NP-MRD: Showing NP-Card for (1s)-5,9,10-trihydroxy-1,2,2-trimethyl-1h-furo[2,3-c]xanthen-6-one (NP0195188)

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Record Information

Version

2.0

Created at

2022-09-04 12:59:51 UTC

Updated at

2022-09-04 12:59:51 UTC

NP-MRD ID

NP0195188

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s)-5,9,10-trihydroxy-1,2,2-trimethyl-1h-furo[2,3-c]xanthen-6-one

Description

(1S)-5,9,10-trihydroxy-1,2,2-trimethyl-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. (1s)-5,9,10-trihydroxy-1,2,2-trimethyl-1h-furo[2,3-c]xanthen-6-one is found in Hypericum japonicum. Based on a literature review very few articles have been published on (1S)-5,9,10-trihydroxy-1,2,2-trimethyl-1H,2H,6H-furo[2,3-c]xanthen-6-one.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309042214592D          

 24 27  0  0  1  0            999 V2000
    4.0562   -3.4530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7155   -2.7016    0.0000 C   0  0  1  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
    8.2091   -3.2811    0.0000 O   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
    2.9073   -2.5356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1035   -2.7211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6496   -3.3193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  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
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 11 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
  3 20  2  0  0  0  0
  8 20  1  0  0  0  0
  4 21  1  0  0  0  0
 21 22  1  0  0  0  0
  2 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0195188

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1C2=C3OC4=C(O)C(O)=CC=C4C(=O)C3=C(O)C=C2OC1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C18H16O6/c1-7-12-11(24-18(7,2)3)6-10(20)13-14(21)8-4-5-9(19)15(22)16(8)23-17(12)13/h4-7,19-20,22H,1-3H3/t7-/m0/s1

> <INCHI_KEY>
CXVIOKUKRAYTPO-ZETCQYMHSA-N

> <FORMULA>
C18H16O6

> <MOLECULAR_WEIGHT>
328.32

> <EXACT_MASS>
328.094688235

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
33.401799116096036

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S)-5,9,10-trihydroxy-1,2,2-trimethyl-1H,2H,6H-furo[2,3-c]xanthen-6-one

> <JCHEM_LOGP>
3.6432860153333326

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.68881150840478

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.513934360031305

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7844587325500645

> <JCHEM_POLAR_SURFACE_AREA>
96.22000000000001

> <JCHEM_REFRACTIVITY>
86.06040000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S)-5,9,10-trihydroxy-1,2,2-trimethyl-1H-furo[2,3-c]xanthen-6-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       7.572  -6.446   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.936  -5.043   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.696  -3.704   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.658  -2.567   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.124  -1.099   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.628  -0.768   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       9.094   0.699   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       9.666  -1.906   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.170  -1.575   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      11.636  -0.107   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      12.209  -2.713   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.713  -2.382   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.751  -3.520   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.285  -4.987   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      15.324  -6.125   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      12.781  -5.318   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      12.315  -6.786   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      11.743  -4.180   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      10.239  -4.511   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       9.201  -3.374   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.256  -3.203   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       5.427  -4.733   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.926  -5.079   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.946  -6.196   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   22                                                  
CONECT    3    2    4   20                                                  
CONECT    4    3    5   21                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   20                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   18                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   11   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19    3    8                                                  
CONECT   21    4   22                                                       
CONECT   22   21    2   23   24                                             
CONECT   23   22                                                            
CONECT   24   22                                                            
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

(1S)-5,9,10-trihydroxy-1,2,2-trimethyl-1H,2H,6H-furo[2,3-c]xanthen-6-one

Traditional Name

(1S)-5,9,10-trihydroxy-1,2,2-trimethyl-1H-furo[2,3-c]xanthen-6-one

CAS Registry Number

Not Available

SMILES

C[C@H]1C2=C3OC4=C(O)C(O)=CC=C4C(=O)C3=C(O)C=C2OC1(C)C

InChI Identifier

InChI=1S/C18H16O6/c1-7-12-11(24-18(7,2)3)6-10(20)13-14(21)8-4-5-9(19)15(22)16(8)23-17(12)13/h4-7,19-20,22H,1-3H3/t7-/m0/s1

InChI Key

CXVIOKUKRAYTPO-ZETCQYMHSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Hypericum japonicum	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
Benzenoid
Pyran
Heteroaromatic compound
Vinylogous acid
Ether
Oxacycle
Polyol
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
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	3.64	ChemAxon
pKa (Strongest Acidic)	7.51	ChemAxon
pKa (Strongest Basic)	-3.8	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	0	ChemAxon
Refractivity	86.06 m³·mol⁻¹	ChemAxon
Polarizability	33.4 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

162956362

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s)-5,9,10-trihydroxy-1,2,2-trimethyl-1h-furo[2,3-c]xanthen-6-one (NP0195188)

MOL for NP0195188 ((1s)-5,9,10-trihydroxy-1,2,2-trimethyl-1h-furo[2,3-c]xanthen-6-one)

3D MOL for NP0195188 ((1s)-5,9,10-trihydroxy-1,2,2-trimethyl-1h-furo[2,3-c]xanthen-6-one)

3D SDF for NP0195188 ((1s)-5,9,10-trihydroxy-1,2,2-trimethyl-1h-furo[2,3-c]xanthen-6-one)

3D-SDF for NP0195188 ((1s)-5,9,10-trihydroxy-1,2,2-trimethyl-1h-furo[2,3-c]xanthen-6-one)

PDB for NP0195188 ((1s)-5,9,10-trihydroxy-1,2,2-trimethyl-1h-furo[2,3-c]xanthen-6-one)

3D PDB for NP0195188 ((1s)-5,9,10-trihydroxy-1,2,2-trimethyl-1h-furo[2,3-c]xanthen-6-one)

SMILES for NP0195188 ((1s)-5,9,10-trihydroxy-1,2,2-trimethyl-1h-furo[2,3-c]xanthen-6-one)

INCHI for NP0195188 ((1s)-5,9,10-trihydroxy-1,2,2-trimethyl-1h-furo[2,3-c]xanthen-6-one)

Structure for NP0195188 ((1s)-5,9,10-trihydroxy-1,2,2-trimethyl-1h-furo[2,3-c]xanthen-6-one)

3D Structure for NP0195188 ((1s)-5,9,10-trihydroxy-1,2,2-trimethyl-1h-furo[2,3-c]xanthen-6-one)