NP-MRD: Showing NP-Card for Isoforbesionic acid (NP0085898)

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Record Information

Version

2.0

Created at

2022-04-29 06:19:54 UTC

Updated at

2022-04-29 06:19:54 UTC

NP-MRD ID

NP0085898

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Isoforbesionic acid

Description

Isoforbesionic acid is found in Garcinia hanburyi . Based on a literature review very few articles have been published on (2E)-4-[(1S,2S,13S,15R)-6,8-dihydroxy-17,17-dimethyl-5-(3-methylbut-2-en-1-yl)-10,14-dioxo-3,16-dioxapentacyclo[11.4.1.0²,¹¹.0²,¹⁵.0⁴,⁹]Octadeca-4,6,8,11-tetraen-15-yl]-2-methylbut-2-enoic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292208192D          

 36 40  0  0  1  0            999 V2000
    1.2333    1.4086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0678    0.6004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7254    0.0764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5506   -0.7299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1614   -1.2844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9866   -2.0906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5975   -2.6452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4227   -3.4514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6370   -3.7032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0335   -4.0059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9471   -1.0326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5579   -1.5871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1219   -0.2263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5110    0.3282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6858    1.1344    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7231   -0.9151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0858   -0.4550    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -4.6025   -1.8098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2580    0.4612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4008   -0.0954    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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  1  2  2  0  0  0  0
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  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
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  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  5 11  2  0  0  0  0
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  3 14  1  0  0  0  0
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  4 16  1  0  0  0  0
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 17 35  1  0  0  0  0
  2 35  1  0  0  0  0
 32 36  2  0  0  0  0
M  END

     RDKit          3D

 66 70  0  0  0  0  0  0  0  0999 V2000
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   -0.1758   -2.2436   -2.0491 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.0116    3.7561    3.6428 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.4125    4.6165    0.7806 H   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0
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  2  4  2  3
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M  END


  Mrv1652304292208192D          

 36 40  0  0  1  0            999 V2000
    1.2333    1.4086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0085898

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC1=C(O)C=C(O)C2=C1O[C@@]13[C@H]4C[C@@H](C=C1C2=O)C(=O)[C@]3(C\C=C(/C)C(O)=O)OC4(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C28H30O8/c1-13(2)6-7-16-18(29)12-19(30)21-22(31)17-10-15-11-20-26(4,5)36-27(24(15)32,9-8-14(3)25(33)34)28(17,20)35-23(16)21/h6,8,10,12,15,20,29-30H,7,9,11H2,1-5H3,(H,33,34)/b14-8+/t15-,20+,27+,28-/m1/s1

> <INCHI_KEY>
POBKAWSSZZYYDY-YAHQMWPKSA-N

> <FORMULA>
C28H30O8

> <MOLECULAR_WEIGHT>
494.54

> <EXACT_MASS>
494.194067926

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
51.0825140080373

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-4-[(1S,2S,13S,15R)-6,8-dihydroxy-17,17-dimethyl-5-(3-methylbut-2-en-1-yl)-10,14-dioxo-3,16-dioxapentacyclo[11.4.1.0^{2,11}.0^{2,15}.0^{4,9}]octadeca-4(9),5,7,11-tetraen-15-yl]-2-methylbut-2-enoic acid

