NP-MRD: Showing NP-Card for (10r)-1,3,6-trihydroxy-2,7-bis(3-methylbut-2-en-1-yl)-10-(prop-1-en-2-yl)-10,11-dihydro-5-oxatetraphene-8,9,12-trione (NP0287530)

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Record Information

Version

2.0

Created at

2022-09-09 16:42:48 UTC

Updated at

2022-09-09 16:42:49 UTC

NP-MRD ID

NP0287530

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(10r)-1,3,6-trihydroxy-2,7-bis(3-methylbut-2-en-1-yl)-10-(prop-1-en-2-yl)-10,11-dihydro-5-oxatetraphene-8,9,12-trione

Description

Artonin O belongs to the class of organic compounds known as xanthones. These are polycyclic aromatic compounds containing a xanthene moiety conjugated to a ketone group at carbon 9. Xanthene is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring. (10r)-1,3,6-trihydroxy-2,7-bis(3-methylbut-2-en-1-yl)-10-(prop-1-en-2-yl)-10,11-dihydro-5-oxatetraphene-8,9,12-trione is found in Artocarpus kemando and Artocarpus rigidus. (10r)-1,3,6-trihydroxy-2,7-bis(3-methylbut-2-en-1-yl)-10-(prop-1-en-2-yl)-10,11-dihydro-5-oxatetraphene-8,9,12-trione was first documented in 2010 (PMID: 20384315). Based on a literature review a small amount of articles have been published on Artonin O.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092218422D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309092218422D          

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  4 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 30 36  2  0  0  0  0
 24 36  1  0  0  0  0
 36 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0287530

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC1=C(O)C=C2OC3=C(C[C@H](C(C)=C)C4=C3C(O)=C(CC=C(C)C)C(=O)C4=O)C(=O)C2=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C30H30O7/c1-13(2)7-9-16-20(31)12-21-23(25(16)32)27(34)19-11-18(15(5)6)22-24(30(19)37-21)26(33)17(10-8-14(3)4)28(35)29(22)36/h7-8,12,18,31-33H,5,9-11H2,1-4,6H3/t18-/m1/s1

> <INCHI_KEY>
RITJEVMEGJQWAA-GOSISDBHSA-N

> <FORMULA>
C30H30O7

> <MOLECULAR_WEIGHT>
502.563

> <EXACT_MASS>
502.199153306

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
54.42379192824734

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(10R)-1,3,6-trihydroxy-2,7-bis(3-methylbut-2-en-1-yl)-10-(prop-1-en-2-yl)-9,10,11,12-tetrahydro-8H-5-oxatetraphene-8,9,12-trione

> <JCHEM_LOGP>
6.034026424

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.973147768927022

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.8242367237167603

> <JCHEM_PKA_STRONGEST_BASIC>
-5.407495018054166

> <JCHEM_POLAR_SURFACE_AREA>
121.12999999999998

> <JCHEM_REFRACTIVITY>
145.3763

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(10R)-1,3,6-trihydroxy-2,7-bis(3-methylbut-2-en-1-yl)-10-(prop-1-en-2-yl)-10,11-dihydro-5-oxatetraphene-8,9,12-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.179  -3.013   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -3.304   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.838  -4.760   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.342  -2.140   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.854  -2.431   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.862  -1.267   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.358   0.188   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       5.366   1.352   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       6.879   1.061   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.887   2.225   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.399   1.934   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      10.407   3.098   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       9.903   0.479   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.415   0.188   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.919  -1.267   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.432  -1.558   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.440  -0.394   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.936  -3.013   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.895  -0.685   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       9.399  -2.140   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       7.383  -0.394   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.375  -1.558   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.879  -3.013   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.846   0.479   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.838  -0.685   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.326  -0.394   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -0.683  -1.558   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -0.179   1.061   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -1.691   1.352   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       0.830   2.225   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.326   3.680   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -1.187   3.971   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -1.691   5.427   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -3.203   5.718   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -0.683   6.591   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       2.342   1.934   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       3.350   3.098   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   25                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   22                                                  
CONECT    7    6    8   24                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   21                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   19                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   13   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19    9   22                                                  
CONECT   22   21    6   23                                                  
CONECT   23   22                                                            
CONECT   24    7   25   36                                                  
CONECT   25   24    4   26                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   36                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36   30   24   37                                                  
CONECT   37   36                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₃₀O₇

Average Mass

502.5630 Da

Monoisotopic Mass

502.19915 Da

IUPAC Name

(10R)-1,3,6-trihydroxy-2,7-bis(3-methylbut-2-en-1-yl)-10-(prop-1-en-2-yl)-9,10,11,12-tetrahydro-8H-5-oxatetraphene-8,9,12-trione

