NP-MRD: Showing NP-Card for methyl 4',9'-bis(acetyloxy)-5'a-hydroxy-6',6',9'a-trimethyl-3-oxo-octahydro-1'h-4,6-dioxaspiro[bicyclo[3.1.0]hexane-2,2'-cyclopenta[a]naphthalene]-3'-carboxylate (NP0245687)

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Record Information

Version

1.0

Created at

2022-09-07 06:51:34 UTC

Updated at

2022-09-07 06:51:34 UTC

NP-MRD ID

NP0245687

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 4',9'-bis(acetyloxy)-5'a-hydroxy-6',6',9'a-trimethyl-3-oxo-octahydro-1'h-4,6-dioxaspiro[bicyclo[3.1.0]hexane-2,2'-cyclopenta[a]naphthalene]-3'-carboxylate

Description

Methyl 4',9'-bis(acetyloxy)-5'a-hydroxy-6',6',9'a-trimethyl-3-oxo-dodecahydro-4,6-dioxaspiro[bicyclo[3.1.0]Hexane-2,2'-cyclopenta[a]naphthalene]-3'-carboxylate belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups. methyl 4',9'-bis(acetyloxy)-5'a-hydroxy-6',6',9'a-trimethyl-3-oxo-octahydro-1'h-4,6-dioxaspiro[bicyclo[3.1.0]hexane-2,2'-cyclopenta[a]naphthalene]-3'-carboxylate is found in Caesalpinia minax. Methyl 4',9'-bis(acetyloxy)-5'a-hydroxy-6',6',9'a-trimethyl-3-oxo-dodecahydro-4,6-dioxaspiro[bicyclo[3.1.0]Hexane-2,2'-cyclopenta[a]naphthalene]-3'-carboxylate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251506562D          

 35 39  0  0  0  0            999 V2000
    5.3666    3.7172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1533004251506562D          

 35 39  0  0  0  0            999 V2000
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  5 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 25 30  1  0  0  0  0
 30 31  2  0  0  0  0
  7 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0245687

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1C2C(CC11C3OC3OC1=O)C1(C)C(CCC(C)(C)C1(O)CC2OC(C)=O)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C25H34O10/c1-11(26)32-14-10-25(30)22(3,4)8-7-15(33-12(2)27)23(25,5)13-9-24(17(16(13)14)19(28)31-6)18-20(34-18)35-21(24)29/h13-18,20,30H,7-10H2,1-6H3

> <INCHI_KEY>
BCESHLQRCAWNOE-UHFFFAOYSA-N

> <FORMULA>
C25H34O10

> <MOLECULAR_WEIGHT>
494.537

> <EXACT_MASS>
494.215197295

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
49.85052553796351

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 4',9'-bis(acetyloxy)-5'a-hydroxy-6',6',9'a-trimethyl-3-oxo-dodecahydro-4,6-dioxaspiro[bicyclo[3.1.0]hexane-2,2'-cyclopenta[a]naphthalene]-3'-carboxylate

> <ALOGPS_LOGP>
1.91

> <JCHEM_LOGP>
1.0735865883333322

> <ALOGPS_LOGS>
-3.47

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.75546784833892

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.8844589384316

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2867067191874852

> <JCHEM_POLAR_SURFACE_AREA>
137.96000000000004

> <JCHEM_REFRACTIVITY>
115.75399999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.66e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 4',9'-bis(acetyloxy)-5'a-hydroxy-6',6',9'a-trimethyl-3-oxo-octahydro-1'H-4,6-dioxaspiro[bicyclo[3.1.0]hexane-2,2'-cyclopenta[a]naphthalene]-3'-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0      10.018   6.939   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      10.677   5.547   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       9.802   4.280   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       8.267   4.405   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      10.461   2.888   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.975   2.604   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.199   3.538   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      14.620   2.945   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      14.817   1.418   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      16.041   2.352   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      16.238   0.825   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      17.777   0.754   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      16.576   2.328   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      16.436  -0.702   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      15.211  -1.637   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.790  -1.044   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      12.566  -1.978   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      12.763  -3.505   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      14.184  -4.098   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      11.539  -4.440   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.593   0.484   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.369  -0.451   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.172   1.077   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.780   0.417   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.723   1.537   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.985   0.185   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       7.981  -0.983   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       7.471   0.470   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       7.274   1.997   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       8.666   2.657   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       7.608   3.776   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      13.002   5.066   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      14.226   6.000   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      14.029   7.527   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      15.647   5.407   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   25                                                  
CONECT    6    5    7   23                                                  
CONECT    7    6    8   32                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11   21                                             
CONECT   10    9                                                            
CONECT   11    9   12   13   14                                             
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   11   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   16    9   22   23                                             
CONECT   22   21                                                            
CONECT   23   21    6   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24    5   26   30                                             
CONECT   26   25   27   28                                                  
CONECT   27   26   28                                                       
CONECT   28   27   26   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29   25   31                                                  
CONECT   31   30                                                            
CONECT   32    7   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

View in JSmol

Synonyms

Value	Source
Methyl 4',9'-bis(acetyloxy)-5'a-hydroxy-6',6',9'a-trimethyl-3-oxo-dodecahydro-4,6-dioxaspiro[bicyclo[3.1.0]hexane-2,2'-cyclopenta[a]naphthalene]-3'-carboxylic acid	Generator

