NP-MRD: Showing NP-Card for Spathelia bischromene (NP0051431)

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Record Information

Version

2.0

Created at

2022-04-27 22:48:01 UTC

Updated at

2022-04-27 22:48:01 UTC

NP-MRD ID

NP0051431

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Spathelia bischromene

Description

2,2,6,10,10-Pentamethyl-8,10-dihydro-2H-1,5,9-trioxatriphenylen-8-one, also known as 2,2,6,6,10-pentamethyl-2H,6H,12H-benzo[1,2-b:3,4-B':5,6-B'']tripyran-12-one, belongs to the class of organic compounds known as pyranochromenes. These are organic heterocyclic compounds containing a pyran ring fused to a chromene (1-benzopyran) moiety. Spathelia bischromene is found in Cneorum pulverulentum, Cneorum tricoccum, family Rutaceae spp., Spathelia glabrescens and Spathelia sorbifolia. 2,2,6,10,10-Pentamethyl-8,10-dihydro-2H-1,5,9-trioxatriphenylen-8-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 44 47  0  0  0  0  0  0  0  0999 V2000
   -0.8038    5.3379    0.0609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1879    3.9569    0.0493 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1814    3.8169    0.0690 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7093    2.5450    0.0577 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9528    2.3603    0.0746 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8589    1.4675    0.0275 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3853    0.1671    0.0157 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4714   -0.8833   -0.0151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8984   -0.6721   -0.0337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3976    0.6127   -0.0217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5134    1.6661    0.0087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9361    2.9010    0.0211 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8421    0.7766   -0.0422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6771   -0.2408   -0.0712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1618   -1.6111   -0.0843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6808   -2.3024   -1.3410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8157   -2.3482    1.0901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7763   -1.7396   -0.0642 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0507   -2.2134   -0.0265 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3475   -2.4169   -0.0090 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3059   -1.3216    0.0232 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3025   -1.4230   -1.1327 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1384   -1.4327    1.2990 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7197   -0.0741    0.0332 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4255    5.3881   -0.8657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5003    5.3596    0.9098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0159    6.0897    0.0978 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8131    4.6961    0.0926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2551    1.7916   -0.0330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7637   -0.1016   -0.0864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0435   -2.1093   -2.2184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7089   -3.3980   -1.1000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7184   -1.9223   -1.5053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3496   -3.3554    1.1126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6076   -1.8032    2.0454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8975   -2.3788    0.9175 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3626   -3.0603   -0.0506 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6828   -3.4821   -0.0202 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6174   -2.4621   -1.2217 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8547   -1.0912   -2.0813 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1471   -0.7490   -0.8459 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5372   -1.2601    2.2023 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9225   -0.6558    1.2657 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6158   -2.4248    1.3964 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 11  2  0
 11 12  1  0
 11 10  1  0
 10  9  2  0
  9 18  1  0
 18 15  1  0
 15 16  1  0
 15 17  1  0
 15 14  1  0
 14 13  2  0
  9  8  1  0
  8  7  2  0
  7 24  1  0
 24 21  1  0
 21 22  1  0
 21 23  1  0
 21 20  1  0
 20 19  2  0
 12  2  1  0
 13 10  1  0
 19  8  1  0
  7  6  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
 16 31  1  0
 16 32  1  0
 16 33  1  0
 17 34  1  0
 17 35  1  0
 17 36  1  0
 14 30  1  0
 13 29  1  0
 22 39  1  0
 22 40  1  0
 22 41  1  0
 23 42  1  0
 23 43  1  0
 23 44  1  0
 20 38  1  0
 19 37  1  0
M  END


  Mrv1533004161508272D          

 24 27  0  0  0  0            999 V2000
    2.0329    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0329   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0329   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9204   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7454   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7899   -0.2947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7899   -1.3553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7454   -1.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9204   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9204   -2.9684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079   -3.6829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829   -3.6829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8261   -4.4954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9076   -3.9651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -2.9684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829   -2.2539    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  2  0  0  0  0
  7  8  1  0  0  0  0
  2  8  1  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
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
  9 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  1  0  0  0  0
  6 24  1  0  0  0  0
 17 24  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0051431

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC(=O)C2=C(O1)C1=C(OC(C)(C)C=C1)C1=C2OC(C)(C)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H20O4/c1-11-10-14(21)15-17(22-11)12-6-8-19(2,3)23-16(12)13-7-9-20(4,5)24-18(13)15/h6-10H,1-5H3

