NP-MRD: Showing NP-Card for Artonin E (NP0048170)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-03-17 20:52:14 UTC

Updated at

2022-03-17 20:52:14 UTC

NP-MRD ID

NP0048170

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Artonin E

Description

Artonin E, also known as 5'-hydroxymorusin or KB 3, belongs to the class of organic compounds known as 3-prenylated flavones. These are flavones that features a C5-isoprenoid substituent at the 3-position. Thus, artonin e is considered to be a flavonoid lipid molecule. Artonin E is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Artonin E has been detected, but not quantified in, breadfruits and fruits. Artonin E is found in Artocarpus chama, Artocarpus kemando , Artocarpus nobilis, Artocarpus rigidus, Artocarpus rotunda (Hout) Panzer and Artocarpus scortechinii King . This could make artonin e a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061308172D          

 32 35  0  0  0  0            999 V2000
   -2.5855    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5855    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6465    0.9428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6465   -0.1178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1730    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1730    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480    3.9849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -1.7309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  8  7  2  0  0  0  0
 12  1  1  0  0  0  0
 12  2  1  0  0  0  0
 12  5  2  0  0  0  0
 13  7  1  0  0  0  0
 14  6  1  0  0  0  0
 15  9  2  0  0  0  0
 16 10  2  0  0  0  0
 16 15  1  0  0  0  0
 17  9  1  0  0  0  0
 18 10  1  0  0  0  0
 18 17  2  0  0  0  0
 19 11  2  0  0  0  0
 20 11  1  0  0  0  0
 20 13  2  0  0  0  0
 21 19  1  0  0  0  0
 22 14  1  0  0  0  0
 22 21  1  0  0  0  0
 23 14  2  0  0  0  0
 23 15  1  0  0  0  0
 24 13  1  0  0  0  0
 24 21  2  0  0  0  0
 25  3  1  0  0  0  0
 25  4  1  0  0  0  0
 25  8  1  0  0  0  0
 26 16  1  0  0  0  0
 27 17  1  0  0  0  0
 28 18  1  0  0  0  0
 29 19  1  0  0  0  0
 30 22  2  0  0  0  0
 31 23  1  0  0  0  0
 31 24  1  0  0  0  0
 32 20  1  0  0  0  0
 32 25  1  0  0  0  0
M  END


  Mrv0541 05061308172D          

 32 35  0  0  0  0            999 V2000
   -2.5855    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5855    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6465    0.9428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6465   -0.1178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1730    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1730    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480    3.9849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -1.7309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  8  7  2  0  0  0  0
 12  1  1  0  0  0  0
 12  2  1  0  0  0  0
 12  5  2  0  0  0  0
 13  7  1  0  0  0  0
 14  6  1  0  0  0  0
 15  9  2  0  0  0  0
 16 10  2  0  0  0  0
 16 15  1  0  0  0  0
 17  9  1  0  0  0  0
 18 10  1  0  0  0  0
 18 17  2  0  0  0  0
 19 11  2  0  0  0  0
 20 11  1  0  0  0  0
 20 13  2  0  0  0  0
 21 19  1  0  0  0  0
 22 14  1  0  0  0  0
 22 21  1  0  0  0  0
 23 14  2  0  0  0  0
 23 15  1  0  0  0  0
 24 13  1  0  0  0  0
 24 21  2  0  0  0  0
 25  3  1  0  0  0  0
 25  4  1  0  0  0  0
 25  8  1  0  0  0  0
 26 16  1  0  0  0  0
 27 17  1  0  0  0  0
 28 18  1  0  0  0  0
 29 19  1  0  0  0  0
 30 22  2  0  0  0  0
 31 23  1  0  0  0  0
 31 24  1  0  0  0  0
 32 20  1  0  0  0  0
 32 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048170

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC1=C(OC2=C(C(O)=CC3=C2C=CC(C)(C)O3)C1=O)C1=CC(O)=C(O)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C25H24O7/c1-12(2)5-6-14-22(30)21-19(29)11-20-13(7-8-25(3,4)32-20)24(21)31-23(14)15-9-17(27)18(28)10-16(15)26/h5,7-11,26-29H,6H2,1-4H3

> <INCHI_KEY>
HDHRTQZSBFUBMJ-UHFFFAOYSA-N

> <FORMULA>
C25H24O7

> <MOLECULAR_WEIGHT>
436.4539

> <EXACT_MASS>
436.152203122

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
46.35754919377386

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-hydroxy-8,8-dimethyl-3-(3-methylbut-2-en-1-yl)-2-(2,4,5-trihydroxyphenyl)-4H,8H-pyrano[2,3-h]chromen-4-one

> <ALOGPS_LOGP>
4.58

> <JCHEM_LOGP>
4.914443313333334

> <ALOGPS_LOGS>
-4.65

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.918796961982688

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.309712714871688

> <JCHEM_PKA_STRONGEST_BASIC>
-4.812496772485264

> <JCHEM_POLAR_SURFACE_AREA>
116.45000000000002

> <JCHEM_REFRACTIVITY>
122.84689999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.72e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
artonin E

