NP-MRD: Showing NP-Card for Dihydrocycloartomunin (NP0049255)

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Record Information

Version

2.0

Created at

2022-03-17 21:09:33 UTC

Updated at

2022-03-17 21:09:33 UTC

NP-MRD ID

NP0049255

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Dihydrocycloartomunin

Description

Dihydrocycloartomunin belongs to the class of organic compounds known as pyranoflavonoids. Pyranoflavonoids are compounds containing a pyran ring fused to a 2-phenyl-1,4-benzopyran skeleton. Thus, dihydrocycloartomunin is considered to be a flavonoid lipid molecule. Dihydrocycloartomunin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Dihydrocycloartomunin has been detected, but not quantified in, breadfruits and fruits. This could make dihydrocycloartomunin a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI

  Mrv0541 05061310432D          

 33 36  0  0  0  0            999 V2000
    6.9086   -1.9359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5583   -1.4682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1279    4.6123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2081    5.5478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5288    0.5586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6385   -0.5327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0984    0.0909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4782    4.1446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3980    1.0264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3178    2.2736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4486    1.8059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3685   -1.3123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9381    4.7682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3685    0.8704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6680    1.8059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5878    0.8704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0477    1.4941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9086    2.4296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1786    1.0264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1279    2.4296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2081    3.3650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0984    2.2736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7482    2.7414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5583    2.8973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8284    1.4941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4782    1.9618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3178    0.0909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2376    1.3382    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1786    3.2091    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8284    3.6768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7187    0.4027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3980    3.2091    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0182    1.3382    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0  0  0  0
 12  1  1  0  0  0  0
 12  2  1  0  0  0  0
 12  6  2  0  0  0  0
 13  3  1  0  0  0  0
 13  4  1  0  0  0  0
 13  8  2  0  0  0  0
 14  7  1  0  0  0  0
 15  9  1  0  0  0  0
 16  9  2  0  0  0  0
 17 10  2  0  0  0  0
 17 16  1  0  0  0  0
 18 11  2  0  0  0  0
 19 11  1  0  0  0  0
 19 14  2  0  0  0  0
 20 10  1  0  0  0  0
 20 15  2  0  0  0  0
 21  8  1  0  0  0  0
 22 18  1  0  0  0  0
 23 21  1  0  0  0  0
 24 22  1  0  0  0  0
 24 23  1  0  0  0  0
 25 14  1  0  0  0  0
 25 22  2  0  0  0  0
 26 15  1  0  0  0  0
 26 23  2  0  0  0  0
 27 16  1  0  0  0  0
 28 17  1  0  0  0  0
 29 18  1  0  0  0  0
 30 24  2  0  0  0  0
 31  5  1  0  0  0  0
 31 19  1  0  0  0  0
 32 20  1  0  0  0  0
 32 21  1  0  0  0  0
 33 25  1  0  0  0  0
 33 26  1  0  0  0  0
M  END

  Mrv0541 05061310432D          

 33 36  0  0  0  0            999 V2000
    6.9086   -1.9359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5583   -1.4682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1279    4.6123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2081    5.5478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5288    0.5586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6385   -0.5327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0984    0.0909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4782    4.1446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3980    1.0264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3178    2.2736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4486    1.8059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3685   -1.3123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9381    4.7682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3685    0.8704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6680    1.8059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5878    0.8704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0477    1.4941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9086    2.4296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1786    1.0264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1279    2.4296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2081    3.3650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0984    2.2736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7482    2.7414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5583    2.8973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8284    1.4941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4782    1.9618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3178    0.0909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2376    1.3382    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1786    3.2091    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8284    3.6768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7187    0.4027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3980    3.2091    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0182    1.3382    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0  0  0  0
 12  1  1  0  0  0  0
 12  2  1  0  0  0  0
 12  6  2  0  0  0  0
 13  3  1  0  0  0  0
 13  4  1  0  0  0  0
 13  8  2  0  0  0  0
 14  7  1  0  0  0  0
 15  9  1  0  0  0  0
 16  9  2  0  0  0  0
 17 10  2  0  0  0  0
 17 16  1  0  0  0  0
 18 11  2  0  0  0  0
 19 11  1  0  0  0  0
 19 14  2  0  0  0  0
 20 10  1  0  0  0  0
 20 15  2  0  0  0  0
 21  8  1  0  0  0  0
 22 18  1  0  0  0  0
 23 21  1  0  0  0  0
 24 22  1  0  0  0  0
 24 23  1  0  0  0  0
 25 14  1  0  0  0  0
 25 22  2  0  0  0  0
 26 15  1  0  0  0  0
 26 23  2  0  0  0  0
 27 16  1  0  0  0  0
 28 17  1  0  0  0  0
 29 18  1  0  0  0  0
 30 24  2  0  0  0  0
 31  5  1  0  0  0  0
 31 19  1  0  0  0  0
 32 20  1  0  0  0  0
 32 21  1  0  0  0  0
 33 25  1  0  0  0  0
 33 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0049255

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(CC=C(C)C)C2=C(C(O)=C1)C(=O)C1=C(O2)C2=C(OC1C=C(C)C)C=C(O)C(O)=C2

> <INCHI_IDENTIFIER>
InChI=1S/C26H26O7/c1-12(2)6-7-14-19(31-5)11-18(29)22-24(30)23-21(8-13(3)4)32-20-10-17(28)16(27)9-15(20)26(23)33-25(14)22/h6,8-11,21,27-29H,7H2,1-5H3

