NP-MRD: Showing NP-Card for (1r,2r)-1,8,10-trihydroxy-2-(2-hydroxypropan-2-yl)-9-(3-methylbut-2-en-1-yl)-1h,2h-furo[3,2-a]xanthen-11-one (NP0224513)

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Record Information

Version

2.0

Created at

2022-09-06 02:53:32 UTC

Updated at

2022-09-06 02:53:33 UTC

NP-MRD ID

NP0224513

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2r)-1,8,10-trihydroxy-2-(2-hydroxypropan-2-yl)-9-(3-methylbut-2-en-1-yl)-1h,2h-furo[3,2-a]xanthen-11-one

Description

(1R,2R)-1,8,10-trihydroxy-2-(2-hydroxypropan-2-yl)-9-(3-methylbut-2-en-1-yl)-1H,2H,11H-furo[3,2-a]xanthen-11-one 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. (1r,2r)-1,8,10-trihydroxy-2-(2-hydroxypropan-2-yl)-9-(3-methylbut-2-en-1-yl)-1h,2h-furo[3,2-a]xanthen-11-one is found in Garcinia mangostana. Based on a literature review very few articles have been published on (1R,2R)-1,8,10-trihydroxy-2-(2-hydroxypropan-2-yl)-9-(3-methylbut-2-en-1-yl)-1H,2H,11H-furo[3,2-a]xanthen-11-one.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062204532D          

 30 33  0  0  1  0            999 V2000
   -0.0815   -4.4997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3310   -3.7133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1368   -3.5363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2252   -3.1040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0310   -3.2811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5872   -2.6718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3376   -1.8854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5319   -1.7084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8939   -1.2761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6996   -1.4532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2559   -0.8439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0616   -1.0210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6179   -0.4117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4236   -0.5887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6732   -1.3751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1170   -1.9844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3112   -1.8073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7550   -2.4166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0045   -3.2030    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9492   -2.2396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3930   -2.8489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6425   -3.6352    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5246   -2.7016    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1838   -3.4530    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3327   -2.5356    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.9420   -3.0919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5513   -3.6481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3858   -3.7012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4982   -2.4826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4245   -1.7158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 10 20  1  0  0  0  0
 20 21  2  0  0  0  0
  6 21  1  0  0  0  0
 21 22  1  0  0  0  0
 16 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 26 29  1  0  0  0  0
 25 30  1  0  0  0  0
 15 30  1  0  0  0  0
M  END


  Mrv1652309062204532D          

 30 33  0  0  1  0            999 V2000
   -0.0815   -4.4997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3310   -3.7133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1368   -3.5363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2252   -3.1040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0310   -3.2811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5872   -2.6718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3376   -1.8854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5319   -1.7084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8939   -1.2761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6996   -1.4532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2559   -0.8439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0616   -1.0210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6179   -0.4117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4236   -0.5887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6732   -1.3751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1170   -1.9844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3112   -1.8073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7550   -2.4166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0045   -3.2030    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9492   -2.2396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3930   -2.8489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6425   -3.6352    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5246   -2.7016    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1838   -3.4530    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3327   -2.5356    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.9420   -3.0919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5513   -3.6481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3858   -3.7012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4982   -2.4826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4245   -1.7158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 10 20  1  0  0  0  0
 20 21  2  0  0  0  0
  6 21  1  0  0  0  0
 21 22  1  0  0  0  0
 16 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 26 29  1  0  0  0  0
 25 30  1  0  0  0  0
 15 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0224513

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC1=C(O)C=C2OC3=CC=C4O[C@H]([C@H](O)C4=C3C(=O)C2=C1O)C(C)(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C23H24O7/c1-10(2)5-6-11-12(24)9-15-18(19(11)25)20(26)16-13(29-15)7-8-14-17(16)21(27)22(30-14)23(3,4)28/h5,7-9,21-22,24-25,27-28H,6H2,1-4H3/t21-,22-/m1/s1

> <INCHI_KEY>
GTFZZWXWNSXLEV-FGZHOGPDSA-N

> <FORMULA>
C23H24O7

> <MOLECULAR_WEIGHT>
412.438

> <EXACT_MASS>
412.152203113

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
44.04061041495678

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2R)-1,8,10-trihydroxy-2-(2-hydroxypropan-2-yl)-9-(3-methylbut-2-en-1-yl)-1H,2H,11H-furo[3,2-a]xanthen-11-one

