NP-MRD: Showing NP-Card for (-)-Thermopsine (NP0051287)

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Record Information

Version

2.0

Created at

2022-04-27 22:40:04 UTC

Updated at

2022-04-27 22:40:04 UTC

NP-MRD ID

NP0051287

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Thermopsine

Description

Thermopsine, also known as anagyrine, belongs to the class of organic compounds known as anagyrine-type alkaloids. These are lupin alkaloids with a structure based on the anagyrine skeleton. Anagyrine is a tetracyclic ketone containing a quinolizidine, and two pyridine rings fused together to form dipyrido[1,2-a:1',2'-E][1,5]diazocin-4-one. (-)-Thermopsine is found in Anagyris foetida, Anarthrophyllum rigidum, Baptisia alba, Baptisia albescens, Baptisia australis, Baptisia bracteata, Baptisia calycosa, Baptisia cinerea, Baptisia sphaerocarpa, Bolusanthus speciosus, Caulophyllum thalictroides, Clathrotropis brachypetala, Clathrotropis glaucophylla, Dermatophyllum secundiflorum, Dichilus gracilis, Dichilus lebeckioides, Dichilus pilosus, Dichilus reflexus, Dichilus strictus, Dicraeopetalum stipulare, Echinosophora koreensis, Genista acanthoclada, Genista cinerascens, Genista ephedroides, Genista lobelii, Genista lydia, Genista pilosa, Gonocytisus pterocladus, Laburnum alpinum, Lamprolobium fruticosum, Lupinus argenteus, Lupinus digitatus, Lupinus hispanicus, Lupinus mutabilis, Lupinus polyphyllus, Lupinus pusillus, Maackia amurensis, Maackia tashiroi, Maackia tenuifolia, Melolobium exudans, Ormosia sumatrana, Osyris alba, Oxytropis glabra, Oxytropis ochrocephala, Petteria ramentacea, Plagiocarpus axillaris, Platycelyphium voense, Polhillia canescens, Retama raetam, Sophora chrysophylla, Sophora flavescens, Sophora secundiflora , Sophora tomentosa, Spartium junceum , Teline maderensis, Templetonia retusa, Thermopsis alpinia, Thermopsis alterniflora Rgl.et Schmalh., Thermopsis chinensis, Thermopsis lanceolata, Thermopsis lupinoides, Thermopsis mongolica, Ulex europaeus and Viscum cruciatum. (-)-Thermopsine was first documented in 2006 (PMID: 16521145). Based on a literature review a small amount of articles have been published on Thermopsine (PMID: 35122885) (PMID: 33397149) (PMID: 24233720) (PMID: 22978215).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 38 41  0  0  0  0  0  0  0  0999 V2000
   -2.9859   -1.0673    2.4959 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9649   -0.2175    1.5463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8791    0.8235    1.5153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7973    1.7031    0.4599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8449    1.5418   -0.5129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9265    0.4766   -0.4615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0510   -0.3604    0.6006 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1058   -1.5234    0.7818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0416   -1.1206   -0.0403 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6791   -1.1570   -1.4426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9272    0.3435   -1.5698 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4518    0.8502   -1.3117 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5419   -0.1230   -1.2917 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7304    0.6086   -0.9968 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8516    1.0868    0.4193 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8616   -0.1043    1.3110 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3534   -1.3538    0.7015 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3370   -1.2587   -0.3487 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.6044    0.9160    2.2884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4747    2.5403    0.3659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7427    2.2089   -1.3615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8926   -1.6068    1.8836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6526   -2.4487    0.5003 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0798   -0.0673    0.4237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6304   -1.6558   -1.5128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0368   -1.5412   -2.2349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3466    0.6150   -2.5439 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5049    1.6223   -0.5487 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7199    1.4322   -2.2585 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7212    1.5099   -1.6449 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6489    0.0276   -1.2258 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8173    1.6674    0.4654 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0759    1.7974    0.7322 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9308   -0.2401    1.6560 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3142    0.1591    2.2575 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2474   -1.9716    0.3855 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9068   -1.9675    1.5417 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4891   -2.1452   -1.0251 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 11  1  0
 11 10  1  0
 10  9  1  0
  9  8  1  0
  8  7  1  0
  9 18  1  0
 18 17  1  0
 17 16  1  0
 16 15  1  0
 15 14  1  0
 14 13  1  0
 13 12  1  0
  7  2  1  0
 13 18  1  0
  7  6  1  0
 12 11  1  0
  3 19  1  0
  4 20  1  0
  5 21  1  0
 11 27  1  6
 10 25  1  0
 10 26  1  0
  9 24  1  1
  8 22  1  0
  8 23  1  0
 18 38  1  6
 17 36  1  0
 17 37  1  0
 16 34  1  0
 16 35  1  0
 15 32  1  0
 15 33  1  0
 14 30  1  0
 14 31  1  0
 12 28  1  0
 12 29  1  0
M  END