> <INCHI_KEY>
FIYIGIGIGDUJQB-UHFFFAOYSA-N

> <FORMULA>
C26H26O7

> <MOLECULAR_WEIGHT>
450.4804

> <EXACT_MASS>
450.167853186

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
48.417395375496554

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,7,8-trihydroxy-3-methoxy-4-(3-methylbut-2-en-1-yl)-11-(2-methylprop-1-en-1-yl)-11,12-dihydro-5,10-dioxatetraphen-12-one

> <ALOGPS_LOGP>
4.13

> <JCHEM_LOGP>
5.174283162666668

> <ALOGPS_LOGS>
-4.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.932141712494833

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.287434355579453

> <JCHEM_PKA_STRONGEST_BASIC>
-4.53919044457617

> <JCHEM_POLAR_SURFACE_AREA>
105.45

> <JCHEM_REFRACTIVITY>
126.74199999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.13e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dihydrocycloartomunin

> <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      12.896  -3.614   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.375  -2.741   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.839   8.610   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.855  10.356   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      15.920   1.043   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.392  -0.994   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.384   0.170   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.359   7.737   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.343   1.916   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.327   4.244   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.904   3.371   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.888  -2.450   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.351   8.901   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.888   1.625   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.847   3.371   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.831   1.625   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.822   2.789   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.896   4.535   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.400   1.916   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.839   4.535   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.855   6.281   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.384   4.244   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.863   5.117   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.375   5.408   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.880   2.789   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.359   3.662   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       4.327   0.170   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       2.310   2.498   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      13.400   5.990   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      10.880   6.863   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      14.408   0.752   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       6.343   5.990   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       9.367   2.498   0.000  0.00  0.00           O+0
CONECT    1   12                                                            
CONECT    2   12                                                            
CONECT    3   13                                                            
CONECT    4   13                                                            
CONECT    5   31                                                            
CONECT    6    7   12                                                       
CONECT    7    6   14                                                       
CONECT    8   13   21                                                       
CONECT    9   15   16                                                       
CONECT   10   17   20                                                       
CONECT   11   18   19                                                       
CONECT   12    1    2    6                                                  
CONECT   13    3    4    8                                                  
CONECT   14    7   19   25                                                  
CONECT   15    9   20   26                                                  
CONECT   16    9   17   27                                                  
CONECT   17   10   16   28                                                  
CONECT   18   11   22   29                                                  
CONECT   19   11   14   31                                                  
CONECT   20   10   15   32                                                  
CONECT   21    8   23   32                                                  
CONECT   22   18   24   25                                                  
CONECT   23   21   24   26                                                  
CONECT   24   22   23   30                                                  
CONECT   25   14   22   33                                                  
CONECT   26   15   23   33                                                  
CONECT   27   16                                                            
CONECT   28   17                                                            
CONECT   29   18                                                            
CONECT   30   24                                                            
CONECT   31    5   19                                                       
CONECT   32   20   21                                                       
CONECT   33   25   26                                                       
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Value	Source
2,3,8-Trihydroxy-10-methoxy-11-(3-methyl-2-butenyl)-6-(2-methyl-1-propenyl)-6H,7H-[1]benzopyrano[4,3-b][1]benzopyran-7-one, 9ci	HMDB

Chemical Formula

C₂₆H₂₆O₇

Average Mass

450.4804 Da

Monoisotopic Mass

450.16785 Da

IUPAC Name

1,7,8-trihydroxy-3-methoxy-4-(3-methylbut-2-en-1-yl)-11-(2-methylprop-1-en-1-yl)-11,12-dihydro-5,10-dioxatetraphen-12-one

Traditional Name

dihydrocycloartomunin

CAS Registry Number

135023-16-4

SMILES

COC1=C(CC=C(C)C)C2=C(C(O)=C1)C(=O)C1=C(O2)C2=C(OC1C=C(C)C)C=C(O)C(O)=C2

InChI Identifier

InChI=1S/C26H26O7/c1-12(2)6-7-14-19(31-5)11-18(29)22-24(30)23-21(8-13(3)4)32-20-10-17(28)16(27)9-15(20)26(23)33-25(14)22/h6,8-11,21,27-29H,7H2,1-5H3

InChI Key

FIYIGIGIGDUJQB-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

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyranoflavonoids. Pyranoflavonoids are compounds containing a pyran ring fused to a 2-phenyl-1,4-benzopyran skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Pyranoflavonoids

Direct Parent

Pyranoflavonoids

Alternative Parents

Substituents

Pyranoflavonoid
Chromone
Benzopyran
1-benzopyran
Anisole
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
Benzenoid
Pyran
Heteroaromatic compound
Vinylogous acid
Oxacycle
Ether
Polyol
Organoheterocyclic compound
Organic oxygen compound
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavones and Flavonols (LMPK12110931 )

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	4.13	ALOGPS
logP	5.17	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	8.29	ChemAxon
pKa (Strongest Basic)	-4.5	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	4	ChemAxon
Refractivity	126.74 m³·mol⁻¹	ChemAxon
Polarizability	48.42 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0038877

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB018323

KNApSAcK ID

C00004041

Chemspider ID

8247994

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10072454

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Dihydrocycloartomunin (NP0049255)

MOL for NP0049255 (Dihydrocycloartomunin)

3D MOL for NP0049255 (Dihydrocycloartomunin)

3D SDF for NP0049255 (Dihydrocycloartomunin)

3D-SDF for NP0049255 (Dihydrocycloartomunin)

PDB for NP0049255 (Dihydrocycloartomunin)

3D PDB for NP0049255 (Dihydrocycloartomunin)

SMILES for NP0049255 (Dihydrocycloartomunin)

INCHI for NP0049255 (Dihydrocycloartomunin)

Structure for NP0049255 (Dihydrocycloartomunin)

3D Structure for NP0049255 (Dihydrocycloartomunin)