> <INCHI_KEY>
CUFLINMPEWUGEH-UHFFFAOYSA-N

> <FORMULA>
C20H20O4

> <MOLECULAR_WEIGHT>
324.376

> <EXACT_MASS>
324.136159124

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
35.653442139772096

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,2,6,10,10-pentamethyl-8,10-dihydro-2H-1,5,9-trioxatriphenylen-8-one

> <ALOGPS_LOGP>
4.31

> <JCHEM_LOGP>
3.6728000733333324

> <ALOGPS_LOGS>
-4.93

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.212016293958403

> <JCHEM_PKA_STRONGEST_BASIC>
-4.5787827976385405

> <JCHEM_POLAR_SURFACE_AREA>
44.760000000000005

> <JCHEM_REFRACTIVITY>
95.894

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.85e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
spathelia bischromene

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0       3.795   1.127   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.565  -0.206   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.795  -1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.565  -2.874   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       3.795  -4.207   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       6.105  -2.874   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.875  -1.540   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       6.105  -0.206   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       8.415  -1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.185  -0.206   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.725  -0.206   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.495  -1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.674  -0.550   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.674  -2.530   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      10.725  -2.874   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       9.185  -2.874   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.415  -4.207   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.185  -5.541   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.415  -6.875   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.875  -6.875   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.142  -8.391   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.428  -7.401   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.105  -5.541   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       6.875  -4.207   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   24                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7    2                                                       
CONECT    9    7   10   16                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14   15                                             
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   12   16                                                       
CONECT   16   15    9   17                                                  
CONECT   17   16   18   24                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22   23                                             
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   20   24                                                       
CONECT   24   23    6   17                                                  
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

View in JSmol

Synonyms

Value	Source
2,2,6,6,10-Pentamethyl-2H,6H,12H-benzo[1,2-b:3,4-b':5,6-b'']tripyran-12-one	Kegg

Chemical Formula

C₂₀H₂₀O₄

Average Mass

324.3760 Da

Monoisotopic Mass

324.13616 Da

IUPAC Name

2,2,6,10,10-pentamethyl-8,10-dihydro-2H-1,5,9-trioxatriphenylen-8-one

Traditional Name

spathelia bischromene

CAS Registry Number

Not Available

SMILES

CC1=CC(=O)C2=C(O1)C1=C(OC(C)(C)C=C1)C1=C2OC(C)(C)C=C1

InChI Identifier

InChI=1S/C20H20O4/c1-11-10-14(21)15-17(22-11)12-6-8-19(2,3)23-16(12)13-7-9-20(4,5)24-18(13)15/h6-10H,1-5H3

InChI Key

CUFLINMPEWUGEH-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, 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
Cneorum pulverulentum	Plant	KNApSAcK
Cneorum tricoccum	Plant	KNApSAcK
family Rutaceae spp.	-	KNApSAcK
Spathelia glabrescens	Plant	KNApSAcK
Spathelia sorbifolia	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyranochromenes. These are organic heterocyclic compounds containing a pyran ring fused to a chromene (1-benzopyran) moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

Pyranochromenes

Alternative Parents

Substituents

Pyranochromene
2,2-dimethyl-1-benzopyran
Chromone
Alkyl aryl ether
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Vinylogous ester
Ether
Oxacycle
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

chromenes (CHEBI:9213 )
chromones (C09048 )

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	4.31	ALOGPS
logP	3.67	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	15.21	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	44.76 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	95.89 m³·mol⁻¹	ChemAxon
Polarizability	35.65 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

C00002446

Chemspider ID

Not Available

KEGG Compound ID

C09048

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

441993

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Spathelia bischromene (NP0051431)

MOL for NP0051431 (Spathelia bischromene)

3D MOL for NP0051431 (Spathelia bischromene)

3D SDF for NP0051431 (Spathelia bischromene)

3D-SDF for NP0051431 (Spathelia bischromene)

PDB for NP0051431 (Spathelia bischromene)

3D PDB for NP0051431 (Spathelia bischromene)

SMILES for NP0051431 (Spathelia bischromene)

INCHI for NP0051431 (Spathelia bischromene)

Structure for NP0051431 (Spathelia bischromene)

3D Structure for NP0051431 (Spathelia bischromene)