NP-MRD: Showing NP-Card for 2-[8-(acetyloxy)-8a-[(acetyloxy)methyl]-4-hydroxy-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-5-yl]-1-(5-oxo-2h-furan-3-yl)ethyl acetate (NP0164495)

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Record Information

Version

2.0

Created at

2022-09-02 23:23:00 UTC

Updated at

2022-09-02 23:23:00 UTC

NP-MRD ID

NP0164495

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-[8-(acetyloxy)-8a-[(acetyloxy)methyl]-4-hydroxy-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-5-yl]-1-(5-oxo-2h-furan-3-yl)ethyl acetate

Description

2-[8-(Acetyloxy)-8a-[(acetyloxy)methyl]-4-hydroxy-5,6-dimethyl-octahydro-2H-spiro[naphthalene-1,2'-oxirane]-5-yl]-1-(5-oxo-2,5-dihydrofuran-3-yl)ethyl acetate belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups. 2-[8-(acetyloxy)-8a-[(acetyloxy)methyl]-4-hydroxy-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-5-yl]-1-(5-oxo-2h-furan-3-yl)ethyl acetate is found in Ajuga taiwanensis. 2-[8-(Acetyloxy)-8a-[(acetyloxy)methyl]-4-hydroxy-5,6-dimethyl-octahydro-2H-spiro[naphthalene-1,2'-oxirane]-5-yl]-1-(5-oxo-2,5-dihydrofuran-3-yl)ethyl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251512472D          

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M  END

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  Mrv1533004251512472D          

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  9 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
  9 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 20 22  1  0  0  0  0
 15 23  1  0  0  0  0
  2 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 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
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 26 31  1  0  0  0  0
 31 32  2  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
 35 36  1  0  0  0  0
 31 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0164495

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CC(OC(C)=O)C2(COC(C)=O)C(C(O)CCC22CO2)C1(C)CC(OC(C)=O)C1=CC(=O)OC1

> <INCHI_IDENTIFIER>
InChI=1S/C26H36O10/c1-14-8-21(36-17(4)29)26(13-33-15(2)27)23(19(30)6-7-25(26)12-34-25)24(14,5)10-20(35-16(3)28)18-9-22(31)32-11-18/h9,14,19-21,23,30H,6-8,10-13H2,1-5H3

> <INCHI_KEY>
FOHKIRFZNTVVEF-UHFFFAOYSA-N

> <FORMULA>
C26H36O10

> <MOLECULAR_WEIGHT>
508.564

> <EXACT_MASS>
508.230847359

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
52.09710607896327

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[8-(acetyloxy)-8a-[(acetyloxy)methyl]-4-hydroxy-5,6-dimethyl-octahydro-2H-spiro[naphthalene-1,2'-oxirane]-5-yl]-1-(5-oxo-2,5-dihydrofuran-3-yl)ethyl acetate

> <ALOGPS_LOGP>
1.68

> <JCHEM_LOGP>
0.5940223506666671

> <ALOGPS_LOGS>
-3.83

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.896608068698772

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.594137825772331

> <JCHEM_PKA_STRONGEST_BASIC>
-2.84402439276768

> <JCHEM_POLAR_SURFACE_AREA>
137.95999999999998

> <JCHEM_REFRACTIVITY>
123.9176

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.56e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[8-(acetyloxy)-8a-[(acetyloxy)methyl]-4-hydroxy-5,6-dimethyl-hexahydro-2H-spiro[naphthalene-1,2'-oxirane]-5-yl]-1-(5-oxo-2H-furan-3-yl)ethyl acetate

> <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      10.054   0.213   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.550  -0.116   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.513   1.023   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.008   0.694   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       4.971   1.833   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       5.439   3.300   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.943   3.629   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.402   4.439   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.541  -0.773   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.371   0.757   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.961   1.376   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.791   2.906   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       3.782   4.446   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.381   3.525   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.577  -1.912   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.110  -3.379   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       6.279  -4.910   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.605  -3.708   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.568  -2.569   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.036  -1.102   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.569  -0.634   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       3.707   0.403   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       8.082  -1.583   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.463  -3.075   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.532  -2.102   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.808  -3.617   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      11.258  -4.135   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      12.432  -3.139   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      12.156  -1.624   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      13.882  -3.657   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.634  -4.613   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       8.750  -6.149   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       7.325  -6.734   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       6.961  -8.230   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       6.329  -5.560   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       7.138  -4.249   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   23                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    4   10   15   20                                             
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15    9   16   23                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19    9   21   22                                             
CONECT   21   20   22                                                       
CONECT   22   21   20                                                       
CONECT   23   15    2   24   25                                             
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27   31                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   26   32   36                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36                                                       
CONECT   36   35   31                                                       
MASTER        0    0    0    0    0    0    0    0   36    0   78    0
END

