NP-MRD: Showing NP-Card for Isothymusin (NP0048855)

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Record Information

Version

2.0

Created at

2022-03-17 21:03:15 UTC

Updated at

2022-03-17 21:03:15 UTC

NP-MRD ID

NP0048855

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Isothymusin

Description

Isothymusin belongs to the class of organic compounds known as 7-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone. Thus, isothymusin is considered to be a flavonoid lipid molecule. Isothymusin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Isothymusin has been detected, but not quantified in, sour cherries. Isothymusin is found in Agastache barberi, Becium grandiflorum, Isodon eriocalyx, Nepeta spp., Ocimum americanum cv.Sacred , Ocimum gratissimum , Ocimum selloi Benth. , Ocimum tenuiflorum and Ocimum tenuiflorum L. . This could make isothymusin a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI

  Mrv1652310061700452D          

 24 26  0  0  0  0            999 V2000
    2.8579    0.0000    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
   -2.1434    2.0625    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
   -2.8579    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
   -1.4289    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
   -3.5724    2.0625    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    0.8250    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
    0.7145   -0.4125    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
    0.0000    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
   -4.2868    2.4750    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
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    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
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
  8  3  2  0  0  0  0
  8  4  1  0  0  0  0
  9  5  2  0  0  0  0
  9  6  1  0  0  0  0
 10  7  1  0  0  0  0
 11  7  2  0  0  0  0
 11  8  1  0  0  0  0
 12 10  1  0  0  0  0
 13 12  2  0  0  0  0
 15 12  1  0  0  0  0
 15 14  2  0  0  0  0
 16 13  1  0  0  0  0
 17 14  1  0  0  0  0
 17 16  2  0  0  0  0
 18  9  1  0  0  0  0
 19 10  2  0  0  0  0
 20 13  1  0  0  0  0
 21 14  1  0  0  0  0
 22  1  1  0  0  0  0
 22 16  1  0  0  0  0
 23  2  1  0  0  0  0
 23 17  1  0  0  0  0
 24 11  1  0  0  0  0
 24 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048855

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(OC)C(O)=C2C(=O)C=C(OC2=C1O)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H14O7/c1-22-16-13(20)12-10(19)7-11(8-3-5-9(18)6-4-8)24-15(12)14(21)17(16)23-2/h3-7,18,20-21H,1-2H3

> <INCHI_KEY>
IODGQWWTJYDCLN-UHFFFAOYSA-N

> <FORMULA>
C17H14O7

> <MOLECULAR_WEIGHT>
330.2889

> <EXACT_MASS>
330.073952802

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
32.67832807370972

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,8-dihydroxy-2-(4-hydroxyphenyl)-6,7-dimethoxy-4H-chromen-4-one

> <ALOGPS_LOGP>
3.00

> <JCHEM_LOGP>
2.391346602333333

> <ALOGPS_LOGS>
-3.67

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.884787270997318

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.234380771143353

> <JCHEM_PKA_STRONGEST_BASIC>
-4.607370800229603

> <JCHEM_POLAR_SURFACE_AREA>
105.45000000000002

> <JCHEM_REFRACTIVITY>
85.8403

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.10e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
isothymusin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-OCT-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-OCT-17         0                                  
HETATM    1  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.668   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -6.668   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -8.002   4.620   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1   22                                                            
CONECT    2   23                                                            
CONECT    3    5    8                                                       
CONECT    4    6    8                                                       
CONECT    5    3    9                                                       
CONECT    6    4    9                                                       
CONECT    7   10   11                                                       
CONECT    8    3    4   11                                                  
CONECT    9    5    6   18                                                  
CONECT   10    7   12   19                                                  
CONECT   11    7    8   24                                                  
CONECT   12   10   13   15                                                  
CONECT   13   12   16   20                                                  
CONECT   14   15   17   21                                                  
CONECT   15   12   14   24                                                  
CONECT   16   13   17   22                                                  
CONECT   17   14   16   23                                                  
CONECT   18    9                                                            
CONECT   19   10                                                            
CONECT   20   13                                                            
CONECT   21   14                                                            
CONECT   22    1   16                                                       
CONECT   23    2   17                                                       
CONECT   24   11   15                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Value	Source
6,7-Dimethoxy-5,8,4'-trihydroxyflavone	MeSH

Chemical Formula

C₁₇H₁₄O₇

Average Mass

330.2889 Da

Monoisotopic Mass

330.07395 Da

IUPAC Name

5,8-dihydroxy-2-(4-hydroxyphenyl)-6,7-dimethoxy-4H-chromen-4-one

Traditional Name

isothymusin

CAS Registry Number

98755-25-0

SMILES

COC1=C(OC)C(O)=C2C(=O)C=C(OC2=C1O)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C17H14O7/c1-22-16-13(20)12-10(19)7-11(8-3-5-9(18)6-4-8)24-15(12)14(21)17(16)23-2/h3-7,18,20-21H,1-2H3

InChI Key

IODGQWWTJYDCLN-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Agastache barberi	Plant	KNApSAcK
Becium grandiflorum	Plant	KNApSAcK
Isodon eriocalyx	LOTUS Database	35616633
Nepeta spp.	Plant	KNApSAcK
Ocimum americanum cv.Sacred	Plant	KNApSAcK
Ocimum gratissimum	Plant	KNApSAcK
Ocimum selloi Benth.	Plant	KNApSAcK
Ocimum tenuiflorum	LOTUS Database	35616633
Ocimum tenuiflorum L.	Plant	KNApSAcK
Prunus cerasus	FooDB	KNAPSACK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 7-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

7-O-methylated flavonoids

Alternative Parents

Substituents

6-methoxyflavonoid-skeleton
7-methoxyflavonoid-skeleton
4'-hydroxyflavonoid
5-hydroxyflavonoid
8-hydroxyflavonoid
Flavone
Hydroxyflavonoid
Chromone
Benzopyran
1-benzopyran
Anisole
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyranone
Benzenoid
Pyran
Monocyclic benzene moiety
Vinylogous acid
Heteroaromatic compound
Ether
Organoheterocyclic compound
Oxacycle
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavones and Flavonols (LMPK12111453 )

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	ALOGPS
logP	2.39	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	8.23	ChemAxon
pKa (Strongest Basic)	-4.6	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	85.84 m³·mol⁻¹	ChemAxon
Polarizability	32.68 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

HMDB0154340

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB016710

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

630253

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Isothymusin (NP0048855)

MOL for NP0048855 (Isothymusin)

3D MOL for NP0048855 (Isothymusin)

3D SDF for NP0048855 (Isothymusin)

3D-SDF for NP0048855 (Isothymusin)

PDB for NP0048855 (Isothymusin)

3D PDB for NP0048855 (Isothymusin)

SMILES for NP0048855 (Isothymusin)

INCHI for NP0048855 (Isothymusin)

Structure for NP0048855 (Isothymusin)

3D Structure for NP0048855 (Isothymusin)