NP-MRD: Showing NP-Card for 12,15,16-trihydroxy-9,13,17-trimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-en-3-yl 2-(acetyloxy)-2-methylbutanoate (NP0300651)

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Record Information

Version

2.0

Created at

2022-09-10 13:09:52 UTC

Updated at

2022-09-10 13:09:53 UTC

NP-MRD ID

NP0300651

Secondary Accession Numbers

None

Natural Product Identification

Common Name

12,15,16-trihydroxy-9,13,17-trimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-en-3-yl 2-(acetyloxy)-2-methylbutanoate

Description

Quassimarin belongs to the class of organic compounds known as quassinoids. These are a group of compounds chemically degraded from triterpenes. According to their basic skeleton, quassinoids are categorized into five distinct groups, C-18, C-19, C-20, C-22 and C-25 types. The C-20 quassinoids can be further classified into two types, tetracyclic and the pentacyclic. The tetracyclic variety does not have oxygenation at C-20, while the pentacyclic quassinoids possess additional oxygenation at C-20 that allows for the formation of an additional ring. Quassimarin is an extremely weak basic (essentially neutral) compound (based on its pKa). 12,15,16-trihydroxy-9,13,17-trimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-en-3-yl 2-(acetyloxy)-2-methylbutanoate is found in Leitneria floridana and Quassia amara. Quassimarin is a constituent of Quassia amara (Surinam quassia).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061309232D          

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M  END

     RDKit          3D

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M  END


  Mrv0541 05061309232D          

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    0.0383    3.1319    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6762    2.7194    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4672    3.1319    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0383    1.4819    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1051    1.0694    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8170    1.2127    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  1  1  0  0  0  0
 11  2  1  0  0  0  0
 11  8  2  0  0  0  0
 12  3  1  0  0  0  0
 13  9  1  0  0  0  0
 13 11  1  0  0  0  0
 14  8  1  0  0  0  0
 15  9  1  0  0  0  0
 18 16  1  0  0  0  0
 19 17  1  0  0  0  0
 20 14  1  0  0  0  0
 21 16  1  0  0  0  0
 22 17  1  0  0  0  0
 24  4  1  0  0  0  0
 24  7  1  0  0  0  0
 24 23  1  0  0  0  0
 25  5  1  0  0  0  0
 25 13  1  0  0  0  0
 25 18  1  0  0  0  0
 25 20  1  0  0  0  0
 26  6  1  0  0  0  0
 26 19  1  0  0  0  0
 26 21  1  0  0  0  0
 27 10  1  0  0  0  0
 27 15  1  0  0  0  0
 27 18  1  0  0  0  0
 27 19  1  0  0  0  0
 28 12  2  0  0  0  0
 29 14  2  0  0  0  0
 30 16  1  0  0  0  0
 31 20  1  0  0  0  0
 32 21  1  0  0  0  0
 33 22  2  0  0  0  0
 34 23  2  0  0  0  0
 35 15  1  0  0  0  0
 35 22  1  0  0  0  0
 36 17  1  0  0  0  0
 36 23  1  0  0  0  0
 37 12  1  0  0  0  0
 37 24  1  0  0  0  0
 26 38  1  0  0  0  0
 10 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0300651

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(C)(OC(C)=O)C(=O)OC1C2C3(C)OCC22C(CC4C(C)=CC(=O)C(O)C4(C)C2C(O)C3O)OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H36O11/c1-7-24(4,38-12(3)28)23(34)37-17-19-26(6)21(32)16(30)18-25(5)13(11(2)8-14(29)20(25)31)9-15(36-22(17)33)27(18,19)10-35-26/h8,13,15-21,30-32H,7,9-10H2,1-6H3

> <INCHI_KEY>
FXMIXHYJCNZLFE-UHFFFAOYSA-N

> <FORMULA>
C27H36O11

> <MOLECULAR_WEIGHT>
536.5681

> <EXACT_MASS>
536.225761994

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
53.543928870446884

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
12,15,16-trihydroxy-9,13,17-trimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-en-3-yl 2-(acetyloxy)-2-methylbutanoate

> <ALOGPS_LOGP>
0.99

> <JCHEM_LOGP>
-0.001342993333333875

> <ALOGPS_LOGS>
-2.83

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.257161409952985

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.660323368875748

> <JCHEM_PKA_STRONGEST_BASIC>
-3.313992437103722

> <JCHEM_POLAR_SURFACE_AREA>
165.88999999999996

> <JCHEM_REFRACTIVITY>
128.01449999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.85e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
12,15,16-trihydroxy-9,13,17-trimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-en-3-yl 2-(acetyloxy)-2-methylbutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -2.596   0.099   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.074   7.386   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.597   1.996   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.366   4.100   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.740   1.996   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.212  -0.221   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.826   1.432   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.407   5.076   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.406   5.846   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.479   3.784   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.074   5.846   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.263   2.766   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.740   5.076   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.407   3.536   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.073   5.076   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.406   1.226   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.405   3.536   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.406   2.766   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.739   2.766   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.074   2.766   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.073   0.456   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.405   5.076   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.262   3.536   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.596   2.766   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.740   3.536   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.739   1.226   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.073   3.536   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -5.263   4.306   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      10.741   2.766   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       6.740   0.456   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       8.074   1.226   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       4.073  -1.084   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       0.071   5.846   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      -1.262   5.076   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       2.739   5.846   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       0.071   2.766   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      -3.930   1.996   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       1.525   2.264   0.000  0.00  0.00           O+0
CONECT    1    7                                                            
CONECT    2   11                                                            
CONECT    3   12                                                            
CONECT    4   24                                                            
CONECT    5   25                                                            
CONECT    6   26                                                            
CONECT    7    1   24                                                       
CONECT    8   11   14                                                       
CONECT    9   13   15                                                       
CONECT   10   27   38                                                       
CONECT   11    2    8   13                                                  
CONECT   12    3   28   37                                                  
CONECT   13    9   11   25                                                  
CONECT   14    8   20   29                                                  
CONECT   15    9   27   35                                                  
CONECT   16   18   21   30                                                  
CONECT   17   19   22   36                                                  
CONECT   18   16   25   27                                                  
CONECT   19   17   26   27                                                  
CONECT   20   14   25   31                                                  
CONECT   21   16   26   32                                                  
CONECT   22   17   33   35                                                  
CONECT   23   24   34   36                                                  
CONECT   24    4    7   23   37                                             
CONECT   25    5   13   18   20                                             
CONECT   26    6   19   21   38                                             
CONECT   27   10   15   18   19                                             
CONECT   28   12                                                            
CONECT   29   14                                                            
CONECT   30   16                                                            
CONECT   31   20                                                            
CONECT   32   21                                                            
CONECT   33   22                                                            
CONECT   34   23                                                            
CONECT   35   15   22                                                       
CONECT   36   17   23                                                       
CONECT   37   12   24                                                       
CONECT   38   26   10                                                       
MASTER        0    0    0    0    0    0    0    0   38    0   84    0
END

