NP-MRD: Showing NP-Card for 12,21,23-trihydroxy-8,8,18,18-tetramethyl-5-(3-methylbut-2-en-1-yl)-3,7,19-trioxahexacyclo[15.6.1.0²,¹⁵.0⁴,¹³.0⁶,¹¹.0²⁰,²⁴]tetracosa-1(23),2(15),4,6(11),9,12,20(24),21-octaen-14-one (NP0154900)

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Record Information

Version

2.0

Created at

2022-09-02 11:52:58 UTC

Updated at

2022-09-02 11:52:58 UTC

NP-MRD ID

NP0154900

Secondary Accession Numbers

None

Natural Product Identification

Common Name

12,21,23-trihydroxy-8,8,18,18-tetramethyl-5-(3-methylbut-2-en-1-yl)-3,7,19-trioxahexacyclo[15.6.1.0²,¹⁵.0⁴,¹³.0⁶,¹¹.0²⁰,²⁴]tetracosa-1(23),2(15),4,6(11),9,12,20(24),21-octaen-14-one

Description

Artonin A 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 A is a very strong basic compound (based on its pKa). Outside of the human body, artonin a has been detected, but not quantified in, fruits. 12,21,23-trihydroxy-8,8,18,18-tetramethyl-5-(3-methylbut-2-en-1-yl)-3,7,19-trioxahexacyclo[15.6.1.0²,¹⁵.0⁴,¹³.0⁶,¹¹.0²⁰,²⁴]tetracosa-1(23),2(15),4,6(11),9,12,20(24),21-octaen-14-one is found in Artocarpus chama, Artocarpus integer, Artocarpus heterophyllus, Artocarpus styracifolius and Artocarpus tonkinensis. This could make artonin a a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061307592D          

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M  END

     RDKit          3D

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M  END


  Mrv0541 05061307592D          

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 20 17  1  0  0  0  0
 21 18  1  0  0  0  0
 21 20  2  0  0  0  0
 23 14  2  0  0  0  0
 23 22  1  0  0  0  0
 24 16  1  0  0  0  0
 24 22  1  0  0  0  0
 25 14  1  0  0  0  0
 25 15  2  0  0  0  0
 26 15  1  0  0  0  0
 26 22  2  0  0  0  0
 27 16  2  0  0  0  0
 27 21  1  0  0  0  0
 28 19  2  0  0  0  0
 28 20  1  0  0  0  0
 29  3  1  0  0  0  0
 29  4  1  0  0  0  0
 29 10  1  0  0  0  0
 30  5  1  0  0  0  0
 30  6  1  0  0  0  0
 30 17  1  0  0  0  0
 31 18  1  0  0  0  0
 32 19  1  0  0  0  0
 33 23  1  0  0  0  0
 34 24  2  0  0  0  0
 35 26  1  0  0  0  0
 35 27  1  0  0  0  0
 36 25  1  0  0  0  0
 36 29  1  0  0  0  0
 37 28  1  0  0  0  0
 37 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0154900

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC1=C2OC(C)(C)C=CC2=C(O)C2=C1OC1=C(CC3C4=C1C(O)=CC(O)=C4OC3(C)C)C2=O

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

> <INCHI_KEY>
CYONWSIQFYQFOS-UHFFFAOYSA-N

> <FORMULA>
C30H30O7

> <MOLECULAR_WEIGHT>
502.555

> <EXACT_MASS>
502.199153314

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
55.44342826509516

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
12,21,23-trihydroxy-8,8,18,18-tetramethyl-5-(3-methylbut-2-en-1-yl)-3,7,19-trioxahexacyclo[15.6.1.0²,¹⁵.0⁴,¹³.0⁶,¹¹.0²⁰,²⁴]tetracosa-1(24),2(15),4(13),5,9,11,20,22-octaen-14-one

