NP-MRD: Showing NP-Card for 8-(acetyloxy)-5-[2-hydroxy-2-(5-oxo-2h-furan-3-yl)ethyl]-8a-(hydroxymethyl)-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-4-yl 2-methylbutanoate (NP0168158)

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Record Information

Version

2.0

Created at

2022-09-03 03:53:10 UTC

Updated at

2022-09-03 03:53:10 UTC

NP-MRD ID

NP0168158

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

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

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004231515342D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004231515342D          

 36 39  0  0  0  0            999 V2000
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    1.5749   -1.5935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1304   -2.2034    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7690   -1.7696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  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
 11 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  2  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
 30 31  1  0  0  0  0
 26 31  1  0  0  0  0
 21 32  1  0  0  0  0
  8 32  1  0  0  0  0
 14 32  1  0  0  0  0
 17 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0168158

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(C)C(=O)OC1CCC2(CO2)C2(CO)C(CC(C)C(C)(CC(O)C3=CC(=O)OC3)C12)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H40O9/c1-6-15(2)24(32)36-20-7-8-26(14-34-26)27(13-28)21(35-17(4)29)9-16(3)25(5,23(20)27)11-19(30)18-10-22(31)33-12-18/h10,15-16,19-21,23,28,30H,6-9,11-14H2,1-5H3

> <INCHI_KEY>
WOINILMQIFGCGI-UHFFFAOYSA-N

> <FORMULA>
C27H40O9

> <MOLECULAR_WEIGHT>
508.608

> <EXACT_MASS>
508.267232868

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
53.65497032441068

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
1.91

> <JCHEM_LOGP>
1.8409877306666655

> <ALOGPS_LOGS>
-3.74

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.677723558138482

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.76697682741644

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8323133701121623

> <JCHEM_POLAR_SURFACE_AREA>
131.89000000000001

> <JCHEM_REFRACTIVITY>
128.56849999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.28e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0       0.093  10.055   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.130   8.916   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.663   7.449   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.842   7.120   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.700   6.310   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       3.204   6.639   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       1.232   4.843   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.269   3.705   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.773   4.033   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.810   2.895   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.343   1.427   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.810   0.960   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.671  -0.077   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.838   1.099   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.875  -0.040   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.285  -0.658   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.371  -0.369   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.866  -0.697   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.171   0.441   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.675   0.113   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.297   1.909   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.234   3.447   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.229   2.114   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.814   3.539   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -0.873   4.758   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -3.341   3.745   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -4.404   2.631   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -5.792   3.298   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -7.148   2.567   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -5.586   4.824   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -4.071   5.100   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.801   2.237   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       3.407  -1.507   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       2.940  -2.975   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       3.977  -4.113   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       1.435  -3.303   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    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   32                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13   14                                             
CONECT   12   11   13                                                       
CONECT   13   12   11                                                       
CONECT   14   11   15   17   32                                             
CONECT   15   14   16                                                       
CONECT   16   15                                                            
CONECT   17   14   18   33                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23   32                                             
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   31                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   26                                                       
CONECT   32   21    8   14                                                  
CONECT   33   17   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   78    0
END

View in JSmol

Synonyms

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

Chemical Formula

C₂₇H₄₀O₉

Average Mass

508.6080 Da

Monoisotopic Mass

508.26723 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CCC(C)C(=O)OC1CCC2(CO2)C2(CO)C(CC(C)C(C)(CC(O)C3=CC(=O)OC3)C12)OC(C)=O

InChI Identifier

InChI=1S/C27H40O9/c1-6-15(2)24(32)36-20-7-8-26(14-34-26)27(13-28)21(35-17(4)29)9-16(3)25(5,23(20)27)11-19(30)18-10-22(31)33-12-18/h10,15-16,19-21,23,28,30H,6-9,11-14H2,1-5H3

InChI Key

WOINILMQIFGCGI-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 ciliata	LOTUS Database	35616633

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tricarboxylic acids and derivatives

Direct Parent

Tricarboxylic acids and derivatives

Alternative Parents

Substituents

Tricarboxylic acid or derivatives
Fatty acid ester
2-furanone
Fatty acyl
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Lactone
Secondary alcohol
Dialkyl ether
Oxirane
Ether
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Alcohol
Organic oxygen compound
Carbonyl group
Organic oxide
Organooxygen compound
Primary alcohol
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	1.84	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	5.77	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	131.89 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	128.57 m³·mol⁻¹	ChemAxon
Polarizability	53.65 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

14356971

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 8-(acetyloxy)-5-[2-hydroxy-2-(5-oxo-2h-furan-3-yl)ethyl]-8a-(hydroxymethyl)-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-4-yl 2-methylbutanoate (NP0168158)

MOL for NP0168158 (8-(acetyloxy)-5-[2-hydroxy-2-(5-oxo-2h-furan-3-yl)ethyl]-8a-(hydroxymethyl)-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-4-yl 2-methylbutanoate)

3D MOL for NP0168158 (8-(acetyloxy)-5-[2-hydroxy-2-(5-oxo-2h-furan-3-yl)ethyl]-8a-(hydroxymethyl)-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-4-yl 2-methylbutanoate)

3D SDF for NP0168158 (8-(acetyloxy)-5-[2-hydroxy-2-(5-oxo-2h-furan-3-yl)ethyl]-8a-(hydroxymethyl)-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-4-yl 2-methylbutanoate)

3D-SDF for NP0168158 (8-(acetyloxy)-5-[2-hydroxy-2-(5-oxo-2h-furan-3-yl)ethyl]-8a-(hydroxymethyl)-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-4-yl 2-methylbutanoate)

PDB for NP0168158 (8-(acetyloxy)-5-[2-hydroxy-2-(5-oxo-2h-furan-3-yl)ethyl]-8a-(hydroxymethyl)-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-4-yl 2-methylbutanoate)

3D PDB for NP0168158 (8-(acetyloxy)-5-[2-hydroxy-2-(5-oxo-2h-furan-3-yl)ethyl]-8a-(hydroxymethyl)-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-4-yl 2-methylbutanoate)

SMILES for NP0168158 (8-(acetyloxy)-5-[2-hydroxy-2-(5-oxo-2h-furan-3-yl)ethyl]-8a-(hydroxymethyl)-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-4-yl 2-methylbutanoate)

INCHI for NP0168158 (8-(acetyloxy)-5-[2-hydroxy-2-(5-oxo-2h-furan-3-yl)ethyl]-8a-(hydroxymethyl)-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-4-yl 2-methylbutanoate)

Structure for NP0168158 (8-(acetyloxy)-5-[2-hydroxy-2-(5-oxo-2h-furan-3-yl)ethyl]-8a-(hydroxymethyl)-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-4-yl 2-methylbutanoate)

3D Structure for NP0168158 (8-(acetyloxy)-5-[2-hydroxy-2-(5-oxo-2h-furan-3-yl)ethyl]-8a-(hydroxymethyl)-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-4-yl 2-methylbutanoate)