NP-MRD: Showing NP-Card for Artonin R (NP0084498)

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Record Information

Version

2.0

Created at

2022-04-29 05:13:27 UTC

Updated at

2022-04-29 05:13:27 UTC

NP-MRD ID

NP0084498

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Artonin R

Description

Artonin R 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 R is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, artonin R has been detected, but not quantified in, fruits. Artonin R is found in Artocarpus integer and Artocarpus heterophyllus . This could make artonin R a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061312242D          

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M  END

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 14  2  1  0  0  0  0
 15  8  1  0  0  0  0
 16  9  1  0  0  0  0
 17 12  2  0  0  0  0
 17 14  1  0  0  0  0
 18 12  1  0  0  0  0
 19 13  1  0  0  0  0
 20 19  1  0  0  0  0
 22 17  1  0  0  0  0
 22 20  2  0  0  0  0
 23 15  2  0  0  0  0
 23 21  1  0  0  0  0
 24 18  1  0  0  0  0
 24 21  1  0  0  0  0
 25 15  1  0  0  0  0
 25 16  2  0  0  0  0
 26 16  1  0  0  0  0
 26 21  2  0  0  0  0
 27 18  2  0  0  0  0
 27 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 11  1  0  0  0  0
 31 13  1  0  0  0  0
 31 22  1  0  0  0  0
 31 28  1  0  0  0  0
 32 19  2  0  0  0  0
 33 23  1  0  0  0  0
 34 24  2  0  0  0  0
 35 28  2  0  0  0  0
 36 31  1  0  0  0  0
 38  7  1  0  0  0  0
 38 28  1  0  0  0  0
 39 26  1  0  0  0  0
 39 27  1  0  0  0  0
 40 25  1  0  0  0  0
 40 29  1  0  0  0  0
 41 30  1  0  0  0  0
 41 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0084498

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1(O)CC(=O)C2=C1C(=CC1=C2OC2=C(C(O)=C3C=CC(C)(C)OC3=C2\C=C\C(C)(C)OO)C1=O)C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C31H30O10/c1-14(2)17-12-18-24(34)21-23(33)15-8-10-29(3,4)40-25(15)16(9-11-30(5,6)41-37)26(21)39-27(18)20-19(32)13-31(36,22(17)20)28(35)38-7/h8-12,33,36-37H,1,13H2,2-7H3/b11-9+

> <INCHI_KEY>
DHSZUELPJXKISQ-PKNBQFBNSA-N

> <FORMULA>
C31H30O10

> <MOLECULAR_WEIGHT>
562.5639

> <EXACT_MASS>
562.18389718

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
59.293172571090835

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 21-[(1E)-3-hydroperoxy-3-methylbut-1-en-1-yl]-7,14-dihydroxy-18,18-dimethyl-5,12-dioxo-9-(prop-1-en-2-yl)-2,19-dioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁵,²⁰]henicosa-1(13),3(11),4(8),9,14,16,20-heptaene-7-carboxylate

> <ALOGPS_LOGP>
3.03

> <JCHEM_LOGP>
4.872279043666666

> <ALOGPS_LOGS>
-5.20

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.825372749062634

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.140535413949333

> <JCHEM_PKA_STRONGEST_BASIC>
-4.242202793851477

> <JCHEM_POLAR_SURFACE_AREA>
148.82

> <JCHEM_REFRACTIVITY>
150.6233

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.56e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 21-[(1E)-3-hydroperoxy-3-methylbut-1-en-1-yl]-7,14-dihydroxy-18,18-dimethyl-5,12-dioxo-9-(prop-1-en-2-yl)-2,19-dioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁵,²⁰]henicosa-1(13),3(11),4(8),9,14,16,20-heptaene-7-carboxylate