> <JCHEM_LOGP>
3.761114421

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.957161242794982

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.351861139370886

> <JCHEM_PKA_STRONGEST_BASIC>
-3.143044350496175

> <JCHEM_POLAR_SURFACE_AREA>
116.45000000000002

> <JCHEM_REFRACTIVITY>
111.02070000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R)-1,8,10-trihydroxy-2-(2-hydroxypropan-2-yl)-9-(3-methylbut-2-en-1-yl)-1H,2H-furo[3,2-a]xanthen-11-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.152  -8.399   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.618  -6.932   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.122  -6.601   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.420  -5.794   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.924  -6.125   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.963  -4.987   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.497  -3.520   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       0.993  -3.189   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       3.535  -2.382   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.039  -2.713   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       6.078  -1.575   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       7.582  -1.906   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.620  -0.768   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.124  -1.099   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.590  -2.567   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.552  -3.704   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.048  -3.374   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.009  -4.511   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       7.475  -5.979   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       5.505  -4.180   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.467  -5.318   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       4.933  -6.786   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      10.313  -5.043   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       9.677  -6.446   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      11.821  -4.733   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      12.958  -5.771   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      14.096  -6.810   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      11.920  -6.909   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      13.997  -4.634   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      11.992  -3.203   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   21                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   20                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   30                                                  
CONECT   16   15   17   23                                                  
CONECT   17   16   12   18                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   10   21                                                  
CONECT   21   20    6   22                                                  
CONECT   22   21                                                            
CONECT   23   16   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   30                                                  
CONECT   26   25   27   28   29                                             
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   26                                                            
CONECT   30   25   15                                                       
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₂₄O₇

Average Mass

412.4380 Da

Monoisotopic Mass

412.15220 Da

IUPAC Name

(1R,2R)-1,8,10-trihydroxy-2-(2-hydroxypropan-2-yl)-9-(3-methylbut-2-en-1-yl)-1H,2H,11H-furo[3,2-a]xanthen-11-one

Traditional Name

(1R,2R)-1,8,10-trihydroxy-2-(2-hydroxypropan-2-yl)-9-(3-methylbut-2-en-1-yl)-1H,2H-furo[3,2-a]xanthen-11-one

CAS Registry Number

Not Available

SMILES

CC(C)=CCC1=C(O)C=C2OC3=CC=C4O[C@H]([C@H](O)C4=C3C(=O)C2=C1O)C(C)(C)O

InChI Identifier

InChI=1S/C23H24O7/c1-10(2)5-6-11-12(24)9-15-18(19(11)25)20(26)16-13(29-15)7-8-14-17(16)21(27)22(30-14)23(3,4)28/h5,7-9,21-22,24-25,27-28H,6H2,1-4H3/t21-,22-/m1/s1

InChI Key

GTFZZWXWNSXLEV-FGZHOGPDSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

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 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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

2-prenylated xanthones

Alternative Parents

Substituents

2-prenylated xanthone
Chromone
Coumaran
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
Benzenoid
Pyran
Heteroaromatic compound
Vinylogous acid
Tertiary alcohol
Secondary alcohol
Ether
Oxacycle
Polyol
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	3.76	ChemAxon
pKa (Strongest Acidic)	7.35	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	116.45 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	111.02 m³·mol⁻¹	ChemAxon
Polarizability	44.04 Å³	ChemAxon
Number of Rings	4	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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

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

163186423

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,2r)-1,8,10-trihydroxy-2-(2-hydroxypropan-2-yl)-9-(3-methylbut-2-en-1-yl)-1h,2h-furo[3,2-a]xanthen-11-one (NP0224513)

MOL for NP0224513 ((1r,2r)-1,8,10-trihydroxy-2-(2-hydroxypropan-2-yl)-9-(3-methylbut-2-en-1-yl)-1h,2h-furo[3,2-a]xanthen-11-one)

3D MOL for NP0224513 ((1r,2r)-1,8,10-trihydroxy-2-(2-hydroxypropan-2-yl)-9-(3-methylbut-2-en-1-yl)-1h,2h-furo[3,2-a]xanthen-11-one)

3D SDF for NP0224513 ((1r,2r)-1,8,10-trihydroxy-2-(2-hydroxypropan-2-yl)-9-(3-methylbut-2-en-1-yl)-1h,2h-furo[3,2-a]xanthen-11-one)

3D-SDF for NP0224513 ((1r,2r)-1,8,10-trihydroxy-2-(2-hydroxypropan-2-yl)-9-(3-methylbut-2-en-1-yl)-1h,2h-furo[3,2-a]xanthen-11-one)

PDB for NP0224513 ((1r,2r)-1,8,10-trihydroxy-2-(2-hydroxypropan-2-yl)-9-(3-methylbut-2-en-1-yl)-1h,2h-furo[3,2-a]xanthen-11-one)

3D PDB for NP0224513 ((1r,2r)-1,8,10-trihydroxy-2-(2-hydroxypropan-2-yl)-9-(3-methylbut-2-en-1-yl)-1h,2h-furo[3,2-a]xanthen-11-one)

SMILES for NP0224513 ((1r,2r)-1,8,10-trihydroxy-2-(2-hydroxypropan-2-yl)-9-(3-methylbut-2-en-1-yl)-1h,2h-furo[3,2-a]xanthen-11-one)

INCHI for NP0224513 ((1r,2r)-1,8,10-trihydroxy-2-(2-hydroxypropan-2-yl)-9-(3-methylbut-2-en-1-yl)-1h,2h-furo[3,2-a]xanthen-11-one)

Structure for NP0224513 ((1r,2r)-1,8,10-trihydroxy-2-(2-hydroxypropan-2-yl)-9-(3-methylbut-2-en-1-yl)-1h,2h-furo[3,2-a]xanthen-11-one)

3D Structure for NP0224513 ((1r,2r)-1,8,10-trihydroxy-2-(2-hydroxypropan-2-yl)-9-(3-methylbut-2-en-1-yl)-1h,2h-furo[3,2-a]xanthen-11-one)