NP-MRD: Showing NP-Card for (+)-Ammodendrine (NP0051112)

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Record Information

Version

2.0

Created at

2022-04-27 22:32:24 UTC

Updated at

2022-04-27 22:32:24 UTC

NP-MRD ID

NP0051112

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Ammodendrine

Description

Ammodendrine, also known as spherocarpine, belongs to the class of organic compounds known as tetrahydropyridines. These are derivatives of pyridine in which two double bonds in the pyridine moiety are reduced by adding four hydrogen atoms. Ammodendrine 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. (+)-Ammodendrine is found in Adenocarpus hispanicus, Ammodendron conollyi, Anarthrophyllum rigidum, Calobota saharae, Castilleja miniata, Cytisus austriacus, Cytisophyllum sessilifolium, Cytisus balansae, Cytisus eriocarpus, Cytisus ingramii, Cytisus scoparius, Cytisus x beanii, Dichilus gracilis, Dichilus lebeckioides, Dichilus pilosus, Dichilus reflexus, Dichilus strictus, Dicraeopetalum stipulare, Echinospartum lusitanicum, Genista cinerea, Genista hispanica, Genista lobelii, Genista lydia, Genista pilosa, Genista sagittalis, Genista spartioides, Genista tinctoria , Hasperolaburnum platycarpum, Hesperolaburnum platycarpum, Laburnum anagyroides , Laburnum x watereri, Lamprolobium grandiflorum, Liparia parva, Liparia splendens, Lotononis alpina, Lotononis bainesii, Lotononis calycina, Lotononis carinata, Lotononis comptonii, Lotononis divaricata, Lotononis eriantha, Lotononis listii, Lotononis longicephala, Lotononis meyeri, Lupinus albescens, Lupinus albus, Lupinus angustifolius, Lupinus arboreus, Lupinus arbustus, Lupinus arcticus, Lupinus argenteus, Lupinus atlanticus, Lupinus cosentinii, Lupinus digitatus, Lupinus formosus, Lupinus hintonii, Lupinus linearis, Lupinus luteus, Lupinus mutabilis, Lupinus palaestinus, Lupinus pilosus, Lupinus polyphyllus, Lupinus pubescens, Lupinus pusillus, Lupinus texensis, Lupinus varius , Maackia amurensis , Maackia amurensis subsp. buergeri , Maackia tashiroi, Melolobium candicans, Melolobium exudans, Melolobium microphyllum, Melolobium obcordatum, Melolobium stipulatum, Ormosia coccinea, Ormosia emarginata, Pearsonia aristata, Pearsonia cajanifolia, Pearsonia obovata, Pearsonia sessilifolia, Petteria ramentacea, Plagiocarpus axillaris, Platycelyphium voense, Retama raetam, Retama sphaerocarpa , Rothia hirsuta, Rothia indica, Sophora chrysophylla, Sophora franchetiana, Sophora mollis , Spartidium saharae, Spartium junceum, Stirtonanthus insignis, Templetonia egena, Thermopsis chinensis, Thermopsis lanceolata, Thermopsis macrophylla, Thermopsis rhombifolia, Virgilia divaricata and Virgilia oroboides. (+)-Ammodendrine was first documented in 2008 (PMID: 18539842). Based on a literature review a small amount of articles have been published on ammodendrine (PMID: 27285814) (PMID: 24339035) (PMID: 20116429) (PMID: 19537792).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 35 36  0  0  0  0  0  0  0  0999 V2000
    4.5914    1.0964   -0.3529 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1787    1.1111   -0.7574 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7852    1.9529   -1.5886 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2692    0.1852   -0.2155 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8768    0.1733   -0.5915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0270   -0.4837    0.1124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4671   -0.5143   -0.2499 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2393    0.0648    0.8833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2984    1.0499    0.4577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9483    0.4541   -0.7950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9106    0.5426   -1.8727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6101    0.1440   -1.5013 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4336   -1.2187    1.3153 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7518   -1.8916    0.9185 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7632   -0.7865    0.7550 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2054    1.8540   -0.8424 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6761    1.2107    0.7548 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0366    0.0949   -0.6158 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5825    0.7233   -1.4774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7235   -1.5998   -0.3905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5966    0.5724    1.6434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7628   -0.7554    1.4336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7719    1.9715    0.1093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0119    1.2264    1.2580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2514   -0.5924   -0.6104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8137    1.0843   -1.1122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2982    0.0150   -2.7846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8678    1.6263   -2.1858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2287   -0.4951   -2.2467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3179   -1.9866    1.6302 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6731   -0.5275    2.1572 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5931   -2.3533   -0.0604 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0649   -2.5705    1.7127 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7650   -1.1629    0.4790 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8987   -0.2146    1.7078 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4 15  1  0
 15 14  1  0
 14 13  1  0
 13  6  1  0
  6  5  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
  5  4  1  0
 12  7  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
 15 34  1  0
 15 35  1  0
 14 32  1  0
 14 33  1  0
 13 30  1  0
 13 31  1  0
  5 19  1  0
  7 20  1  6
  8 21  1  0
  8 22  1  0
  9 23  1  0
  9 24  1  0
 10 25  1  0
 10 26  1  0
 11 27  1  0
 11 28  1  0
 12 29  1  0
M  END