> <ALOGPS_LOGP>
3.93

> <JCHEM_LOGP>
4.841900419999999

> <ALOGPS_LOGS>
-4.57

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.7528004772723795

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.7666460842949556

> <JCHEM_PKA_STRONGEST_BASIC>
-4.209292275954546

> <JCHEM_POLAR_SURFACE_AREA>
130.36

> <JCHEM_REFRACTIVITY>
133.0235

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.32e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-4-[(1S,2S,13S,15R)-6,8-dihydroxy-17,17-dimethyl-5-(3-methylbut-2-en-1-yl)-10,14-dioxo-3,16-dioxapentacyclo[11.4.1.0^{2,11}.0^{2,15}.0^{4,9}]octadeca-4(9),5,7,11-tetraen-15-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       2.302   2.629   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.993   1.121   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.221   0.143   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.894  -1.362   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.035  -2.397   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.708  -3.903   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.849  -4.938   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.522  -6.443   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.056  -6.913   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.663  -7.478   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.501  -1.928   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       6.641  -2.963   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       5.827  -0.423   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.687   0.613   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.014   2.118   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       1.350  -1.708   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -0.160  -0.849   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.302  -1.033   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -2.510  -2.652   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -1.124  -3.402   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.935  -4.711   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.136  -4.289   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.179  -2.214   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.696  -1.941   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -3.840  -0.953   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -4.678  -2.245   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -6.216  -2.166   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -6.916  -0.794   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -7.053  -3.458   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -6.353  -4.830   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -8.591  -3.378   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -2.348   0.861   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -2.615  -0.178   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -1.178   1.294   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       0.337   0.664   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -2.174   2.391   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   35                                                  
CONECT    3    2    4   14                                                  
CONECT    4    3    5   16                                                  
CONECT    5    4    6   11                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    5   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13    3   15                                                  
CONECT   15   14                                                            
CONECT   16    4   17                                                       
CONECT   17   16   18   23   35                                             
CONECT   18   17   19   25   32                                             
CONECT   19   18   20                                                       
CONECT   20   19   21   22   23                                             
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   20   17   24                                                  
CONECT   24   23   33                                                       
CONECT   25   18   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   18   33   36                                                  
CONECT   33   32   24   34                                                  
CONECT   34   33   35                                                       
CONECT   35   34   17    2                                                  
CONECT   36   32                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

View in JSmol

Synonyms

Value	Source
(2E)-4-[(1S,2S,13S,15R)-6,8-Dihydroxy-17,17-dimethyl-5-(3-methylbut-2-en-1-yl)-10,14-dioxo-3,16-dioxapentacyclo[11.4.1.0,.0,.0,]octadeca-4,6,8,11-tetraen-15-yl]-2-methylbut-2-enoate	Generator

Chemical Formula

C₂₈H₃₀O₈

Average Mass

494.5400 Da

Monoisotopic Mass

494.19407 Da

IUPAC Name

(2E)-4-[(1S,2S,13S,15R)-6,8-dihydroxy-17,17-dimethyl-5-(3-methylbut-2-en-1-yl)-10,14-dioxo-3,16-dioxapentacyclo[11.4.1.0^{2,11}.0^{2,15}.0^{4,9}]octadeca-4(9),5,7,11-tetraen-15-yl]-2-methylbut-2-enoic acid

Traditional Name

CAS Registry Number

Not Available

SMILES

CC(C)=CCC1=C(O)C=C(O)C2=C1O[C@@]13[C@H]4C[C@@H](C=C1C2=O)C(=O)[C@]3(C\C=C(/C)C(O)=O)OC4(C)C

InChI Identifier

InChI=1S/C28H30O8/c1-13(2)6-7-16-18(29)12-19(30)21-22(31)17-10-15-11-20-26(4,5)36-27(24(15)32,9-8-14(3)25(33)34)28(17,20)35-23(16)21/h6,8,10,12,15,20,29-30H,7,9,11H2,1-5H3,(H,33,34)/b14-8+/t15-,20+,27+,28-/m1/s1

InChI Key

POBKAWSSZZYYDY-YAHQMWPKSA-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 hanburyi	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	3.93	ALOGPS
logP	4.84	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	3.77	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	130.36 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	133.02 m³·mol⁻¹	ChemAxon
Polarizability	51.08 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

C00055945

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

163184040

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Isoforbesionic acid (NP0085898)

MOL for NP0085898 (Isoforbesionic acid)

3D MOL for NP0085898 (Isoforbesionic acid)

3D SDF for NP0085898 (Isoforbesionic acid)

3D-SDF for NP0085898 (Isoforbesionic acid)

PDB for NP0085898 (Isoforbesionic acid)

3D PDB for NP0085898 (Isoforbesionic acid)

SMILES for NP0085898 (Isoforbesionic acid)

INCHI for NP0085898 (Isoforbesionic acid)

Structure for NP0085898 (Isoforbesionic acid)

3D Structure for NP0085898 (Isoforbesionic acid)