Chemical Formula

C₂₅H₃₄O₁₀

Average Mass

494.5370 Da

Monoisotopic Mass

494.21520 Da

IUPAC Name

methyl 4',9'-bis(acetyloxy)-5'a-hydroxy-6',6',9'a-trimethyl-3-oxo-dodecahydro-4,6-dioxaspiro[bicyclo[3.1.0]hexane-2,2'-cyclopenta[a]naphthalene]-3'-carboxylate

Traditional Name

methyl 4',9'-bis(acetyloxy)-5'a-hydroxy-6',6',9'a-trimethyl-3-oxo-octahydro-1'H-4,6-dioxaspiro[bicyclo[3.1.0]hexane-2,2'-cyclopenta[a]naphthalene]-3'-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1C2C(CC11C3OC3OC1=O)C1(C)C(CCC(C)(C)C1(O)CC2OC(C)=O)OC(C)=O

InChI Identifier

InChI=1S/C25H34O10/c1-11(26)32-14-10-25(30)22(3,4)8-7-15(33-12(2)27)23(25,5)13-9-24(17(16(13)14)19(28)31-6)18-20(34-18)35-21(24)29/h13-18,20,30H,7-10H2,1-6H3

InChI Key

BCESHLQRCAWNOE-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
Caesalpinia minax	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tetracarboxylic acids and derivatives

Direct Parent

Tetracarboxylic acids and derivatives

Alternative Parents

Substituents

Tetracarboxylic acid or derivatives
Meta-dioxane
Gamma butyrolactone
Cyclic alcohol
Tertiary alcohol
Methyl ester
Tetrahydrofuran
Carboxylic acid ester
Lactone
Oxirane
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
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	1.91	ALOGPS
logP	1.07	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	13.88	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	137.96 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	115.75 m³·mol⁻¹	ChemAxon
Polarizability	49.85 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	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 methyl 4',9'-bis(acetyloxy)-5'a-hydroxy-6',6',9'a-trimethyl-3-oxo-octahydro-1'h-4,6-dioxaspiro[bicyclo[3.1.0]hexane-2,2'-cyclopenta[a]naphthalene]-3'-carboxylate (NP0245687)

MOL for NP0245687 (methyl 4',9'-bis(acetyloxy)-5'a-hydroxy-6',6',9'a-trimethyl-3-oxo-octahydro-1'h-4,6-dioxaspiro[bicyclo[3.1.0]hexane-2,2'-cyclopenta[a]naphthalene]-3'-carboxylate)

3D MOL for NP0245687 (methyl 4',9'-bis(acetyloxy)-5'a-hydroxy-6',6',9'a-trimethyl-3-oxo-octahydro-1'h-4,6-dioxaspiro[bicyclo[3.1.0]hexane-2,2'-cyclopenta[a]naphthalene]-3'-carboxylate)

3D SDF for NP0245687 (methyl 4',9'-bis(acetyloxy)-5'a-hydroxy-6',6',9'a-trimethyl-3-oxo-octahydro-1'h-4,6-dioxaspiro[bicyclo[3.1.0]hexane-2,2'-cyclopenta[a]naphthalene]-3'-carboxylate)

3D-SDF for NP0245687 (methyl 4',9'-bis(acetyloxy)-5'a-hydroxy-6',6',9'a-trimethyl-3-oxo-octahydro-1'h-4,6-dioxaspiro[bicyclo[3.1.0]hexane-2,2'-cyclopenta[a]naphthalene]-3'-carboxylate)

PDB for NP0245687 (methyl 4',9'-bis(acetyloxy)-5'a-hydroxy-6',6',9'a-trimethyl-3-oxo-octahydro-1'h-4,6-dioxaspiro[bicyclo[3.1.0]hexane-2,2'-cyclopenta[a]naphthalene]-3'-carboxylate)

3D PDB for NP0245687 (methyl 4',9'-bis(acetyloxy)-5'a-hydroxy-6',6',9'a-trimethyl-3-oxo-octahydro-1'h-4,6-dioxaspiro[bicyclo[3.1.0]hexane-2,2'-cyclopenta[a]naphthalene]-3'-carboxylate)

SMILES for NP0245687 (methyl 4',9'-bis(acetyloxy)-5'a-hydroxy-6',6',9'a-trimethyl-3-oxo-octahydro-1'h-4,6-dioxaspiro[bicyclo[3.1.0]hexane-2,2'-cyclopenta[a]naphthalene]-3'-carboxylate)

INCHI for NP0245687 (methyl 4',9'-bis(acetyloxy)-5'a-hydroxy-6',6',9'a-trimethyl-3-oxo-octahydro-1'h-4,6-dioxaspiro[bicyclo[3.1.0]hexane-2,2'-cyclopenta[a]naphthalene]-3'-carboxylate)

Structure for NP0245687 (methyl 4',9'-bis(acetyloxy)-5'a-hydroxy-6',6',9'a-trimethyl-3-oxo-octahydro-1'h-4,6-dioxaspiro[bicyclo[3.1.0]hexane-2,2'-cyclopenta[a]naphthalene]-3'-carboxylate)

3D Structure for NP0245687 (methyl 4',9'-bis(acetyloxy)-5'a-hydroxy-6',6',9'a-trimethyl-3-oxo-octahydro-1'h-4,6-dioxaspiro[bicyclo[3.1.0]hexane-2,2'-cyclopenta[a]naphthalene]-3'-carboxylate)