> <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      -4.641  -0.547   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.832  -2.507   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.569   3.960   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.227   5.415   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.915   8.146   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.911   7.469   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -7.667   1.282   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.238   1.340   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.620   5.261   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.369   2.385   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.752   6.305   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.569  -0.419   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.419   3.806   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.171  -1.005   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.767   1.799   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.958   3.759   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.039   0.039   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.563   0.626   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.889   3.985   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.246   2.586   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.165   1.212   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.378   1.542   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.635   0.754   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.033   0.168   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.429   3.301   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.827   2.715   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.225   2.128   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -5.255   2.422   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.031   3.887   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.413   7.808   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -3.721   2.295   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -1.136   5.328   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       4.974  -0.748   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       2.372  -1.334   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      -5.913   3.814   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      -4.624   1.048   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       2.604   9.768   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      -6.132   1.156   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0       1.356   3.172   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0       6.561   4.345   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0       4.075   9.310   0.000  0.00  0.00           O+0
CONECT    1   14                                                            
CONECT    2   14                                                            
CONECT    3   29                                                            
CONECT    4   29                                                            
CONECT    5   30                                                            
CONECT    6   30                                                            
CONECT    7   38                                                            
CONECT    8   10   15                                                       
CONECT    9   11   16                                                       
CONECT   10    8   29                                                       
CONECT   11    9   30                                                       
CONECT   12   17   18                                                       
CONECT   13   19   31                                                       
CONECT   14    1    2   17                                                  
CONECT   15    8   23   25                                                  
CONECT   16    9   25   26                                                  
CONECT   17   12   14   22                                                  
CONECT   18   12   24   27                                                  
CONECT   19   13   20   32                                                  
CONECT   20   19   22   27                                                  
CONECT   21   23   24   26                                                  
CONECT   22   17   20   31                                                  
CONECT   23   15   21   33                                                  
CONECT   24   18   21   34                                                  
CONECT   25   15   16   40                                                  
CONECT   26   16   21   39                                                  
CONECT   27   18   20   39                                                  
CONECT   28   31   35   38                                                  
CONECT   29    3    4   10   40                                             
CONECT   30    5    6   11   41                                             
CONECT   31   13   22   28   36                                             
CONECT   32   19                                                            
CONECT   33   23                                                            
CONECT   34   24                                                            
CONECT   35   28                                                            
CONECT   36   31                                                            
CONECT   37   41                                                            
CONECT   38    7   28                                                       
CONECT   39   26   27                                                       
CONECT   40   25   29                                                       
CONECT   41   30   37                                                       
MASTER        0    0    0    0    0    0    0    0   41    0   90    0
END

View in JSmol

Synonyms

Value	Source
Methyl 21-[(1E)-3-hydroperoxy-3-methylbut-1-en-1-yl]-7,14-dihydroxy-18,18-dimethyl-5,12-dioxo-9-(prop-1-en-2-yl)-2,19-dioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁵,²⁰]henicosa-1(13),3(11),4(8),9,14,16,20-heptaene-7-carboxylic acid	Generator

Chemical Formula

C₃₁H₃₀O₁₀

Average Mass

562.5639 Da

Monoisotopic Mass

562.18390 Da

IUPAC Name

methyl 21-[(1E)-3-hydroperoxy-3-methylbut-1-en-1-yl]-7,14-dihydroxy-18,18-dimethyl-5,12-dioxo-9-(prop-1-en-2-yl)-2,19-dioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁵,²⁰]henicosa-1(13),3(11),4(8),9,14,16,20-heptaene-7-carboxylate

Traditional Name

CAS Registry Number

Not Available

SMILES

COC(=O)C1(O)CC(=O)C2=C1C(=CC1=C2OC2=C(C(O)=C3C=CC(C)(C)OC3=C2\C=C\C(C)(C)OO)C1=O)C(C)=C

InChI Identifier

InChI=1S/C31H30O10/c1-14(2)17-12-18-24(34)21-23(33)15-8-10-29(3,4)40-25(15)16(9-11-30(5,6)41-37)26(21)39-27(18)20-19(32)13-31(36,22(17)20)28(35)38-7/h8-12,33,36-37H,1,13H2,2-7H3/b11-9+

InChI Key

DHSZUELPJXKISQ-PKNBQFBNSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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	Plant	KNApSAcK

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

Not Available

Substituents

Not Available

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	3.03	ALOGPS
logP	4.87	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	9.14	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	148.82 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	150.62 m³·mol⁻¹	ChemAxon
Polarizability	59.29 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0041125

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB021007

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131753035

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Artonin R (NP0084498)

MOL for NP0084498 (Artonin R)

3D MOL for NP0084498 (Artonin R)

3D SDF for NP0084498 (Artonin R)

3D-SDF for NP0084498 (Artonin R)

PDB for NP0084498 (Artonin R)

3D PDB for NP0084498 (Artonin R)

SMILES for NP0084498 (Artonin R)

INCHI for NP0084498 (Artonin R)

Structure for NP0084498 (Artonin R)

3D Structure for NP0084498 (Artonin R)