NP-MRD: Showing NP-Card for Cajaisoflavone (NP0047820)

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Record Information

Version

2.0

Created at

2022-03-17 20:46:30 UTC

Updated at

2022-03-17 20:46:30 UTC

NP-MRD ID

NP0047820

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cajaisoflavone

Description

Cajaisoflavone belongs to the class of organic compounds known as 6-prenylated isoflavanones. These are isoflavanones featuring a C5-isoprenoid unit at the 6-position. Thus, cajaisoflavone is considered to be a flavonoid lipid molecule. Cajaisoflavone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Cajaisoflavone has been detected, but not quantified in, pigeon pea and pulses. This could make cajaisoflavone a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061307302D          

 33 36  0  0  0  0            999 V2000
   -1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0993    0.6817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5690    1.6002    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
   -2.1434   -2.8875    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
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    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
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    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
    2.8579    0.8250    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
    1.4289    0.8250    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
    1.4289    0.0000    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
    2.1434   -0.4125    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
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0  0  0  0
  9  8  2  0  0  0  0
 13  1  1  0  0  0  0
 13  2  1  0  0  0  0
 13  6  2  0  0  0  0
 14  7  1  0  0  0  0
 15  8  1  0  0  0  0
 16 12  2  0  0  0  0
 17 10  2  0  0  0  0
 17 14  1  0  0  0  0
 18 11  2  0  0  0  0
 18 15  1  0  0  0  0
 19 10  1  0  0  0  0
 20 11  1  0  0  0  0
 21 16  1  0  0  0  0
 21 19  2  0  0  0  0
 22 20  2  0  0  0  0
 23 14  2  0  0  0  0
 23 21  1  0  0  0  0
 24 15  2  0  0  0  0
 24 22  1  0  0  0  0
 25 16  1  0  0  0  0
 25 22  1  0  0  0  0
 26  3  1  0  0  0  0
 26  4  1  0  0  0  0
 26  9  1  0  0  0  0
 27 17  1  0  0  0  0
 28 23  1  0  0  0  0
 29 24  1  0  0  0  0
 30 25  2  0  0  0  0
 31  5  1  0  0  0  0
 31 19  1  0  0  0  0
 32 12  1  0  0  0  0
 32 20  1  0  0  0  0
 33 18  1  0  0  0  0
 33 26  1  0  0  0  0
M  END


  Mrv0541 05061307302D          

 33 36  0  0  0  0            999 V2000
   -1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0993    0.6817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5690    1.6002    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
   -2.1434   -2.8875    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
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    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
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    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
    2.8579    0.8250    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
    1.4289    0.8250    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
    1.4289    0.0000    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
    2.1434   -0.4125    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
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0  0  0  0
  9  8  2  0  0  0  0
 13  1  1  0  0  0  0
 13  2  1  0  0  0  0
 13  6  2  0  0  0  0
 14  7  1  0  0  0  0
 15  8  1  0  0  0  0
 16 12  2  0  0  0  0
 17 10  2  0  0  0  0
 17 14  1  0  0  0  0
 18 11  2  0  0  0  0
 18 15  1  0  0  0  0
 19 10  1  0  0  0  0
 20 11  1  0  0  0  0
 21 16  1  0  0  0  0
 21 19  2  0  0  0  0
 22 20  2  0  0  0  0
 23 14  2  0  0  0  0
 23 21  1  0  0  0  0
 24 15  2  0  0  0  0
 24 22  1  0  0  0  0
 25 16  1  0  0  0  0
 25 22  1  0  0  0  0
 26  3  1  0  0  0  0
 26  4  1  0  0  0  0
 26  9  1  0  0  0  0
 27 17  1  0  0  0  0
 28 23  1  0  0  0  0
 29 24  1  0  0  0  0
 30 25  2  0  0  0  0
 31  5  1  0  0  0  0
 31 19  1  0  0  0  0
 32 12  1  0  0  0  0
 32 20  1  0  0  0  0
 33 18  1  0  0  0  0
 33 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047820

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(C(O)=C(CC=C(C)C)C(O)=C1)C1=COC2=C(C(O)=C3C=CC(C)(C)OC3=C2)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C26H26O7/c1-13(2)6-7-14-17(27)10-19(31-5)21(23(14)28)16-12-32-20-11-18-15(8-9-26(3,4)33-18)24(29)22(20)25(16)30/h6,8-12,27-29H,7H2,1-5H3

> <INCHI_KEY>
ZCGBVHBPKBFGFW-UHFFFAOYSA-N

> <FORMULA>
C26H26O7

> <MOLECULAR_WEIGHT>
450.4804

> <EXACT_MASS>
450.167853186

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
48.65538442229963

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-[2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-en-1-yl)phenyl]-5-hydroxy-8,8-dimethyl-4H,8H-pyrano[3,2-g]chromen-4-one

