NP-MRD: Showing NP-Card for coronal (NP0197985)

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Record Information

Version

2.0

Created at

2022-09-04 16:21:10 UTC

Updated at

2022-09-04 16:21:10 UTC

NP-MRD ID

NP0197985

Secondary Accession Numbers

None

Natural Product Identification

Common Name

coronal

Description

(R)-dyphylline belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety. coronal is found in Cleistanthus collinus, Haplophyllum patavinum, Haplophyllum tuberculatum and Phyllanthus oligospermus. Based on a literature review very few articles have been published on (R)-dyphylline.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 32 33  0  0  0  0  0  0  0  0999 V2000
   -2.2778    2.7088   -1.1604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0239    1.3502   -0.6912 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7844    0.8597   -0.7255 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1896    1.5311   -1.1525 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5287   -0.4191   -0.2868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5967   -1.1566    0.1820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0892   -2.3472    0.5426 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2342   -2.3294    0.3010 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6063   -1.1385   -0.2159 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9205   -0.7279   -0.6045 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6921   -0.0733    0.5143 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8601   -0.9198    1.6034 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0424    0.3667   -0.0142 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7666    1.0455    0.9577 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8528   -0.6729    0.2218 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9419   -1.4857    0.7228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0359    0.5844   -0.2217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2080    1.0383   -0.1855 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5972    2.9544   -1.9993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3221    2.7397   -1.5384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1296    3.4006   -0.3204 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8972   -3.1578    0.4969 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5234   -1.5941   -0.9475 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9265   -0.0032   -1.4574 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1923    0.8559    0.8775 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1766   -0.3514    2.3603 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8390    1.1032   -0.8298 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5999   -0.4991   -0.4245 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6129    1.3386    0.5429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8961   -1.0215    0.4478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9289   -2.5114    0.3445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8663   -1.4686    1.8286 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 15  1  0
 15  6  1  0
  6  5  2  0
  5  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
  9  8  1  0
  8  7  2  0
  5  3  1  0
  3  4  2  0
  3  2  1  0
  2  1  1  0
  2 17  1  0
 17 18  2  0
 17 15  1  0
  7  6  1  0
 16 30  1  0
 16 31  1  0
 16 32  1  0
 10 23  1  0
 10 24  1  0
 11 25  1  1
 12 26  1  0
 13 27  1  0
 13 28  1  0
 14 29  1  0
  8 22  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
M  END


  Mrv1652309042218212D          

 18 19  0  0  1  0            999 V2000
    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 N   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
    1.3556   -0.1271    0.0000 O   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
   -0.1435    2.1904    0.0000 N   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 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984    0.0709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2054   -0.1006    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7575    0.5124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4604   -0.8853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2673   -1.0568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    2.3479    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    3.1729    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
    2.7845    2.3479    0.0000 O   0  0  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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  5  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
  6 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
  2 17  1  0  0  0  0
 17 18  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0197985

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C2=C(N(C[C@@H](O)CO)C=N2)C(=O)N(C)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H14N4O4/c1-12-8-7(9(17)13(2)10(12)18)14(5-11-8)3-6(16)4-15/h5-6,15-16H,3-4H2,1-2H3/t6-/m1/s1

> <INCHI_KEY>
KSCFJBIXMNOVSH-ZCFIWIBFSA-N

> <FORMULA>
C10H14N4O4

> <MOLECULAR_WEIGHT>
254.246

> <EXACT_MASS>
254.101504947

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
24.61017919239426

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
7-[(2R)-2,3-dihydroxypropyl]-1,3-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione

> <JCHEM_LOGP>
-1.8660825456666665

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.629258284029333

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.909130036369692

> <JCHEM_PKA_STRONGEST_BASIC>
-0.9737219913339484

> <JCHEM_POLAR_SURFACE_AREA>
98.9

> <JCHEM_REFRACTIVITY>
62.086

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
coronal

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       5.198   1.303   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       3.864   2.073   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       2.530   1.303   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.530  -0.237   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.197   2.073   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.197   3.613   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      -0.268   4.089   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      -1.173   2.843   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      -0.268   1.597   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      -0.744   0.132   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.250  -0.188   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -3.281   0.957   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -2.726  -1.652   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -4.232  -1.973   0.000  0.00  0.00           O+0
HETATM   15  N   UNK     0       2.530   4.383   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       2.530   5.923   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.864   3.613   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.198   4.383   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   17                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    9                                                  
CONECT    6    5    7   15                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    5   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13                                                            
CONECT   15    6   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15    2   18                                                  
CONECT   18   17                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

View in JSmol

Synonyms

Value	Source
(R)-Diprophylline	ChEBI
1,3-Dimethyl-7-[(2R)-2,3-dihydroxypropyl]xanthine	ChEBI
7-[(2R)-2,3-Dihydroxypropyl]-1,3-dimethylxanthine	ChEBI
7-[(2R)-2,3-Dihydroxypropyl]-3,7-dihydro-1,3-dimethyl-1H-purine-2,6-dione	ChEBI
7-[(2R)-2,3-Dihydroxypropyl]theophylline	ChEBI
[(2R)-1,2-Dihydroxy-3-propyl]thiophyllin	ChEBI

Chemical Formula

C₁₀H₁₄N₄O₄

Average Mass

254.2460 Da

Monoisotopic Mass

254.10150 Da

IUPAC Name

7-[(2R)-2,3-dihydroxypropyl]-1,3-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione

Traditional Name

coronal

CAS Registry Number

Not Available

SMILES

CN1C2=C(N(C[C@@H](O)CO)C=N2)C(=O)N(C)C1=O

InChI Identifier

InChI=1S/C10H14N4O4/c1-12-8-7(9(17)13(2)10(12)18)14(5-11-8)3-6(16)4-15/h5-6,15-16H,3-4H2,1-2H3/t6-/m1/s1

InChI Key

KSCFJBIXMNOVSH-ZCFIWIBFSA-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
Cleistanthus collinus	LOTUS Database	35616633
Haplophyllum patavinum	LOTUS Database	35616633
Haplophyllum tuberculatum	LOTUS Database	35616633
Phyllanthus oligospermus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Imidazopyrimidines

Sub Class

Purines and purine derivatives

Direct Parent

Xanthines

Alternative Parents

Substituents

Xanthine
6-oxopurine
Purinone
Alkaloid or derivatives
Pyrimidone
N-substituted imidazole
Pyrimidine
Azole
Imidazole
Heteroaromatic compound
Vinylogous amide
1,2-diol
Lactam
Urea
Secondary alcohol
Azacycle
Primary alcohol
Organooxygen compound
Organonitrogen compound
Organic oxide
Organic nitrogen compound
Organopnictogen compound
Organic oxygen compound
Hydrocarbon derivative
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

dyphylline (CHEBI:59846 )

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	-1.9	ChemAxon
pKa (Strongest Acidic)	13.91	ChemAxon
pKa (Strongest Basic)	-0.97	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	98.9 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	62.09 m³·mol⁻¹	ChemAxon
Polarizability	24.61 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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

599827

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

688353

PDB ID

Not Available

ChEBI ID

59846

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for coronal (NP0197985)

MOL for NP0197985 (coronal)

3D MOL for NP0197985 (coronal)

3D SDF for NP0197985 (coronal)

3D-SDF for NP0197985 (coronal)

PDB for NP0197985 (coronal)

3D PDB for NP0197985 (coronal)

SMILES for NP0197985 (coronal)

INCHI for NP0197985 (coronal)

Structure for NP0197985 (coronal)

3D Structure for NP0197985 (coronal)