View in JSmol

Synonyms

Value	Source
12,15,16-Trihydroxy-9,13,17-trimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-en-3-yl 2-(acetyloxy)-2-methylbutanoic acid	Generator
Quassimarin	MeSH

Chemical Formula

C₂₇H₃₆O₁₁

Average Mass

536.5681 Da

Monoisotopic Mass

536.22576 Da

IUPAC Name

12,15,16-trihydroxy-9,13,17-trimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-en-3-yl 2-(acetyloxy)-2-methylbutanoate

Traditional Name

12,15,16-trihydroxy-9,13,17-trimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-en-3-yl 2-(acetyloxy)-2-methylbutanoate

CAS Registry Number

Not Available

SMILES

CCC(C)(OC(C)=O)C(=O)OC1C2C3(C)OCC22C(CC4C(C)=CC(=O)C(O)C4(C)C2C(O)C3O)OC1=O

InChI Identifier

InChI=1S/C27H36O11/c1-7-24(4,38-12(3)28)23(34)37-17-19-26(6)21(32)16(30)18-25(5)13(11(2)8-14(29)20(25)31)9-15(36-22(17)33)27(18,19)10-35-26/h8,13,15-21,30-32H,7,9-10H2,1-6H3

InChI Key

FXMIXHYJCNZLFE-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
Leitneria floridana	LOTUS Database	35616633
Quassia amara	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as quassinoids. These are a group of compounds chemically degraded from triterpenes. According to their basic skeleton, quassinoids are categorized into five distinct groups, C-18, C-19, C-20, C-22 and C-25 types. The C-20 quassinoids can be further classified into two types, tetracyclic and the pentacyclic. The tetracyclic variety does not have oxygenation at C-20, while the pentacyclic quassinoids possess additional oxygenation at C-20 that allows for the formation of an additional ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Quassinoids

Alternative Parents

Substituents

C-20 quassinoid skeleton
Quassinoid
Naphthopyran
Naphthalene
Furopyran
Tricarboxylic acid or derivatives
Delta_valerolactone
Cyclohexenone
Delta valerolactone
Fatty acid ester
Oxepane
Fatty acyl
Oxane
Pyran
Furan
Cyclic alcohol
Tetrahydrofuran
Cyclic ketone
Lactone
Ketone
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Dialkyl ether
Ether
Oxacycle
Organoheterocyclic compound
Polyol
Hydrocarbon derivative
Carbonyl group
Alcohol
Organic oxygen compound
Organic oxide
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	0.99	ALOGPS
logP	-0.0013	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	12.66	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	165.89 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	128.01 m³·mol⁻¹	ChemAxon
Polarizability	53.54 Å³	ChemAxon
Number of Rings	5	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

HMDB0036888

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

429906

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 12,15,16-trihydroxy-9,13,17-trimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-en-3-yl 2-(acetyloxy)-2-methylbutanoate (NP0300651)

MOL for NP0300651 (12,15,16-trihydroxy-9,13,17-trimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-en-3-yl 2-(acetyloxy)-2-methylbutanoate)

3D MOL for NP0300651 (12,15,16-trihydroxy-9,13,17-trimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-en-3-yl 2-(acetyloxy)-2-methylbutanoate)

3D SDF for NP0300651 (12,15,16-trihydroxy-9,13,17-trimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-en-3-yl 2-(acetyloxy)-2-methylbutanoate)

3D-SDF for NP0300651 (12,15,16-trihydroxy-9,13,17-trimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-en-3-yl 2-(acetyloxy)-2-methylbutanoate)

PDB for NP0300651 (12,15,16-trihydroxy-9,13,17-trimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-en-3-yl 2-(acetyloxy)-2-methylbutanoate)

3D PDB for NP0300651 (12,15,16-trihydroxy-9,13,17-trimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-en-3-yl 2-(acetyloxy)-2-methylbutanoate)

SMILES for NP0300651 (12,15,16-trihydroxy-9,13,17-trimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-en-3-yl 2-(acetyloxy)-2-methylbutanoate)

INCHI for NP0300651 (12,15,16-trihydroxy-9,13,17-trimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-en-3-yl 2-(acetyloxy)-2-methylbutanoate)

Structure for NP0300651 (12,15,16-trihydroxy-9,13,17-trimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-en-3-yl 2-(acetyloxy)-2-methylbutanoate)

3D Structure for NP0300651 (12,15,16-trihydroxy-9,13,17-trimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-en-3-yl 2-(acetyloxy)-2-methylbutanoate)