NP-MRD: Showing NP-Card for Isomorellic acid (NP0071366)

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Record Information

Version

2.0

Created at

2022-04-28 16:45:05 UTC

Updated at

2022-04-28 16:45:05 UTC

NP-MRD ID

NP0071366

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Isomorellic acid

Description

Isomorellic acid, also known as isomorellate, 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. Isomorellic acid is found in Garcinia gaudichaudii, Garcinia gummi-gutta, Garcinia hanburyi and Garcinia morella . Isomorellic acid was first documented in 2007 (PMID: 17534879). Based on a literature review very few articles have been published on Isomorellic acid (PMID: 18254140).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282218452D          

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M  END

     RDKit          3D

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M  END


  Mrv1652304282218452D          

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    2.6167   -1.0804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    2.7355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7785    3.5717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1287    3.1688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2537    1.9499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8326    1.3620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6128    0.5668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8143    0.3595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4947    0.4336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8633   -0.2888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  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
  9 11  1  0  0  0  0
  5 12  1  0  0  0  0
 13 12  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 16 15  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 13 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 13 22  1  0  0  0  0
 22 23  1  6  0  0  0
 16 23  1  0  0  0  0
 21 24  1  0  0  0  0
 21 25  1  0  0  0  0
 19 26  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 28 32  1  0  0  0  0
 14 33  1  0  0  0  0
  4 33  1  0  0  0  0
 33 34  2  0  0  0  0
  3 35  1  0  0  0  0
  2 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
  1 39  1  0  0  0  0
 38 40  1  0  0  0  0
 38 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0071366

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC1=C2O[C@@]34[C@H]5C[C@@H](C=C3C(=O)C2=C(O)C2=C1OC(C)(C)C=C2)C(=O)[C@]4(C\C=C(/C)C(O)=O)OC5(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C33H36O8/c1-16(2)8-9-20-26-19(11-12-30(4,5)39-26)24(34)23-25(35)21-14-18-15-22-31(6,7)41-32(28(18)36,13-10-17(3)29(37)38)33(21,22)40-27(20)23/h8,10-12,14,18,22,34H,9,13,15H2,1-7H3,(H,37,38)/b17-10+/t18-,22+,32+,33-/m1/s1

> <INCHI_KEY>
COVMVPHACFXMAX-UERHWIFRSA-N

> <FORMULA>
C33H36O8

> <MOLECULAR_WEIGHT>
560.643

> <EXACT_MASS>
560.241018119

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
60.03437641963869

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-4-[(1S,2S,17S,19R)-12-hydroxy-8,8,21,21-tetramethyl-5-(3-methylbut-2-en-1-yl)-14,18-dioxo-3,7,20-trioxahexacyclo[15.4.1.0^{2,15}.0^{2,19}.0^{4,13}.0^{6,11}]docosa-4,6(11),9,12,15-pentaen-19-yl]-2-methylbut-2-enoic acid

> <ALOGPS_LOGP>
4.62

> <JCHEM_LOGP>
6.046089143666666

> <ALOGPS_LOGS>
-5.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.582151616184376

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.756892258520436

> <JCHEM_PKA_STRONGEST_BASIC>
-4.135570183967039

> <JCHEM_POLAR_SURFACE_AREA>
119.36000000000001

> <JCHEM_REFRACTIVITY>
155.43599999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.47e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-4-[(1S,2S,17S,19R)-12-hydroxy-8,8,21,21-tetramethyl-5-(3-methylbut-2-en-1-yl)-14,18-dioxo-3,7,20-trioxahexacyclo[15.4.1.0^{2,15}.0^{2,19}.0^{4,13}.0^{6,11}]docosa-4,6(11),9,12,15-pentaen-19-yl]-2-methylbut-2-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      11.640   1.768   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.050   3.253   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.969   4.350   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.479   3.963   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.069   2.479   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.149   1.381   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.052  -0.323   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.583  -1.857   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.095  -2.148   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.104  -0.984   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.599  -3.603   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       7.525   2.169   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       6.109   3.046   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.929   4.500   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.093   5.885   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.607   5.332   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.426   4.301   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       1.930   4.816   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       4.274   2.930   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       3.005   1.938   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       4.067   0.829   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.058   2.035   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.054   3.811   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.651  -0.206   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.979  -0.809   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.110   1.125   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.462   0.135   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.294  -1.396   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.536  -2.307   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       8.946  -1.686   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       7.369  -3.838   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       4.885  -2.017   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.415   5.106   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       8.920   6.667   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      11.440   5.915   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      13.540   3.640   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      14.621   2.542   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      14.211   1.058   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      12.720   0.671   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      15.857   0.809   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      14.678  -0.539   0.000  0.00  0.00           C+0
CONECT    1    2    6   39                                                  
CONECT    2    1    3   36                                                  
CONECT    3    2    4   35                                                  
CONECT    4    3    5   33                                                  
CONECT    5    4    6   12                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    5   13                                                       
CONECT   13   12   14   19   22                                             
CONECT   14   13   15   33                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   23                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   13   20   26                                             
CONECT   20   19   21                                                       
CONECT   21   20   22   24   25                                             
CONECT   22   21   13   23                                                  
CONECT   23   22   16                                                       
CONECT   24   21                                                            
CONECT   25   21                                                            
CONECT   26   19   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   32                                                  
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   28                                                            
CONECT   33   14    4   34                                                  
CONECT   34   33                                                            
CONECT   35    3                                                            
CONECT   36    2   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39   40   41                                             
CONECT   39   38    1                                                       
CONECT   40   38                                                            
CONECT   41   38                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   92    0
END