  Mrv1652304282200322D          

 15 16  0  0  1  0            999 V2000
    0.0000   -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  1  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 N   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 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    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 N   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
   -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 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    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
  2  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
M  END
> <DATABASE_ID>
NP0051112

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C12H20N2O/c1-10(15)14-8-4-5-11(9-14)12-6-2-3-7-13-12/h9,12-13H,2-8H2,1H3/t12-/m1/s1

> <INCHI_KEY>
APKLQIQRPUDADG-GFCCVEGCSA-N

> <FORMULA>
C12H20N2O

> <MOLECULAR_WEIGHT>
208.305

> <EXACT_MASS>
208.157563272

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
24.435545187748104

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-{5-[(2R)-piperidin-2-yl]-1,2,3,4-tetrahydropyridin-1-yl}ethan-1-one

> <ALOGPS_LOGP>
1.02

> <JCHEM_LOGP>
0.4778308936666669

> <ALOGPS_LOGS>
-1.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.63392167436348

> <JCHEM_POLAR_SURFACE_AREA>
32.34

> <JCHEM_REFRACTIVITY>
60.79540000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.50e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ammodendrine

> <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       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       2.667  -3.080   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       0.000   1.540   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    2    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                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

View in JSmol

Synonyms

Value	Source
1-Acetyl-5-[(2R)-piperidin-2-yl]-1,2,3,4-tetrahydropyridine	ChEBI
Spherocarpine	ChEBI

Chemical Formula

C₁₂H₂₀N₂O

Average Mass

208.3050 Da

Monoisotopic Mass

208.15756 Da

IUPAC Name

1-{5-[(2R)-piperidin-2-yl]-1,2,3,4-tetrahydropyridin-1-yl}ethan-1-one

Traditional Name

ammodendrine

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C12H20N2O/c1-10(15)14-8-4-5-11(9-14)12-6-2-3-7-13-12/h9,12-13H,2-8H2,1H3/t12-/m1/s1

