NP-MRD: Showing NP-Card for Trifoliol (NP0047868)

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Record Information

Version

2.0

Created at

2022-03-17 20:47:17 UTC

Updated at

2022-03-17 20:47:17 UTC

NP-MRD ID

NP0047868

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Trifoliol

Description

Trifoliol 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, trifoliol is considered to be a flavonoid lipid molecule. Trifoliol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Trifoliol has been detected, but not quantified in, several different foods, such as alfalfa, green vegetables, herbs and spices, pulses, and tea. Trifoliol is found in Ascochyta imperfecta and Trifolium repens . This could make trifoliol a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061307362D          

 22 25  0  0  0  0            999 V2000
   -1.9532    2.4880    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
    3.4655    2.0613    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
   -0.4867    3.2441    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
    4.6601    2.8453    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
    3.0128    2.7510    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
    3.3838    3.4879    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
    0.9407    3.1762    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
    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
    5.4838    2.8924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2858    4.4463    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
   -1.2591    2.0420    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
  3  2  2  0  0  0  0
  7  2  1  0  0  0  0
  7  4  2  0  0  0  0
  8  5  2  0  0  0  0
  8  6  1  0  0  0  0
  9  3  1  0  0  0  0
 10  5  1  0  0  0  0
 11  4  1  0  0  0  0
 11  9  2  0  0  0  0
 12  6  2  0  0  0  0
 13 10  2  0  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15  9  1  0  0  0  0
 15 14  2  0  0  0  0
 16 14  1  0  0  0  0
 17  7  1  0  0  0  0
 18 10  1  0  0  0  0
 19 16  2  0  0  0  0
 20  1  1  0  0  0  0
 20  8  1  0  0  0  0
 21 12  1  0  0  0  0
 21 15  1  0  0  0  0
 22 11  1  0  0  0  0
 22 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047868

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O)=C2C(OC3=C2C(=O)OC2=C3C=CC(O)=C2)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H10O6/c1-20-8-5-10(18)13-12(6-8)21-15-9-3-2-7(17)4-11(9)22-16(19)14(13)15/h2-6,17-18H,1H3

> <INCHI_KEY>
YFVNQUXNYCREJW-UHFFFAOYSA-N

> <FORMULA>
C16H10O6

> <MOLECULAR_WEIGHT>
298.247

> <EXACT_MASS>
298.047738052

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
29.3887073250744

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,12-dihydroxy-14-methoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11,13,15-heptaen-9-one

> <ALOGPS_LOGP>
2.50

> <JCHEM_LOGP>
2.239650056666666

> <ALOGPS_LOGS>
-2.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
7.976468872581998

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.076151283140327

> <JCHEM_PKA_STRONGEST_BASIC>
-3.8894800369498364

> <JCHEM_POLAR_SURFACE_AREA>
89.13000000000001

> <JCHEM_REFRACTIVITY>
76.0827

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.26e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
trifoliol

> <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      -3.646   4.644   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.006   3.936   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.469   3.848   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.854   6.599   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.909   6.056   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.314   3.685   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.699   5.311   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.982   4.518   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.624   5.135   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.460   6.761   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.316   6.511   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.683   4.391   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       3.241   6.335   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.087   5.047   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.934   7.710   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      10.236   5.399   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       0.533   8.300   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       3.089   8.998   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -2.350   3.812   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       3.123   3.846   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       5.472   7.798   0.000  0.00  0.00           O+0
CONECT    1   20                                                            
CONECT    2    3    7                                                       
CONECT    3    2    9                                                       
CONECT    4    7   11                                                       
CONECT    5    8   10                                                       
CONECT    6    8   12                                                       
CONECT    7    2    4   17                                                  
CONECT    8    5    6   20                                                  
CONECT    9    3   11   15                                                  
CONECT   10    5   13   18                                                  
CONECT   11    4    9   22                                                  
CONECT   12    6   13   21                                                  
CONECT   13   10   12   14                                                  
CONECT   14   13   15   16                                                  
CONECT   15    9   14   21                                                  
CONECT   16   14   19   22                                                  
CONECT   17    7                                                            
CONECT   18   10                                                            
CONECT   19   16                                                            
CONECT   20    1    8                                                       
CONECT   21   12   15                                                       
CONECT   22   11   16                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

View in JSmol

Synonyms

Value	Source
3,7-Dihydroxy-9-methoxycoumestan	HMDB
7,10-Dihydroxy-12-methoxycoumestan	HMDB

Chemical Formula

C₁₆H₁₀O₆

Average Mass

298.2470 Da

Monoisotopic Mass

298.04774 Da

IUPAC Name

5,12-dihydroxy-14-methoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11,13,15-heptaen-9-one

Traditional Name

trifoliol

CAS Registry Number

1857-26-7

SMILES

COC1=CC(O)=C2C(OC3=C2C(=O)OC2=C3C=CC(O)=C2)=C1

InChI Identifier

InChI=1S/C16H10O6/c1-20-8-5-10(18)13-12(6-8)21-15-9-3-2-7(17)4-11(9)22-16(19)14(13)15/h2-6,17-18H,1H3

InChI Key

YFVNQUXNYCREJW-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Ascochyta imperfecta	Fungi	KNApSAcK
Medicago sativa	FooDB	KNAPSACK
Trifolium repens	Plant	KNApSAcK

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
Anisole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
Benzenoid
Pyran
Furan
Heteroaromatic compound
Lactone
Oxacycle
Organoheterocyclic compound
Ether
Organic oxygen compound
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Coumestan flavonoids (LMPK12090030 )

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	2.5	ALOGPS
logP	2.24	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	7.08	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	89.13 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	76.08 m³·mol⁻¹	ChemAxon
Polarizability	29.39 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

External Links

HMDB ID

HMDB0034139

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB012414

KNApSAcK ID

C00009762

Chemspider ID

4589482

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5487671

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Trifoliol (NP0047868)

MOL for NP0047868 (Trifoliol)

3D MOL for NP0047868 (Trifoliol)

3D SDF for NP0047868 (Trifoliol)

3D-SDF for NP0047868 (Trifoliol)

PDB for NP0047868 (Trifoliol)

3D PDB for NP0047868 (Trifoliol)

SMILES for NP0047868 (Trifoliol)

INCHI for NP0047868 (Trifoliol)

Structure for NP0047868 (Trifoliol)

3D Structure for NP0047868 (Trifoliol)