NP-MRD: Showing NP-Card for (2r)-5,10-dihydroxy-2-(2-hydroxypropan-2-yl)-1h,2h-furo[2,3-c]xanthen-6-one (NP0233002)

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Record Information

Version

2.0

Created at

2022-09-06 14:26:20 UTC

Updated at

2022-09-06 14:26:20 UTC

NP-MRD ID

NP0233002

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r)-5,10-dihydroxy-2-(2-hydroxypropan-2-yl)-1h,2h-furo[2,3-c]xanthen-6-one

Description

(2R)-5,10-dihydroxy-2-(2-hydroxypropan-2-yl)-1H,2H,6H-furo[2,3-c]xanthen-6-one 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. (2r)-5,10-dihydroxy-2-(2-hydroxypropan-2-yl)-1h,2h-furo[2,3-c]xanthen-6-one is found in Cratoxylum sumatranum. Based on a literature review very few articles have been published on (2R)-5,10-dihydroxy-2-(2-hydroxypropan-2-yl)-1H,2H,6H-furo[2,3-c]xanthen-6-one.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062216262D          

 24 27  0  0  1  0            999 V2000
    1.6887   -3.6481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2980   -3.0919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8543   -3.7012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7418   -2.4826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9073   -2.5356    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7155   -2.7016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1231   -1.9844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5668   -1.3751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8164   -0.5887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6222   -0.4117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8717    0.3747    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1784   -1.0210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9842   -0.8439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2337   -0.0576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5404   -1.4532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3462   -1.2761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9024   -1.8854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6528   -2.6718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8471   -2.8489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5975   -3.6352    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2908   -2.2396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4851   -2.4166    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9288   -1.8073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8155   -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  1  0  0  0  0
  5  2  1  6  0  0  0
  5  6  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
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 15 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
  7 23  2  0  0  0  0
 12 23  1  0  0  0  0
  8 24  1  0  0  0  0
  5 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0233002

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)(O)[C@H]1CC2=C3OC4=C(O)C=CC=C4C(=O)C3=C(O)C=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C18H16O6/c1-18(2,22)13-6-9-12(23-13)7-11(20)14-15(21)8-4-3-5-10(19)16(8)24-17(9)14/h3-5,7,13,19-20,22H,6H2,1-2H3/t13-/m1/s1

> <INCHI_KEY>
QOMATUMHCQRUDT-CYBMUJFWSA-N

> <FORMULA>
C18H16O6

> <MOLECULAR_WEIGHT>
328.32

> <EXACT_MASS>
328.094688235

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
33.349933580400496

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R)-5,10-dihydroxy-2-(2-hydroxypropan-2-yl)-1H,2H,6H-furo[2,3-c]xanthen-6-one

> <JCHEM_LOGP>
2.9515435686666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.729906242158084

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.812348961905178

> <JCHEM_PKA_STRONGEST_BASIC>
-3.106437461643047

> <JCHEM_POLAR_SURFACE_AREA>
96.22000000000001

> <JCHEM_REFRACTIVITY>
85.5704

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-5,10-dihydroxy-2-(2-hydroxypropan-2-yl)-1H,2H-furo[2,3-c]xanthen-6-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       3.152  -6.810   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.290  -5.771   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.328  -6.909   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       3.251  -4.634   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       5.427  -4.733   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.936  -5.043   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.696  -3.704   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.658  -2.567   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.124  -1.099   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.628  -0.768   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       9.094   0.699   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       9.666  -1.906   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.170  -1.575   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      11.636  -0.107   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      12.209  -2.713   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.713  -2.382   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.751  -3.520   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.285  -4.987   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.781  -5.318   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      12.315  -6.786   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      11.743  -4.180   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      10.239  -4.511   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       9.201  -3.374   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       5.256  -3.203   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4    5                                             
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5    2    6   24                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   23                                                  
CONECT    8    7    9   24                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   23                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   21                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   15   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22    7   12                                                  
CONECT   24    8    5                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₁₆O₆

Average Mass

328.3200 Da

Monoisotopic Mass

328.09469 Da

IUPAC Name

(2R)-5,10-dihydroxy-2-(2-hydroxypropan-2-yl)-1H,2H,6H-furo[2,3-c]xanthen-6-one

Traditional Name

(2R)-5,10-dihydroxy-2-(2-hydroxypropan-2-yl)-1H,2H-furo[2,3-c]xanthen-6-one

CAS Registry Number

Not Available

SMILES

CC(C)(O)[C@H]1CC2=C3OC4=C(O)C=CC=C4C(=O)C3=C(O)C=C2O1

InChI Identifier

InChI=1S/C18H16O6/c1-18(2,22)13-6-9-12(23-13)7-11(20)14-15(21)8-4-3-5-10(19)16(8)24-17(9)14/h3-5,7,13,19-20,22H,6H2,1-2H3/t13-/m1/s1

InChI Key

QOMATUMHCQRUDT-CYBMUJFWSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Cratoxylum sumatranum	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

Xanthone
Chromone
Coumaran
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Tertiary alcohol
Vinylogous acid
Ether
Oxacycle
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Organooxygen compound
Organic oxide
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	2.95	ChemAxon
pKa (Strongest Acidic)	7.81	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	96.22 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	85.57 m³·mol⁻¹	ChemAxon
Polarizability	33.35 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

163191216

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r)-5,10-dihydroxy-2-(2-hydroxypropan-2-yl)-1h,2h-furo[2,3-c]xanthen-6-one (NP0233002)

MOL for NP0233002 ((2r)-5,10-dihydroxy-2-(2-hydroxypropan-2-yl)-1h,2h-furo[2,3-c]xanthen-6-one)

3D MOL for NP0233002 ((2r)-5,10-dihydroxy-2-(2-hydroxypropan-2-yl)-1h,2h-furo[2,3-c]xanthen-6-one)

3D SDF for NP0233002 ((2r)-5,10-dihydroxy-2-(2-hydroxypropan-2-yl)-1h,2h-furo[2,3-c]xanthen-6-one)

3D-SDF for NP0233002 ((2r)-5,10-dihydroxy-2-(2-hydroxypropan-2-yl)-1h,2h-furo[2,3-c]xanthen-6-one)

PDB for NP0233002 ((2r)-5,10-dihydroxy-2-(2-hydroxypropan-2-yl)-1h,2h-furo[2,3-c]xanthen-6-one)

3D PDB for NP0233002 ((2r)-5,10-dihydroxy-2-(2-hydroxypropan-2-yl)-1h,2h-furo[2,3-c]xanthen-6-one)

SMILES for NP0233002 ((2r)-5,10-dihydroxy-2-(2-hydroxypropan-2-yl)-1h,2h-furo[2,3-c]xanthen-6-one)

INCHI for NP0233002 ((2r)-5,10-dihydroxy-2-(2-hydroxypropan-2-yl)-1h,2h-furo[2,3-c]xanthen-6-one)

Structure for NP0233002 ((2r)-5,10-dihydroxy-2-(2-hydroxypropan-2-yl)-1h,2h-furo[2,3-c]xanthen-6-one)

3D Structure for NP0233002 ((2r)-5,10-dihydroxy-2-(2-hydroxypropan-2-yl)-1h,2h-furo[2,3-c]xanthen-6-one)