View in JSmol

Synonyms

Value	Source
Isomorellate	Generator

Chemical Formula

C₃₃H₃₆O₈

Average Mass

560.6430 Da

Monoisotopic Mass

560.24102 Da

IUPAC Name

(2E)-4-[(1S,2S,17S,19R)-12-hydroxy-8,8,21,21-tetramethyl-5-(3-methylbut-2-en-1-yl)-14,18-dioxo-3,7,20-trioxahexacyclo[15.4.1.0^{2,15}.0^{2,19}.0^{4,13}.0^{6,11}]docosa-4,6(11),9,12,15-pentaen-19-yl]-2-methylbut-2-enoic acid

Traditional Name

CAS Registry Number

Not Available

SMILES

CC(C)=CCC1=C2O[C@@]34[C@H]5C[C@@H](C=C3C(=O)C2=C(O)C2=C1OC(C)(C)C=C2)C(=O)[C@]4(C\C=C(/C)C(O)=O)OC5(C)C

InChI Identifier

InChI=1S/C33H36O8/c1-16(2)8-9-20-26-19(11-12-30(4,5)39-26)24(34)23-25(35)21-14-18-15-22-31(6,7)41-32(28(18)36,13-10-17(3)29(37)38)33(21,22)40-27(20)23/h8,10-12,14,18,22,34H,9,13,15H2,1-7H3,(H,37,38)/b17-10+/t18-,22+,32+,33-/m1/s1

InChI Key

COVMVPHACFXMAX-UERHWIFRSA-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
Garcinia gaudichaudii	LOTUS Database	35616633
Garcinia gummi-gutta	Plant	KNApSAcK
Garcinia hanburyi	Plant	KNApSAcK
Garcinia morella	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
Aromatic monoterpenoid
Monoterpenoid
Aryl ketone
Alkyl aryl ether
Cyclohexenone
Oxepane
Phenol
Benzenoid
Oxolane
Vinylogous acid
Ketone
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid
Carboxylic acid derivative
Oxacycle
Carbonyl group
Organic oxygen compound
Organooxygen compound
Organic oxide
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	4.62	ALOGPS
logP	6.05	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	3.76	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	119.36 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	155.44 m³·mol⁻¹	ChemAxon
Polarizability	60.03 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

C00030538

Chemspider ID

58802217

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101389907

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Rajagopal Rao D, Gurudutt KN, Mamatha S, Mohan Rao LJ: Guttiferic acid, a novel rearrangement product from minor chromenoxanthone pigments of Garcinia morella Desr. Magn Reson Chem. 2007 Jul;45(7):578-82. doi: 10.1002/mrc.2011. [PubMed:17534879 ]
Li SL, Song JZ, Han QB, Qiao CF, Xu HX: Improved high-performance liquid chromatographic method for simultaneous determination of 12 cytotoxic caged xanthones in gamboges, a potential anticancer resin from Garcinia hanburyi. Biomed Chromatogr. 2008 Jun;22(6):637-44. doi: 10.1002/bmc.981. [PubMed:18254140 ]

Showing NP-Card for Isomorellic acid (NP0071366)

MOL for NP0071366 (Isomorellic acid)

3D MOL for NP0071366 (Isomorellic acid)

3D SDF for NP0071366 (Isomorellic acid)

3D-SDF for NP0071366 (Isomorellic acid)

PDB for NP0071366 (Isomorellic acid)

3D PDB for NP0071366 (Isomorellic acid)

SMILES for NP0071366 (Isomorellic acid)

INCHI for NP0071366 (Isomorellic acid)

Structure for NP0071366 (Isomorellic acid)

3D Structure for NP0071366 (Isomorellic acid)