NP-MRD: Showing NP-Card for Matrine (NP0137282)

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Record Information

Version

2.0

Created at

2022-05-30 16:47:38 UTC

Updated at

2022-05-30 16:47:38 UTC

NP-MRD ID

NP0137282

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Matrine

Description

Sophoridine, also known as matrine, belongs to the class of organic compounds known as matrine alkaloids. These are lupin alkaloids with a structure based on the matrine skeleton, a four-ring skeleton that based on a saturated dipyrido[2,1-f:3',2',1'-Ij][1,6]naphthyridin-10-one skeleton. Matrine is found in Euchresta japonica, Gymnospermium albertii, Gymnospermium darwasicum, Sophora alopecuroides, Sophora chrysophylla, Sophora flavescens, Sophora microphylla, Sophora pachycarpa, Sophora tetraptera, Sophora tonkinensis and Sophora viciifolia. Sophoridine is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 42 45  0  0  0  0  0  0  0  0999 V2000
    2.4827   -3.1208    0.2060 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4705   -1.8480    0.1625 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7293   -1.1652    0.5633 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5469    0.2781    0.8939 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5393    0.9028   -0.0196 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1919    0.2343    0.1644 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2059    1.0035   -0.6875 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0384    2.3614   -0.0715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3695    2.8684   -0.1578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3131    1.9032    0.4865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7813    0.5296    0.5125 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9348   -0.3037    0.7855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3844   -1.7236    0.8864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9973   -2.1040   -0.5156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9930   -1.1561   -1.1306 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3592   -1.7708   -1.0444 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3252   -1.1222   -0.2438 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1396    0.2579   -0.7448 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4876   -1.2450   -0.2559 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1612   -1.7558    1.4117 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1881    0.3562    1.9428 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4878    0.8567    0.8186 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8752    0.8396   -1.0693 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4754    1.9913    0.2476 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9231    0.3562    1.2407 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5670    1.0322   -1.7365 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6990    3.1087   -0.5417 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2981    2.3137    1.0258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4031    3.8470    0.3814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6420    3.0986   -1.2084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2340    1.8344   -0.1593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6411    2.2196    1.4840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4048    0.0393    1.7054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6266   -0.3136   -0.0877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2423   -2.3637    1.1741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5726   -1.8111    1.6142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9361   -2.1798   -1.1032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5816   -3.1381   -0.4678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2517   -1.2055   -2.2397 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8445   -1.9326   -2.0563 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2785   -2.8334   -0.6586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7257    0.8600   -1.5075 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  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
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 15 18  1  0
 17  2  1  0
 17  6  1  0
 18  7  1  0
 18 11  1  0
  3 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  1
  7 26  1  6
  8 27  1  0
  8 28  1  0
  9 29  1  0
  9 30  1  0
 10 31  1  0
 10 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 14 38  1  0
 15 39  1  6
 16 40  1  0
 16 41  1  0
 18 42  1  6
M  END


  Mrv1533004181502192D          

 18 21  0  0  0  0            999 V2000
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   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 N   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
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 N   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  2  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
  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
 11 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
  2 17  1  0  0  0  0
  6 17  1  0  0  0  0
 15 18  1  0  0  0  0
  7 18  1  0  0  0  0
 11 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0137282

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O=C1CCCC2C3CCCN4CCCC(CN12)C34

> <INCHI_IDENTIFIER>
InChI=1S/C15H24N2O/c18-14-7-1-6-13-12-5-3-9-16-8-2-4-11(15(12)16)10-17(13)14/h11-13,15H,1-10H2

> <INCHI_KEY>
ZSBXGIUJOOQZMP-UHFFFAOYSA-N

> <FORMULA>
C15H24N2O

> <MOLECULAR_WEIGHT>
248.37

> <EXACT_MASS>
248.188863401

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
29.172902716127993

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7,13-diazatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadecan-6-one

> <ALOGPS_LOGP>
1.92

> <JCHEM_LOGP>
1.0759273119999997

> <ALOGPS_LOGS>
-1.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.75220211509645

> <JCHEM_POLAR_SURFACE_AREA>
23.550000000000004

> <JCHEM_REFRACTIVITY>
71.4485

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.24e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
matrine

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 18-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-APR-15         0                                  
HETATM    1  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       1.334  -0.770   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       5.335   1.540   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   17                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   17                                                  
CONECT    7    6    8   18                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   18                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16    2    6                                                  
CONECT   18   15    7   11                                                  
MASTER        0    0    0    0    0    0    0    0   18    0   42    0
END

View in JSmol

Synonyms

Value	Source
Matrine, (5beta)-isomer	MeSH
Matrine	MeSH

Chemical Formula

C₁₅H₂₄N₂O

Average Mass

248.3700 Da

Monoisotopic Mass

248.18886 Da

IUPAC Name

7,13-diazatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadecan-6-one

Traditional Name

matrine

CAS Registry Number

Not Available

SMILES

O=C1CCCC2C3CCCN4CCCC(CN12)C34

InChI Identifier

InChI=1S/C15H24N2O/c18-14-7-1-6-13-12-5-3-9-16-8-2-4-11(15(12)16)10-17(13)14/h11-13,15H,1-10H2

InChI Key

ZSBXGIUJOOQZMP-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
Euchresta japonica	LOTUS Database	35616633
Gymnospermium albertii	LOTUS Database	35616633
Gymnospermium darwasicum	LOTUS Database	35616633
Sophora alopecuroides	LOTUS Database	35616633
Sophora chrysophylla	LOTUS Database	35616633
Sophora flavescens	LOTUS Database	35616633
Sophora microphylla	LOTUS Database	35616633
Sophora pachycarpa	LOTUS Database	35616633
Sophora tetraptera	LOTUS Database	35616633
Sophora tonkinensis	LOTUS Database	35616633
Sophora viciifolia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as matrine alkaloids. These are lupin alkaloids with a structure based on the matrine skeleton, a four-ring skeleton that based on a saturated dipyrido[2,1-f:3',2',1'-Ij][1,6]naphthyridin-10-one skeleton.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Lupin alkaloids

Sub Class

Matrine alkaloids

Direct Parent

Matrine alkaloids

Alternative Parents

Substituents

Matrine
Quinolizidinone
Diazanaphthalene
Naphthyridine
Quinolizidine
Delta-lactam
Piperidinone
Piperidine
Tertiary carboxylic acid amide
Tertiary aliphatic amine
Tertiary amine
Amino acid or derivatives
Carboxamide group
Lactam
Organoheterocyclic compound
Azacycle
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxygen compound
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Amine
Carbonyl group
Organopnictogen compound
Organic oxide
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	1.92	ALOGPS
logP	1.08	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Basic)	9.75	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	71.45 m³·mol⁻¹	ChemAxon
Polarizability	29.17 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

285698

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Matrine (NP0137282)

MOL for NP0137282 (Matrine)

3D MOL for NP0137282 (Matrine)

3D SDF for NP0137282 (Matrine)

3D-SDF for NP0137282 (Matrine)

PDB for NP0137282 (Matrine)

3D PDB for NP0137282 (Matrine)

SMILES for NP0137282 (Matrine)

INCHI for NP0137282 (Matrine)

Structure for NP0137282 (Matrine)

3D Structure for NP0137282 (Matrine)