NP-MRD: Showing NP-Card for 5-Deoxykievitone (NP0047901)

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Record Information

Version

2.0

Created at

2022-03-17 20:47:48 UTC

Updated at

2022-03-17 20:47:48 UTC

NP-MRD ID

NP0047901

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-Deoxykievitone

Description

5-Deoxykievitone belongs to the class of organic compounds known as 8-prenylated isoflavanones. These are isoflavanones featuring a C5-isoprenoid unit at the 8-position. Thus, 5-deoxykievitone is considered to be a flavonoid lipid molecule. 5-Deoxykievitone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, 5-Deoxykievitone has been detected, but not quantified in, several different foods, such as mung beans, lima beans, green beans, pulses, and yellow wax beans. This could make 5-deoxykievitone a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061307392D          

 25 27  0  0  0  0            999 V2000
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
  8  7  2  0  0  0  0
 11  1  1  0  0  0  0
 11  2  1  0  0  0  0
 11  3  2  0  0  0  0
 12  4  1  0  0  0  0
 12  9  2  0  0  0  0
 13  6  1  0  0  0  0
 14  5  1  0  0  0  0
 15  7  1  0  0  0  0
 16 10  1  0  0  0  0
 16 13  1  0  0  0  0
 17  8  1  0  0  0  0
 17 14  2  0  0  0  0
 18  9  1  0  0  0  0
 18 13  2  0  0  0  0
 19 15  1  0  0  0  0
 19 16  1  0  0  0  0
 20 14  1  0  0  0  0
 20 15  2  0  0  0  0
 21 12  1  0  0  0  0
 22 17  1  0  0  0  0
 23 18  1  0  0  0  0
 24 19  2  0  0  0  0
 25 10  1  0  0  0  0
 25 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047901

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC1=C(O)C=CC2=C1OCC(C2=O)C1=C(O)C=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H20O5/c1-11(2)3-5-14-17(22)8-7-15-19(24)16(10-25-20(14)15)13-6-4-12(21)9-18(13)23/h3-4,6-9,16,21-23H,5,10H2,1-2H3

> <INCHI_KEY>
JIJYZALGIIQXKE-UHFFFAOYSA-N

> <FORMULA>
C20H20O5

> <MOLECULAR_WEIGHT>
340.3698

> <EXACT_MASS>
340.13107375

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
35.82580427776575

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(2,4-dihydroxyphenyl)-7-hydroxy-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2H-1-benzopyran-4-one

> <ALOGPS_LOGP>
3.29

> <JCHEM_LOGP>
3.8062251133333334

> <ALOGPS_LOGS>
-4.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.094738153743638

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.580432499107878

> <JCHEM_PKA_STRONGEST_BASIC>
-4.916512593990683

> <JCHEM_POLAR_SURFACE_AREA>
86.99

> <JCHEM_REFRACTIVITY>
95.91929999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.57e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(+-)-5-deoxykievitone

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -3.080   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       9.336   6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.669   6.160   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      12.003   6.930   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
CONECT    1   11                                                            
CONECT    2   11                                                            
CONECT    3    5   11                                                       
CONECT    4    6   12                                                       
CONECT    5    3   14                                                       
CONECT    6    4   13                                                       
CONECT    7    8   15                                                       
CONECT    8    7   17                                                       
CONECT    9   12   18                                                       
CONECT   10   16   25                                                       
CONECT   11    1    2    3                                                  
CONECT   12    4    9   21                                                  
CONECT   13    6   16   18                                                  
CONECT   14    5   17   20                                                  
CONECT   15    7   19   20                                                  
CONECT   16   10   13   19                                                  
CONECT   17    8   14   22                                                  
CONECT   18    9   13   23                                                  
CONECT   19   15   16   24                                                  
CONECT   20   14   15   25                                                  
CONECT   21   12                                                            
CONECT   22   17                                                            
CONECT   23   18                                                            
CONECT   24   19                                                            
CONECT   25   10   20                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

View in JSmol

Synonyms

Value	Source
(+-)-5-Deoxykievitone	Kegg
2',4',7-Trihydroxy-8-prenylisoflavanone	HMDB

Chemical Formula

C₂₀H₂₀O₅

Average Mass

340.3698 Da

Monoisotopic Mass

340.13107 Da

IUPAC Name

3-(2,4-dihydroxyphenyl)-7-hydroxy-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

(+-)-5-deoxykievitone

CAS Registry Number

74161-24-3

SMILES

CC(C)=CCC1=C(O)C=CC2=C1OCC(C2=O)C1=C(O)C=C(O)C=C1

InChI Identifier

InChI=1S/C20H20O5/c1-11(2)3-5-14-17(22)8-7-15-19(24)16(10-25-20(14)15)13-6-4-12(21)9-18(13)23/h3-4,6-9,16,21-23H,5,10H2,1-2H3

InChI Key

JIJYZALGIIQXKE-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Phaseolus lunatus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Phaseolus vulgaris	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Vigna mungo	FooDB	KNAPSACK
Vigna radiata	FooDB	KNAPSACK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 8-prenylated isoflavanones. These are isoflavanones featuring a C5-isoprenoid unit at the 8-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Isoflavans

Direct Parent

8-prenylated isoflavanones

Alternative Parents

Substituents

8-prenylated isoflavanone
Isoflavanol
Hydroxyisoflavonoid
Chromone
1-benzopyran
Benzopyran
Chromane
Aryl alkyl ketone
Aryl ketone
Resorcinol
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Phenol
Benzenoid
Monocyclic benzene moiety
Ketone
Oxacycle
Organoheterocyclic compound
Ether
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

isoflavanones (CHEBI:63 )
isoflavanones (C10418 )
Isoflavonoids (C10418 )
Isoflavonoids (LMPK12050458 )

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	3.29	ALOGPS
logP	3.81	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	7.58	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	95.92 m³·mol⁻¹	ChemAxon
Polarizability	35.83 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0034214

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

442770

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 5-Deoxykievitone (NP0047901)

MOL for NP0047901 (5-Deoxykievitone)

3D MOL for NP0047901 (5-Deoxykievitone)

3D SDF for NP0047901 (5-Deoxykievitone)

3D-SDF for NP0047901 (5-Deoxykievitone)

PDB for NP0047901 (5-Deoxykievitone)

3D PDB for NP0047901 (5-Deoxykievitone)

SMILES for NP0047901 (5-Deoxykievitone)

INCHI for NP0047901 (5-Deoxykievitone)

Structure for NP0047901 (5-Deoxykievitone)

3D Structure for NP0047901 (5-Deoxykievitone)