NP-MRD: Showing NP-Card for 5,7,8,15-tetrahydroxy-19,19-dimethyl-22-(3-methylbut-2-en-1-yl)-10-(prop-1-en-2-yl)-2,20-dioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁶,²¹]docosa-1(22),3(12),4,6,8,14,16(21),17-octaen-13-one (NP0210367)

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Record Information

Version

2.0

Created at

2022-09-05 08:08:42 UTC

Updated at

2022-09-05 08:08:42 UTC

NP-MRD ID

NP0210367

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5,7,8,15-tetrahydroxy-19,19-dimethyl-22-(3-methylbut-2-en-1-yl)-10-(prop-1-en-2-yl)-2,20-dioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁶,²¹]docosa-1(22),3(12),4,6,8,14,16(21),17-octaen-13-one

Description

Artonin B belongs to the class of organic compounds known as pyranoxanthones. These are organic aromatic compounds containing a pyran or a hydrogenated derivative fused to a xanthone ring system. Artonin B is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, artonin b has been detected, but not quantified in, fruits. 5,7,8,15-tetrahydroxy-19,19-dimethyl-22-(3-methylbut-2-en-1-yl)-10-(prop-1-en-2-yl)-2,20-dioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁶,²¹]docosa-1(22),3(12),4,6,8,14,16(21),17-octaen-13-one is found in Artocarpus integer, Artocarpus heterophyllus and Artocarpus styracifolius. This could make artonin b a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061307592D          

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  Mrv0541 05061307592D          

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 25 18  1  0  0  0  0
 25 23  1  0  0  0  0
 26 20  2  0  0  0  0
 26 21  1  0  0  0  0
 27 15  1  0  0  0  0
 27 16  2  0  0  0  0
 28 16  1  0  0  0  0
 28 23  2  0  0  0  0
 29 18  2  0  0  0  0
 29 22  1  0  0  0  0
 30  5  1  0  0  0  0
 30  6  1  0  0  0  0
 30 10  1  0  0  0  0
 31 19  1  0  0  0  0
 32 20  1  0  0  0  0
 33 24  1  0  0  0  0
 34 25  2  0  0  0  0
 35 26  1  0  0  0  0
 36 28  1  0  0  0  0
 36 29  1  0  0  0  0
 37 27  1  0  0  0  0
 37 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0210367

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC1=C2OC(C)(C)C=CC2=C(O)C2=C1OC1=C(CC(C(C)=C)C3=C1C(O)=CC(O)=C3O)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H30O7/c1-13(2)7-8-16-27-15(9-10-30(5,6)37-27)24(33)23-25(34)18-11-17(14(3)4)21-22(29(18)36-28(16)23)19(31)12-20(32)26(21)35/h7,9-10,12,17,31-33,35H,3,8,11H2,1-2,4-6H3

> <INCHI_KEY>
IGNKZOMBJGAKHN-UHFFFAOYSA-N

> <FORMULA>
C30H30O7

> <MOLECULAR_WEIGHT>
502.555

> <EXACT_MASS>
502.199153314

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
54.85630319283595

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5,7,8,15-tetrahydroxy-19,19-dimethyl-22-(3-methylbut-2-en-1-yl)-10-(prop-1-en-2-yl)-2,20-dioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁶,²¹]docosa-1(14),3(12),4(9),5,7,15,17,21-octaen-13-one

