NP-MRD: Showing NP-Card for anagyrine (NP0264891)

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Record Information

Version

2.0

Created at

2022-09-08 08:40:22 UTC

Updated at

2022-09-08 08:40:22 UTC

NP-MRD ID

NP0264891

Secondary Accession Numbers

None

Natural Product Identification

Common Name

anagyrine

Description

7,15-Diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]Heptadeca-2,4-dien-6-one 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. anagyrine is found in Anagyris foetida, Baptisia perfoliata, Bolusanthus speciosus, Echinosophora koreensis, Genista lydia, Lupinus pusillus, Maackia amurensis, Maackia tenuifolia, Ormosia fordiana, Petteria ramentacea, Sophora chrysophylla, Sophora flavescens, Sophora tomentosa, Spartium junceum, Thermopsis rhombifolia, Ulex europaeus and Uresiphita reversalis. 7,15-Diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]Heptadeca-2,4-dien-6-one is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 38 41  0  0  0  0  0  0  0  0999 V2000
    3.0655    2.7568    0.1366 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0876    1.5002    0.3609 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0907    0.9768    1.1243 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1034   -0.3804    1.3590 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0875   -1.1133    0.7963 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0698   -0.5569    0.0176 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0803    0.7559   -0.1942 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0716    1.4495   -0.9910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0738    0.5922   -1.3848 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4713   -0.7720   -1.7878 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0046   -1.4525   -0.5485 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1173   -1.5769    0.4322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3382   -0.9459   -0.0172 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2784   -1.0200    1.1019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6414   -0.5296    0.7049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5338    0.8825    0.1856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4165    1.0681   -0.7872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1208    0.4433   -0.3240 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8777    1.5811    1.5542 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8877   -0.8309    1.9628 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0684   -2.1829    0.9616 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6108    1.7716   -1.9276 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7822    2.3918   -0.4871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5319    1.0169   -2.3043 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2769   -0.6554   -2.5269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3872   -1.3752   -2.1556 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4439   -2.4347   -0.8121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3500   -2.6586    0.5892 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1675   -1.1077    1.3945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8897   -0.2984    1.8681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3483   -2.0421    1.4808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1514   -1.2144   -0.0038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2608   -0.4937    1.6227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4815    1.5802    1.0238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4918    1.1118   -0.3550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7422    0.6470   -1.7696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2484    2.1574   -0.9239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8441    0.9583    0.6232 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  6
  8 22  1  0
  8 23  1  0
 18 38  1  1
 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


  Mrv1533004161502292D          

 18 21  0  0  0  0            999 V2000
    6.1269   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1269   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8413    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8413    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1269    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4124    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8290    1.4084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6655    0.3094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0040   -0.5834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8290   -0.5834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4124   -0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4207   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7062   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9917    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9917    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7062    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4207    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0040    1.4084    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
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  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
  2 11  1  0  0  0  0
  6 11  1  0  0  0  0
  9 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
 16 17  1  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
  7 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0264891

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O=C1C=CC=C2C3CC(CN12)C1CCCCN1C3

> <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

> <INCHI_KEY>
FQEQMASDZFXSJI-UHFFFAOYSA-N

> <FORMULA>
C15H20N2O

> <MOLECULAR_WEIGHT>
244.338

> <EXACT_MASS>
244.157563272

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
27.280644343459137

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]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>
74.03519999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.02e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
anagyrine

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  O   UNK     0      11.437  -2.310   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      11.437  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.770   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.770   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.437   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.103   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.014   2.629   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.709   0.577   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.474  -1.089   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.014  -1.089   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      10.103  -0.000   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       6.385  -0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.052  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.718   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.718   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.052   2.310   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       6.385   1.540   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       7.474   2.629   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    8   18                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10    2    6                                                  
CONECT   12    9   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12   18                                                  
CONECT   18   17    7                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   42    0
END

View in JSmol

Synonyms

Value	Source
Thermospine	MeSH

Chemical Formula

C₁₅H₂₀N₂O

Average Mass

244.3380 Da

Monoisotopic Mass

244.15756 Da

IUPAC Name

7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadeca-2,4-dien-6-one

Traditional Name

anagyrine

CAS Registry Number

Not Available

SMILES

O=C1C=CC=C2C3CC(CN12)C1CCCCN1C3

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

InChI Key

FQEQMASDZFXSJI-UHFFFAOYSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Baptisia perfoliata	LOTUS Database	35616633
Bolusanthus speciosus	LOTUS Database	35616633
Echinosophora koreensis	LOTUS Database	35616633
Genista lydia	LOTUS Database	35616633
Lupinus pusillus	LOTUS Database	35616633
Maackia amurensis	LOTUS Database	35616633
Maackia tenuifolia	LOTUS Database	35616633
Ormosia fordiana	LOTUS Database	35616633
Petteria ramentacea	LOTUS Database	35616633
Sophora chrysophylla	LOTUS Database	35616633
Sophora flavescens	LOTUS Database	35616633
Sophora tomentosa	LOTUS Database	35616633
Spartium junceum	LOTUS Database	35616633
Thermopsis rhombifolia	LOTUS Database	35616633
Ulex europaeus	LOTUS Database	35616633
Uresiphita reversalis	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
Organoheterocyclic compound
Azacycle
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Amine
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	27.28 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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

92768

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for anagyrine (NP0264891)

MOL for NP0264891 (anagyrine)

3D MOL for NP0264891 (anagyrine)

3D SDF for NP0264891 (anagyrine)

3D-SDF for NP0264891 (anagyrine)

PDB for NP0264891 (anagyrine)

3D PDB for NP0264891 (anagyrine)

SMILES for NP0264891 (anagyrine)

INCHI for NP0264891 (anagyrine)

Structure for NP0264891 (anagyrine)

3D Structure for NP0264891 (anagyrine)