View in JSmol

Synonyms

Value	Source
2-[8-(Acetyloxy)-8a-[(acetyloxy)methyl]-4-hydroxy-5,6-dimethyl-octahydro-2H-spiro[naphthalene-1,2'-oxirane]-5-yl]-1-(5-oxo-2,5-dihydrofuran-3-yl)ethyl acetic acid	Generator

Chemical Formula

C₂₆H₃₆O₁₀

Average Mass

508.5640 Da

Monoisotopic Mass

508.23085 Da

IUPAC Name

2-[8-(acetyloxy)-8a-[(acetyloxy)methyl]-4-hydroxy-5,6-dimethyl-octahydro-2H-spiro[naphthalene-1,2'-oxirane]-5-yl]-1-(5-oxo-2,5-dihydrofuran-3-yl)ethyl acetate

Traditional Name

2-[8-(acetyloxy)-8a-[(acetyloxy)methyl]-4-hydroxy-5,6-dimethyl-hexahydro-2H-spiro[naphthalene-1,2'-oxirane]-5-yl]-1-(5-oxo-2H-furan-3-yl)ethyl acetate

CAS Registry Number

Not Available

SMILES

CC1CC(OC(C)=O)C2(COC(C)=O)C(C(O)CCC22CO2)C1(C)CC(OC(C)=O)C1=CC(=O)OC1

InChI Identifier

InChI=1S/C26H36O10/c1-14-8-21(36-17(4)29)26(13-33-15(2)27)23(19(30)6-7-25(26)12-34-25)24(14,5)10-20(35-16(3)28)18-9-22(31)32-11-18/h9,14,19-21,23,30H,6-8,10-13H2,1-5H3

InChI Key

FOHKIRFZNTVVEF-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
Ajuga taiwanensis	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
2-furanone
Cyclic alcohol
Dihydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Lactone
Carboxylic acid ester
Ether
Oxirane
Dialkyl ether
Organoheterocyclic compound
Oxacycle
Organic oxygen compound
Organic oxide
Organooxygen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
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	1.68	ALOGPS
logP	0.59	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	5.59	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	137.96 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	123.92 m³·mol⁻¹	ChemAxon
Polarizability	52.1 Å³	ChemAxon
Number of Rings	4	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

72954729

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-[8-(acetyloxy)-8a-[(acetyloxy)methyl]-4-hydroxy-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-5-yl]-1-(5-oxo-2h-furan-3-yl)ethyl acetate (NP0164495)

MOL for NP0164495 (2-[8-(acetyloxy)-8a-[(acetyloxy)methyl]-4-hydroxy-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-5-yl]-1-(5-oxo-2h-furan-3-yl)ethyl acetate)

3D MOL for NP0164495 (2-[8-(acetyloxy)-8a-[(acetyloxy)methyl]-4-hydroxy-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-5-yl]-1-(5-oxo-2h-furan-3-yl)ethyl acetate)

3D SDF for NP0164495 (2-[8-(acetyloxy)-8a-[(acetyloxy)methyl]-4-hydroxy-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-5-yl]-1-(5-oxo-2h-furan-3-yl)ethyl acetate)

3D-SDF for NP0164495 (2-[8-(acetyloxy)-8a-[(acetyloxy)methyl]-4-hydroxy-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-5-yl]-1-(5-oxo-2h-furan-3-yl)ethyl acetate)

PDB for NP0164495 (2-[8-(acetyloxy)-8a-[(acetyloxy)methyl]-4-hydroxy-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-5-yl]-1-(5-oxo-2h-furan-3-yl)ethyl acetate)

3D PDB for NP0164495 (2-[8-(acetyloxy)-8a-[(acetyloxy)methyl]-4-hydroxy-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-5-yl]-1-(5-oxo-2h-furan-3-yl)ethyl acetate)

SMILES for NP0164495 (2-[8-(acetyloxy)-8a-[(acetyloxy)methyl]-4-hydroxy-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-5-yl]-1-(5-oxo-2h-furan-3-yl)ethyl acetate)

INCHI for NP0164495 (2-[8-(acetyloxy)-8a-[(acetyloxy)methyl]-4-hydroxy-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-5-yl]-1-(5-oxo-2h-furan-3-yl)ethyl acetate)

Structure for NP0164495 (2-[8-(acetyloxy)-8a-[(acetyloxy)methyl]-4-hydroxy-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-5-yl]-1-(5-oxo-2h-furan-3-yl)ethyl acetate)

3D Structure for NP0164495 (2-[8-(acetyloxy)-8a-[(acetyloxy)methyl]-4-hydroxy-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-5-yl]-1-(5-oxo-2h-furan-3-yl)ethyl acetate)