InChI Key

APKLQIQRPUDADG-GFCCVEGCSA-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 hispanicus	LOTUS Database	35616633
Ammodendron conollyi	Plant	KNApSAcK
Anarthrophyllum rigidum	LOTUS Database	35616633
Calobota saharae	LOTUS Database	35616633
Castilleja miniata	LOTUS Database	35616633
Chamaecytisus austriacus	Plant	KNApSAcK
Cytisophyllum sessilifolium	Plant	KNApSAcK
Cytisus balansae	Plant	KNApSAcK
Cytisus eriocarpus	Plant	KNApSAcK
Cytisus ingramii	Plant	KNApSAcK
Cytisus scoparius	LOTUS Database	35616633
Cytisus x beanii	Plant	KNApSAcK
Dichilus gracilis	Plant	KNApSAcK
Dichilus lebeckioides	Plant	KNApSAcK
Dichilus pilosus	Plant	KNApSAcK
Dichilus reflexus	Plant	KNApSAcK
Dichilus strictus	Plant	KNApSAcK
Dicraeopetalum stipulare	LOTUS Database	35616633
Echinospartum lusitanicum	Plant	KNApSAcK
Genista cinerea	Plant	KNApSAcK
Genista hispanica	Plant	KNApSAcK
Genista lobelii	LOTUS Database	35616633
Genista lydia	Plant	KNApSAcK
Genista pilosa	LOTUS Database	35616633
Genista sagittalis	Plant	KNApSAcK
Genista spartioides	Plant	KNApSAcK
Genista tinctoria	Plant	KNApSAcK
Hasperolaburnum platycarpum	-	KNApSAcK
Hesperolaburnum platycarpum	LOTUS Database	35616633
Laburnum anagyroides	Plant	KNApSAcK
Laburnum watereri	Plant	KNApSAcK
Lamprolobium grandiflorum	LOTUS Database	35616633
Liparia parva	Plant	KNApSAcK
Liparia splendens	Plant	KNApSAcK
Lotononis alpina	Plant	KNApSAcK
Lotononis bainesii	Plant	KNApSAcK
Lotononis calycina	Plant	KNApSAcK
Lotononis carinata	Plant	KNApSAcK
Lotononis comptonii	Plant	KNApSAcK
Lotononis divaricata	Plant	KNApSAcK
Lotononis eriantha	Plant	KNApSAcK
Lotononis listii	Plant	KNApSAcK
Lotononis longicephala	Plant	KNApSAcK
Lotononis meyeri	Plant	KNApSAcK
Lupinus albescens	LOTUS Database	35616633
Lupinus albus	LOTUS Database	35616633
Lupinus angustifolius	LOTUS Database	35616633
Lupinus arboreus	Plant	KNApSAcK
Lupinus arbustus	LOTUS Database	35616633
Lupinus arcticus	LOTUS Database	35616633
Lupinus argenteus	LOTUS Database	35616633
Lupinus atlanticus	Plant	KNApSAcK
Lupinus cosentinii	Plant	KNApSAcK
Lupinus digitatus	LOTUS Database	35616633
Lupinus formosus	LOTUS Database	35616633
Lupinus hintonii	LOTUS Database	35616633
Lupinus linearis	LOTUS Database	35616633
Lupinus luteus	LOTUS Database	35616633
Lupinus mutabilis	Plant	KNApSAcK
Lupinus palaestinus	Plant	KNApSAcK
Lupinus pilosus	Plant	KNApSAcK
Lupinus polyphyllus	LOTUS Database	35616633
Lupinus pubescens	LOTUS Database	35616633
Lupinus pusillus	LOTUS Database	35616633
Lupinus texensis	LOTUS Database	35616633
Lupinus varius	Plant	KNApSAcK
Maackia amurensis	Plant	KNApSAcK
Maackia amurensis subsp. buergeri	Plant	KNApSAcK
Maackia tashiroi	Plant	KNApSAcK
Melolobium candicans	Plant	KNApSAcK
Melolobium exudans	Plant	KNApSAcK
Melolobium microphyllum	Plant	KNApSAcK
Melolobium obcordatum	Plant	KNApSAcK
Melolobium stipulatum	Plant	KNApSAcK
Ormosia coccinea	Plant	KNApSAcK
Ormosia emarginata	LOTUS Database	35616633
Pearsonia aristata	Plant	KNApSAcK
Pearsonia cajanifolia	Plant	KNApSAcK
Pearsonia obovata	Plant	KNApSAcK
Pearsonia sessilifolia	Plant	KNApSAcK
Petteria ramentacea	Plant	KNApSAcK
Plagiocarpus axillaris	LOTUS Database	35616633
Platycelyphium voense	LOTUS Database	35616633
Retama raetam	LOTUS Database	35616633
Retama sphaerocarpa	Plant	KNApSAcK
Rothia hirsuta	LOTUS Database	35616633
Rothia indica	Plant	KNApSAcK
Sophora chrysophylla	Plant	KNApSAcK
Sophora franchetiana	Plant	KNApSAcK
Sophora mollis	Plant	KNApSAcK
Spartidium saharae	Plant	KNApSAcK
Spartium junceum	LOTUS Database	35616633
Stirtonanthus insignis	LOTUS Database	35616633
Templetonia egena	Plant	KNApSAcK
Thermopsis chinensis	Plant	KNApSAcK
Thermopsis lanceolata	Plant	KNApSAcK
Thermopsis macrophylla	Plant	KNApSAcK
Thermopsis rhombifolia	Plant	KNApSAcK
Virgilia divaricata	Plant	KNApSAcK
Virgilia oroboides	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetrahydropyridines. These are derivatives of pyridine in which two double bonds in the pyridine moiety are reduced by adding four hydrogen atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridines and derivatives

