NP-MRD: Showing NP-Card for Euchrenone a12 (NP0055778)

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Record Information

Version

2.0

Created at

2022-04-28 01:43:55 UTC

Updated at

2022-04-28 01:43:55 UTC

NP-MRD ID

NP0055778

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Euchrenone a12

Description

(2R)-5-hydroxy-2-(7-hydroxy-2,2-dimethyl-2H-chromen-6-yl)-8,8-dimethyl-6-(3-methylbut-2-en-1-yl)-2H,3H,4H,8H-pyrano[2,3-f]chromen-4-one belongs to the class of organic compounds known as 6-prenylated flavanones. These are flavanones that features a C5-isoprenoid substituent at the 6-position. Euchrenone a12 is found in Euchresta formosana and Euchresta japonica . Based on a literature review very few articles have been published on (2R)-5-hydroxy-2-(7-hydroxy-2,2-dimethyl-2H-chromen-6-yl)-8,8-dimethyl-6-(3-methylbut-2-en-1-yl)-2H,3H,4H,8H-pyrano[2,3-f]chromen-4-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282203432D          

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M  END

     RDKit          3D

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 26 29  1  0  0  0  0
 26 30  1  0  0  0  0
  2 31  1  0  0  0  0
  1 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0055778

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC1=C(O)C2=C(O[C@H](CC2=O)C2=CC3=C(OC(C)(C)C=C3)C=C2O)C2=C1OC(C)(C)C=C2

> <INCHI_IDENTIFIER>
InChI=1S/C30H32O6/c1-16(2)7-8-18-26(33)25-22(32)15-24(34-28(25)19-10-12-30(5,6)36-27(18)19)20-13-17-9-11-29(3,4)35-23(17)14-21(20)31/h7,9-14,24,31,33H,8,15H2,1-6H3/t24-/m1/s1

> <INCHI_KEY>
AFNMVZWHERFZJC-XMMPIXPASA-N

> <FORMULA>
C30H32O6

> <MOLECULAR_WEIGHT>
488.58

> <EXACT_MASS>
488.21988875

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
54.55661721082164

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4R)-8-hydroxy-4-(7-hydroxy-2,2-dimethyl-2H-chromen-6-yl)-12,12-dimethyl-9-(3-methylbut-2-en-1-yl)-3,11-dioxatricyclo[8.4.0.0^{2,7}]tetradeca-1(10),2(7),8,13-tetraen-6-one

> <ALOGPS_LOGP>
5.62

> <JCHEM_LOGP>
6.668487175333333

> <ALOGPS_LOGS>
-5.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.267978331058444

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.576934819869614

> <JCHEM_PKA_STRONGEST_BASIC>
-4.465295502311697

> <JCHEM_POLAR_SURFACE_AREA>
85.22000000000001

> <JCHEM_REFRACTIVITY>
142.33850000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.51e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4R)-8-hydroxy-4-(7-hydroxy-2,2-dimethylchromen-6-yl)-12,12-dimethyl-9-(3-methylbut-2-en-1-yl)-3,11-dioxatricyclo[8.4.0.0^{2,7}]tetradeca-1(10),2(7),8,13-tetraen-6-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -4.001  -6.930   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.540  -5.336   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.817  -4.084   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.334 -11.550   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       8.002  -4.620   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      10.152  -4.084   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      10.875  -5.336   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -1.334 -11.550   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -5.335 -12.320   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -5.335 -13.860   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -6.668 -11.550   0.000  0.00  0.00           C+0
CONECT    1    2    6   32                                                  
CONECT    2    1    3   31                                                  
CONECT    3    2    4   16                                                  
CONECT    4    3    5   13                                                  
CONECT    5    4    6   10                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   11   12                                             
CONECT    9    8   10                                                       
CONECT   10    9    5                                                       
CONECT   11    8                                                            
CONECT   12    8                                                            
CONECT   13    4   14                                                       
CONECT   14   13   15   18                                                  
CONECT   15   14   16                                                       
CONECT   16   15    3   17                                                  
CONECT   17   16                                                            
CONECT   18   14   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   28                                                  
CONECT   21   20   22   25                                                  
CONECT   22   21   23                                                       
CONECT   23   22   18   24                                                  
CONECT   24   23                                                            
CONECT   25   21   26                                                       
CONECT   26   25   27   29   30                                             
CONECT   27   26   28                                                       
CONECT   28   27   20                                                       
CONECT   29   26                                                            
CONECT   30   26                                                            
CONECT   31    2                                                            
CONECT   32    1   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₃₂O₆

Average Mass

488.5800 Da

Monoisotopic Mass

488.21989 Da

IUPAC Name

(4R)-8-hydroxy-4-(7-hydroxy-2,2-dimethyl-2H-chromen-6-yl)-12,12-dimethyl-9-(3-methylbut-2-en-1-yl)-3,11-dioxatricyclo[8.4.0.0^{2,7}]tetradeca-1(10),2(7),8,13-tetraen-6-one

Traditional Name

(4R)-8-hydroxy-4-(7-hydroxy-2,2-dimethylchromen-6-yl)-12,12-dimethyl-9-(3-methylbut-2-en-1-yl)-3,11-dioxatricyclo[8.4.0.0^{2,7}]tetradeca-1(10),2(7),8,13-tetraen-6-one

CAS Registry Number

Not Available

SMILES

CC(C)=CCC1=C(O)C2=C(O[C@H](CC2=O)C2=CC3=C(OC(C)(C)C=C3)C=C2O)C2=C1OC(C)(C)C=C2

InChI Identifier

InChI=1S/C30H32O6/c1-16(2)7-8-18-26(33)25-22(32)15-24(34-28(25)19-10-12-30(5,6)36-27(18)19)20-13-17-9-11-29(3,4)35-23(17)14-21(20)31/h7,9-14,24,31,33H,8,15H2,1-6H3/t24-/m1/s1

InChI Key

AFNMVZWHERFZJC-XMMPIXPASA-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
Euchresta formosana	Plant	KNApSAcK
Euchresta japonica	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 6-prenylated flavanones. These are flavanones that features a C5-isoprenoid substituent at the 6-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

6-prenylated flavanones

Alternative Parents

Substituents

6-prenylated flavanone
Pyranoflavonoid
Hydroxyflavonoid
Flavanone
5-hydroxyflavonoid
Pyranochromene
2,2-dimethyl-1-benzopyran
Chromone
1-benzopyran
Benzopyran
Chromane
Aryl alkyl ketone
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Vinylogous acid
Ketone
Oxacycle
Organoheterocyclic compound
Ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen 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	5.62	ALOGPS
logP	6.67	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	8.58	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	85.22 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	142.34 m³·mol⁻¹	ChemAxon
Polarizability	54.56 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

162848105

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Euchrenone a12 (NP0055778)

MOL for NP0055778 (Euchrenone a12)

3D MOL for NP0055778 (Euchrenone a12)

3D SDF for NP0055778 (Euchrenone a12)

3D-SDF for NP0055778 (Euchrenone a12)

PDB for NP0055778 (Euchrenone a12)

3D PDB for NP0055778 (Euchrenone a12)

SMILES for NP0055778 (Euchrenone a12)

INCHI for NP0055778 (Euchrenone a12)

Structure for NP0055778 (Euchrenone a12)

3D Structure for NP0055778 (Euchrenone a12)