NP-MRD: Showing NP-Card for 5,6,12,14-tetrahydroxy-13-(7-hydroxy-3,7-dimethyloct-2-en-1-yl)-7-(3-methylbut-2-en-1-yl)-2,9-dioxatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3(8),4,6,12,14-hexaen-10-one (NP0200607)

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Record Information

Version

2.0

Created at

2022-09-04 19:29:21 UTC

Updated at

2022-09-04 19:29:22 UTC

NP-MRD ID

NP0200607

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5,6,12,14-tetrahydroxy-13-(7-hydroxy-3,7-dimethyloct-2-en-1-yl)-7-(3-methylbut-2-en-1-yl)-2,9-dioxatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3(8),4,6,12,14-hexaen-10-one

Description

5,6,12,14-Tetrahydroxy-13-(7-hydroxy-3,7-dimethyloct-2-en-1-yl)-7-(3-methylbut-2-en-1-yl)-2,9-dioxatricyclo[9.4.0.0³,⁸]Pentadeca-1(11),3(8),4,6,12,14-hexaen-10-one belongs to the class of organic compounds known as depsides and depsidones. These are polycyclic compounds that is either a polyphenolic compound composed of two or more monocyclic aromatic units linked by an ester bond (depside), or a compound containing the depsidone structure (depsidone). 5,6,12,14-tetrahydroxy-13-(7-hydroxy-3,7-dimethyloct-2-en-1-yl)-7-(3-methylbut-2-en-1-yl)-2,9-dioxatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3(8),4,6,12,14-hexaen-10-one is found in Garcinia parvifolia. 5,6,12,14-Tetrahydroxy-13-(7-hydroxy-3,7-dimethyloct-2-en-1-yl)-7-(3-methylbut-2-en-1-yl)-2,9-dioxatricyclo[9.4.0.0³,⁸]Pentadeca-1(11),3(8),4,6,12,14-hexaen-10-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241514192D          

 36 38  0  0  0  0            999 V2000
    0.4718   -4.3364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.3705   -1.6055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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 11 35  2  0  0  0  0
  2 36  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1533004241514192D          

 36 38  0  0  0  0            999 V2000
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  8 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  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
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 17 18  1  0  0  0  0
 19 18  1  4  0  0  0
 19 20  2  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
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 25 28  1  0  0  0  0
 17 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
 13 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
  5 35  1  0  0  0  0
 11 35  2  0  0  0  0
  2 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0200607

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC1=C(O)C(O)=CC2=C1OC(=O)C1=C(O)C(CC=C(C)CCCC(C)(C)O)=C(O)C=C1O2

> <INCHI_IDENTIFIER>
InChI=1S/C28H34O8/c1-15(2)8-10-18-24(31)20(30)14-22-26(18)36-27(33)23-21(35-22)13-19(29)17(25(23)32)11-9-16(3)7-6-12-28(4,5)34/h8-9,13-14,29-32,34H,6-7,10-12H2,1-5H3

> <INCHI_KEY>
OORBCMGHEZSSMO-UHFFFAOYSA-N

> <FORMULA>
C28H34O8

> <MOLECULAR_WEIGHT>
498.572

> <EXACT_MASS>
498.225368055

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
53.576991765230936

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5,6,12,14-tetrahydroxy-13-(7-hydroxy-3,7-dimethyloct-2-en-1-yl)-7-(3-methylbut-2-en-1-yl)-2,9-dioxatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3(8),4,6,11,13-hexaen-10-one

> <ALOGPS_LOGP>
4.79

> <JCHEM_LOGP>
6.448774379

> <ALOGPS_LOGS>
-4.89

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.839469860722126

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.945523155002425

> <JCHEM_PKA_STRONGEST_BASIC>
-1.2195838751431816

> <JCHEM_POLAR_SURFACE_AREA>
136.68

> <JCHEM_REFRACTIVITY>
139.2416

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.43e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,6,12,14-tetrahydroxy-13-(7-hydroxy-3,7-dimethyloct-2-en-1-yl)-7-(3-methylbut-2-en-1-yl)-2,9-dioxatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3(8),4,6,11,13-hexaen-10-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       0.881  -8.095   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.248  -7.047   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.095  -5.546   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.566  -5.092   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.909  -3.590   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.780  -2.543   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.692  -2.997   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.123  -1.042   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.006   0.006   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.594  -0.588   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.723  -1.635   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.111  -0.967   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       6.498  -1.635   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.627  -0.588   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.099  -1.042   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      10.227   0.006   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       9.441  -2.543   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.913  -2.997   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.042  -1.949   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.513  -2.403   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.856  -3.905   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      14.642  -1.356   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      14.299   0.145   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      15.428   1.193   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      15.086   2.694   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      14.743   4.196   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      16.587   3.037   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      13.584   2.352   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       8.312  -3.590   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       8.655  -5.092   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       6.841  -3.137   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.881  -4.341   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       6.549  -5.728   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       4.341  -4.341   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       3.380  -3.137   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -1.720  -7.501   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   36                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   35                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   35                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   31                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   29                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27   28                                             
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   25                                                            
CONECT   29   17   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   13   32                                                  
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34    5   11                                                  
CONECT   36    2                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₄O₈

