NP-MRD: Showing NP-Card for Dioxamine (NP0069828)

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Record Information

Version

2.0

Created at

2022-04-28 15:09:23 UTC

Updated at

2022-04-28 15:09:23 UTC

NP-MRD ID

NP0069828

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Dioxamine

Description

SCHEMBL108118 belongs to the class of organic compounds known as cinnamic acid amides. These are amides of cinnamic acids. Cinnamic acid is an aromatic compound containing a benzene and a carboxylic acid group forming 3-phenylprop-2-enoic acid. Dioxamine is found in Beilschmiedia erythrophloia and Zanthoxylum rubescens. Based on a literature review very few articles have been published on SCHEMBL108118.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 42 45  0  0  0  0  0  0  0  0999 V2000
   -0.0042    1.3803   -1.9172 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5253    0.7260   -0.9578 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9434    0.5764   -0.9688 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5932   -0.0749   -0.0359 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0396   -0.2326   -0.0389 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6241   -0.9499    1.0121 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0007   -1.1121    1.0287 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8053   -0.5863    0.0392 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2177    0.1220   -0.9966 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8262    0.2928   -1.0244 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2538    0.5242   -1.8281 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4236    0.5089   -1.0307 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1836   -0.5996   -0.1841 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2683    0.1730    0.0734 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7238    0.4069   -0.0446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4561   -0.2312    1.1127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8947    0.0415    0.9301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4869    1.1584    1.4528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8324    1.4220    1.2872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5954    0.5277    0.5722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0167   -0.6062    0.0361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6613   -0.8445    0.2192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9713   -1.3539   -0.6376 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0747   -0.4678   -0.8281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9465    0.4682    0.2130 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5070    1.0165   -1.7775 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0217   -0.5278    0.7948 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9969   -1.3633    1.7890 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4272   -1.6757    1.8602 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4425    0.8516   -1.8564 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4722    1.4599   -0.4515 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3243    0.3615   -1.6606 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0977   -0.3626    0.8706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9673    1.4707   -0.0664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0134   -0.0356   -1.0169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0821    0.1078    2.0789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2952   -1.3406    1.0279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8961    1.8649    2.0148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3209    2.2845    1.6834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2481   -1.7555   -0.2237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9700   -0.0025   -1.8332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0006   -1.0542   -0.7172 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 22  2  0
 22 21  1  0
 21 20  2  0
 20 25  1  0
 25 24  1  0
 24 23  1  0
 20 19  1  0
 19 18  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5 10  2  0
 10  9  1  0
  9  8  2  0
  8 13  1  0
 13 12  1  0
 12 11  1  0
  8  7  1  0
  7  6  2  0
 18 17  1  0
  6  5  1  0
 23 21  1  0
 11  9  1  0
 14 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  0
 16 37  1  0
 22 40  1  0
 24 41  1  0
 24 42  1  0
 19 39  1  0
 18 38  1  0
  3 26  1  0
  4 27  1  0
 10 30  1  0
 12 31  1  0
 12 32  1  0
  7 29  1  0
  6 28  1  0
M  END


  Mrv1652304282217092D          

 25 28  0  0  0  0            999 V2000
    6.3569   -3.0146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3569   -3.8396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6424   -4.2521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9279   -3.8396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9279   -3.0146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6424   -2.6021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135   -2.6021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135   -1.7771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990   -1.3646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845   -1.7771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990   -0.5396    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845   -0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    0.8555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1415   -4.0945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6264   -3.4271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1415   -2.7596    0.0000 O   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
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 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  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 16 22  1  0  0  0  0
  2 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
  1 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0069828

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O=C(NCCC1=CC2=C(OCO2)C=C1)\C=C\C1=CC2=C(OCO2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H17NO5/c21-19(6-3-13-1-4-15-17(9-13)24-11-22-15)20-8-7-14-2-5-16-18(10-14)25-12-23-16/h1-6,9-10H,7-8,11-12H2,(H,20,21)/b6-3+

> <INCHI_KEY>
YQKXNEWHNMPIKL-ZZXKWVIFSA-N

> <FORMULA>
C19H17NO5

> <MOLECULAR_WEIGHT>
339.347

> <EXACT_MASS>
339.110672651

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
36.248418388994324

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-3-(2H-1,3-benzodioxol-5-yl)-N-[2-(2H-1,3-benzodioxol-5-yl)ethyl]prop-2-enamide

