NP-MRD: Showing NP-Card for Isoetin (NP0050618)

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Record Information

Version

2.0

Created at

2022-04-27 21:59:14 UTC

Updated at

2022-04-27 21:59:14 UTC

NP-MRD ID

NP0050618

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Isoetin

Description

5,7-Dihydroxy-2-(2,4,5-trihydroxyphenyl)-4H-chromen-4-one, also known as 5,7,2',4',5'-pentahydroxyflavone, belongs to the class of organic compounds known as flavones. These are flavonoids with a structure based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one). Thus, 5,7-dihydroxy-2-(2,4,5-trihydroxyphenyl)-4H-chromen-4-one is considered to be a flavonoid lipid molecule. A pentahydroxyflavone that is flavone substituted by hydroxy groups at positions 5, 7, 2', 4' and 5'. Isoetin is found in Isoetes spp. and Taraxacum platycarpum. Isoetin was first documented in 2008 (PMID: 18720865). 5,7-Dihydroxy-2-(2,4,5-trihydroxyphenyl)-4H-chromen-4-one is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (PMID: 19624011).

Structure

MOL SDF PDB SMILES InChI

  Mrv1652308201902152D          

 22 24  0  0  0  0            999 V2000
    1.4289    0.8250    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
    5.7158    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    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
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    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    1.2375    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
    2.8579    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
    0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  2  0  0  0  0
  6  2  1  0  0  0  0
  7  3  2  0  0  0  0
  8  4  2  0  0  0  0
  8  7  1  0  0  0  0
  9  3  1  0  0  0  0
 10  4  1  0  0  0  0
 10  9  2  0  0  0  0
 11  1  1  0  0  0  0
 12  5  1  0  0  0  0
 13  5  2  0  0  0  0
 13  7  1  0  0  0  0
 14  2  2  0  0  0  0
 15 11  2  0  0  0  0
 15 12  1  0  0  0  0
 15 14  1  0  0  0  0
 16  6  1  0  0  0  0
 17  8  1  0  0  0  0
 18  9  1  0  0  0  0
 19 10  1  0  0  0  0
 20 11  1  0  0  0  0
 21 12  2  0  0  0  0
 22 13  1  0  0  0  0
 22 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0050618

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC(O)=C2C(=O)C=C(OC2=C1)C1=CC(O)=C(O)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C15H10O7/c16-6-1-11(20)15-12(21)5-13(22-14(15)2-6)7-3-9(18)10(19)4-8(7)17/h1-5,16-20H

> <INCHI_KEY>
DSNIERNBMAVNJI-UHFFFAOYSA-N

> <FORMULA>
C15H10O7

> <MOLECULAR_WEIGHT>
302.238

> <EXACT_MASS>
302.042652662

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
28.531200580248697

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,7-dihydroxy-2-(2,4,5-trihydroxyphenyl)-4H-chromen-4-one

> <ALOGPS_LOGP>
2.22

> <JCHEM_LOGP>
2.099558490333333

> <ALOGPS_LOGS>
-3.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.022164186599891

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.57205345580343

> <JCHEM_PKA_STRONGEST_BASIC>
-5.392974477654585

> <JCHEM_POLAR_SURFACE_AREA>
127.45

> <JCHEM_REFRACTIVITY>
76.87570000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.06e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
isoetin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-AUG-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-AUG-19         0                                  
HETATM    1  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.003  -2.310   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       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      13.337   0.000   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      13.337  -3.080   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
CONECT    1    6   11                                                       
CONECT    2    6   14                                                       
CONECT    3    7    9                                                       
CONECT    4    8   10                                                       
CONECT    5   12   13                                                       
CONECT    6    1    2   16                                                  
CONECT    7    3    8   13                                                  
CONECT    8    4    7   17                                                  
CONECT    9    3   10   18                                                  
CONECT   10    4    9   19                                                  
CONECT   11    1   15   20                                                  
CONECT   12    5   15   21                                                  
CONECT   13    5    7   22                                                  
CONECT   14    2   15   22                                                  
CONECT   15   11   12   14                                                  
CONECT   16    6                                                            
CONECT   17    8                                                            
CONECT   18    9                                                            
CONECT   19   10                                                            
CONECT   20   11                                                            
CONECT   21   12                                                            
CONECT   22   13   14                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Value	Source
5,7,2',4',5'-Pentahydroxyflavone	ChEBI

Chemical Formula

C₁₅H₁₀O₇

Average Mass

302.2380 Da

Monoisotopic Mass

302.04265 Da

IUPAC Name

5,7-dihydroxy-2-(2,4,5-trihydroxyphenyl)-4H-chromen-4-one

Traditional Name

isoetin

CAS Registry Number

Not Available

SMILES

OC1=CC(O)=C2C(=O)C=C(OC2=C1)C1=CC(O)=C(O)C=C1O

InChI Identifier

InChI=1S/C15H10O7/c16-6-1-11(20)15-12(21)5-13(22-14(15)2-6)7-3-9(18)10(19)4-8(7)17/h1-5,16-20H

InChI Key

DSNIERNBMAVNJI-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Isoetes spp.	Plant	KNApSAcK
Taraxacum platycarpum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavones. These are flavonoids with a structure based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavones

Direct Parent

Flavones

Alternative Parents

Substituents

3'-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
Flavone
7-hydroxyflavonoid
Hydroxyflavonoid
Chromone
1-benzopyran
Benzopyran
Hydroxyquinol derivative
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyranone
Monocyclic benzene moiety
Benzenoid
Pyran
Heteroaromatic compound
Vinylogous acid
Oxacycle
Organoheterocyclic compound
Polyol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

pentahydroxyflavone (CHEBI:6006 )
flavones (C10079 )
Flavones and Flavonols (C10079 )
Flavones and Flavonols (LMPK12110940 )

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	2.22	ALOGPS
logP	2.1	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	6.57	ChemAxon
pKa (Strongest Basic)	-5.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	127.45 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	76.88 m³·mol⁻¹	ChemAxon
Polarizability	28.53 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

HMDB0126017

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB084895

KNApSAcK ID

C00001054

Chemspider ID

Not Available

KEGG Compound ID

C10079

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5281649

PDB ID

Not Available

ChEBI ID

6006

Good Scents ID

Not Available

References

General References

Huang W, Li Y, Jiang J: [Chemical constituents from Hedyotis diffusa]. Zhongguo Zhong Yao Za Zhi. 2009 Mar;34(6):712-4. [PubMed:19624011 ]
Shi SY, Zhou CX, Xu Y, Tao QF, Bai H, Lu FS, Lin WY, Chen HY, Zheng W, Wang LW, Wu YH, Zeng S, Huang KX, Zhao Y, Li XK, Qu J: [Studies on chemical constituents from herbs of Taraxacum mongolicum]. Zhongguo Zhong Yao Za Zhi. 2008 May;33(10):1147-57. [PubMed:18720865 ]

Showing NP-Card for Isoetin (NP0050618)

MOL for NP0050618 (Isoetin)

3D MOL for NP0050618 (Isoetin)

3D SDF for NP0050618 (Isoetin)

3D-SDF for NP0050618 (Isoetin)

PDB for NP0050618 (Isoetin)

3D PDB for NP0050618 (Isoetin)

SMILES for NP0050618 (Isoetin)

INCHI for NP0050618 (Isoetin)

Structure for NP0050618 (Isoetin)

3D Structure for NP0050618 (Isoetin)