Traditional Name

(10R)-1,3,6-trihydroxy-2,7-bis(3-methylbut-2-en-1-yl)-10-(prop-1-en-2-yl)-10,11-dihydro-5-oxatetraphene-8,9,12-trione

CAS Registry Number

Not Available

SMILES

CC(C)=CCC1=C(O)C=C2OC3=C(C[C@H](C(C)=C)C4=C3C(O)=C(CC=C(C)C)C(=O)C4=O)C(=O)C2=C1O

InChI Identifier

InChI=1S/C30H30O7/c1-13(2)7-9-16-20(31)12-21-23(25(16)32)27(34)19-11-18(15(5)6)22-24(30(19)37-21)26(33)17(10-8-14(3)4)28(35)29(22)36/h7-8,12,18,31-33H,5,9-11H2,1-4,6H3/t18-/m1/s1

InChI Key

RITJEVMEGJQWAA-GOSISDBHSA-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 kemando	LOTUS Database	35616633
Artocarpus rigidus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as xanthones. These are polycyclic aromatic compounds containing a xanthene moiety conjugated to a ketone group at carbon 9. Xanthene is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

Xanthones

Alternative Parents

Substituents

Naphthopyranone
Xanthone
Naphthopyran
Chromone
Naphthalene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyranone
Pyran
Benzenoid
Vinylogous acid
Heteroaromatic compound
Ketone
Cyclic ketone
Polyol
Oxacycle
Enol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
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	6.03	ChemAxon
pKa (Strongest Acidic)	3.82	ChemAxon
pKa (Strongest Basic)	-5.4	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	121.13 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	145.38 m³·mol⁻¹	ChemAxon
Polarizability	54.42 Å³	ChemAxon
Number of Rings	4	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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00013493

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

46887814

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ren Y, Kardono LB, Riswan S, Chai H, Farnsworth NR, Soejarto DD, Carcache de Blanco EJ, Kinghorn AD: Cytotoxic and NF-kappaB inhibitory constituents of Artocarpus rigida. J Nat Prod. 2010 May 28;73(5):949-55. doi: 10.1021/np1002065. [PubMed:20384315 ]
LOTUS database [Link]

Showing NP-Card for (10r)-1,3,6-trihydroxy-2,7-bis(3-methylbut-2-en-1-yl)-10-(prop-1-en-2-yl)-10,11-dihydro-5-oxatetraphene-8,9,12-trione (NP0287530)

MOL for NP0287530 ((10r)-1,3,6-trihydroxy-2,7-bis(3-methylbut-2-en-1-yl)-10-(prop-1-en-2-yl)-10,11-dihydro-5-oxatetraphene-8,9,12-trione)

3D MOL for NP0287530 ((10r)-1,3,6-trihydroxy-2,7-bis(3-methylbut-2-en-1-yl)-10-(prop-1-en-2-yl)-10,11-dihydro-5-oxatetraphene-8,9,12-trione)

3D SDF for NP0287530 ((10r)-1,3,6-trihydroxy-2,7-bis(3-methylbut-2-en-1-yl)-10-(prop-1-en-2-yl)-10,11-dihydro-5-oxatetraphene-8,9,12-trione)

3D-SDF for NP0287530 ((10r)-1,3,6-trihydroxy-2,7-bis(3-methylbut-2-en-1-yl)-10-(prop-1-en-2-yl)-10,11-dihydro-5-oxatetraphene-8,9,12-trione)

PDB for NP0287530 ((10r)-1,3,6-trihydroxy-2,7-bis(3-methylbut-2-en-1-yl)-10-(prop-1-en-2-yl)-10,11-dihydro-5-oxatetraphene-8,9,12-trione)

3D PDB for NP0287530 ((10r)-1,3,6-trihydroxy-2,7-bis(3-methylbut-2-en-1-yl)-10-(prop-1-en-2-yl)-10,11-dihydro-5-oxatetraphene-8,9,12-trione)

SMILES for NP0287530 ((10r)-1,3,6-trihydroxy-2,7-bis(3-methylbut-2-en-1-yl)-10-(prop-1-en-2-yl)-10,11-dihydro-5-oxatetraphene-8,9,12-trione)

INCHI for NP0287530 ((10r)-1,3,6-trihydroxy-2,7-bis(3-methylbut-2-en-1-yl)-10-(prop-1-en-2-yl)-10,11-dihydro-5-oxatetraphene-8,9,12-trione)

Structure for NP0287530 ((10r)-1,3,6-trihydroxy-2,7-bis(3-methylbut-2-en-1-yl)-10-(prop-1-en-2-yl)-10,11-dihydro-5-oxatetraphene-8,9,12-trione)

3D Structure for NP0287530 ((10r)-1,3,6-trihydroxy-2,7-bis(3-methylbut-2-en-1-yl)-10-(prop-1-en-2-yl)-10,11-dihydro-5-oxatetraphene-8,9,12-trione)