> <ALOGPS_LOGP>
4.86

> <JCHEM_LOGP>
6.148521235999999

> <ALOGPS_LOGS>
-4.87

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.707432718236879

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.122758984364465

> <JCHEM_PKA_STRONGEST_BASIC>
-4.818247591030992

> <JCHEM_POLAR_SURFACE_AREA>
116.45

> <JCHEM_REFRACTIVITY>
144.6028

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.80e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,7,8,15-tetrahydroxy-19,19-dimethyl-22-(3-methylbut-2-en-1-yl)-10-(prop-1-en-2-yl)-2,20-dioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁶,²¹]docosa-1(14),3(12),4(9),5,7,15,17,21-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       2.881   8.419   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.470   9.060   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667  -2.473   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.517  -0.550   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.596   4.252   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.223   5.679   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.731   6.497   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.621   5.429   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.320   1.585   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.429   2.653   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.448  -0.337   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.037   4.575   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.361   7.992   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.037  -0.978   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.840   2.012   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.991   3.934   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.928   0.090   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.662   0.731   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.558   4.148   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.147   3.507   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.297   1.585   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.188   2.653   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.251   1.371   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.731   0.944   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.141   0.304   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -3.777   2.012   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.470   3.507   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.881   2.866   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.292   2.226   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.060   4.148   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -0.448   5.216   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -5.627   3.934   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       5.100  -0.550   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       2.511  -1.191   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      -4.887   0.944   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       1.401   3.294   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       6.580   4.575   0.000  0.00  0.00           O+0
CONECT    1   13                                                            
CONECT    2   13                                                            
CONECT    3   14                                                            
CONECT    4   14                                                            
CONECT    5   30                                                            
CONECT    6   30                                                            
CONECT    7    8   13                                                       
CONECT    8    7   16                                                       
CONECT    9   10   15                                                       
CONECT   10    9   30                                                       
CONECT   11   17   18                                                       
CONECT   12   19   20                                                       
CONECT   13    1    2    7                                                  
CONECT   14    3    4   17                                                  
CONECT   15    9   24   27                                                  
CONECT   16    8   27   28                                                  
CONECT   17   11   14   21                                                  
CONECT   18   11   25   29                                                  
CONECT   19   12   22   31                                                  
CONECT   20   12   26   32                                                  
CONECT   21   17   22   26                                                  
CONECT   22   19   21   29                                                  
CONECT   23   24   25   28                                                  
CONECT   24   15   23   33                                                  
CONECT   25   18   23   34                                                  
CONECT   26   20   21   35                                                  
CONECT   27   15   16   37                                                  
CONECT   28   16   23   36                                                  
CONECT   29   18   22   36                                                  
CONECT   30    5    6   10   37                                             
CONECT   31   19                                                            
CONECT   32   20                                                            
CONECT   33   24                                                            
CONECT   34   25                                                            
CONECT   35   26                                                            
CONECT   36   28   29                                                       
CONECT   37   27   30                                                       
MASTER        0    0    0    0    0    0    0    0   37    0   82    0
END

View in JSmol

Synonyms

Value	Source
Artonin b	MeSH

Chemical Formula

C₃₀H₃₀O₇

Average Mass

502.5550 Da

Monoisotopic Mass

502.19915 Da

IUPAC Name

5,7,8,15-tetrahydroxy-19,19-dimethyl-22-(3-methylbut-2-en-1-yl)-10-(prop-1-en-2-yl)-2,20-dioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁶,²¹]docosa-1(14),3(12),4(9),5,7,15,17,21-octaen-13-one

Traditional Name

5,7,8,15-tetrahydroxy-19,19-dimethyl-22-(3-methylbut-2-en-1-yl)-10-(prop-1-en-2-yl)-2,20-dioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁶,²¹]docosa-1(14),3(12),4(9),5,7,15,17,21-octaen-13-one

CAS Registry Number

Not Available

SMILES

CC(C)=CCC1=C2OC(C)(C)C=CC2=C(O)C2=C1OC1=C(CC(C(C)=C)C3=C1C(O)=CC(O)=C3O)C2=O

InChI Identifier

InChI=1S/C30H30O7/c1-13(2)7-8-16-27-15(9-10-30(5,6)37-27)24(33)23-25(34)18-11-17(14(3)4)21-22(29(18)36-28(16)23)19(31)12-20(32)26(21)35/h7,9-10,12,17,31-33,35H,3,8,11H2,1-2,4-6H3

InChI Key

IGNKZOMBJGAKHN-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Artocarpus champeden	LOTUS Database	35616633
Artocarpus heterophyllus	LOTUS Database	35616633
Artocarpus styracifolius	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyranoxanthones. These are organic aromatic compounds containing a pyran or a hydrogenated derivative fused to a xanthone ring system.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