> <ALOGPS_LOGP>
4.64

> <JCHEM_LOGP>
5.548391525333333

> <ALOGPS_LOGS>
-4.99

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.709577768047863

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.119307413497102

> <JCHEM_PKA_STRONGEST_BASIC>
-4.5321792921632555

> <JCHEM_POLAR_SURFACE_AREA>
105.45

> <JCHEM_REFRACTIVITY>
126.78229999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.59e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cajaisoflavone

> <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  -7.700   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.519   1.273   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.529   2.987   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.001  -5.390   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       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.667   1.540   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  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       6.668   2.310   0.000  0.00  0.00           O+0
CONECT    1   13                                                            
CONECT    2   13                                                            
CONECT    3   26                                                            
CONECT    4   26                                                            
CONECT    5   31                                                            
CONECT    6    7   13                                                       
CONECT    7    6   14                                                       
CONECT    8    9   15                                                       
CONECT    9    8   26                                                       
CONECT   10   17   19                                                       
CONECT   11   18   20                                                       
CONECT   12   16   32                                                       
CONECT   13    1    2    6                                                  
CONECT   14    7   17   23                                                  
CONECT   15    8   18   24                                                  
CONECT   16   12   21   25                                                  
CONECT   17   10   14   27                                                  
CONECT   18   11   15   33                                                  
CONECT   19   10   21   31                                                  
CONECT   20   11   22   32                                                  
CONECT   21   16   19   23                                                  
CONECT   22   20   24   25                                                  
CONECT   23   14   21   28                                                  
CONECT   24   15   22   29                                                  
CONECT   25   16   22   30                                                  
CONECT   26    3    4    9   33                                             
CONECT   27   17                                                            
CONECT   28   23                                                            
CONECT   29   24                                                            
CONECT   30   25                                                            
CONECT   31    5   19                                                       
CONECT   32   12   20                                                       
CONECT   33   18   26                                                       
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Value	Source
7-[2,4-Dihydroxy-6-methoxy-3-(3-methyl-2-butenyl)phenyl]-5-hydroxy-2,2-dimethyl-2H,6H-benzo[1,2-b:5,4-b']dipyran-6-one, 9ci	HMDB

Chemical Formula

C₂₆H₂₆O₇

Average Mass

450.4804 Da

Monoisotopic Mass

450.16785 Da

IUPAC Name

3-[2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-en-1-yl)phenyl]-5-hydroxy-8,8-dimethyl-4H,8H-pyrano[3,2-g]chromen-4-one

Traditional Name

cajaisoflavone

CAS Registry Number

72578-99-5

SMILES

COC1=C(C(O)=C(CC=C(C)C)C(O)=C1)C1=COC2=C(C(O)=C3C=CC(C)(C)OC3=C2)C1=O

InChI Identifier

InChI=1S/C26H26O7/c1-13(2)6-7-14-17(27)10-19(31-5)21(23(14)28)16-12-32-20-11-18-15(8-9-26(3,4)33-18)24(29)22(20)25(16)30/h6,8-12,27-29H,7H2,1-5H3

InChI Key

ZCGBVHBPKBFGFW-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Cajanus cajan	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

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
Hydroxyisoflavonoid
Pyranochromene
2,2-dimethyl-1-benzopyran
Chromone
Benzopyran
Methoxyphenol
1-benzopyran
Methoxybenzene
Phenoxy compound
Anisole
Phenol ether
Resorcinol
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
Phenol
Pyranone
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Pyran
Vinylogous acid
Heteroaromatic compound
Oxacycle
Ether
Organoheterocyclic compound
Organooxygen compound
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Isoflavonoids (LMPK12050308 )

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	4.64	ALOGPS
logP	5.55	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	8.12	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	105.45 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	126.78 m³·mol⁻¹	ChemAxon
Polarizability	48.66 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0034020

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB012258

KNApSAcK ID

C00009448

Chemspider ID

24842827

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44257320

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Cajaisoflavone (NP0047820)

MOL for NP0047820 (Cajaisoflavone)

3D MOL for NP0047820 (Cajaisoflavone)

3D SDF for NP0047820 (Cajaisoflavone)

3D-SDF for NP0047820 (Cajaisoflavone)

PDB for NP0047820 (Cajaisoflavone)

3D PDB for NP0047820 (Cajaisoflavone)

SMILES for NP0047820 (Cajaisoflavone)

INCHI for NP0047820 (Cajaisoflavone)

Structure for NP0047820 (Cajaisoflavone)

3D Structure for NP0047820 (Cajaisoflavone)