NP-MRD: Showing NP-Card for 4-hydroxy-5,5,5',8a-tetramethyl-2-{[(3-methylbutanoyl)oxy]methyl}-4a,6,7,8-tetrahydro-4h-spiro[naphthalene-1,2'-oxolan]-5'-ylacetic acid (NP0279964)

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Record Information

Version

2.0

Created at

2022-09-09 05:32:34 UTC

Updated at

2022-09-09 05:32:34 UTC

NP-MRD ID

NP0279964

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-hydroxy-5,5,5',8a-tetramethyl-2-{[(3-methylbutanoyl)oxy]methyl}-4a,6,7,8-tetrahydro-4h-spiro[naphthalene-1,2'-oxolan]-5'-ylacetic acid

Description

2-(4-Hydroxy-5,5,5',8a-tetramethyl-2-{[(3-methylbutanoyl)oxy]methyl}-4a,5,6,7,8,8a-hexahydro-4H-spiro[naphthalene-1,2'-oxolane]-5'-yl)acetic acid belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. 4-hydroxy-5,5,5',8a-tetramethyl-2-{[(3-methylbutanoyl)oxy]methyl}-4a,6,7,8-tetrahydro-4h-spiro[naphthalene-1,2'-oxolan]-5'-ylacetic acid is found in Grindelia hirsutula. 2-(4-Hydroxy-5,5,5',8a-tetramethyl-2-{[(3-methylbutanoyl)oxy]methyl}-4a,5,6,7,8,8a-hexahydro-4H-spiro[naphthalene-1,2'-oxolane]-5'-yl)acetic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004231518392D          

 31 33  0  0  0  0            999 V2000
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    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.8592   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   10.0026   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5329   -1.8430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4723   -1.8430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
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  2  4  1  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1533004231518392D          

 31 33  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0279964

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)CC(=O)OCC1=CC(O)C2C(C)(C)CCCC2(C)C11CCC(C)(CC(O)=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C25H40O6/c1-16(2)12-20(29)30-15-17-13-18(26)21-22(3,4)8-7-9-24(21,6)25(17)11-10-23(5,31-25)14-19(27)28/h13,16,18,21,26H,7-12,14-15H2,1-6H3,(H,27,28)

> <INCHI_KEY>
MCWMHXJEXJBWNW-UHFFFAOYSA-N

> <FORMULA>
C25H40O6

> <MOLECULAR_WEIGHT>
436.589

> <EXACT_MASS>
436.282489008

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
48.76855073872262

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(4-hydroxy-5,5,5',8a-tetramethyl-2-{[(3-methylbutanoyl)oxy]methyl}-4a,5,6,7,8,8a-hexahydro-4H-spiro[naphthalene-1,2'-oxolane]-5'-yl)acetic acid

> <ALOGPS_LOGP>
3.86

> <JCHEM_LOGP>
3.828163946333332

> <ALOGPS_LOGS>
-4.95

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.505926932522943

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.398939603854893

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0149076796946304

> <JCHEM_POLAR_SURFACE_AREA>
93.06

> <JCHEM_REFRACTIVITY>
117.77729999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.94e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-hydroxy-5,5,5',8a-tetramethyl-2-{[(3-methylbutanoyl)oxy]methyl}-4a,6,7,8-tetrahydro-4H-spiro[naphthalene-1,2'-oxolane]-5'-ylacetic acid

