NP-MRD: Showing NP-Card for Phaseol (NP0048940)

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Record Information

Version

2.0

Created at

2022-03-17 21:04:35 UTC

Updated at

2022-03-17 21:04:35 UTC

NP-MRD ID

NP0048940

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Phaseol

Description

Phaseol belongs to the class of organic compounds known as coumestans. These are polycyclic aromatic compounds containing a coumestan moiety, which consists of a benzoxole fused to a chromen-2-one to form 1-Benzoxolo[3,2-c]chromen-6-one. They are oxidation products of pterocarpan. Thus, phaseol is considered to be a flavonoid lipid molecule. Phaseol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Phaseol has been detected, but not quantified in, pulses and soy beans. Phaseol is found in Cadophora gregata, Glycyrrhiza glabra , Glycyrrhiza sp., Phaseolus aureus and Vigna radiata. This could make phaseol a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061310052D          

 25 28  0  0  0  0            999 V2000
    5.3205    5.7457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5968    5.1031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4021    4.3190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4867    3.2441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5785    4.2719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2466    3.6222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4655    2.0613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2891    2.1084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1682    1.9741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7731    5.0559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5259    2.4201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2075    3.5350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9407    3.1762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0128    2.7510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6601    2.8453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9014    2.3522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7365    3.3936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3838    3.4879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1892    2.7039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1075    4.1305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2591    2.0420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4838    2.8924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6548    4.8202    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6731    2.0602    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9312    4.1776    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
 10  1  1  0  0  0  0
 10  2  1  0  0  0  0
 10  3  2  0  0  0  0
 11  4  1  0  0  0  0
 11  9  2  0  0  0  0
 12  5  1  0  0  0  0
 13  6  1  0  0  0  0
 14  7  1  0  0  0  0
 15  8  1  0  0  0  0
 15 12  2  0  0  0  0
 16  9  1  0  0  0  0
 16 13  2  0  0  0  0
 17 13  1  0  0  0  0
 18 12  1  0  0  0  0
 18 14  2  0  0  0  0
 19 14  1  0  0  0  0
 19 17  2  0  0  0  0
 20 17  1  0  0  0  0
 21 11  1  0  0  0  0
 22 15  1  0  0  0  0
 23 20  2  0  0  0  0
 24 16  1  0  0  0  0
 24 19  1  0  0  0  0
 25 18  1  0  0  0  0
 25 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048940

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC1=C(O)C=CC2=C1OC(=O)C1=C2OC2=C1C=CC(O)=C2

> <INCHI_IDENTIFIER>
InChI=1S/C20H16O5/c1-10(2)3-5-12-15(22)8-7-14-18(12)25-20(23)17-13-6-4-11(21)9-16(13)24-19(14)17/h3-4,6-9,21-22H,5H2,1-2H3

> <INCHI_KEY>
FRXPSBUCIWPZMH-UHFFFAOYSA-N

> <FORMULA>
C20H16O5

> <MOLECULAR_WEIGHT>
336.338

> <EXACT_MASS>
336.099773622

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
35.9896798274789

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,14-dihydroxy-6-(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-9-one

> <ALOGPS_LOGP>
4.59

> <JCHEM_LOGP>
4.125888321666666

> <ALOGPS_LOGS>
-3.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.109957681263777

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.9225789415810315

> <JCHEM_PKA_STRONGEST_BASIC>
-4.325585151569688

> <JCHEM_POLAR_SURFACE_AREA>
79.9

> <JCHEM_REFRACTIVITY>
93.86229999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.81e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
phaseol

> <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       9.932  10.725   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.314   9.526   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.084   8.062   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.909   6.056   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.547   7.974   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.460   6.761   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.469   3.848   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.006   3.936   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.314   3.685   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.776   9.438   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.982   4.518   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.854   6.599   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.756   5.929   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.624   5.135   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.699   5.311   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.683   4.391   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.241   6.335   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.316   6.511   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.087   5.047   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.934   7.710   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -2.350   3.812   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      10.236   5.399   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       3.089   8.998   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       3.123   3.846   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       5.472   7.798   0.000  0.00  0.00           O+0
CONECT    1   10                                                            
CONECT    2   10                                                            
CONECT    3    5   10                                                       
CONECT    4    6   11                                                       
CONECT    5    3   12                                                       
CONECT    6    4   13                                                       
CONECT    7    8   14                                                       
CONECT    8    7   15                                                       
CONECT    9   11   16                                                       
CONECT   10    1    2    3                                                  
CONECT   11    4    9   21                                                  
CONECT   12    5   15   18                                                  
CONECT   13    6   16   17                                                  
CONECT   14    7   18   19                                                  
CONECT   15    8   12   22                                                  
CONECT   16    9   13   24                                                  
CONECT   17   13   19   20                                                  
CONECT   18   12   14   25                                                  
CONECT   19   14   17   24                                                  
CONECT   20   17   23   25                                                  
CONECT   21   11                                                            
CONECT   22   15                                                            
CONECT   23   20                                                            
CONECT   24   16   19                                                       
CONECT   25   18   20                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

View in JSmol

Synonyms

Value	Source
3,9-Dihydroxy-4-(3-methyl-2-butenyl)-6H-benzofuro[3,2-c][1]benzopyran-6-one, 9ci	HMDB
3,9-Dihydroxy-4-prenylcoumestan	HMDB
Phaseollidin hydrate	HMDB

Chemical Formula

C₂₀H₁₆O₅

Average Mass

336.3380 Da

Monoisotopic Mass

336.09977 Da

IUPAC Name

5,14-dihydroxy-6-(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-9-one

Traditional Name

phaseol

CAS Registry Number

88478-02-8

SMILES

CC(C)=CCC1=C(O)C=CC2=C1OC(=O)C1=C2OC2=C1C=CC(O)=C2

InChI Identifier

InChI=1S/C20H16O5/c1-10(2)3-5-12-15(22)8-7-14-18(12)25-20(23)17-13-6-4-11(21)9-16(13)24-19(14)17/h3-4,6-9,21-22H,5H2,1-2H3

InChI Key

FRXPSBUCIWPZMH-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Cadophora gregata	LOTUS Database	35616633
Glycine max	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Glycyrrhiza glabra	Plant	KNApSAcK
Glycyrrhiza sp.	Plant	KNApSAcK
Phaseolus aureus	Plant	KNApSAcK
Vigna radiata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumestans. These are polycyclic aromatic compounds containing a coumestan moiety, which consists of a benzoxole fused to a chromen-2-one to form 1-Benzoxolo[3,2-c]chromen-6-one. They are oxidation products of pterocarpan.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Coumestans

Direct Parent

Coumestans

Alternative Parents

Substituents

Coumestan
Angular furanocoumarin
Furanocoumarin
Coumarin
Benzopyran
1-benzopyran
Benzofuran
Furopyran
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Pyran
Benzenoid
Furan
Heteroaromatic compound
Lactone
Organoheterocyclic compound
Oxacycle
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Coumestan flavonoids (LMPK12090010 )

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	4.59	ALOGPS
logP	4.13	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	6.92	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	79.9 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	93.86 m³·mol⁻¹	ChemAxon
Polarizability	35.99 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon