NP-MRD: Showing NP-Card for Oxysophoridine (NP0140061)

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Record Information

Version

2.0

Created at

2022-06-29 20:44:18 UTC

Updated at

2022-06-29 20:44:18 UTC

NP-MRD ID

NP0140061

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Oxysophoridine

Description

Oxymatrine, also known as matrine N-oxide, 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. Oxysophoridine is found in Ammodendron bifolium, Sophora alopecuroides, Sophora chrysophylla, Sophora flavescens, Sophora macrocarpa, Sophora pachycarpa, Sophora tomentosa, Sophora tonkinensis and Sophora viciifolia. Based on a literature review very few articles have been published on Oxymatrine.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 43 46  0  0  0  0  0  0  0  0999 V2000
    2.8473    2.8270    0.0390 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7412    1.5724   -0.0163 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9635    0.7893    0.3129 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -0.6169    0.7683 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5756   -1.1441   -0.2106 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2769   -0.3842    0.1000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1237   -1.0626   -0.5584 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1643   -2.3525    0.1225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2325   -2.3140    1.1722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4600   -1.6691    0.5195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0375   -0.2691    0.3484 N   0  0  2  0  0  4  0  0  0  0  0  0
   -1.5369    0.1189    1.5170 O   0  0  0  0  0  1  0  0  0  0  0  0
   -3.2332    0.4474   -0.0532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9366    1.9160    0.1586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4752    2.1812   -0.0283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8304    1.2312   -1.0329 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5919    1.6478   -1.1821 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5181    0.9479   -0.3741 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0831   -0.1999   -0.7515 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5683    1.2885    1.0697 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5911    0.6701   -0.6010 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4902   -1.2633    0.8336 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1320   -0.5128    1.7761 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9276   -0.8184   -1.2329 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4683   -2.2193   -0.2201 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1431   -0.3857    1.2032 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4885   -1.3317   -1.5974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4547   -3.1312   -0.6251 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7362   -2.7832    0.6363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4318   -3.3293    1.5084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9029   -1.6344    1.9969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6112   -2.1667   -0.4553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3359   -1.7110    1.1850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0837    0.0933    0.5659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4301    0.2480   -1.1181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2521    2.1705    1.1916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5775    2.4780   -0.5424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4011    3.1985   -0.5180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8957    2.2754    0.9032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3397    1.5075   -2.0080 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8903    1.6195   -2.2654 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6850    2.7453   -0.9267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6545   -0.6744   -1.6103 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 12  1  1
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18  6  1  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  7 19  1  0
 10 11  1  0
 19 11  1  0
 19 16  1  0
  2 18  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  0
 15 39  1  0
 16 40  1  6
 17 41  1  0
 17 42  1  0
  6 26  1  1
  5 24  1  0
  5 25  1  0
  4 22  1  0
  4 23  1  0
  3 20  1  0
  3 21  1  0
  7 27  1  6
  8 28  1  0
  8 29  1  0
  9 30  1  0
  9 31  1  0
 10 32  1  0
 10 33  1  0
 19 43  1  6
M  CHG  2  11   1  12  -1
M  END


  Mrv1652306292222442D          

 19 22  0  0  1  0            999 V2000
    4.2868    0.8250    0.0000 C   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
    2.8579    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    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    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  1  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
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 N   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
    3.5724   -1.2375    0.0000 O   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
   -0.0000    1.6500    0.0000 O   0  5  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  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  6  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  8 13  1  0  0  0  0
 10 14  1  0  0  0  0
 14 15  1  0  0  0  0
  3 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
  1 18  1  0  0  0  0
  8 19  1  0  0  0  0
M  CHG  2   8   1  19  -1
M  END
> <DATABASE_ID>
NP0140061

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[O-][N+]12CCC[C@H]3CN4[C@H](CCCC4=O)[C@@H](CCC1)[C@@H]23

> <INCHI_IDENTIFIER>
InChI=1S/C15H24N2O2/c18-14-7-1-6-13-12-5-3-9-17(19)8-2-4-11(15(12)17)10-16(13)14/h11-13,15H,1-10H2/t11-,12+,13+,15-,17?/m0/s1

> <INCHI_KEY>
XVPBINOPNYFXID-LHDUFFHYSA-N

> <FORMULA>
C15H24N2O2

> <MOLECULAR_WEIGHT>
264.369

> <EXACT_MASS>
264.183778021

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
29.452310390832952

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2R,9S,17S)-6-oxo-7,13-diazatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadecan-13-ium-13-olate

> <ALOGPS_LOGP>
-0.33

> <JCHEM_LOGP>
-0.04844787133333345

> <ALOGPS_LOGS>
-2.24

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
3.8188790175929146

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
73.4934

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.52e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,9S,17S)-6-oxo-7,13-diazatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadecan-13-ium-13-olate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-JUN-22         0                                  
HETATM    1  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       1.334   2.310   0.000  0.00  0.00           N+1
HETATM    9  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+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       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       5.335   0.000   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -0.000   3.080   0.000  0.00  0.00           O-1
CONECT    1    2   18                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   15                                                  
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   13   19                                             
CONECT    9    8    4   10                                                  
CONECT   10    9   11   14                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    8                                                       
CONECT   14   10   15                                                       
CONECT   15   14    3   16                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16    1                                                       
CONECT   19    8                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   44    0
END

View in JSmol

Synonyms

Value	Source
Matrine N-oxide	Kegg

Chemical Formula

C₁₅H₂₄N₂O₂

Average Mass

264.3690 Da

Monoisotopic Mass

264.18378 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

[O-][N+]12CCC[C@H]3CN4[C@H](CCCC4=O)[C@@H](CCC1)[C@@H]23

InChI Identifier

InChI=1S/C15H24N2O2/c18-14-7-1-6-13-12-5-3-9-17(19)8-2-4-11(15(12)17)10-16(13)14/h11-13,15H,1-10H2/t11-,12+,13+,15-,17?/m0/s1

InChI Key

XVPBINOPNYFXID-LHDUFFHYSA-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
Ammodendron bifolium	LOTUS Database	35616633
Sophora alopecuroides	LOTUS Database	35616633
Sophora chrysophylla	LOTUS Database	35616633
Sophora flavescens	LOTUS Database	35616633
Sophora macrocarpa	LOTUS Database	35616633
Sophora pachycarpa	LOTUS Database	35616633
Sophora tomentosa	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
Trialkyl amine oxide
Tertiary carboxylic acid amide
Carboxamide group
Lactam
Organoheterocyclic compound
Azacycle
N-oxide
Carboxylic acid derivative
Trisubstituted n-oxide
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Organic zwitterion
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

alkaloid (CHEBI:2672 )
Quinolizidine alkaloids (C10749 )

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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00007758

Chemspider ID

102808

KEGG Compound ID

C10749

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Oxymatrine

METLIN ID

Not Available

PubChem Compound

114850

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Oxysophoridine (NP0140061)

MOL for NP0140061 (Oxysophoridine)

3D MOL for NP0140061 (Oxysophoridine)

3D SDF for NP0140061 (Oxysophoridine)

3D-SDF for NP0140061 (Oxysophoridine)

PDB for NP0140061 (Oxysophoridine)

3D PDB for NP0140061 (Oxysophoridine)

SMILES for NP0140061 (Oxysophoridine)

INCHI for NP0140061 (Oxysophoridine)

Structure for NP0140061 (Oxysophoridine)

3D Structure for NP0140061 (Oxysophoridine)