NP-MRD: Showing NP-Card for Cajanin (NP0047438)

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Record Information

Version

2.0

Created at

2022-03-17 20:40:12 UTC

Updated at

2022-03-17 20:40:13 UTC

NP-MRD ID

NP0047438

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cajanin

Description

Cajanin, also known as cajinin, belongs to the class of organic compounds known as 7-o-methylisoflavones. These are isoflavones with methoxy groups attached to the C7 atom of the isoflavone backbone. Thus, cajanin is considered to be a flavonoid lipid molecule. Cajanin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Cajanin has been detected, but not quantified in, a few different foods, such as coffee and coffee products, pigeon pea, and pulses. Cajanin is found in Butea monosperma, Cajanus scarabaeoides, Camptosema rubicundum, Canavalia ensiformis , Canavalia gladiata , Caragana jubata, Centrosema pascuorum, Centrosema pubescens, Clitoria falcata, Crotalaria lachnophora, Dalbergia parviflora , Dunbaria villosa, Eriophorum scheuchzeri, Eriosema glomeratum , Eriosema psoraleoides, Erythrina indica , Fagelia bituminosa, Ficus nervosa, Ficus nymphaeifolia , Galactia jussiaeana, Rhynchosia caribaea, Rhynchosia densiflora, Rhynchosia hirsuta, Rhynchosia phaseoloides, Rhynchosia pyramidalis and Spatholobus suberectus . This could make cajanin a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061306382D          

 22 24  0  0  0  0            999 V2000
    0.0000    0.0000    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
    4.2868    3.3000    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
    0.7145    2.0625    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
    3.5724    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
    0.7145    1.2375    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
    3.5724    2.0625    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
    1.4289    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
    2.1434    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
    6.4302    3.7125    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
    1.4289    3.3000    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
    0.0000    0.8250    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
  3  2  2  0  0  0  0
  8  2  1  0  0  0  0
  8  4  2  0  0  0  0
  9  5  2  0  0  0  0
  9  6  1  0  0  0  0
 10  3  1  0  0  0  0
 11  7  2  0  0  0  0
 11 10  1  0  0  0  0
 12  4  1  0  0  0  0
 12 10  2  0  0  0  0
 13  5  1  0  0  0  0
 14  6  2  0  0  0  0
 15 13  2  0  0  0  0
 15 14  1  0  0  0  0
 16 11  1  0  0  0  0
 16 15  1  0  0  0  0
 17  8  1  0  0  0  0
 18 12  1  0  0  0  0
 19 13  1  0  0  0  0
 20 16  2  0  0  0  0
 21  1  1  0  0  0  0
 21  9  1  0  0  0  0
 22  7  1  0  0  0  0
 22 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047438

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O)=C2C(=O)C(=COC2=C1)C1=C(O)C=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H12O6/c1-21-9-5-13(19)15-14(6-9)22-7-11(16(15)20)10-3-2-8(17)4-12(10)18/h2-7,17-19H,1H3

> <INCHI_KEY>
ALFNTRJPGFNJQV-UHFFFAOYSA-N

> <FORMULA>
C16H12O6

> <MOLECULAR_WEIGHT>
300.2629

> <EXACT_MASS>
300.063388116

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
29.527843152815638

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(2,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-4H-chromen-4-one

> <ALOGPS_LOGP>
3.01

> <JCHEM_LOGP>
2.9192011239999993

> <ALOGPS_LOGS>
-3.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.811340459872458

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.220480818016382

> <JCHEM_PKA_STRONGEST_BASIC>
-4.7379282267558676

> <JCHEM_POLAR_SURFACE_AREA>
96.22

> <JCHEM_REFRACTIVITY>
78.1461

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.44e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cajanin

