NP-MRD: Showing NP-Card for Ugaxanthone (NP0075867)

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Record Information

Version

2.0

Created at

2022-04-28 21:05:07 UTC

Updated at

2022-04-28 21:05:07 UTC

NP-MRD ID

NP0075867

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Ugaxanthone

Description

Ugaxanthone belongs to the class of organic compounds known as 4-prenylated xanthones. These are organic compounds containing a C5-isoprenoid group linked to a xanthone moiety at the 4-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. Ugaxanthone is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Ugaxanthone has been detected, but not quantified in, fruits. Ugaxanthone is found in Garcinia cowa , Garcinia dulcis , Hypericum beanii, Hypericum henryi, Hypericum japonicum, Morus insignis, Symphonia globulifera and Syphonia globifera. This could make ugaxanthone a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 40 42  0  0  0  0  0  0  0  0999 V2000
    3.7914   -1.1045    0.7550 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9059    0.3602    0.9322 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2072    0.9942    1.1777 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7986    1.0906    0.8611 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4839    0.5478    0.6219 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7075    0.8931   -0.5581 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1927    1.6052   -1.6139 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4430    2.1239   -1.7813 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2859    1.8366   -2.6810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0035    1.3759   -2.6621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8671    1.6252   -3.7333 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4533    0.6588   -1.5750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7581    0.1598   -1.5030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5355    0.3710   -2.4462 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1502   -0.5535   -0.3905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4219   -1.0752   -0.2572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8107   -1.7941    0.8636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9216   -2.0128    1.8985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2713   -2.7280    3.0389 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6565   -1.4895    1.7583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7168   -1.6840    2.7823 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2599   -0.7701    0.6399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0494   -0.2827    0.5265 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6279    0.4073   -0.5233 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7780   -1.6064    0.6932 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2888   -1.3429   -0.2254 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2272   -1.5870    1.5789 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4029    1.6897    0.3126 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2994    1.5181    2.1462 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0375    0.2545    1.1141 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9226    2.1730    1.0280 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8631    0.6879    1.5688 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5992   -0.5877    0.6045 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2097    2.0799   -1.2182 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6412    2.3984   -3.5270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5198    2.1593   -4.5350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1052   -0.8901   -1.0852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8103   -2.1714    0.9074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1752   -3.1283    3.1869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9714   -2.2018    3.6162 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6 24  2  0
 24 23  1  0
 23 22  1  0
 22 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 15 13  1  0
 13 14  2  0
 13 12  1  0
 12 10  2  0
 10 11  1  0
 10  9  1  0
  9  7  2  0
  7  8  1  0
  7  6  1  0
 12 24  1  0
 20 22  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
 16 37  1  0
 17 38  1  0
 19 39  1  0
 21 40  1  0
 11 36  1  0
  9 35  1  0
  8 34  1  0
M  END


  Mrv0541 05061305222D          

 24 26  0  0  0  0            999 V2000
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  6  5  2  0  0  0  0
  8  1  1  0  0  0  0
  8  2  1  0  0  0  0
  8  3  2  0  0  0  0
  9  4  1  0  0  0  0
 10  5  1  0  0  0  0
 11  6  1  0  0  0  0
 12  7  2  0  0  0  0
 12  9  1  0  0  0  0
 13  7  1  0  0  0  0
 14 13  2  0  0  0  0
 15 10  1  0  0  0  0
 15 14  1  0  0  0  0
 16 11  2  0  0  0  0
 17  9  2  0  0  0  0
 17 14  1  0  0  0  0
 18 10  2  0  0  0  0
 18 16  1  0  0  0  0
 19 11  1  0  0  0  0
 20 12  1  0  0  0  0
 21 13  1  0  0  0  0
 22 15  2  0  0  0  0
 23 16  1  0  0  0  0
 24 17  1  0  0  0  0
 24 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0075867

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC1=C2OC3=C(C=CC(O)=C3O)C(=O)C2=C(O)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C18H16O6/c1-8(2)3-4-9-12(20)7-13(21)14-15(22)10-5-6-11(19)16(23)18(10)24-17(9)14/h3,5-7,19-21,23H,4H2,1-2H3

> <INCHI_KEY>
ZZUFNBISWJNCEE-UHFFFAOYSA-N

> <FORMULA>
C18H16O6

> <MOLECULAR_WEIGHT>
328.316

> <EXACT_MASS>
328.094688244

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
33.42056822802541

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,3,5,6-tetrahydroxy-4-(3-methylbut-2-en-1-yl)-9H-xanthen-9-one

