NP-MRD: Showing NP-Card for 12-ethoxy-6,6,10,11-tetramethyl-4-phenyl-11,12-dihydro-10h-1,5,9-trioxatriphenylen-2-one (NP0192153)

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Record Information

Version

2.0

Created at

2022-09-04 09:17:54 UTC

Updated at

2022-09-04 09:17:54 UTC

NP-MRD ID

NP0192153

Secondary Accession Numbers

None

Natural Product Identification

Common Name

12-ethoxy-6,6,10,11-tetramethyl-4-phenyl-11,12-dihydro-10h-1,5,9-trioxatriphenylen-2-one

Description

12-Ethoxy-6,6,10,11-tetramethyl-4-phenyl-6,10,11,12-tetrahydro-2H-1,5,9-trioxatriphenylen-2-one belongs to the class of organic compounds known as prenylated neoflavonoids. These are neoflavonoids that features a C5-isoprenoid substituent at any position of the A, B, or C ring. Neoflavonoids are compounds with a structure based on the 4-phenylchromene backbone. 12-ethoxy-6,6,10,11-tetramethyl-4-phenyl-11,12-dihydro-10h-1,5,9-trioxatriphenylen-2-one is found in Calophyllum inophyllum. 12-Ethoxy-6,6,10,11-tetramethyl-4-phenyl-6,10,11,12-tetrahydro-2H-1,5,9-trioxatriphenylen-2-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241514032D          

 32 36  0  0  0  0            999 V2000
    0.7954   -2.9684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2079   -2.2539    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
    2.4454   -1.5395    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
    1.2079   -0.8250    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    0.6039    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
    3.6829   -0.8250    0.0000 C   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
    3.2704   -4.3974    0.0000 O   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
    3.2704   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7454   -2.9684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1579   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9829   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.9829   -3.6829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1579   -3.6829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1533004241514032D          

 32 36  0  0  0  0            999 V2000
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    1.2079   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.4454   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0192153

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCOC1C(C)C(C)OC2=C3C=CC(C)(C)OC3=C3C(OC(=O)C=C3C3=CC=CC=C3)=C12

> <INCHI_IDENTIFIER>
InChI=1S/C27H28O5/c1-6-29-23-15(2)16(3)30-24-18-12-13-27(4,5)32-25(18)21-19(17-10-8-7-9-11-17)14-20(28)31-26(21)22(23)24/h7-16,23H,6H2,1-5H3

> <INCHI_KEY>
ACUWSEQRCCAKLO-UHFFFAOYSA-N

> <FORMULA>
C27H28O5

> <MOLECULAR_WEIGHT>
432.516

> <EXACT_MASS>
432.193674002

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
47.664323228035016

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
12-ethoxy-6,6,10,11-tetramethyl-4-phenyl-6,10,11,12-tetrahydro-2H-1,5,9-trioxatriphenylen-2-one

> <ALOGPS_LOGP>
5.73

> <JCHEM_LOGP>
5.036195469999999

> <ALOGPS_LOGS>
-5.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.0458986750913715

> <JCHEM_POLAR_SURFACE_AREA>
53.99000000000001

> <JCHEM_REFRACTIVITY>
133.67539999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.56e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
12-ethoxy-6,6,10,11-tetramethyl-4-phenyl-11,12-dihydro-10H-1,5,9-trioxatriphenylen-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       1.485  -5.541   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.255  -4.207   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       3.795  -4.207   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       4.565  -2.874   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.795  -1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.255  -1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.565  -0.206   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.795   1.127   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.105  -0.206   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       6.875  -1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.415  -1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.185  -0.206   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.725  -0.206   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.495  -1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.674  -0.550   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.674  -2.530   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      10.725  -2.874   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       9.185  -2.874   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.415  -4.207   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.185  -5.541   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.415  -6.875   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.875  -6.875   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.105  -8.208   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       6.105  -5.541   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       6.875  -4.207   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.105  -2.874   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.725  -5.541   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      11.495  -4.207   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      13.035  -4.207   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      13.805  -5.541   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      13.035  -6.875   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      11.495  -6.875   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   26                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   26                                                  
CONECT   11   10   12   18                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16   17                                             
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   14   18                                                       
CONECT   18   17   11   19                                                  
CONECT   19   18   20   25                                                  
CONECT   20   19   21   27                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   19   26                                                  
CONECT   26   25    4   10                                                  
CONECT   27   20   28   32                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   27                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₂₈O₅

