NP-MRD: Showing NP-Card for Gaudichaudiic acid E (NP0084052)

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Record Information

Version

2.0

Created at

2022-04-29 04:54:29 UTC

Updated at

2022-04-29 04:54:29 UTC

NP-MRD ID

NP0084052

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Gaudichaudiic acid E

Description

Gaudichaudiic acid E is found in Garcinia gaudichaudii. Based on a literature review very few articles have been published on (2Z)-4-[(1S,2S,17S,19R)-12-hydroxy-5-(2-hydroxy-3-methylbut-3-en-1-yl)-8,8,21,21-tetramethyl-14,18-dioxo-3,7,20-trioxahexacyclo[15.4.1.0²,¹⁵.0²,¹⁹.0⁴,¹³.0⁶,¹¹]Docosa-4(13),5,9,11,15-pentaen-19-yl]-2-methylbut-2-enoic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292206542D          

 42 47  0  0  1  0            999 V2000
   -0.0392   -0.7786    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7075   -0.2388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.0621    0.9982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7309    0.5039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4975    0.8088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6758    1.6456    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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 40 41  1  6  0  0  0
  3 41  1  0  0  0  0
  6 42  2  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652304292206542D          

 42 47  0  0  1  0            999 V2000
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    1.5998   -0.5407    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2292   -1.5152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4512   -2.0944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5470   -2.9139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3046   -3.2406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9663   -2.7479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4004   -4.0600    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8853   -3.4066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1097   -1.3600    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8501   -1.4146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6929   -1.1819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0543   -2.3398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0889   -0.7674    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2738   -0.1267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0574    1.8811    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  6  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
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 13 16  1  0  0  0  0
 10 17  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 18 25  2  0  0  0  0
  7 25  1  0  0  0  0
 25 26  1  0  0  0  0
 27 26  1  1  0  0  0
  5 27  1  0  0  0  0
 27 28  1  0  0  0  0
  2 28  1  0  0  0  0
 28 29  1  6  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
 31 35  1  0  0  0  0
 28 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
 37 40  1  0  0  0  0
 27 40  1  0  0  0  0
 40 41  1  6  0  0  0
  3 41  1  0  0  0  0
  6 42  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0084052

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=C)C(O)CC1=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/C33H36O9/c1-15(2)21(34)14-19-26-18(9-10-30(4,5)40-26)24(35)23-25(36)20-12-17-13-22-31(6,7)42-32(28(17)37,11-8-16(3)29(38)39)33(20,22)41-27(19)23/h8-10,12,17,21-22,34-35H,1,11,13-14H2,2-7H3,(H,38,39)/b16-8-/t17-,21?,22+,32+,33-/m1/s1

> <INCHI_KEY>
QQVYMSAUAKNMII-SIOHMWQTSA-N

> <FORMULA>
C33H36O9

> <MOLECULAR_WEIGHT>
576.642

> <EXACT_MASS>
576.235932739

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
60.14493631485091

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2Z)-4-[(1S,2S,17S,19R)-12-hydroxy-5-(2-hydroxy-3-methylbut-3-en-1-yl)-8,8,21,21-tetramethyl-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>
3.40

