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Showing NP-Card for Mangostinone (NP0049821)

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Record Information
Version2.0
Created at2022-03-17 21:18:40 UTC
Updated at2022-03-17 21:18:40 UTC
NP-MRD IDNP0049821
Secondary Accession NumbersNone
Natural Product Identification
Common NameMangostinone
DescriptionMangostinone belongs to the class of organic compounds known as 2-prenylated xanthones. These are organic compounds containing a C5-isoprenoid group linked to a xanthone moiety at the 2-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. Mangostinone is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Mangostinone has been detected, but not quantified in, fruits and purple mangosteens. Mangostinone is found in Garcinia cowa and Garcinia xipshuanbannaensis. This could make mangostinone a potential biomarker for the consumption of these foods.
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0049821 (Mangostinone)


  Mrv1652309272007382D          

 28 30  0  0  0  0            999 V2000
 2511.5511 2512.4547    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2512.9799 2512.4547    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2514.4088 2513.2798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2515.1231 2513.6913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2515.8376 2513.2798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2516.5519 2513.6913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2517.2663 2513.2798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2517.9806 2513.6913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2518.6951 2513.2798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2519.4093 2513.6913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2518.6951 2512.4547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2515.8376 2512.4547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2514.4088 2514.9297    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2510.1209 2513.2791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2509.4063 2513.6916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2509.4063 2514.5165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2510.1208 2514.9291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2511.5505 2513.2793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2510.8361 2513.6918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2510.8361 2514.5168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2511.5505 2514.9293    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2512.2650 2514.5168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2512.2650 2513.6918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2513.6944 2513.6913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2512.9800 2513.2790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2512.9798 2514.9291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2513.6944 2514.5165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2510.1204 2515.7562    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5 12  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 18 19  1  0  0  0  0
 18 23  1  0  0  0  0
 19 20  1  0  0  0  0
 22 23  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 24 25  2  0  0  0  0
 26 27  2  0  0  0  0
 27 24  1  0  0  0  0
 25  2  1  0  0  0  0
 24  3  1  0  0  0  0
 27 13  1  0  0  0  0
  1 18  2  0  0  0  0
 19 14  2  0  0  0  0
 17 20  2  0  0  0  0
 25 23  1  0  0  0  0
 22 26  1  0  0  0  0
 17 28  1  0  0  0  0
M  END
Download

3D MOL for NP0049821 (Mangostinone)

Download
3D SDF for NP0049821 (Mangostinone)

  Mrv1652309272007382D          

 28 30  0  0  0  0            999 V2000
 2511.5511 2512.4547    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2512.9799 2512.4547    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2514.4088 2513.2798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2515.1231 2513.6913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2515.8376 2513.2798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2516.5519 2513.6913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2517.2663 2513.2798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2517.9806 2513.6913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2518.6951 2513.2798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2519.4093 2513.6913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2518.6951 2512.4547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2515.8376 2512.4547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2514.4088 2514.9297    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2510.1209 2513.2791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2509.4063 2513.6916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2509.4063 2514.5165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2510.1208 2514.9291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2511.5505 2513.2793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2510.8361 2513.6918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2510.8361 2514.5168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2511.5505 2514.9293    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2512.2650 2514.5168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2512.2650 2513.6918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2513.6944 2513.6913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2512.9800 2513.2790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2512.9798 2514.9291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2513.6944 2514.5165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2510.1204 2515.7562    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5 12  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 18 19  1  0  0  0  0
 18 23  1  0  0  0  0
 19 20  1  0  0  0  0
 22 23  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 24 25  2  0  0  0  0
 26 27  2  0  0  0  0
 27 24  1  0  0  0  0
 25  2  1  0  0  0  0
 24  3  1  0  0  0  0
 27 13  1  0  0  0  0
  1 18  2  0  0  0  0
 19 14  2  0  0  0  0
 17 20  2  0  0  0  0
 25 23  1  0  0  0  0
 22 26  1  0  0  0  0
 17 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0049821

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC\C(C)=C\CC1=C(O)C2=C(OC3=C(O)C=CC=C3C2=O)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C23H24O5/c1-13(2)6-4-7-14(3)10-11-15-18(25)12-19-20(21(15)26)22(27)16-8-5-9-17(24)23(16)28-19/h5-6,8-10,12,24-26H,4,7,11H2,1-3H3/b14-10+

> <INCHI_KEY>
RJLWIAOXQDZMTB-GXDHUFHOSA-N

> <FORMULA>
C23H24O5

> <MOLECULAR_WEIGHT>
380.4337

> <EXACT_MASS>
380.162373878

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
41.89250268382335

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-1,3,5-trihydroxy-9H-xanthen-9-one