> <ALOGPS_LOGP>
5.64

> <JCHEM_LOGP>
5.767477216666666

> <ALOGPS_LOGS>
-5.04

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
6.255343136042513

> <JCHEM_PKA_STRONGEST_ACIDIC>
-8.21632997037283

> <JCHEM_PKA_STRONGEST_BASIC>
10.74024641395223

> <JCHEM_POLAR_SURFACE_AREA>
105.45

> <JCHEM_REFRACTIVITY>
142.8054

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.61e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
12,21,23-trihydroxy-8,8,18,18-tetramethyl-5-(3-methylbut-2-en-1-yl)-3,7,19-trioxahexacyclo[15.6.1.0²,¹⁵.0⁴,¹³.0⁶,¹¹.0²⁰,²⁴]tetracosa-1(24),2(15),4(13),5,9,11,20,22-octaen-14-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       2.423  -8.765   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.086 -11.073   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.238 -10.705   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.258 -10.708   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.181   2.423   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.492   3.610   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.245  -8.762   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.243  -7.222   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.577  -7.215   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.579  -8.755   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.570  -0.290   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.760  -1.830   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.088  -9.533   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.243  -6.447   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.575  -6.450   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.570  -1.830   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.240   0.480   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.430  -2.600   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.760  -0.290   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.090  -0.290   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.090  -1.830   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.906  -4.138   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -4.241  -4.907   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.905  -2.598   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.910  -7.218   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.574  -4.910   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.237  -2.602   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.430   0.480   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -4.246  -9.527   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.320   2.080   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       2.432  -4.140   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       5.094   0.479   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -5.574  -4.135   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      -4.237  -1.827   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      -0.239  -4.142   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      -2.912  -8.758   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       1.860   2.080   0.000  0.00  0.00           O+0
CONECT    1   13                                                            
CONECT    2   13                                                            
CONECT    3   29                                                            
CONECT    4   29                                                            
CONECT    5   30                                                            
CONECT    6   30                                                            
CONECT    7    8   13                                                       
CONECT    8    7   15                                                       
CONECT    9   10   14                                                       
CONECT   10    9   29                                                       
CONECT   11   16   17                                                       
CONECT   12   18   19                                                       
CONECT   13    1    2    7                                                  
CONECT   14    9   23   25                                                  
CONECT   15    8   25   26                                                  
CONECT   16   11   24   27                                                  
CONECT   17   11   20   30                                                  
CONECT   18   12   21   31                                                  
CONECT   19   12   28   32                                                  
CONECT   20   17   21   28                                                  
CONECT   21   18   20   27                                                  
CONECT   22   23   24   26                                                  
CONECT   23   14   22   33                                                  
CONECT   24   16   22   34                                                  
CONECT   25   14   15   36                                                  
CONECT   26   15   22   35                                                  
CONECT   27   16   21   35                                                  
CONECT   28   19   20   37                                                  
CONECT   29    3    4   10   36                                             
CONECT   30    5    6   17   37                                             
CONECT   31   18                                                            
CONECT   32   19                                                            
CONECT   33   23                                                            
CONECT   34   24                                                            
CONECT   35   26   27                                                       
CONECT   36   25   29                                                       
CONECT   37   28   30                                                       
MASTER        0    0    0    0    0    0    0    0   37    0   84    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₃₀O₇

Average Mass

502.5550 Da

Monoisotopic Mass

502.19915 Da

IUPAC Name

12,21,23-trihydroxy-8,8,18,18-tetramethyl-5-(3-methylbut-2-en-1-yl)-3,7,19-trioxahexacyclo[15.6.1.0²,¹⁵.0⁴,¹³.0⁶,¹¹.0²⁰,²⁴]tetracosa-1(24),2(15),4(13),5,9,11,20,22-octaen-14-one

Traditional Name

12,21,23-trihydroxy-8,8,18,18-tetramethyl-5-(3-methylbut-2-en-1-yl)-3,7,19-trioxahexacyclo[15.6.1.0²,¹⁵.0⁴,¹³.0⁶,¹¹.0²⁰,²⁴]tetracosa-1(24),2(15),4(13),5,9,11,20,22-octaen-14-one

CAS Registry Number

Not Available

SMILES

CC(C)=CCC1=C2OC(C)(C)C=CC2=C(O)C2=C1OC1=C(CC3C4=C1C(O)=CC(O)=C4OC3(C)C)C2=O

InChI Identifier

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

InChI Key

CYONWSIQFYQFOS-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 chama	LOTUS Database	35616633
Artocarpus champeden	LOTUS Database	35616633
Artocarpus heterophyllus	LOTUS Database	35616633
Artocarpus styracifolius	LOTUS Database	35616633
Artocarpus tonkinensis	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
Coumaran
Alkyl aryl ether
Pyranone
1-hydroxy-2-unsubstituted benzenoid
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	5.64	ALOGPS
logP	5.77	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	-8.2	ChemAxon
pKa (Strongest Basic)	10.74	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	2	ChemAxon
Refractivity	142.81 m³·mol⁻¹	ChemAxon
Polarizability	55.44 Å³	ChemAxon
Number of Rings	6	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

