamide group
Carboxylic acid derivative
Secondary aliphatic amine
Azacycle
Secondary amine
Organoheterocyclic compound
Hydrocarbon derivative
Organic nitrogen compound
Organic oxide
Amine
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Carbonyl group
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

cinnamamides (CHEBI:2471 )
Piperidine alkaloids (C10123 )

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	2.82	ALOGPS
logP	2.84	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Basic)	9.63	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	32.34 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	91.21 m³·mol⁻¹	ChemAxon
Polarizability	35.28 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

C00002012

Chemspider ID

4445000

KEGG Compound ID

C10123

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5281681

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Adenocarpine (NP0051111)

MOL for NP0051111 (Adenocarpine)

3D MOL for NP0051111 (Adenocarpine)

3D SDF for NP0051111 (Adenocarpine)

3D-SDF for NP0051111 (Adenocarpine)

PDB for NP0051111 (Adenocarpine)

3D PDB for NP0051111 (Adenocarpine)

SMILES for NP0051111 (Adenocarpine)

INCHI for NP0051111 (Adenocarpine)

Structure for NP0051111 (Adenocarpine)

3D Structure for NP0051111 (Adenocarpine)