Pyranoxanthones

Alternative Parents

Substituents

Pyranoxanthone
Naphthopyranone
Naphthopyran
Pyranochromene
2,2-dimethyl-1-benzopyran
Chromone
1-naphthol
Naphthalene
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
Benzenoid
Pyran
Vinylogous acid
Heteroaromatic compound
Polyol
Oxacycle
Ether
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

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	4.86	ALOGPS
logP	6.15	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	8.12	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	144.6 m³·mol⁻¹	ChemAxon
Polarizability	54.86 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0034667

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB013192

KNApSAcK ID

C00029738

Chemspider ID

10138595

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11964501

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5,7,8,15-tetrahydroxy-19,19-dimethyl-22-(3-methylbut-2-en-1-yl)-10-(prop-1-en-2-yl)-2,20-dioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁶,²¹]docosa-1(22),3(12),4,6,8,14,16(21),17-octaen-13-one (NP0210367)

MOL for NP0210367 (5,7,8,15-tetrahydroxy-19,19-dimethyl-22-(3-methylbut-2-en-1-yl)-10-(prop-1-en-2-yl)-2,20-dioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁶,²¹]docosa-1(22),3(12),4,6,8,14,16(21),17-octaen-13-one)

3D MOL for NP0210367 (5,7,8,15-tetrahydroxy-19,19-dimethyl-22-(3-methylbut-2-en-1-yl)-10-(prop-1-en-2-yl)-2,20-dioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁶,²¹]docosa-1(22),3(12),4,6,8,14,16(21),17-octaen-13-one)

3D SDF for NP0210367 (5,7,8,15-tetrahydroxy-19,19-dimethyl-22-(3-methylbut-2-en-1-yl)-10-(prop-1-en-2-yl)-2,20-dioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁶,²¹]docosa-1(22),3(12),4,6,8,14,16(21),17-octaen-13-one)

3D-SDF for NP0210367 (5,7,8,15-tetrahydroxy-19,19-dimethyl-22-(3-methylbut-2-en-1-yl)-10-(prop-1-en-2-yl)-2,20-dioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁶,²¹]docosa-1(22),3(12),4,6,8,14,16(21),17-octaen-13-one)

PDB for NP0210367 (5,7,8,15-tetrahydroxy-19,19-dimethyl-22-(3-methylbut-2-en-1-yl)-10-(prop-1-en-2-yl)-2,20-dioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁶,²¹]docosa-1(22),3(12),4,6,8,14,16(21),17-octaen-13-one)

3D PDB for NP0210367 (5,7,8,15-tetrahydroxy-19,19-dimethyl-22-(3-methylbut-2-en-1-yl)-10-(prop-1-en-2-yl)-2,20-dioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁶,²¹]docosa-1(22),3(12),4,6,8,14,16(21),17-octaen-13-one)

SMILES for NP0210367 (5,7,8,15-tetrahydroxy-19,19-dimethyl-22-(3-methylbut-2-en-1-yl)-10-(prop-1-en-2-yl)-2,20-dioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁶,²¹]docosa-1(22),3(12),4,6,8,14,16(21),17-octaen-13-one)

INCHI for NP0210367 (5,7,8,15-tetrahydroxy-19,19-dimethyl-22-(3-methylbut-2-en-1-yl)-10-(prop-1-en-2-yl)-2,20-dioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁶,²¹]docosa-1(22),3(12),4,6,8,14,16(21),17-octaen-13-one)

Structure for NP0210367 (5,7,8,15-tetrahydroxy-19,19-dimethyl-22-(3-methylbut-2-en-1-yl)-10-(prop-1-en-2-yl)-2,20-dioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁶,²¹]docosa-1(22),3(12),4,6,8,14,16(21),17-octaen-13-one)

3D Structure for NP0210367 (5,7,8,15-tetrahydroxy-19,19-dimethyl-22-(3-methylbut-2-en-1-yl)-10-(prop-1-en-2-yl)-2,20-dioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁶,²¹]docosa-1(22),3(12),4,6,8,14,16(21),17-octaen-13-one)