  Mrv1652304282200402D          

 18 21  0  0  1  0            999 V2000
    6.3404    2.0344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3404    1.2094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6259    0.7969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6259   -0.0281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9114    1.2094    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9114    2.0344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6259    2.4469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3281    2.6178    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1646    1.5188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5031    0.6260    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3281    0.6260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9197    1.2094    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9197    2.0344    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5031    2.6178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2053    2.4469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4908    2.0344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4908    1.2094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2053    0.7969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  1  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  1  0  0  0
 10  9  1  6  0  0  0
 10 11  1  0  0  0  0
  5 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  1  0  0  0  0
  8 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 12 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051287

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O=C1C=CC=C2[C@@H]3C[C@@H](CN12)[C@@H]1CCCCN1C3

> <INCHI_IDENTIFIER>
InChI=1S/C15H20N2O/c18-15-6-3-5-14-11-8-12(10-17(14)15)13-4-1-2-7-16(13)9-11/h3,5-6,11-13H,1-2,4,7-10H2/t11-,12+,13+/m1/s1

> <INCHI_KEY>
FQEQMASDZFXSJI-AGIUHOORSA-N

> <FORMULA>
C15H20N2O

> <MOLECULAR_WEIGHT>
244.338

> <EXACT_MASS>
244.157563272

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
27.947754115375137

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,9S,10S)-7,15-diazatetracyclo[7.7.1.0^{2,7}.0^{10,15}]heptadeca-2,4-dien-6-one

> <ALOGPS_LOGP>
2.58

> <JCHEM_LOGP>
1.0133275319999986

> <ALOGPS_LOGS>
-1.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.196367600103125

> <JCHEM_POLAR_SURFACE_AREA>
23.550000000000004

> <JCHEM_REFRACTIVITY>
74.0352

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.02e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,9S,10S)-7,15-diazatetracyclo[7.7.1.0^{2,7}.0^{10,15}]heptadeca-2,4-dien-6-one

> <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      11.835   3.798   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.835   2.258   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.502   1.488   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      10.502  -0.052   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       9.168   2.258   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       9.168   3.798   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.502   4.568   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.079   4.886   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.774   2.835   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.539   1.169   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.079   1.169   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.450   2.258   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       5.450   3.798   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       6.539   4.886   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.116   4.568   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.783   3.798   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.783   2.258   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.116   1.488   0.000  0.00  0.00           C+0
CONECT    1    2    7                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   11                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6    1                                                       
CONECT    8    6    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10    5                                                       
CONECT   12   10   13   18                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13    8                                                       
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   12                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   42    0
END

View in JSmol

Synonyms

Value	Source
Anagyrine	MeSH
Thermospine	MeSH

Chemical Formula

C₁₅H₂₀N₂O

Average Mass

244.3380 Da

Monoisotopic Mass

244.15756 Da

IUPAC Name

(1R,9S,10S)-7,15-diazatetracyclo[7.7.1.0^{2,7}.0^{10,15}]heptadeca-2,4-dien-6-one

Traditional Name

(1R,9S,10S)-7,15-diazatetracyclo[7.7.1.0^{2,7}.0^{10,15}]heptadeca-2,4-dien-6-one

CAS Registry Number

Not Available

SMILES

O=C1C=CC=C2[C@@H]3C[C@@H](CN12)[C@@H]1CCCCN1C3

InChI Identifier

InChI=1S/C15H20N2O/c18-15-6-3-5-14-11-8-12(10-17(14)15)13-4-1-2-7-16(13)9-11/h3,5-6,11-13H,1-2,4,7-10H2/t11-,12+,13+/m1/s1

