NP-MRD: Showing NP-Card for 2-methyl-8h-1,11-dioxa-8-azatetraphene-4,5,10-trione (NP0259369)

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Record Information

Version

2.0

Created at

2022-09-08 01:13:09 UTC

Updated at

2022-09-08 01:13:09 UTC

NP-MRD ID

NP0259369

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-methyl-8h-1,11-dioxa-8-azatetraphene-4,5,10-trione

Description

Schumanniophytine belongs to the class of organic compounds known as linear pyranocoumarins. These are organic compounds containing a pyran (or a hydrogenated derivative) linearly fused to a coumarin moiety. 2-methyl-8h-1,11-dioxa-8-azatetraphene-4,5,10-trione is found in Schumanniophyton magnificum and Schumanniophyton problematicum. 2-methyl-8h-1,11-dioxa-8-azatetraphene-4,5,10-trione was first documented in 1985 (PMID: 17340393). Based on a literature review very few articles have been published on Schumanniophytine (PMID: 17269014).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 31 34  0  0  0  0  0  0  0  0999 V2000
    5.4533    0.7288    0.1940 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0462    0.3224   -0.0360 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7697   -0.8292   -0.7496 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4367   -1.1970   -0.9568 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1383   -2.2354   -1.5995 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4718   -0.3875   -0.4359 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1310   -0.7290   -0.6265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0898   -1.7627   -1.2676 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8854    0.0448   -0.1270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5682    1.2045    0.5910 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7754    1.5177    0.7640 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7901    0.7377    0.2606 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0564    1.0256    0.4191 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5158    1.9435    1.0677 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7884    1.6923    0.9322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6706    2.4372    1.4115 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1861    0.5675    0.2373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5185    0.2572    0.0659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8550   -0.8475   -0.6175 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9219   -1.6608   -1.1402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5708   -1.4062   -1.0039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2031   -0.2807   -0.3081 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6935    1.5748   -0.5100 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6017    1.1515    1.2171 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1716   -0.0684    0.0017 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5583   -1.4550   -1.1530 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9877    2.4234    1.3253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2714    0.9266    0.4960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8805   -1.0340   -0.7167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2452   -2.5534   -1.6916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9109   -2.1084   -1.4529 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6 12  2  0
 12 13  1  0
 12 11  1  0
 11 10  2  0
 10 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22  9  2  0
  9  7  1  0
  7  8  2  0
 13  2  1  0
  9 10  1  0
  7  6  1  0
 22 17  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
 11 27  1  0
 18 28  1  0
 19 29  1  0
 20 30  1  0
 21 31  1  0
M  END


  Mrv1652309082203132D          

 22 25  0  0  0  0            999 V2000
    6.1154    0.1007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3052    0.2566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0352    1.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2251    1.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9550    1.9716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6850    0.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8748    0.7243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6048    1.5039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3347    0.1007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6048   -0.6789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4149   -0.8348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9550   -0.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7651   -0.3671    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0647   -1.3025    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2546   -1.1466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.7702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9845   -0.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1744   -0.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0957    0.5684    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4444    1.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2546    1.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5246    0.2566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
  6 12  2  0  0  0  0
 12 13  1  0  0  0  0
  2 13  1  0  0  0  0
 10 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 17 22  1  0  0  0  0
  9 22  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0259369

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC(=O)C2=C(O1)C=C1OC(=O)C3=CNC=CC3=C1C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H9NO5/c1-7-4-10(18)14-12(21-7)5-11-13(15(14)19)8-2-3-17-6-9(8)16(20)22-11/h2-6,17H,1H3

> <INCHI_KEY>
JTMSAVQTVBHKAP-UHFFFAOYSA-N

> <FORMULA>
C16H9NO5

> <MOLECULAR_WEIGHT>
295.25

> <EXACT_MASS>
295.048072394

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
28.649983484893983

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-methyl-4,5,8,10-tetrahydro-1,11-dioxa-8-azatetraphene-4,5,10-trione

