NP-MRD: Showing NP-Card for 1,6-dihydroxy-8-(2-hydroxy-3-methylbut-3-en-1-yl)-3,7-dimethoxy-2-(3-methylbut-2-en-1-yl)xanthen-9-one (NP0142141)

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Record Information

Version

2.0

Created at

2022-09-01 20:36:44 UTC

Updated at

2022-09-01 20:36:44 UTC

NP-MRD ID

NP0142141

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1,6-dihydroxy-8-(2-hydroxy-3-methylbut-3-en-1-yl)-3,7-dimethoxy-2-(3-methylbut-2-en-1-yl)xanthen-9-one

Description

1,6-Dihydroxy-3,7-dimethoxy-2-(3-methyl-2-butenyl)-8-(2-hydroxy-3-methyl-3-butenyl)-xanthone belongs to the class of organic compounds known as 8-prenylated xanthones. These are organic compounds containing a C5-isoprenoid group linked to a xanthone moiety at the 8-position. Xanthone is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring that carries a ketone group. 1,6-Dihydroxy-3,7-dimethoxy-2-(3-methyl-2-butenyl)-8-(2-hydroxy-3-methyl-3-butenyl)-xanthone is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 1,6-Dihydroxy-3,7-dimethoxy-2-(3-methyl-2-butenyl)-8-(2-hydroxy-3-methyl-3-butenyl)-xanthone has been detected, but not quantified in, fruits. 1,6-dihydroxy-8-(2-hydroxy-3-methylbut-3-en-1-yl)-3,7-dimethoxy-2-(3-methylbut-2-en-1-yl)xanthen-9-one is found in Garcinia mangostana. This could make 1,6-dihydroxy-3,7-dimethoxy-2-(3-methyl-2-butenyl)-8-(2-hydroxy-3-methyl-3-butenyl)-xanthone a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061311292D          

 32 34  0  0  0  0            999 V2000
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M  END

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M  END


  Mrv0541 05061311292D          

 32 34  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0142141

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C(O)=C1CC=C(C)C)C(=O)C1=C(CC(O)C(C)=C)C(OC)=C(O)C=C1O2

> <INCHI_IDENTIFIER>
InChI=1S/C25H28O7/c1-12(2)7-8-14-18(30-5)11-20-22(23(14)28)24(29)21-15(9-16(26)13(3)4)25(31-6)17(27)10-19(21)32-20/h7,10-11,16,26-28H,3,8-9H2,1-2,4-6H3

> <INCHI_KEY>
OHGAQNFIUCKPAY-UHFFFAOYSA-N

> <FORMULA>
C25H28O7

> <MOLECULAR_WEIGHT>
440.4856

> <EXACT_MASS>
440.18350325

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
47.98603032786271

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,6-dihydroxy-8-(2-hydroxy-3-methylbut-3-en-1-yl)-3,7-dimethoxy-2-(3-methylbut-2-en-1-yl)-9H-xanthen-9-one

> <ALOGPS_LOGP>
3.47

> <JCHEM_LOGP>
4.971423647666667

> <ALOGPS_LOGS>
-4.42

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.414950251957853

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.959310644472528

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0735772915367248

> <JCHEM_POLAR_SURFACE_AREA>
105.45

> <JCHEM_REFRACTIVITY>
122.63309999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.68e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,6-dihydroxy-8-(2-hydroxy-3-methylbut-3-en-1-yl)-3,7-dimethoxy-2-(3-methylbut-2-en-1-yl)xanthen-9-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      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.669   9.240   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002   9.240   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.003   3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.336   8.470   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.336   6.930   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      10.669   6.160   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      10.669   1.540   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      10.669   4.620   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
CONECT    1   12                                                            
CONECT    2   12                                                            
CONECT    3   13                                                            
CONECT    4   13                                                            
CONECT    5   30                                                            
CONECT    6   31                                                            
CONECT    7    8   12                                                       
CONECT    8    7   14                                                       
CONECT    9   15   16                                                       
CONECT   10   17   19                                                       
CONECT   11   18   20                                                       
CONECT   12    1    2    7                                                  
CONECT   13    3    4   16                                                  
CONECT   14    8   18   23                                                  
CONECT   15    9   21   25                                                  
CONECT   16    9   13   26                                                  
CONECT   17   10   25   27                                                  
CONECT   18   11   14   30                                                  
CONECT   19   10   21   32                                                  
CONECT   20   11   22   32                                                  
CONECT   21   15   19   24                                                  
CONECT   22   20   23   24                                                  
CONECT   23   14   22   28                                                  
CONECT   24   21   22   29                                                  
CONECT   25   15   17   31                                                  
CONECT   26   16                                                            
CONECT   27   17                                                            
CONECT   28   23                                                            
CONECT   29   24                                                            
CONECT   30    5   18                                                       
CONECT   31    6   25                                                       
CONECT   32   19   20                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₂₈O₇