> <ALOGPS_LOGP>
4.82

> <JCHEM_LOGP>
6.087225529666666

> <ALOGPS_LOGS>
-4.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
7.973658706294423

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.2438491576597555

> <JCHEM_PKA_STRONGEST_BASIC>
-3.808528561440108

> <JCHEM_POLAR_SURFACE_AREA>
86.99

> <JCHEM_REFRACTIVITY>
110.80439999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.65e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
mangostinone

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0049821 (Mangostinone)
Download
PDB for NP0049821 (Mangostinone)
HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  O   UNK     0    4688.2294689.915   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0    4690.8964689.915   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0    4693.5634691.456   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    4694.8964692.224   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    4696.2304691.456   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    4697.5644692.224   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    4698.8974691.456   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    4700.2304692.224   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    4701.5644691.456   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    4702.8974692.224   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    4701.5644689.915   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    4696.2304689.915   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0    4693.5634694.535   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0    4685.5594691.454   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    4684.2254692.224   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    4684.2254693.764   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    4685.5594694.534   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    4688.2284691.455   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    4686.8944692.225   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    4686.8944693.765   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0    4688.2284694.535   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0    4689.5614693.765   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    4689.5614692.225   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    4692.2304692.224   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    4690.8964691.454   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    4690.8964694.534   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    4692.2304693.764   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0    4685.5584696.078   0.000  0.00  0.00           O+0
CONECT    1   18                                                            
CONECT    2   25                                                            
CONECT    3    4   24                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    5                                                            
CONECT   13   27                                                            
CONECT   14   15   19                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   20   28                                                  
CONECT   18   19   23    1                                                  
CONECT   19   18   20   14                                                  
CONECT   20   19   21   17                                                  
CONECT   21   20   22                                                       
CONECT   22   23   21   26                                                  
CONECT   23   18   22   25                                                  
CONECT   24   25   27    3                                                  
CONECT   25   24    2   23                                                  
CONECT   26   27   22                                                       
CONECT   27   26   24   13                                                  
CONECT   28   17                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   60    0
END

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3D PDB for NP0049821 (Mangostinone)
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SMILES for NP0049821 (Mangostinone)
CC(C)=CCC\C(C)=C\CC1=C(O)C2=C(OC3=C(O)C=CC=C3C2=O)C=C1O
Download
INCHI for NP0049821 (Mangostinone)
InChI=1S/C23H24O5/c1-13(2)6-4-7-14(3)10-11-15-18(25)12-19-20(21(15)26)22(27)16-8-5-9-17(24)23(16)28-19/h5-6,8-10,12,24-26H,4,7,11H2,1-3H3/b14-10+
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View in JSmol
Synonyms
ValueSource
2-Geranyl-1,3,5-trihydroxyxanthoneHMDB
Chemical FormulaC23H24O5
Average Mass380.4337 Da
Monoisotopic Mass380.16237 Da
IUPAC Name2-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-1,3,5-trihydroxy-9H-xanthen-9-one
Traditional Namemangostinone
CAS Registry Number166197-40-6
SMILES
CC(C)=CCC\C(C)=C\CC1=C(O)C2=C(OC3=C(O)C=CC=C3C2=O)C=C1O
InChI Identifier
InChI=1S/C23H24O5/c1-13(2)6-4-7-14(3)10-11-15-18(25)12-19-20(21(15)26)22(27)16-8-5-9-17(24)23(16)28-19/h5-6,8-10,12,24-26H,4,7,11H2,1-3H3/b14-10+
InChI KeyRJLWIAOXQDZMTB-GXDHUFHOSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Garcinia cowaPlant
Garcinia mangostanaFooDB
Garcinia xipshuanbannaensisLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 2-prenylated xanthones. These are organic compounds containing a C5-isoprenoid group linked to a xanthone moiety at the 2-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.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassBenzopyrans  
Sub Class1-benzopyrans  
Direct Parent2-prenylated xanthones  
Alternative Parents
Substituents
  • 2-prenylated xanthone
    • 

  • Chromone
    • 

  • Aromatic monoterpenoid
    • 

  • Monoterpenoid
    • 

  • 1-hydroxy-4-unsubstituted benzenoid
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Pyranone
    • 

  • Benzenoid
    • 

  • Pyran
    • 

  • Heteroaromatic compound
    • 

  • Vinylogous acid
    • 

  • Oxacycle
    • 

  • Polyol
    • 

  • Organic oxygen compound
    • 

  • Organooxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP4.82ALOGPS
logP6.09ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)7.24ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.99 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity110.8 m³·mol⁻¹ChemAxon
Polarizability41.89 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0041292  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB021209  
KNApSAcK IDC00030726  
Chemspider ID4979848  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6478778  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available