> <JCHEM_LOGP>
0.20850648266666655

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.531768278002154

> <JCHEM_PKA_STRONGEST_BASIC>
-5.079574510582865

> <JCHEM_POLAR_SURFACE_AREA>
81.70000000000002

> <JCHEM_REFRACTIVITY>
81.05850000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
2-methyl-8H-1,11-dioxa-8-azatetraphene-4,5,10-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      11.415   0.188   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.903   0.479   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.399   1.934   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.887   2.225   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       7.383   3.680   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       6.879   1.061   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.366   1.352   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.862   2.807   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.358   0.188   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.862  -1.267   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.375  -1.558   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.383  -0.394   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       8.895  -0.685   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       3.854  -2.431   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.342  -2.140   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.334  -3.304   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.838  -0.685   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.326  -0.394   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0      -0.179   1.061   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       0.830   2.225   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.342   1.934   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.846   0.479   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   12                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   22                                                  
CONECT   10    9   11   14                                                  
CONECT   11   10   12                                                       
CONECT   12   11    6   13                                                  
CONECT   13   12    2                                                       
CONECT   14   10   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   17    9                                                  
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₉NO₅

Average Mass

295.2500 Da

Monoisotopic Mass

295.04807 Da

IUPAC Name

2-methyl-4,5,8,10-tetrahydro-1,11-dioxa-8-azatetraphene-4,5,10-trione

Traditional Name

2-methyl-8H-1,11-dioxa-8-azatetraphene-4,5,10-trione

CAS Registry Number

Not Available

SMILES

CC1=CC(=O)C2=C(O1)C=C1OC(=O)C3=CNC=CC3=C1C2=O

InChI Identifier

InChI=1S/C16H9NO5/c1-7-4-10(18)14-12(21-7)5-11-13(15(14)19)8-2-3-17-6-9(8)16(20)22-11/h2-6,17H,1H3

InChI Key

JTMSAVQTVBHKAP-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
Schumanniophyton magnificum	LOTUS Database	35616633
Schumanniophyton problematicum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as linear pyranocoumarins. These are organic compounds containing a pyran (or a hydrogenated derivative) linearly fused to a coumarin moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Pyranocoumarins

Direct Parent

Linear pyranocoumarins

Alternative Parents

Substituents

Linear pyranocoumarin
Pyranochromene
Chromone
1-benzopyran
Benzopyran
Pyranone
Benzenoid
Pyridine
Pyran
Heteroaromatic compound
Vinylogous amide
Lactone
Oxacycle
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen 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	0.21	ChemAxon
pKa (Strongest Acidic)	12.53	ChemAxon
pKa (Strongest Basic)	-5.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	81.7 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	81.06 m³·mol⁻¹	ChemAxon
Polarizability	28.65 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

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

13892290

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Houghton PJ, Hairong Y: Further Chromone Alkaloids from Schumanniophyton magnificum. Planta Med. 1987 Jun;53(3):262-4. doi: 10.1055/s-2006-962698. [PubMed:17269014 ]
Houghton PJ, Hairong Y: Novel Chromone Alkaloids from Schumanniophyton magnificum. Planta Med. 1985 Feb;51(1):23-7. doi: 10.1055/s-2007-969383. [PubMed:17340393 ]
LOTUS database [Link]

Showing NP-Card for 2-methyl-8h-1,11-dioxa-8-azatetraphene-4,5,10-trione (NP0259369)

MOL for NP0259369 (2-methyl-8h-1,11-dioxa-8-azatetraphene-4,5,10-trione)

3D MOL for NP0259369 (2-methyl-8h-1,11-dioxa-8-azatetraphene-4,5,10-trione)

3D SDF for NP0259369 (2-methyl-8h-1,11-dioxa-8-azatetraphene-4,5,10-trione)

3D-SDF for NP0259369 (2-methyl-8h-1,11-dioxa-8-azatetraphene-4,5,10-trione)

PDB for NP0259369 (2-methyl-8h-1,11-dioxa-8-azatetraphene-4,5,10-trione)

3D PDB for NP0259369 (2-methyl-8h-1,11-dioxa-8-azatetraphene-4,5,10-trione)

SMILES for NP0259369 (2-methyl-8h-1,11-dioxa-8-azatetraphene-4,5,10-trione)

INCHI for NP0259369 (2-methyl-8h-1,11-dioxa-8-azatetraphene-4,5,10-trione)

Structure for NP0259369 (2-methyl-8h-1,11-dioxa-8-azatetraphene-4,5,10-trione)

3D Structure for NP0259369 (2-methyl-8h-1,11-dioxa-8-azatetraphene-4,5,10-trione)