> <JCHEM_LOGP>
4.873211747000003

> <ALOGPS_LOGS>
-4.99

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.93615536286792

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.7826867249223324

> <JCHEM_PKA_STRONGEST_BASIC>
-3.05414424004341

> <JCHEM_POLAR_SURFACE_AREA>
139.59000000000003

> <JCHEM_REFRACTIVITY>
155.879

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.93e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2Z)-4-[(1S,2S,17S,19R)-12-hydroxy-5-(2-hydroxy-3-methylbut-3-en-1-yl)-8,8,21,21-tetramethyl-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                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  O   UNK     0      -0.073  -1.453   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.321  -0.446   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.462   1.102   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.821   1.982   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.211   1.243   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.716   1.863   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.964   0.941   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.395   1.510   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       8.728   3.072   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       9.604   0.555   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.035   1.124   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.243   0.170   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.020  -1.354   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.655  -1.306   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.698  -2.827   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      10.590  -1.923   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       9.381  -0.969   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.950  -1.538   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.355  -3.206   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.265  -4.522   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       8.607  -5.914   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      10.800  -4.396   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.459  -3.004   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.676  -5.662   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.742  -0.583   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       5.277  -1.111   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       3.857  -0.375   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.986  -1.009   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.161  -2.828   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.709  -3.910   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.888  -5.439   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.302  -6.049   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       5.537  -5.129   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       4.481  -7.579   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       1.653  -6.359   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       2.071  -2.539   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       3.453  -2.641   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       5.027  -2.206   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       3.835  -4.368   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       2.033  -1.432   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       0.511  -0.236   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       5.707   3.511   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   28                                                  
CONECT    3    2    4   41                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   27                                                  
CONECT    6    5    7   42                                                  
CONECT    7    6    8   25                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   17                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15   16                                             
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   13   17                                                       
CONECT   17   10   16   18                                                  
CONECT   18   17   19   25                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   18    7   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26    5   28   40                                             
CONECT   28   27    2   29   36                                             
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   35                                                  
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35   31                                                            
CONECT   36   28   37                                                       
CONECT   37   36   38   39   40                                             
CONECT   38   37                                                            
CONECT   39   37                                                            
CONECT   40   37   27   41                                                  
CONECT   41   40    3                                                       
CONECT   42    6                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   94    0
END

View in JSmol

Synonyms

Value	Source
(2Z)-4-[(1S,2S,17S,19R)-12-Hydroxy-5-(2-hydroxy-3-methylbut-3-en-1-yl)-8,8,21,21-tetramethyl-14,18-dioxo-3,7,20-trioxahexacyclo[15.4.1.0,.0,.0,.0,]docosa-4(13),5,9,11,15-pentaen-19-yl]-2-methylbut-2-enoate	Generator

Chemical Formula

C₃₃H₃₆O₉

Average Mass

576.6420 Da

Monoisotopic Mass

576.23593 Da

IUPAC Name

(2Z)-4-[(1S,2S,17S,19R)-12-hydroxy-5-(2-hydroxy-3-methylbut-3-en-1-yl)-8,8,21,21-tetramethyl-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)C(O)CC1=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/C33H36O9/c1-15(2)21(34)14-19-26-18(9-10-30(4,5)40-26)24(35)23-25(36)20-12-17-13-22-31(6,7)42-32(28(17)37,11-8-16(3)29(38)39)33(20,22)41-27(19)23/h8-10,12,17,21-22,34-35H,1,11,13-14H2,2-7H3,(H,38,39)/b16-8-/t17-,21?,22+,32+,33-/m1/s1

InChI Key

QQVYMSAUAKNMII-SIOHMWQTSA-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	Plant	KNApSAcK

Chemical Taxonomy

Classification

Not classified

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	3.4	ALOGPS
logP	4.87	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	3.78	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	139.59 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	155.88 m³·mol⁻¹	ChemAxon
Polarizability	60.14 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00053243

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

163184222

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Gaudichaudiic acid E (NP0084052)

MOL for NP0084052 (Gaudichaudiic acid E)

3D MOL for NP0084052 (Gaudichaudiic acid E)

3D SDF for NP0084052 (Gaudichaudiic acid E)

3D-SDF for NP0084052 (Gaudichaudiic acid E)

PDB for NP0084052 (Gaudichaudiic acid E)

3D PDB for NP0084052 (Gaudichaudiic acid E)

SMILES for NP0084052 (Gaudichaudiic acid E)

INCHI for NP0084052 (Gaudichaudiic acid E)

Structure for NP0084052 (Gaudichaudiic acid E)

3D Structure for NP0084052 (Gaudichaudiic acid E)