Average Mass

432.5160 Da

Monoisotopic Mass

432.19367 Da

IUPAC Name

12-ethoxy-6,6,10,11-tetramethyl-4-phenyl-6,10,11,12-tetrahydro-2H-1,5,9-trioxatriphenylen-2-one

Traditional Name

12-ethoxy-6,6,10,11-tetramethyl-4-phenyl-11,12-dihydro-10H-1,5,9-trioxatriphenylen-2-one

CAS Registry Number

Not Available

SMILES

CCOC1C(C)C(C)OC2=C3C=CC(C)(C)OC3=C3C(OC(=O)C=C3C3=CC=CC=C3)=C12

InChI Identifier

InChI=1S/C27H28O5/c1-6-29-23-15(2)16(3)30-24-18-12-13-27(4,5)32-25(18)21-19(17-10-8-7-9-11-17)14-20(28)31-26(21)22(23)24/h7-16,23H,6H2,1-5H3

InChI Key

ACUWSEQRCCAKLO-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
Calophyllum inophyllum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as prenylated neoflavonoids. These are neoflavonoids that features a C5-isoprenoid substituent at any position of the A, B, or C ring. Neoflavonoids are compounds with a structure based on the 4-phenylchromene backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Neoflavonoids

Sub Class

Prenylated neoflavonoids

Direct Parent

Prenylated neoflavonoids

Alternative Parents

Substituents

Prenylated neoflavonoid
Pyranoneoflavonoid
4-phenylcoumarin
Pyranocoumarin
Angular pyranocoumarin
Pyranochromene
2,2-dimethyl-1-benzopyran
Coumarin
Chromane
Benzopyran
1-benzopyran
Pyranone
Alkyl aryl ether
Monocyclic benzene moiety
Pyran
Benzenoid
Heteroaromatic compound
Lactone
Ether
Dialkyl ether
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen 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	5.73	ALOGPS
logP	5.04	ChemAxon
logS	-5.9	ALOGPS
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	53.99 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	133.68 m³·mol⁻¹	ChemAxon
Polarizability	47.66 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 12-ethoxy-6,6,10,11-tetramethyl-4-phenyl-11,12-dihydro-10h-1,5,9-trioxatriphenylen-2-one (NP0192153)

MOL for NP0192153 (12-ethoxy-6,6,10,11-tetramethyl-4-phenyl-11,12-dihydro-10h-1,5,9-trioxatriphenylen-2-one)

3D MOL for NP0192153 (12-ethoxy-6,6,10,11-tetramethyl-4-phenyl-11,12-dihydro-10h-1,5,9-trioxatriphenylen-2-one)

3D SDF for NP0192153 (12-ethoxy-6,6,10,11-tetramethyl-4-phenyl-11,12-dihydro-10h-1,5,9-trioxatriphenylen-2-one)

3D-SDF for NP0192153 (12-ethoxy-6,6,10,11-tetramethyl-4-phenyl-11,12-dihydro-10h-1,5,9-trioxatriphenylen-2-one)

PDB for NP0192153 (12-ethoxy-6,6,10,11-tetramethyl-4-phenyl-11,12-dihydro-10h-1,5,9-trioxatriphenylen-2-one)

3D PDB for NP0192153 (12-ethoxy-6,6,10,11-tetramethyl-4-phenyl-11,12-dihydro-10h-1,5,9-trioxatriphenylen-2-one)

SMILES for NP0192153 (12-ethoxy-6,6,10,11-tetramethyl-4-phenyl-11,12-dihydro-10h-1,5,9-trioxatriphenylen-2-one)

INCHI for NP0192153 (12-ethoxy-6,6,10,11-tetramethyl-4-phenyl-11,12-dihydro-10h-1,5,9-trioxatriphenylen-2-one)

Structure for NP0192153 (12-ethoxy-6,6,10,11-tetramethyl-4-phenyl-11,12-dihydro-10h-1,5,9-trioxatriphenylen-2-one)

3D Structure for NP0192153 (12-ethoxy-6,6,10,11-tetramethyl-4-phenyl-11,12-dihydro-10h-1,5,9-trioxatriphenylen-2-one)