Sub Class

Hydropyridines

Direct Parent

Tetrahydropyridines

Alternative Parents

Substituents

Tetrahydropyridine
Piperidine
Tertiary carboxylic acid amide
Acetamide
Amino acid or derivatives
Carboxamide group
Carboxylic acid derivative
Secondary aliphatic amine
Secondary amine
Azacycle
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Amine
Organic oxygen compound
Organic nitrogen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

N-acylpiperidine (CHEBI:2670 )
acetamides (CHEBI:2670 )
piperidine alkaloid (CHEBI:2670 )
Piperidine alkaloids (C10125 )

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	1.02	ALOGPS
logP	0.48	ChemAxon
logS	-1.3	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	1	ChemAxon
Refractivity	60.8 m³·mol⁻¹	ChemAxon
Polarizability	24.44 Å³	ChemAxon
Number of Rings	2	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

C00002014

Chemspider ID

390990

KEGG Compound ID

C10125

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

442625

PDB ID

Not Available

ChEBI ID

2670

Good Scents ID

Not Available

References

General References

Jan S, Kamili AN, Parray JA, Bedi YS, Ahmad P: Microclimatic variation in UV perception and related disparity in tropane and quinolizidine alkaloid composition of Atropa acuminata, Lupinus polyphyllus and Hyoscyamus niger. J Photochem Photobiol B. 2016 Aug;161:230-5. doi: 10.1016/j.jphotobiol.2016.04.028. Epub 2016 Apr 30. [PubMed:27285814 ]
Green BT, Lee ST, Welch KD, Panter KE: Plant alkaloids that cause developmental defects through the disruption of cholinergic neurotransmission. Birth Defects Res C Embryo Today. 2013 Dec;99(4):235-46. doi: 10.1002/bdrc.21049. [PubMed:24339035 ]
Green BT, Lee ST, Panter KE, Welch KD, Cook D, Pfister JA, Kem WR: Actions of piperidine alkaloid teratogens at fetal nicotinic acetylcholine receptors. Neurotoxicol Teratol. 2010 May-Jun;32(3):383-90. doi: 10.1016/j.ntt.2010.01.011. Epub 2010 Jan 29. [PubMed:20116429 ]
Chludil HD, Vilarino Mdel P, Franco ML, Leicach SR: Changes in Lupinus albus and Lupinus angustifolius alkaloid profiles in response to mechanical damage. J Agric Food Chem. 2009 Jul 22;57(14):6107-13. doi: 10.1021/jf901232c. [PubMed:19537792 ]
Lee ST, Panter KE, Pfister JA, Gardner DR, Welch KD: The effect of body condition on serum concentrations of two teratogenic alkaloids (anagyrine and ammodendrine) from lupines (Lupinus species) that cause crooked calf disease. J Anim Sci. 2008 Oct;86(10):2771-8. doi: 10.2527/jas.2007-0610. Epub 2008 Jun 6. [PubMed:18539842 ]

Showing NP-Card for (+)-Ammodendrine (NP0051112)

MOL for NP0051112 ((+)-Ammodendrine)

3D MOL for NP0051112 ((+)-Ammodendrine)

3D SDF for NP0051112 ((+)-Ammodendrine)

3D-SDF for NP0051112 ((+)-Ammodendrine)

PDB for NP0051112 ((+)-Ammodendrine)

3D PDB for NP0051112 ((+)-Ammodendrine)

SMILES for NP0051112 ((+)-Ammodendrine)

INCHI for NP0051112 ((+)-Ammodendrine)

Structure for NP0051112 ((+)-Ammodendrine)

3D Structure for NP0051112 ((+)-Ammodendrine)