NP-MRD: Showing NP-Card for Cycloartomunin (NP0049256)

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Record Information

Version

2.0

Created at

2022-03-17 21:09:34 UTC

Updated at

2022-03-17 21:09:34 UTC

NP-MRD ID

NP0049256

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cycloartomunin

Description

Cycloartomunin 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, cycloartomunin is considered to be a flavonoid lipid molecule. Cycloartomunin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, cycloartomunin has been detected, but not quantified in, breadfruits and fruits. This could make cycloartomunin a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061310432D          

 33 37  0  0  0  0            999 V2000
    2.8579    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1413    0.4623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6716    1.3808    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
    6.4302    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    4.5375    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
    7.1447    3.3000    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    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    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
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    3.7125    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
    7.1447    2.4750    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    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  2  0  0  0  0
 12  1  1  0  0  0  0
 12  2  1  0  0  0  0
 12  8  2  0  0  0  0
 13  6  1  0  0  0  0
 14  9  2  0  0  0  0
 15  9  1  0  0  0  0
 16 10  2  0  0  0  0
 17 11  2  0  0  0  0
 17 14  1  0  0  0  0
 18 10  1  0  0  0  0
 18 13  2  0  0  0  0
 19 11  1  0  0  0  0
 19 15  2  0  0  0  0
 20  8  1  0  0  0  0
 21 16  1  0  0  0  0
 22 20  1  0  0  0  0
 23 21  1  0  0  0  0
 23 22  1  0  0  0  0
 24 13  1  0  0  0  0
 24 21  2  0  0  0  0
 25 14  1  0  0  0  0
 25 22  2  0  0  0  0
 26  3  1  0  0  0  0
 26  4  1  0  0  0  0
 26  7  1  0  0  0  0
 27 15  1  0  0  0  0
 28 16  1  0  0  0  0
 29 23  2  0  0  0  0
 30  5  1  0  0  0  0
 30 19  1  0  0  0  0
 31 17  1  0  0  0  0
 31 20  1  0  0  0  0
 32 24  1  0  0  0  0
 32 25  1  0  0  0  0
 33 18  1  0  0  0  0
 33 26  1  0  0  0  0
M  END


  Mrv0541 05061310432D          

 33 37  0  0  0  0            999 V2000
    2.8579    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1413    0.4623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6716    1.3808    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
    6.4302    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    4.5375    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
    7.1447    3.3000    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    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    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
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    3.7125    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
    7.1447    2.4750    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    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  2  0  0  0  0
 12  1  1  0  0  0  0
 12  2  1  0  0  0  0
 12  8  2  0  0  0  0
 13  6  1  0  0  0  0
 14  9  2  0  0  0  0
 15  9  1  0  0  0  0
 16 10  2  0  0  0  0
 17 11  2  0  0  0  0
 17 14  1  0  0  0  0
 18 10  1  0  0  0  0
 18 13  2  0  0  0  0
 19 11  1  0  0  0  0
 19 15  2  0  0  0  0
 20  8  1  0  0  0  0
 21 16  1  0  0  0  0
 22 20  1  0  0  0  0
 23 21  1  0  0  0  0
 23 22  1  0  0  0  0
 24 13  1  0  0  0  0
 24 21  2  0  0  0  0
 25 14  1  0  0  0  0
 25 22  2  0  0  0  0
 26  3  1  0  0  0  0
 26  4  1  0  0  0  0
 26  7  1  0  0  0  0
 27 15  1  0  0  0  0
 28 16  1  0  0  0  0
 29 23  2  0  0  0  0
 30  5  1  0  0  0  0
 30 19  1  0  0  0  0
 31 17  1  0  0  0  0
 31 20  1  0  0  0  0
 32 24  1  0  0  0  0
 32 25  1  0  0  0  0
 33 18  1  0  0  0  0
 33 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0049256

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=C2C(OC(C=C(C)C)C3=C2OC2=C(C(O)=CC4=C2C=CC(C)(C)O4)C3=O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C26H24O7/c1-12(2)8-20-22-23(29)21-16(28)10-18-13(6-7-26(3,4)33-18)24(21)32-25(22)14-9-15(27)19(30-5)11-17(14)31-20/h6-11,20,27-28H,1-5H3

> <INCHI_KEY>
WQSBCGFYYIWXHK-UHFFFAOYSA-N

> <FORMULA>
C26H24O7

> <MOLECULAR_WEIGHT>
448.4646

> <EXACT_MASS>
448.152203122

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
48.22461799077537

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
11,20-dihydroxy-19-methoxy-7,7-dimethyl-15-(2-methylprop-1-en-1-yl)-2,8,16-trioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁷,²²]docosa-1(14),3(12),4(9),5,10,17,19,21-octaen-13-one

> <ALOGPS_LOGP>
3.91

> <JCHEM_LOGP>
4.649904887

> <ALOGPS_LOGS>
-4.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.9949982372806

