NP-MRD: Showing NP-Card for 5,7,4'-Trihydroxy-5'-methoxy-6,8,3'-triprenylcoumaronochromone (NP0062741)

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Record Information

Version

2.0

Created at

2022-04-28 07:19:09 UTC

Updated at

2022-04-28 07:19:09 UTC

NP-MRD ID

NP0062741

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5,7,4'-Trihydroxy-5'-methoxy-6,8,3'-triprenylcoumaronochromone

Description

5,7,14-Trihydroxy-13-methoxy-4,6,15-tris(3-methylbut-2-en-1-yl)-2,17-dioxatetracyclo[8.7.0.0³,⁸.0¹¹,¹⁶]Heptadeca-1(10),3,5,7,11(16),12,14-heptaen-9-one belongs to the class of organic compounds known as 6-prenylated isoflavanones. These are isoflavanones featuring a C5-isoprenoid unit at the 6-position. 5,7,4'-Trihydroxy-5'-methoxy-6,8,3'-triprenylcoumaronochromone is found in Euchresta formosana. Based on a literature review very few articles have been published on 5,7,14-trihydroxy-13-methoxy-4,6,15-tris(3-methylbut-2-en-1-yl)-2,17-dioxatetracyclo[8.7.0.0³,⁸.0¹¹,¹⁶]Heptadeca-1(10),3,5,7,11(16),12,14-heptaen-9-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282209192D          

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M  END

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M  END


  Mrv1652304282209192D          

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  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
  5 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
  4 15  1  0  0  0  0
 15 16  2  0  0  0  0
 14 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 13 19  1  0  0  0  0
 18 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 17 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 21 26  1  0  0  0  0
 20 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
  3 32  1  0  0  0  0
  2 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
  1 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0062741

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C(CC=C(C)C)=C2OC3=C(C2=C1)C(=O)C1=C(O)C(CC=C(C)C)=C(O)C(CC=C(C)C)=C1O3

> <INCHI_IDENTIFIER>
InChI=1S/C31H34O7/c1-15(2)8-11-18-25(32)19(12-9-16(3)4)30-24(27(18)34)28(35)23-21-14-22(36-7)26(33)20(13-10-17(5)6)29(21)37-31(23)38-30/h8-10,14,32-34H,11-13H2,1-7H3

> <INCHI_KEY>
YXEFHDJSTWXKFZ-UHFFFAOYSA-N

> <FORMULA>
C31H34O7

> <MOLECULAR_WEIGHT>
518.606

> <EXACT_MASS>
518.230453435

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
57.65136062583256

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5,7,14-trihydroxy-13-methoxy-4,6,15-tris(3-methylbut-2-en-1-yl)-2,17-dioxatetracyclo[8.7.0.0^{3,8}.0^{11,16}]heptadeca-1(10),3,5,7,11,13,15-heptaen-9-one

> <ALOGPS_LOGP>
5.70

> <JCHEM_LOGP>
7.975388397000002

> <ALOGPS_LOGS>
-4.20

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.439868562065758

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.099198981452179

> <JCHEM_PKA_STRONGEST_BASIC>
-3.024703223159942

> <JCHEM_POLAR_SURFACE_AREA>
109.36000000000001

> <JCHEM_REFRACTIVITY>
150.04500000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.24e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,7,14-trihydroxy-13-methoxy-4,6,15-tris(3-methylbut-2-en-1-yl)-2,17-dioxatetracyclo[8.7.0.0^{3,8}.0^{11,16}]heptadeca-1(10),3,5,7,11,13,15-heptaen-9-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       9.930   0.278   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.627   1.788   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.167   2.280   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.012   1.262   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.315  -0.248   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.774  -0.740   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.078  -2.250   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.537  -2.742   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.841  -4.251   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.685  -5.269   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.300  -4.743   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       6.159  -1.266   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.700  -0.774   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.397   0.736   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.552   1.754   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.249   3.264   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.867   0.914   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.225  -0.486   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.358  -1.529   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       0.692  -0.630   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.200   0.626   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.442   2.026   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.976   2.170   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -0.449   3.282   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       0.193   4.681   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -1.733   0.482   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       0.050  -2.030   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.483  -2.174   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -2.125  -3.574   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -1.234  -4.829   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -3.658  -3.718   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       7.864   3.790   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      10.782   2.806   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      10.479   4.315   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      11.635   5.333   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      11.331   6.843   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      13.094   4.841   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      11.390  -0.214   0.000  0.00  0.00           O+0
CONECT    1    2    6   38                                                  
CONECT    2    1    3   33                                                  
CONECT    3    2    4   32                                                  
CONECT    4    3    5   15                                                  
CONECT    5    4    6   12                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    5   13                                                       
CONECT   13   12   14   19                                                  
CONECT   14   13   15   17                                                  
CONECT   15   14    4   16                                                  
CONECT   16   15                                                            
CONECT   17   14   18   23                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18   13                                                       
CONECT   20   18   21   27                                                  
CONECT   21   20   22   26                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22   17                                                       
CONECT   24   22   25                                                       
CONECT   25   24                                                            
CONECT   26   21                                                            
CONECT   27   20   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32    3                                                            
CONECT   33    2   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35                                                            
CONECT   38    1                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₁H₃₄O₇