> <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      -4.826   0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.826   3.437   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.673   1.760   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.673  -0.220   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.516   2.104   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.746   0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.746   3.437   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.206   6.105   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.414  -1.897   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.056   2.104   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.206   3.437   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.564   4.771   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.516   4.771   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.746   6.105   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.874  -1.897   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.104   4.771   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -4.056   4.771   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -2.516   7.438   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       2.104  -3.231   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -0.206  -1.897   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       2.104   2.104   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       6.724  -0.564   0.000  0.00  0.00           O+0
CONECT    1   12                                                            
CONECT    2   12                                                            
CONECT    3   25                                                            
CONECT    4   25                                                            
CONECT    5    6   12                                                       
CONECT    6    5   14                                                       
CONECT    7    8   13                                                       
CONECT    8    7   25                                                       
CONECT    9   15   17                                                       
CONECT   10   16   18                                                       
CONECT   11   19   20                                                       
CONECT   12    1    2    5                                                  
CONECT   13    7   20   24                                                  
CONECT   14    6   22   23                                                  
CONECT   15    9   16   23                                                  
CONECT   16   10   15   26                                                  
CONECT   17    9   18   27                                                  
CONECT   18   10   17   28                                                  
CONECT   19   11   21   29                                                  
CONECT   20   11   13   32                                                  
CONECT   21   19   22   24                                                  
CONECT   22   14   21   30                                                  
CONECT   23   14   15   31                                                  
CONECT   24   13   21   31                                                  
CONECT   25    3    4    8   32                                             
CONECT   26   16                                                            
CONECT   27   17                                                            
CONECT   28   18                                                            
CONECT   29   19                                                            
CONECT   30   22                                                            
CONECT   31   23   24                                                       
CONECT   32   20   25                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Value	Source
5'-Hydroxymorusin	HMDB
KB 3	HMDB

Chemical Formula

C₂₅H₂₄O₇

Average Mass

436.4539 Da

Monoisotopic Mass

436.15220 Da

IUPAC Name

5-hydroxy-8,8-dimethyl-3-(3-methylbut-2-en-1-yl)-2-(2,4,5-trihydroxyphenyl)-4H,8H-pyrano[2,3-h]chromen-4-one

Traditional Name

artonin E

CAS Registry Number

129683-93-8

SMILES

CC(C)=CCC1=C(OC2=C(C(O)=CC3=C2C=CC(C)(C)O3)C1=O)C1=CC(O)=C(O)C=C1O

InChI Identifier

InChI=1S/C25H24O7/c1-12(2)5-6-14-22(30)21-19(29)11-20-13(7-8-25(3,4)32-20)24(21)31-23(14)15-9-17(27)18(28)10-16(15)26/h5,7-11,26-29H,6H2,1-4H3

InChI Key

HDHRTQZSBFUBMJ-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Artocarpus altilis	FooDB	KNAPSACK
Artocarpus chama	Plant	KNApSAcK
Artocarpus kemando	Plant	KNApSAcK
Artocarpus nobilis	LOTUS Database	35616633
Artocarpus rigidus	LOTUS Database	35616633
Artocarpus rotunda (Hout) Panzer	Plant	KNApSAcK
Artocarpus scortechinii King	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3-prenylated flavones. These are flavones that features a C5-isoprenoid substituent at the 3-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavones

Direct Parent

3-prenylated flavones

Alternative Parents

Substituents

3-prenylated flavone
Pyranoflavonoid
3'-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
Hydroxyflavonoid
Pyranochromene
2,2-dimethyl-1-benzopyran
Chromone
Benzopyran
1-benzopyran
Hydroxyquinol derivative
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Pyranone
Monocyclic benzene moiety
Benzenoid
Pyran
Vinylogous acid
Heteroaromatic compound
Ether
Organoheterocyclic compound
Oxacycle
Polyol
Organic oxide
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavones and Flavonols (LMPK12110925 )

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	4.58	ALOGPS
logP	4.91	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	8.31	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	116.45 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	122.85 m³·mol⁻¹	ChemAxon
Polarizability	46.36 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

HMDB0035186

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB013832

KNApSAcK ID

C00004106

Chemspider ID

4587690

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5481962

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Artonin E (NP0048170)

MOL for NP0048170 (Artonin E)

3D MOL for NP0048170 (Artonin E)

3D SDF for NP0048170 (Artonin E)

3D-SDF for NP0048170 (Artonin E)

PDB for NP0048170 (Artonin E)

3D PDB for NP0048170 (Artonin E)

SMILES for NP0048170 (Artonin E)

INCHI for NP0048170 (Artonin E)

Structure for NP0048170 (Artonin E)

3D Structure for NP0048170 (Artonin E)