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.706413334831554

> <JCHEM_PKA_STRONGEST_BASIC>
-4.4062655154833985

> <JCHEM_POLAR_SURFACE_AREA>
94.45000000000002

> <JCHEM_REFRACTIVITY>
124.91169999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.25e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
11,20-dihydroxy-19-methoxy-7,7-dimethyl-15-(2-methylprop-1-en-1-yl)-2,8,16-trioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁷,²²]docosa-1(14),3(12),4(9),5,10,17,19,21-octaen-13-one

> <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       5.335  10.780   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001   8.470   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      15.197   0.863   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      16.187   2.577   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.003   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.337   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668   8.470   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.337   6.160   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335   9.240   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.003   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668   3.850   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  C   UNK     0      12.003   6.930   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.337   4.620   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.669   6.160   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.336   6.930   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      14.671   2.310   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      12.003   8.470   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       9.336   8.470   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       9.336   3.850   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      14.671   3.850   0.000  0.00  0.00           O+0
CONECT    1   12                                                            
CONECT    2   12                                                            
CONECT    3   26                                                            
CONECT    4   26                                                            
CONECT    5   30                                                            
CONECT    6    7   13                                                       
CONECT    7    6   26                                                       
CONECT    8   12   20                                                       
CONECT    9   14   15                                                       
CONECT   10   16   18                                                       
CONECT   11   17   19                                                       
CONECT   12    1    2    8                                                  
CONECT   13    6   18   24                                                  
CONECT   14    9   17   25                                                  
CONECT   15    9   19   27                                                  
CONECT   16   10   21   28                                                  
CONECT   17   11   14   31                                                  
CONECT   18   10   13   33                                                  
CONECT   19   11   15   30                                                  
CONECT   20    8   22   31                                                  
CONECT   21   16   23   24                                                  
CONECT   22   20   23   25                                                  
CONECT   23   21   22   29                                                  
CONECT   24   13   21   32                                                  
CONECT   25   14   22   32                                                  
CONECT   26    3    4    7   33                                             
CONECT   27   15                                                            
CONECT   28   16                                                            
CONECT   29   23                                                            
CONECT   30    5   19                                                       
CONECT   31   17   20                                                       
CONECT   32   24   25                                                       
CONECT   33   18   26                                                       
MASTER        0    0    0    0    0    0    0    0   33    0   74    0
END

View in JSmol

Synonyms

Value	Source
3-(9H-Fluoren-9-yl(hydroxy)methyl)dihydro-2(3H)-furanone	HMDB
6,12-Dihydroxy-11-methoxy-3,3-dimethyl-8-(2-methyl-1-propenyl)-3H,7H,8H-bis[1]benzopyrano[4,3-b:6',5'-e]pyran-7-one	HMDB
6,12-Dihydroxy-11-methoxy-3,3-dimethyl-8-(2-methyl-1-propenyl)-3H,7H,8H-bis[1]benzopyrano[4,3-b:6',5'-e]pyran-7-one, 9ci	HMDB

Chemical Formula

C₂₆H₂₄O₇

Average Mass

448.4646 Da

Monoisotopic Mass

448.15220 Da

IUPAC Name

11,20-dihydroxy-19-methoxy-7,7-dimethyl-15-(2-methylprop-1-en-1-yl)-2,8,16-trioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁷,²²]docosa-1(14),3(12),4(9),5,10,17,19,21-octaen-13-one

Traditional Name

11,20-dihydroxy-19-methoxy-7,7-dimethyl-15-(2-methylprop-1-en-1-yl)-2,8,16-trioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁷,²²]docosa-1(14),3(12),4(9),5,10,17,19,21-octaen-13-one

CAS Registry Number

135023-19-7

SMILES

COC1=C(O)C=C2C(OC(C=C(C)C)C3=C2OC2=C(C(O)=CC4=C2C=CC(C)(C)O4)C3=O)=C1

InChI Identifier

InChI=1S/C26H24O7/c1-12(2)8-20-22-23(29)21-16(28)10-18-13(6-7-26(3,4)33-18)24(21)32-25(22)14-9-15(27)19(30-5)11-17(14)31-20/h6-11,20,27-28H,1-5H3

InChI Key

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavones and Flavonols (LMPK12110916 )

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	3.91	ALOGPS
logP	4.65	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	8.71	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	94.45 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	124.91 m³·mol⁻¹	ChemAxon
Polarizability	48.22 Å³	ChemAxon
Number of Rings	5	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

HMDB0038878

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB018324

KNApSAcK ID

C00004055

Chemspider ID

8631727

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10456312

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Cycloartomunin (NP0049256)

MOL for NP0049256 (Cycloartomunin)

3D MOL for NP0049256 (Cycloartomunin)

3D SDF for NP0049256 (Cycloartomunin)

3D-SDF for NP0049256 (Cycloartomunin)

PDB for NP0049256 (Cycloartomunin)

3D PDB for NP0049256 (Cycloartomunin)

SMILES for NP0049256 (Cycloartomunin)

INCHI for NP0049256 (Cycloartomunin)

Structure for NP0049256 (Cycloartomunin)

3D Structure for NP0049256 (Cycloartomunin)