NP-MRD: Showing NP-Card for Isojacareubin (NP0073557)

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Record Information

Version

2.0

Created at

2022-04-28 18:47:15 UTC

Updated at

2022-04-28 18:47:15 UTC

NP-MRD ID

NP0073557

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Isojacareubin

Description

Isojacareubin belongs to the class of organic compounds known as pyranoxanthones. These are organic aromatic compounds containing a pyran or a hydrogenated derivative fused to a xanthone ring system. Isojacareubin is an extremely weak basic (essentially neutral) compound (based on its pKa). Isojacareubin is found in Garcina xipshuanbannaensis, Garcinia cowa , Garcinia fusca, Garcinia xipshuanbannaensis, Hypericum japonicum and Hypericum roeperanum . Isojacareubin is an antibacterial isolate of Hypericum japonicum.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 38 41  0  0  0  0  0  0  0  0999 V2000
    4.6797    1.0621   -1.1489 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7818    0.5570   -0.0120 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7251    0.3309    1.1584 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7298    1.5189    0.2972 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4294    1.2987    0.2770 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9737   -0.0335   -0.0885 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9102   -0.9893   -0.3922 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4874   -2.2524   -0.7390 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1270   -2.6004   -0.7938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2024   -3.8768   -1.1475 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7736   -1.5914   -0.4761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1285   -1.8636   -0.5094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5776   -2.9867   -0.8154 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9999   -0.8273   -0.1849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3626   -1.0636   -0.2077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2623   -0.0647    0.1071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7618    1.1984    0.4514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7065    2.1601    0.7570 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4122    1.4582    0.4813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9176    2.7073    0.8218 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5278    0.4197    0.1557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2459    0.6598    0.1823 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3862   -0.3092   -0.1227 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2554   -0.6879   -0.3502 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3600    0.5155   -2.0777 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7311    0.8089   -0.9898 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4725    2.1442   -1.2409 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2959    1.2311    1.4042 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4107   -0.4910    0.8402 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1089   -0.0503    1.9967 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0080    2.5475    0.5818 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7054    2.0822    0.5245 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2105   -3.0095   -0.9790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0479   -4.2927   -1.2386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7534   -2.0358   -0.4725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3353   -0.2518    0.0889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4898    3.1038    1.0194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5113    3.4736    1.0601 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2 24  1  0
 24  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  2  0
 21 22  1  0
 22 23  1  0
 23  6  2  0
  6  5  1  0
  5  4  2  0
  4  2  1  0
  6  7  1  0
 23 11  1  0
 21 14  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
  8 33  1  0
 10 34  1  0
 15 35  1  0
 16 36  1  0
 18 37  1  0
 20 38  1  0
  5 32  1  0
  4 31  1  0
M  END


  Mrv1533004171507062D          

 24 27  0  0  0  0            999 V2000
    2.0414   -1.8171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7622   -2.2184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2418   -2.8586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0323   -1.4389    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8424   -1.2829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1124   -0.5034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9226   -0.3475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1926    0.4321    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4627   -0.9711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2728   -0.8152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5428   -0.0357    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8129   -1.4389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6230   -1.2829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1631   -1.9066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8931   -2.6861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4332   -3.3098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0829   -2.8421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8129   -3.6216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5428   -2.2184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7327   -2.3743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1926   -1.7507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3825   -1.9066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1124   -2.6861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3023   -2.8421    0.0000 C   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
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 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
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 12 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  9 21  1  0  0  0  0
 21 22  2  0  0  0  0
  5 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
  2 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0073557

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)OC2=CC(O)=C3C(=O)C4=CC=C(O)C(O)=C4OC3=C2C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H14O6/c1-18(2)6-5-8-12(24-18)7-11(20)13-14(21)9-3-4-10(19)15(22)17(9)23-16(8)13/h3-7,19-20,22H,1-2H3