> <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       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.336   6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.669   6.160   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001   2.310   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       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      12.003   6.930   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
CONECT    1   21                                                            
CONECT    2    3    8                                                       
CONECT    3    2   10                                                       
CONECT    4    8   12                                                       
CONECT    5    9   13                                                       
CONECT    6    9   14                                                       
CONECT    7   11   22                                                       
CONECT    8    2    4   17                                                  
CONECT    9    5    6   21                                                  
CONECT   10    3   11   12                                                  
CONECT   11    7   10   16                                                  
CONECT   12    4   10   18                                                  
CONECT   13    5   15   19                                                  
CONECT   14    6   15   22                                                  
CONECT   15   13   14   16                                                  
CONECT   16   11   15   20                                                  
CONECT   17    8                                                            
CONECT   18   12                                                            
CONECT   19   13                                                            
CONECT   20   16                                                            
CONECT   21    1    9                                                       
CONECT   22    7   14                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Value	Source
2',4',5-Trihydroxy-7-methoxyisoflavone	HMDB
Cajinin	HMDB

Chemical Formula

C₁₆H₁₂O₆

Average Mass

300.2629 Da

Monoisotopic Mass

300.06339 Da

IUPAC Name

3-(2,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-4H-chromen-4-one

Traditional Name

cajanin

CAS Registry Number

32884-36-9

SMILES

COC1=CC(O)=C2C(=O)C(=COC2=C1)C1=C(O)C=C(O)C=C1

InChI Identifier

InChI=1S/C16H12O6/c1-21-9-5-13(19)15-14(6-9)22-7-11(16(15)20)10-3-2-8(17)4-12(10)18/h2-7,17-19H,1H3

InChI Key

ALFNTRJPGFNJQV-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Butea monosperma	LOTUS Database	35616633
Cajanus cajan	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Cajanus scarabaeoides	Plant	KNApSAcK
Camptosema rubicundum	Plant	KNApSAcK
Canavalia ensiformis	Plant	KNApSAcK
Canavalia gladiata	Plant	KNApSAcK
Caragana jubata	Plant	KNApSAcK
Centrosema pascuorum	Plant	KNApSAcK
Centrosema pubescens	Plant	KNApSAcK
Clitoria falcata	Plant	KNApSAcK
Coffea arabica L.	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Coffea canephora	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Crotalaria lachnophora	LOTUS Database	35616633
Dalbergia parviflora	Plant	KNApSAcK
Dunbaria villosa	Plant	KNApSAcK
Eriophorum scheuchzeri	Plant	KNApSAcK
Eriosema glomeratum	Plant	KNApSAcK
Eriosema psoraleoides	Plant	KNApSAcK
Erythrina variegata	Plant	KNApSAcK
Fagelia bituminosa	-	KNApSAcK
Ficus nervosa	LOTUS Database	35616633
Ficus nymphaeifolia	Plant	KNApSAcK
Galactia jussiaeana	Plant	KNApSAcK
Rhynchosia caribaea	Plant	KNApSAcK
Rhynchosia densiflora	Plant	KNApSAcK
Rhynchosia hirsuta	Plant	KNApSAcK
Rhynchosia phaseoloides	Plant	KNApSAcK
Rhynchosia pyramidalis	Plant	KNApSAcK
Spatholobus suberectus	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 7-o-methylisoflavones. These are isoflavones with methoxy groups attached to the C7 atom of the isoflavone backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

O-methylated isoflavonoids

Direct Parent

7-O-methylisoflavones

Alternative Parents

Substituents

7-o-methylisoflavone
Isoflavone
Hydroxyisoflavonoid
Chromone
Benzopyran
1-benzopyran
Anisole
Resorcinol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyranone
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Pyran
Vinylogous acid
Heteroaromatic compound
Ether
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

methoxyisoflavone (CHEBI:70036 )
isoflavones (C10203 )
Isoflavonoids (C10203 )
Isoflavonoids (LMPK12050326 )

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	3.01	ALOGPS
logP	2.92	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	8.22	ChemAxon
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	96.22 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	78.15 m³·mol⁻¹	ChemAxon
Polarizability	29.53 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

HMDB0032696

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

5281706

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Cajanin (NP0047438)

MOL for NP0047438 (Cajanin)

3D MOL for NP0047438 (Cajanin)

3D SDF for NP0047438 (Cajanin)

3D-SDF for NP0047438 (Cajanin)

PDB for NP0047438 (Cajanin)

3D PDB for NP0047438 (Cajanin)

SMILES for NP0047438 (Cajanin)

INCHI for NP0047438 (Cajanin)

Structure for NP0047438 (Cajanin)

3D Structure for NP0047438 (Cajanin)