> <ALOGPS_LOGP>
2.93

> <JCHEM_LOGP>
4.123945933

> <ALOGPS_LOGS>
-3.63

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
7.799980531299641

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.180643430617394

> <JCHEM_PKA_STRONGEST_BASIC>
-4.18127892194421

> <JCHEM_POLAR_SURFACE_AREA>
107.22

> <JCHEM_REFRACTIVITY>
88.98269999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.72e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,3,5,6-tetrahydroxy-4-(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       4.001   6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   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       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -4.001   2.310   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       6.668   2.310   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2    8                                                            
CONECT    3    4    8                                                       
CONECT    4    3    9                                                       
CONECT    5    6   10                                                       
CONECT    6    5   11                                                       
CONECT    7   12   13                                                       
CONECT    8    1    2    3                                                  
CONECT    9    4   12   17                                                  
CONECT   10    5   15   18                                                  
CONECT   11    6   16   19                                                  
CONECT   12    7    9   20                                                  
CONECT   13    7   14   21                                                  
CONECT   14   13   15   17                                                  
CONECT   15   10   14   22                                                  
CONECT   16   11   18   23                                                  
CONECT   17    9   14   24                                                  
CONECT   18   10   16   24                                                  
CONECT   19   11                                                            
CONECT   20   12                                                            
CONECT   21   13                                                            
CONECT   22   15                                                            
CONECT   23   16                                                            
CONECT   24   17   18                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Value	Source
1,3,5,6-Tetrahydroxy-4-(3-methyl-2-butenyl)-9H-xanthen-9-one, 9ci	HMDB

Chemical Formula

C₁₈H₁₆O₆

Average Mass

328.3160 Da

Monoisotopic Mass

328.09469 Da

IUPAC Name

1,3,5,6-tetrahydroxy-4-(3-methylbut-2-en-1-yl)-9H-xanthen-9-one

Traditional Name

1,3,5,6-tetrahydroxy-4-(3-methylbut-2-en-1-yl)xanthen-9-one

CAS Registry Number

Not Available

SMILES

CC(C)=CCC1=C2OC3=C(C=CC(O)=C3O)C(=O)C2=C(O)C=C1O

InChI Identifier

InChI=1S/C18H16O6/c1-8(2)3-4-9-12(20)7-13(21)14-15(22)10-5-6-11(19)16(23)18(10)24-17(9)14/h3,5-7,19-21,23H,4H2,1-2H3

InChI Key

ZZUFNBISWJNCEE-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, 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
Garcinia cowa	Plant	KNApSAcK
Garcinia dulcis	Plant	KNApSAcK
Hypericum beanii	LOTUS Database	35616633
Hypericum henryi	LOTUS Database	35616633
Hypericum japonicum	LOTUS Database	35616633
Morus insignis	LOTUS Database	35616633
Symphonia globulifera	Plant	KNApSAcK
Syphonia globifera	-	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 4-prenylated xanthones. These are organic compounds containing a C5-isoprenoid group linked to a xanthone moiety at the 4-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

4-prenylated xanthones

Alternative Parents

Substituents

4-prenylated xanthone
Chromone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Vinylogous acid
Polyol
Oxacycle
Hydrocarbon derivative
Organic oxide
Organooxygen compound
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	2.93	ALOGPS
logP	4.12	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	7.18	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	107.22 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	88.98 m³·mol⁻¹	ChemAxon
Polarizability	33.42 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	No	ChemAxon

External Links

HMDB ID

HMDB0030596

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB002490

KNApSAcK ID

C00037969

Chemspider ID

4479504

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5321880

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Ugaxanthone (NP0075867)

MOL for NP0075867 (Ugaxanthone)

3D MOL for NP0075867 (Ugaxanthone)

3D SDF for NP0075867 (Ugaxanthone)

3D-SDF for NP0075867 (Ugaxanthone)

PDB for NP0075867 (Ugaxanthone)

3D PDB for NP0075867 (Ugaxanthone)

SMILES for NP0075867 (Ugaxanthone)

INCHI for NP0075867 (Ugaxanthone)

Structure for NP0075867 (Ugaxanthone)

3D Structure for NP0075867 (Ugaxanthone)