HMDB0034665

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB013190

KNApSAcK ID

C00029737

Chemspider ID

10211393

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14557102

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 12,21,23-trihydroxy-8,8,18,18-tetramethyl-5-(3-methylbut-2-en-1-yl)-3,7,19-trioxahexacyclo[15.6.1.0²,¹⁵.0⁴,¹³.0⁶,¹¹.0²⁰,²⁴]tetracosa-1(23),2(15),4,6(11),9,12,20(24),21-octaen-14-one (NP0154900)

MOL for NP0154900 (12,21,23-trihydroxy-8,8,18,18-tetramethyl-5-(3-methylbut-2-en-1-yl)-3,7,19-trioxahexacyclo[15.6.1.0²,¹⁵.0⁴,¹³.0⁶,¹¹.0²⁰,²⁴]tetracosa-1(23),2(15),4,6(11),9,12,20(24),21-octaen-14-one)

3D MOL for NP0154900 (12,21,23-trihydroxy-8,8,18,18-tetramethyl-5-(3-methylbut-2-en-1-yl)-3,7,19-trioxahexacyclo[15.6.1.0²,¹⁵.0⁴,¹³.0⁶,¹¹.0²⁰,²⁴]tetracosa-1(23),2(15),4,6(11),9,12,20(24),21-octaen-14-one)

3D SDF for NP0154900 (12,21,23-trihydroxy-8,8,18,18-tetramethyl-5-(3-methylbut-2-en-1-yl)-3,7,19-trioxahexacyclo[15.6.1.0²,¹⁵.0⁴,¹³.0⁶,¹¹.0²⁰,²⁴]tetracosa-1(23),2(15),4,6(11),9,12,20(24),21-octaen-14-one)

3D-SDF for NP0154900 (12,21,23-trihydroxy-8,8,18,18-tetramethyl-5-(3-methylbut-2-en-1-yl)-3,7,19-trioxahexacyclo[15.6.1.0²,¹⁵.0⁴,¹³.0⁶,¹¹.0²⁰,²⁴]tetracosa-1(23),2(15),4,6(11),9,12,20(24),21-octaen-14-one)

PDB for NP0154900 (12,21,23-trihydroxy-8,8,18,18-tetramethyl-5-(3-methylbut-2-en-1-yl)-3,7,19-trioxahexacyclo[15.6.1.0²,¹⁵.0⁴,¹³.0⁶,¹¹.0²⁰,²⁴]tetracosa-1(23),2(15),4,6(11),9,12,20(24),21-octaen-14-one)

3D PDB for NP0154900 (12,21,23-trihydroxy-8,8,18,18-tetramethyl-5-(3-methylbut-2-en-1-yl)-3,7,19-trioxahexacyclo[15.6.1.0²,¹⁵.0⁴,¹³.0⁶,¹¹.0²⁰,²⁴]tetracosa-1(23),2(15),4,6(11),9,12,20(24),21-octaen-14-one)

SMILES for NP0154900 (12,21,23-trihydroxy-8,8,18,18-tetramethyl-5-(3-methylbut-2-en-1-yl)-3,7,19-trioxahexacyclo[15.6.1.0²,¹⁵.0⁴,¹³.0⁶,¹¹.0²⁰,²⁴]tetracosa-1(23),2(15),4,6(11),9,12,20(24),21-octaen-14-one)

INCHI for NP0154900 (12,21,23-trihydroxy-8,8,18,18-tetramethyl-5-(3-methylbut-2-en-1-yl)-3,7,19-trioxahexacyclo[15.6.1.0²,¹⁵.0⁴,¹³.0⁶,¹¹.0²⁰,²⁴]tetracosa-1(23),2(15),4,6(11),9,12,20(24),21-octaen-14-one)

Structure for NP0154900 (12,21,23-trihydroxy-8,8,18,18-tetramethyl-5-(3-methylbut-2-en-1-yl)-3,7,19-trioxahexacyclo[15.6.1.0²,¹⁵.0⁴,¹³.0⁶,¹¹.0²⁰,²⁴]tetracosa-1(23),2(15),4,6(11),9,12,20(24),21-octaen-14-one)

3D Structure for NP0154900 (12,21,23-trihydroxy-8,8,18,18-tetramethyl-5-(3-methylbut-2-en-1-yl)-3,7,19-trioxahexacyclo[15.6.1.0²,¹⁵.0⁴,¹³.0⁶,¹¹.0²⁰,²⁴]tetracosa-1(23),2(15),4,6(11),9,12,20(24),21-octaen-14-one)