InChI Key

FQEQMASDZFXSJI-AGIUHOORSA-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
Anagyris foetida	LOTUS Database	35616633
Anarthrophyllum rigidum	LOTUS Database	35616633
Baptisia alba	Plant	KNApSAcK
Baptisia albescens	LOTUS Database	35616633
Baptisia australis	LOTUS Database	35616633
Baptisia bracteata	Plant	KNApSAcK
Baptisia calycosa	LOTUS Database	35616633
Baptisia cinerea	Plant	KNApSAcK
Baptisia sphaerocarpa	Plant	KNApSAcK
Bolusanthus speciosus	LOTUS Database	35616633
Caulophyllum thalictroides	LOTUS Database	35616633
Clathrotropis brachypetala	LOTUS Database	35616633
Clathrotropis glaucophylla	Plant	KNApSAcK
Dermatophyllum secundiflorum	LOTUS Database	35616633
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
Echinosophora koreensis	LOTUS Database	35616633
Genista acanthoclada	LOTUS Database	35616633
Genista cinerascens	LOTUS Database	35616633
Genista ephedroides	LOTUS Database	35616633
Genista lobelii	LOTUS Database	35616633
Genista lydia	LOTUS Database	35616633
Genista pilosa	LOTUS Database	35616633
Gonocytisus pterocladus	LOTUS Database	35616633
Laburnum alpinum	Plant	KNApSAcK
Lamprolobium fruticosum	LOTUS Database	35616633
Lupinus argenteus	Plant	KNApSAcK
Lupinus digitatus	LOTUS Database	35616633
Lupinus hispanicus	LOTUS Database	35616633
Lupinus mutabilis	LOTUS Database	35616633
Lupinus polyphyllus	LOTUS Database	35616633
Lupinus pusillus	LOTUS Database	35616633
Maackia amurensis	LOTUS Database	35616633
Maackia tashiroi	LOTUS Database	35616633
Maackia tenuifolia	LOTUS Database	35616633
Melolobium exudans	LOTUS Database	35616633
Ormosia sumatrana	LOTUS Database	35616633
Osyris alba	LOTUS Database	35616633
Oxytropis glabra	Plant	KNApSAcK
Oxytropis ochrocephala	LOTUS Database	35616633
Petteria ramentacea	LOTUS Database	35616633
Plagiocarpus axillaris	LOTUS Database	35616633
Platycelyphium voense	LOTUS Database	35616633
Polhillia canescens	LOTUS Database	35616633
Retama raetam	LOTUS Database	35616633
Sophora chrysophylla	LOTUS Database	35616633
Sophora flavescens	LOTUS Database	35616633
Sophora secundiflora	Plant	KNApSAcK
Sophora tomentosa	LOTUS Database	35616633
Spartium junceum	Plant	KNApSAcK
Teline maderensis	LOTUS Database	35616633
Templetonia retusa	LOTUS Database	35616633
Thermopsis alpinia	Plant	KNApSAcK
Thermopsis alterniflora Rgl.et Schmalh.	Plant	KNApSAcK
Thermopsis chinensis	LOTUS Database	35616633
Thermopsis lanceolata	Plant	KNApSAcK
Thermopsis lupinoides	Plant	KNApSAcK
Thermopsis mongolica	Plant	KNApSAcK
Ulex europaeus	LOTUS Database	35616633
Viscum cruciatum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anagyrine-type alkaloids. These are lupin alkaloids with a structure based on the anagyrine skeleton. Anagyrine is a tetracyclic ketone containing a quinolizidine, and two pyridine rings fused together to form dipyrido[1,2-a:1',2'-E][1,5]diazocin-4-one.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Lupin alkaloids

Sub Class

Anagyrine-type alkaloids

Direct Parent

Anagyrine-type alkaloids

Alternative Parents

Substituents

Anagyrine-type alkaloid
Quinolizidine
Pyridinone
Aralkylamine
Piperidine
Pyridine
Heteroaromatic compound
Lactam
Tertiary amine
Tertiary aliphatic amine
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Amine
Organic nitrogen 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
logP	2.58	ALOGPS
logP	1.01	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Basic)	9.2	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	23.55 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	74.04 m³·mol⁻¹	ChemAxon
Polarizability	27.95 Å³	ChemAxon
Number of Rings	4	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

C00002238

Chemspider ID

65047958

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6920824

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zhang P, An Q, Yi P, Cui Y, Zou JB, Yuan CM, Zhang Y, Gu W, Huang LJ, Zhao LH, Hu ZX, Hao XJ: Thermlanseedlines A-G, seven thermopsine-based alkaloids with antiviral and insecticidal activities from the seeds of Thermopsis lanceolata R. Br. Fitoterapia. 2022 Apr;158:105140. doi: 10.1016/j.fitote.2022.105140. Epub 2022 Feb 2. [PubMed:35122885 ]
Koval'skaya AV, Petrova PR, Tsypyshev DO, Lobov AN, Tsypysheva IP: Thionation of quinolizidine alkaloids and their derivatives via Lawesson's reagent. Nat Prod Res. 2021 Jan 4:1-6. doi: 10.1080/14786419.2020.1868460. [PubMed:33397149 ]
Brimioulle R, Bach T: Enantioselective Lewis acid catalysis of intramolecular enone [2+2] photocycloaddition reactions. Science. 2013 Nov 15;342(6160):840-3. doi: 10.1126/science.1244809. [PubMed:24233720 ]
Korir E, Kiplimo JJ, Crouch NR, Moodley N, Koorbanally NA: Quinolizidine alkaloids from Sophora velutina subsp. zimbabweensis (Fabaceae: Sophoreae). Nat Prod Commun. 2012 Aug;7(8):999-1003. [PubMed:22978215 ]
Gray D, Gallagher T: A flexible strategy for the synthesis of tri- and tetracyclic lupin alkaloids: synthesis of (+)-cytisine, (+/-)-anagyrine, and (+/-)-thermopsine. Angew Chem Int Ed Engl. 2006 Apr 3;45(15):2419-23. doi: 10.1002/anie.200504015. [PubMed:16521145 ]

Showing NP-Card for (-)-Thermopsine (NP0051287)

MOL for NP0051287 ((-)-Thermopsine)

3D MOL for NP0051287 ((-)-Thermopsine)

3D SDF for NP0051287 ((-)-Thermopsine)

3D-SDF for NP0051287 ((-)-Thermopsine)

PDB for NP0051287 ((-)-Thermopsine)

3D PDB for NP0051287 ((-)-Thermopsine)

SMILES for NP0051287 ((-)-Thermopsine)

INCHI for NP0051287 ((-)-Thermopsine)

Structure for NP0051287 ((-)-Thermopsine)

3D Structure for NP0051287 ((-)-Thermopsine)