> <INCHI_KEY>
FSTNFJKGRSHPBO-UHFFFAOYSA-N

> <FORMULA>
C18H14O6

> <MOLECULAR_WEIGHT>
326.304

> <EXACT_MASS>
326.079038171

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
32.93513224709127

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6,7,11-trihydroxy-2,2-dimethyl-2,10-dihydro-1,5-dioxatetraphen-10-one

> <ALOGPS_LOGP>
3.57

> <JCHEM_LOGP>
3.599567657333333

> <ALOGPS_LOGS>
-3.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.635524805685977

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.507286885441602

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7925566032423537

> <JCHEM_POLAR_SURFACE_AREA>
96.22000000000001

> <JCHEM_REFRACTIVITY>
87.1524

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.17e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6,7,11-trihydroxy-2,2-dimethyl-1,5-dioxatetraphen-10-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       3.811  -3.392   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.156  -4.141   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.185  -5.336   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       5.660  -2.686   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       7.172  -2.395   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.677  -0.940   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.189  -0.649   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       9.693   0.807   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      10.197  -1.813   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.709  -1.522   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      12.213  -0.067   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      12.717  -2.686   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.230  -2.395   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      15.238  -3.559   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.734  -5.014   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      15.742  -6.178   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      13.221  -5.305   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      12.717  -6.760   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      12.213  -4.141   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      10.701  -4.432   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       9.693  -3.268   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.181  -3.559   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.677  -5.014   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.164  -5.305   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4   24                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   22                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   21                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   19                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   12   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20    9   22                                                  
CONECT   22   21    5   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23    2                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₁₄O₆

Average Mass

326.3040 Da

Monoisotopic Mass

326.07904 Da

IUPAC Name

6,7,11-trihydroxy-2,2-dimethyl-2,10-dihydro-1,5-dioxatetraphen-10-one

Traditional Name

6,7,11-trihydroxy-2,2-dimethyl-1,5-dioxatetraphen-10-one

CAS Registry Number

Not Available

SMILES

CC1(C)OC2=CC(O)=C3C(=O)C4=CC=C(O)C(O)=C4OC3=C2C=C1

InChI Identifier

InChI=1S/C18H14O6/c1-18(2)6-5-8-12(24-18)7-11(20)13-14(21)9-3-4-10(19)15(22)17(9)23-16(8)13/h3-7,19-20,22H,1-2H3

InChI Key

FSTNFJKGRSHPBO-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
Garcina xipshuanbannaensis	-	KNApSAcK
Garcinia cowa	Plant	KNApSAcK
Garcinia fusca	Plant	KNApSAcK
Garcinia xipshuanbannaensis	Plant	KNApSAcK
Hypericum japonicum	LOTUS Database	35616633
Hypericum roeperanum	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyranoxanthones. These are organic aromatic compounds containing a pyran or a hydrogenated derivative fused to a xanthone ring system.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

Pyranoxanthones

Alternative Parents

Substituents

Pyranoxanthone
Pyranochromene
2,2-dimethyl-1-benzopyran
Chromone
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
Phenol
Pyranone
1-hydroxy-2-unsubstituted benzenoid
Pyran
Benzenoid
Vinylogous acid
Heteroaromatic compound
Ether
Polyol
Oxacycle
Organic oxide
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
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	3.57	ALOGPS
logP	3.6	ChemAxon
logS	-3.7	ALOGPS
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	87.15 m³·mol⁻¹	ChemAxon
Polarizability	32.94 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

Isojacareubin

METLIN ID

Not Available

PubChem Compound

9996463

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Isojacareubin (NP0073557)

MOL for NP0073557 (Isojacareubin)

3D MOL for NP0073557 (Isojacareubin)

3D SDF for NP0073557 (Isojacareubin)

3D-SDF for NP0073557 (Isojacareubin)

PDB for NP0073557 (Isojacareubin)

3D PDB for NP0073557 (Isojacareubin)

SMILES for NP0073557 (Isojacareubin)

INCHI for NP0073557 (Isojacareubin)

Structure for NP0073557 (Isojacareubin)

3D Structure for NP0073557 (Isojacareubin)