Average Mass

518.6060 Da

Monoisotopic Mass

518.23045 Da

IUPAC Name

5,7,14-trihydroxy-13-methoxy-4,6,15-tris(3-methylbut-2-en-1-yl)-2,17-dioxatetracyclo[8.7.0.0^{3,8}.0^{11,16}]heptadeca-1(10),3,5,7,11,13,15-heptaen-9-one

Traditional Name

5,7,14-trihydroxy-13-methoxy-4,6,15-tris(3-methylbut-2-en-1-yl)-2,17-dioxatetracyclo[8.7.0.0^{3,8}.0^{11,16}]heptadeca-1(10),3,5,7,11,13,15-heptaen-9-one

CAS Registry Number

Not Available

SMILES

COC1=C(O)C(CC=C(C)C)=C2OC3=C(C2=C1)C(=O)C1=C(O)C(CC=C(C)C)=C(O)C(CC=C(C)C)=C1O3

InChI Identifier

InChI=1S/C31H34O7/c1-15(2)8-11-18-25(32)19(12-9-16(3)4)30-24(27(18)34)28(35)23-21-14-22(36-7)26(33)20(13-10-17(5)6)29(21)37-31(23)38-30/h8-10,14,32-34H,11-13H2,1-7H3

InChI Key

YXEFHDJSTWXKFZ-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
Euchresta formosana	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 6-prenylated isoflavanones. These are isoflavanones featuring a C5-isoprenoid unit at the 6-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Isoflavans

Direct Parent

6-prenylated isoflavanones

Alternative Parents

Substituents

6-prenylated isoflavanone
Isoflavone
Coumaronochromene
Chromone
Coumarin
Benzopyran
1-benzopyran
Benzofuran
Furopyran
Anisole
Alkyl aryl ether
Pyranone
Pyran
Benzenoid
Vinylogous acid
Furan
Heteroaromatic compound
Polyol
Organoheterocyclic compound
Ether
Oxacycle
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
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	5.7	ALOGPS
logP	7.98	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	7.1	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	109.36 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	150.04 m³·mol⁻¹	ChemAxon
Polarizability	57.65 Å³	ChemAxon
Number of Rings	4	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

C00019412

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

163067573

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 5,7,4'-Trihydroxy-5'-methoxy-6,8,3'-triprenylcoumaronochromone (NP0062741)

MOL for NP0062741 (5,7,4'-Trihydroxy-5'-methoxy-6,8,3'-triprenylcoumaronochromone)

3D MOL for NP0062741 (5,7,4'-Trihydroxy-5'-methoxy-6,8,3'-triprenylcoumaronochromone)

3D SDF for NP0062741 (5,7,4'-Trihydroxy-5'-methoxy-6,8,3'-triprenylcoumaronochromone)

3D-SDF for NP0062741 (5,7,4'-Trihydroxy-5'-methoxy-6,8,3'-triprenylcoumaronochromone)

PDB for NP0062741 (5,7,4'-Trihydroxy-5'-methoxy-6,8,3'-triprenylcoumaronochromone)

3D PDB for NP0062741 (5,7,4'-Trihydroxy-5'-methoxy-6,8,3'-triprenylcoumaronochromone)

SMILES for NP0062741 (5,7,4'-Trihydroxy-5'-methoxy-6,8,3'-triprenylcoumaronochromone)

INCHI for NP0062741 (5,7,4'-Trihydroxy-5'-methoxy-6,8,3'-triprenylcoumaronochromone)

Structure for NP0062741 (5,7,4'-Trihydroxy-5'-methoxy-6,8,3'-triprenylcoumaronochromone)

3D Structure for NP0062741 (5,7,4'-Trihydroxy-5'-methoxy-6,8,3'-triprenylcoumaronochromone)