> <ALOGPS_LOGP>
2.52

> <JCHEM_LOGP>
2.8124209696666664

> <ALOGPS_LOGS>
-4.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.954701658104735

> <JCHEM_PKA_STRONGEST_BASIC>
-0.38802901957295755

> <JCHEM_POLAR_SURFACE_AREA>
66.02000000000001

> <JCHEM_REFRACTIVITY>
90.68020000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.92e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-3-(2H-1,3-benzodioxol-5-yl)-N-[2-(2H-1,3-benzodioxol-5-yl)ethyl]prop-2-enamide

> <JCHEM_VEBER_RULE>
0

$$$$

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      11.866  -5.627   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.866  -7.167   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.533  -7.937   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.199  -7.167   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.199  -5.627   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.533  -4.857   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.865  -4.857   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.865  -3.317   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.531  -2.547   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.198  -3.317   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0       6.531  -1.007   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       5.198  -0.237   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.198   1.303   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.864   2.073   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.530   1.303   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.197   2.073   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.197   3.613   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.530   4.383   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.864   3.613   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -0.268   4.089   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -1.173   2.843   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -0.268   1.597   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      13.331  -7.643   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      14.236  -6.397   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      13.331  -5.151   0.000  0.00  0.00           O+0
CONECT    1    2    6   25                                                  
CONECT    2    1    3   23                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   22                                                  
CONECT   17   16   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18   14                                                       
CONECT   20   17   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   16                                                       
CONECT   23    2   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24    1                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₁₇NO₅

Average Mass

339.3470 Da

Monoisotopic Mass

339.11067 Da

IUPAC Name

(2E)-3-(2H-1,3-benzodioxol-5-yl)-N-[2-(2H-1,3-benzodioxol-5-yl)ethyl]prop-2-enamide

Traditional Name

(2E)-3-(2H-1,3-benzodioxol-5-yl)-N-[2-(2H-1,3-benzodioxol-5-yl)ethyl]prop-2-enamide

CAS Registry Number

Not Available

SMILES

O=C(NCCC1=CC2=C(OCO2)C=C1)\C=C\C1=CC2=C(OCO2)C=C1

InChI Identifier

InChI=1S/C19H17NO5/c21-19(6-3-13-1-4-15-17(9-13)24-11-22-15)20-8-7-14-2-5-16-18(10-14)25-12-23-16/h1-6,9-10H,7-8,11-12H2,(H,20,21)/b6-3+

InChI Key

YQKXNEWHNMPIKL-ZZXKWVIFSA-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
Beilschmiedia erythrophloia	Plant	KNApSAcK
Zanthoxylum rubescens	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cinnamic acid amides. These are amides of cinnamic acids. Cinnamic acid is an aromatic compound containing a benzene and a carboxylic acid group forming 3-phenylprop-2-enoic acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Cinnamic acid amides

Direct Parent

Cinnamic acid amides

Alternative Parents

Substituents

Cinnamic acid amide
Benzodioxole
Styrene
Benzenoid
Carboxamide group
Secondary carboxylic acid amide
Organoheterocyclic compound
Carboxylic acid derivative
Acetal
Oxacycle
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Hydrocarbon derivative
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	2.52	ALOGPS
logP	2.81	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	14.95	ChemAxon
pKa (Strongest Basic)	-0.39	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	66.02 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	90.68 m³·mol⁻¹	ChemAxon
Polarizability	36.25 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	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

C00028200

Chemspider ID

59650667

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14237548

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Dioxamine (NP0069828)

MOL for NP0069828 (Dioxamine)

3D MOL for NP0069828 (Dioxamine)

3D SDF for NP0069828 (Dioxamine)

3D-SDF for NP0069828 (Dioxamine)

PDB for NP0069828 (Dioxamine)

3D PDB for NP0069828 (Dioxamine)

SMILES for NP0069828 (Dioxamine)

INCHI for NP0069828 (Dioxamine)

Structure for NP0069828 (Dioxamine)

3D Structure for NP0069828 (Dioxamine)