NP-MRD: Showing NP-Card for 5'-Prenylaliarin (NP0138276)

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Record Information

Version

1.0

Created at

2022-05-31 17:51:44 UTC

Updated at

2022-05-31 17:51:44 UTC

NP-MRD ID

NP0138276

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5'-Prenylaliarin

Description

5,7-Dihydroxy-2-[4-hydroxy-3-(4-hydroxy-3-methylbutyl)-5-(3-methylbut-2-en-1-yl)phenyl]-3,6-dimethoxy-4H-chromen-4-one belongs to the class of organic compounds known as 3'-prenylated flavones. These are flavones that features a C5-isoprenoid substituent at the 3'-position. 5'-Prenylaliarin is found in Dodonaea viscosa. 5,7-Dihydroxy-2-[4-hydroxy-3-(4-hydroxy-3-methylbutyl)-5-(3-methylbut-2-en-1-yl)phenyl]-3,6-dimethoxy-4H-chromen-4-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004201501012D          

 35 37  0  0  0  0            999 V2000
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
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  3 16  1  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1533004201501012D          

 35 37  0  0  0  0            999 V2000
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0138276

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=C2OC(C3=CC(CCC(C)CO)=C(O)C(CC=C(C)C)=C3)=C(OC)C(=O)C2=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C27H32O8/c1-14(2)6-8-16-10-18(11-17(22(16)30)9-7-15(3)13-28)25-27(34-5)24(32)21-20(35-25)12-19(29)26(33-4)23(21)31/h6,10-12,15,28-31H,7-9,13H2,1-5H3

> <INCHI_KEY>
HZKQZIBQTUUPIQ-UHFFFAOYSA-N

> <FORMULA>
C27H32O8

> <MOLECULAR_WEIGHT>
484.545

> <EXACT_MASS>
484.20971799

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
52.77827714881232

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5,7-dihydroxy-2-[4-hydroxy-3-(4-hydroxy-3-methylbutyl)-5-(3-methylbut-2-en-1-yl)phenyl]-3,6-dimethoxy-4H-chromen-4-one

> <ALOGPS_LOGP>
4.41

> <JCHEM_LOGP>
4.9190095026666665

> <ALOGPS_LOGS>
-5.02

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.262614509884648

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.903578753742574

> <JCHEM_PKA_STRONGEST_BASIC>
-2.5889011394008303

> <JCHEM_POLAR_SURFACE_AREA>
125.68

> <JCHEM_REFRACTIVITY>
135.583

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.66e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,7-dihydroxy-2-[4-hydroxy-3-(4-hydroxy-3-methylbutyl)-5-(3-methylbut-2-en-1-yl)phenyl]-3,6-dimethoxychromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-15         0                                  
HETATM    1  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.000  -6.160   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -8.470   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -2.667  -9.240   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -4.001  -8.470   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -6.668  -8.470   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -8.002  -9.240   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -8.002  -6.160   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -5.335  -6.160   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.667  -6.160   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334  -8.470   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.001  -8.470   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.668  -8.470   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       9.336  -8.470   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       2.667 -10.780   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       4.001 -11.550   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.334 -13.090   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.000 -13.860   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.000 -15.400   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -1.334 -16.170   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       1.334 -16.170   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       0.000 -10.780   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   16                                                  
CONECT    4    3    5   18                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   15                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13   10   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    6   16                                                  
CONECT   16   15    3   17                                                  
CONECT   17   16                                                            
CONECT   18    4   19   35                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   27                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25                                                            
CONECT   27   20   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   35                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35   29   18                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₂O₈

Average Mass

484.5450 Da

Monoisotopic Mass

484.20972 Da

IUPAC Name

5,7-dihydroxy-2-[4-hydroxy-3-(4-hydroxy-3-methylbutyl)-5-(3-methylbut-2-en-1-yl)phenyl]-3,6-dimethoxy-4H-chromen-4-one

Traditional Name

5,7-dihydroxy-2-[4-hydroxy-3-(4-hydroxy-3-methylbutyl)-5-(3-methylbut-2-en-1-yl)phenyl]-3,6-dimethoxychromen-4-one

CAS Registry Number

1246926-09-9

SMILES

COC1=C(O)C=C2OC(C3=CC(CCC(C)CO)=C(O)C(CC=C(C)C)=C3)=C(OC)C(=O)C2=C1O

InChI Identifier

InChI=1S/C27H32O8/c1-14(2)6-8-16-10-18(11-17(22(16)30)9-7-15(3)13-28)25-27(34-5)24(32)21-20(35-25)12-19(29)26(33-4)23(21)31/h6,10-12,15,28-31H,7-9,13H2,1-5H3

InChI Key

HZKQZIBQTUUPIQ-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
Dodonaea viscosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3'-prenylated flavones. These are flavones that features a C5-isoprenoid substituent at the 3'-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavones

Direct Parent

3'-prenylated flavones

Alternative Parents

Substituents

3'-prenylated flavone
3-methoxyflavonoid-skeleton
6-methoxyflavonoid-skeleton
4'-hydroxyflavonoid
5-hydroxyflavonoid
Hydroxyflavonoid
7-hydroxyflavonoid
3-methoxychromone
Chromone
Benzopyran
1-benzopyran
Anisole
Phenol ether
Pyranone
Alkyl aryl ether
Phenol
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Pyran
Monocyclic benzene moiety
Benzenoid
Heteroaromatic compound
Vinylogous acid
Oxacycle
Organoheterocyclic compound
Ether
Primary alcohol
Alcohol
Organic oxide
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
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	4.41	ALOGPS
logP	4.92	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	6.9	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	125.68 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	135.58 m³·mol⁻¹	ChemAxon
Polarizability	52.78 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

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

46218174

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 5'-Prenylaliarin (NP0138276)

MOL for NP0138276 (5'-Prenylaliarin)

3D MOL for NP0138276 (5'-Prenylaliarin)

3D SDF for NP0138276 (5'-Prenylaliarin)

3D-SDF for NP0138276 (5'-Prenylaliarin)

PDB for NP0138276 (5'-Prenylaliarin)

3D PDB for NP0138276 (5'-Prenylaliarin)

SMILES for NP0138276 (5'-Prenylaliarin)

INCHI for NP0138276 (5'-Prenylaliarin)

Structure for NP0138276 (5'-Prenylaliarin)

3D Structure for NP0138276 (5'-Prenylaliarin)