Average Mass

440.4856 Da

Monoisotopic Mass

440.18350 Da

IUPAC Name

1,6-dihydroxy-8-(2-hydroxy-3-methylbut-3-en-1-yl)-3,7-dimethoxy-2-(3-methylbut-2-en-1-yl)-9H-xanthen-9-one

Traditional Name

1,6-dihydroxy-8-(2-hydroxy-3-methylbut-3-en-1-yl)-3,7-dimethoxy-2-(3-methylbut-2-en-1-yl)xanthen-9-one

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C(O)=C1CC=C(C)C)C(=O)C1=C(CC(O)C(C)=C)C(OC)=C(O)C=C1O2

InChI Identifier

InChI=1S/C25H28O7/c1-12(2)7-8-14-18(30-5)11-20-22(23(14)28)24(29)21-15(9-16(26)13(3)4)25(31-6)17(27)10-19(21)32-20/h7,10-11,16,26-28H,3,8-9H2,1-2,4-6H3

InChI Key

OHGAQNFIUCKPAY-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
Garcinia mangostana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 8-prenylated xanthones. These are organic compounds containing a C5-isoprenoid group linked to a xanthone moiety at the 8-position. Xanthone is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring that carries a ketone group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

8-prenylated xanthones

Alternative Parents

Substituents

2-prenylated xanthone
8-prenylated xanthone
Chromone
Anisole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Vinylogous acid
Secondary alcohol
Oxacycle
Ether
Alcohol
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	3.47	ALOGPS
logP	4.97	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	7.96	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	105.45 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	122.63 m³·mol⁻¹	ChemAxon
Polarizability	47.99 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0039916

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB019578

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

101193826

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1,6-dihydroxy-8-(2-hydroxy-3-methylbut-3-en-1-yl)-3,7-dimethoxy-2-(3-methylbut-2-en-1-yl)xanthen-9-one (NP0142141)

MOL for NP0142141 (1,6-dihydroxy-8-(2-hydroxy-3-methylbut-3-en-1-yl)-3,7-dimethoxy-2-(3-methylbut-2-en-1-yl)xanthen-9-one)

3D MOL for NP0142141 (1,6-dihydroxy-8-(2-hydroxy-3-methylbut-3-en-1-yl)-3,7-dimethoxy-2-(3-methylbut-2-en-1-yl)xanthen-9-one)

3D SDF for NP0142141 (1,6-dihydroxy-8-(2-hydroxy-3-methylbut-3-en-1-yl)-3,7-dimethoxy-2-(3-methylbut-2-en-1-yl)xanthen-9-one)

3D-SDF for NP0142141 (1,6-dihydroxy-8-(2-hydroxy-3-methylbut-3-en-1-yl)-3,7-dimethoxy-2-(3-methylbut-2-en-1-yl)xanthen-9-one)

PDB for NP0142141 (1,6-dihydroxy-8-(2-hydroxy-3-methylbut-3-en-1-yl)-3,7-dimethoxy-2-(3-methylbut-2-en-1-yl)xanthen-9-one)

3D PDB for NP0142141 (1,6-dihydroxy-8-(2-hydroxy-3-methylbut-3-en-1-yl)-3,7-dimethoxy-2-(3-methylbut-2-en-1-yl)xanthen-9-one)

SMILES for NP0142141 (1,6-dihydroxy-8-(2-hydroxy-3-methylbut-3-en-1-yl)-3,7-dimethoxy-2-(3-methylbut-2-en-1-yl)xanthen-9-one)

INCHI for NP0142141 (1,6-dihydroxy-8-(2-hydroxy-3-methylbut-3-en-1-yl)-3,7-dimethoxy-2-(3-methylbut-2-en-1-yl)xanthen-9-one)

Structure for NP0142141 (1,6-dihydroxy-8-(2-hydroxy-3-methylbut-3-en-1-yl)-3,7-dimethoxy-2-(3-methylbut-2-en-1-yl)xanthen-9-one)

3D Structure for NP0142141 (1,6-dihydroxy-8-(2-hydroxy-3-methylbut-3-en-1-yl)-3,7-dimethoxy-2-(3-methylbut-2-en-1-yl)xanthen-9-one)