Average Mass

498.5720 Da

Monoisotopic Mass

498.22537 Da

IUPAC Name

5,6,12,14-tetrahydroxy-13-(7-hydroxy-3,7-dimethyloct-2-en-1-yl)-7-(3-methylbut-2-en-1-yl)-2,9-dioxatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3(8),4,6,11,13-hexaen-10-one

Traditional Name

5,6,12,14-tetrahydroxy-13-(7-hydroxy-3,7-dimethyloct-2-en-1-yl)-7-(3-methylbut-2-en-1-yl)-2,9-dioxatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3(8),4,6,11,13-hexaen-10-one

CAS Registry Number

Not Available

SMILES

CC(C)=CCC1=C(O)C(O)=CC2=C1OC(=O)C1=C(O)C(CC=C(C)CCCC(C)(C)O)=C(O)C=C1O2

InChI Identifier

InChI=1S/C28H34O8/c1-15(2)8-10-18-24(31)20(30)14-22-26(18)36-27(33)23-21(35-22)13-19(29)17(25(23)32)11-9-16(3)7-6-12-28(4,5)34/h8-9,13-14,29-32,34H,6-7,10-12H2,1-5H3

InChI Key

OORBCMGHEZSSMO-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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 parvifolia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as depsides and depsidones. These are polycyclic compounds that is either a polyphenolic compound composed of two or more monocyclic aromatic units linked by an ester bond (depside), or a compound containing the depsidone structure (depsidone).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Depsides and depsidones

Sub Class

Not Available

Direct Parent

Depsides and depsidones

Alternative Parents

Substituents

Depsidone
Diaryl ether
Dihydroxybenzoic acid
1,4-dioxepine
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Dioxepine
Phenol
Benzenoid
Tertiary alcohol
Vinylogous acid
Carboxylic acid ester
Lactone
Polyol
Ether
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Organooxygen compound
Organic oxygen compound
Alcohol
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	4.79	ALOGPS
logP	6.45	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	7.95	ChemAxon
pKa (Strongest Basic)	-1.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	136.68 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	139.24 m³·mol⁻¹	ChemAxon
Polarizability	53.58 Å³	ChemAxon
Number of Rings	3	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

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5,6,12,14-tetrahydroxy-13-(7-hydroxy-3,7-dimethyloct-2-en-1-yl)-7-(3-methylbut-2-en-1-yl)-2,9-dioxatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3(8),4,6,12,14-hexaen-10-one (NP0200607)

MOL for NP0200607 (5,6,12,14-tetrahydroxy-13-(7-hydroxy-3,7-dimethyloct-2-en-1-yl)-7-(3-methylbut-2-en-1-yl)-2,9-dioxatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3(8),4,6,12,14-hexaen-10-one)

3D MOL for NP0200607 (5,6,12,14-tetrahydroxy-13-(7-hydroxy-3,7-dimethyloct-2-en-1-yl)-7-(3-methylbut-2-en-1-yl)-2,9-dioxatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3(8),4,6,12,14-hexaen-10-one)

3D SDF for NP0200607 (5,6,12,14-tetrahydroxy-13-(7-hydroxy-3,7-dimethyloct-2-en-1-yl)-7-(3-methylbut-2-en-1-yl)-2,9-dioxatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3(8),4,6,12,14-hexaen-10-one)

3D-SDF for NP0200607 (5,6,12,14-tetrahydroxy-13-(7-hydroxy-3,7-dimethyloct-2-en-1-yl)-7-(3-methylbut-2-en-1-yl)-2,9-dioxatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3(8),4,6,12,14-hexaen-10-one)

PDB for NP0200607 (5,6,12,14-tetrahydroxy-13-(7-hydroxy-3,7-dimethyloct-2-en-1-yl)-7-(3-methylbut-2-en-1-yl)-2,9-dioxatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3(8),4,6,12,14-hexaen-10-one)

3D PDB for NP0200607 (5,6,12,14-tetrahydroxy-13-(7-hydroxy-3,7-dimethyloct-2-en-1-yl)-7-(3-methylbut-2-en-1-yl)-2,9-dioxatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3(8),4,6,12,14-hexaen-10-one)

SMILES for NP0200607 (5,6,12,14-tetrahydroxy-13-(7-hydroxy-3,7-dimethyloct-2-en-1-yl)-7-(3-methylbut-2-en-1-yl)-2,9-dioxatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3(8),4,6,12,14-hexaen-10-one)

INCHI for NP0200607 (5,6,12,14-tetrahydroxy-13-(7-hydroxy-3,7-dimethyloct-2-en-1-yl)-7-(3-methylbut-2-en-1-yl)-2,9-dioxatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3(8),4,6,12,14-hexaen-10-one)

Structure for NP0200607 (5,6,12,14-tetrahydroxy-13-(7-hydroxy-3,7-dimethyloct-2-en-1-yl)-7-(3-methylbut-2-en-1-yl)-2,9-dioxatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3(8),4,6,12,14-hexaen-10-one)

3D Structure for NP0200607 (5,6,12,14-tetrahydroxy-13-(7-hydroxy-3,7-dimethyloct-2-en-1-yl)-7-(3-methylbut-2-en-1-yl)-2,9-dioxatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3(8),4,6,12,14-hexaen-10-one)