NP-MRD: Showing NP-Card for 2-(acetyloxy)-4-[5,7-bis(acetyloxy)-4-oxochromen-3-yl]-5-(2-methylbut-3-en-2-yl)phenyl acetate (NP0226549)

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Record Information

Version

2.0

Created at

2022-09-06 05:37:44 UTC

Updated at

2022-09-06 05:37:44 UTC

NP-MRD ID

NP0226549

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-(acetyloxy)-4-[5,7-bis(acetyloxy)-4-oxochromen-3-yl]-5-(2-methylbut-3-en-2-yl)phenyl acetate

Description

Fremontin tetraacetate belongs to the class of organic compounds known as isoflavones. These are polycyclic compounds containing a 2-isoflavene skeleton which bears a ketone group at the C4 carbon atom. 2-(acetyloxy)-4-[5,7-bis(acetyloxy)-4-oxochromen-3-yl]-5-(2-methylbut-3-en-2-yl)phenyl acetate is found in Psorothamnus arborescens. Based on a literature review very few articles have been published on Fremontin tetraacetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062207372D          

 38 40  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309062207372D          

 38 40  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0226549

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC1=CC(OC(C)=O)=C2C(=O)C(=COC2=C1)C1=CC(OC(C)=O)=C(OC(C)=O)C=C1C(C)(C)C=C

> <INCHI_IDENTIFIER>
InChI=1S/C28H26O10/c1-8-28(6,7)21-12-23(37-16(4)31)22(36-15(3)30)11-19(21)20-13-34-24-9-18(35-14(2)29)10-25(38-17(5)32)26(24)27(20)33/h8-13H,1H2,2-7H3

> <INCHI_KEY>
GXUDMRDICMYDQL-UHFFFAOYSA-N

> <FORMULA>
C28H26O10

> <MOLECULAR_WEIGHT>
522.506

> <EXACT_MASS>
522.152597037

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
53.83007076843987

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(acetyloxy)-4-[5,7-bis(acetyloxy)-4-oxo-4H-chromen-3-yl]-5-(2-methylbut-3-en-2-yl)phenyl acetate

> <JCHEM_LOGP>
3.452249201333334

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-5.32163105125866

> <JCHEM_POLAR_SURFACE_AREA>
131.5

> <JCHEM_REFRACTIVITY>
133.5808

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
2-(acetyloxy)-4-[5,7-bis(acetyloxy)-4-oxochromen-3-yl]-5-(2-methylbut-3-en-2-yl)phenyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       0.976   0.564   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.206  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.874  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       9.336  -2.310   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       8.002  -4.620   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5    6                                             
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    3    7   19                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    8   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   13   19                                                       
CONECT   19   18    6   20                                                  
CONECT   20   19   21   37                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   36                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   30                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   25   31                                                       
CONECT   31   30   32   36                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36   31   23   37                                                  
CONECT   37   36   20   38                                                  
CONECT   38   37                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   80    0
END

View in JSmol

Synonyms

Value	Source
Fremontin tetraacetic acid	Generator

Chemical Formula

C₂₈H₂₆O₁₀

Average Mass

522.5060 Da

Monoisotopic Mass

522.15260 Da

IUPAC Name

2-(acetyloxy)-4-[5,7-bis(acetyloxy)-4-oxo-4H-chromen-3-yl]-5-(2-methylbut-3-en-2-yl)phenyl acetate

Traditional Name

2-(acetyloxy)-4-[5,7-bis(acetyloxy)-4-oxochromen-3-yl]-5-(2-methylbut-3-en-2-yl)phenyl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OC1=CC(OC(C)=O)=C2C(=O)C(=COC2=C1)C1=CC(OC(C)=O)=C(OC(C)=O)C=C1C(C)(C)C=C

InChI Identifier

InChI=1S/C28H26O10/c1-8-28(6,7)21-12-23(37-16(4)31)22(36-15(3)30)11-19(21)20-13-34-24-9-18(35-14(2)29)10-25(38-17(5)32)26(24)27(20)33/h8-13H,1H2,2-7H3

InChI Key

GXUDMRDICMYDQL-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
Psorothamnus arborescens	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoflavones. These are polycyclic compounds containing a 2-isoflavene skeleton which bears a ketone group at the C4 carbon atom.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Isoflav-2-enes

Direct Parent

Isoflavones

Alternative Parents

Substituents

Isoflavone
Tetracarboxylic acid or derivatives
Chromone
Benzopyran
Phenol ester
1-benzopyran
Phenylpropane
Phenoxy compound
Pyranone
Monocyclic benzene moiety
Benzenoid
Pyran
Heteroaromatic compound
Carboxylic acid ester
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
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	3.45	ChemAxon
pKa (Strongest Basic)	-5.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	131.5 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	133.58 m³·mol⁻¹	ChemAxon
Polarizability	53.83 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

23338890

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44566227

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-(acetyloxy)-4-[5,7-bis(acetyloxy)-4-oxochromen-3-yl]-5-(2-methylbut-3-en-2-yl)phenyl acetate (NP0226549)

MOL for NP0226549 (2-(acetyloxy)-4-[5,7-bis(acetyloxy)-4-oxochromen-3-yl]-5-(2-methylbut-3-en-2-yl)phenyl acetate)

3D MOL for NP0226549 (2-(acetyloxy)-4-[5,7-bis(acetyloxy)-4-oxochromen-3-yl]-5-(2-methylbut-3-en-2-yl)phenyl acetate)

3D SDF for NP0226549 (2-(acetyloxy)-4-[5,7-bis(acetyloxy)-4-oxochromen-3-yl]-5-(2-methylbut-3-en-2-yl)phenyl acetate)

3D-SDF for NP0226549 (2-(acetyloxy)-4-[5,7-bis(acetyloxy)-4-oxochromen-3-yl]-5-(2-methylbut-3-en-2-yl)phenyl acetate)

PDB for NP0226549 (2-(acetyloxy)-4-[5,7-bis(acetyloxy)-4-oxochromen-3-yl]-5-(2-methylbut-3-en-2-yl)phenyl acetate)

3D PDB for NP0226549 (2-(acetyloxy)-4-[5,7-bis(acetyloxy)-4-oxochromen-3-yl]-5-(2-methylbut-3-en-2-yl)phenyl acetate)

SMILES for NP0226549 (2-(acetyloxy)-4-[5,7-bis(acetyloxy)-4-oxochromen-3-yl]-5-(2-methylbut-3-en-2-yl)phenyl acetate)

INCHI for NP0226549 (2-(acetyloxy)-4-[5,7-bis(acetyloxy)-4-oxochromen-3-yl]-5-(2-methylbut-3-en-2-yl)phenyl acetate)

Structure for NP0226549 (2-(acetyloxy)-4-[5,7-bis(acetyloxy)-4-oxochromen-3-yl]-5-(2-methylbut-3-en-2-yl)phenyl acetate)

3D Structure for NP0226549 (2-(acetyloxy)-4-[5,7-bis(acetyloxy)-4-oxochromen-3-yl]-5-(2-methylbut-3-en-2-yl)phenyl acetate)