> <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       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      10.669  -9.240   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      12.003  -6.930   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      13.337  -7.700   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      14.670  -6.930   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.670  -5.390   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      16.004  -4.620   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      16.004  -3.080   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      17.338  -5.390   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      18.672  -4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      19.661  -3.440   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      17.682  -3.440   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      20.005  -5.390   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      20.005  -6.930   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      18.672  -7.700   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      17.338  -6.930   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      17.814  -8.395   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      16.004  -7.700   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      17.250  -8.605   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      16.774 -10.070   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      15.234 -10.070   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      13.728 -10.390   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      15.395 -11.601   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      14.149 -12.507   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      12.742 -11.880   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      14.310 -14.038   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      14.758  -8.605   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   22                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   20                                                  
CONECT   14   13   15   16   17                                             
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   14   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   13   21   22                                             
CONECT   21   20                                                            
CONECT   22   20    9   23   31                                             
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27   31                                             
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   25   22                                                       
MASTER        0    0    0    0    0    0    0    0   31    0   66    0
END

View in JSmol

Synonyms

Value	Source
2-(4-Hydroxy-5,5,5',8a-tetramethyl-2-{[(3-methylbutanoyl)oxy]methyl}-4a,5,6,7,8,8a-hexahydro-4H-spiro[naphthalene-1,2'-oxolane]-5'-yl)acetate	Generator

Chemical Formula

C₂₅H₄₀O₆

Average Mass

436.5890 Da

Monoisotopic Mass

436.28249 Da

IUPAC Name

2-(4-hydroxy-5,5,5',8a-tetramethyl-2-{[(3-methylbutanoyl)oxy]methyl}-4a,5,6,7,8,8a-hexahydro-4H-spiro[naphthalene-1,2'-oxolane]-5'-yl)acetic acid

Traditional Name

4-hydroxy-5,5,5',8a-tetramethyl-2-{[(3-methylbutanoyl)oxy]methyl}-4a,6,7,8-tetrahydro-4H-spiro[naphthalene-1,2'-oxolane]-5'-ylacetic acid

CAS Registry Number

Not Available

SMILES

CC(C)CC(=O)OCC1=CC(O)C2C(C)(C)CCCC2(C)C11CCC(C)(CC(O)=O)O1

InChI Identifier

InChI=1S/C25H40O6/c1-16(2)12-20(29)30-15-17-13-18(26)21-22(3,4)8-7-9-24(21,6)25(17)11-10-23(5,31-25)14-19(27)28/h13,16,18,21,26H,7-12,14-15H2,1-6H3,(H,27,28)

InChI Key

MCWMHXJEXJBWNW-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
Grindelia hirsutula	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Diterpenoid
Grindelane diterpenoid
Abscisic acid
Fatty acid ester
Dicarboxylic acid or derivatives
Fatty acyl
Tetrahydrofuran
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Oxacycle
Organoheterocyclic compound
Ether
Alcohol
Hydrocarbon derivative
Carbonyl group
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	3.86	ALOGPS
logP	3.83	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	4.4	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	117.78 m³·mol⁻¹	ChemAxon
Polarizability	48.77 Å³	ChemAxon
Number of Rings	3	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 4-hydroxy-5,5,5',8a-tetramethyl-2-{[(3-methylbutanoyl)oxy]methyl}-4a,6,7,8-tetrahydro-4h-spiro[naphthalene-1,2'-oxolan]-5'-ylacetic acid (NP0279964)

MOL for NP0279964 (4-hydroxy-5,5,5',8a-tetramethyl-2-{[(3-methylbutanoyl)oxy]methyl}-4a,6,7,8-tetrahydro-4h-spiro[naphthalene-1,2'-oxolan]-5'-ylacetic acid)

3D MOL for NP0279964 (4-hydroxy-5,5,5',8a-tetramethyl-2-{[(3-methylbutanoyl)oxy]methyl}-4a,6,7,8-tetrahydro-4h-spiro[naphthalene-1,2'-oxolan]-5'-ylacetic acid)

3D SDF for NP0279964 (4-hydroxy-5,5,5',8a-tetramethyl-2-{[(3-methylbutanoyl)oxy]methyl}-4a,6,7,8-tetrahydro-4h-spiro[naphthalene-1,2'-oxolan]-5'-ylacetic acid)

3D-SDF for NP0279964 (4-hydroxy-5,5,5',8a-tetramethyl-2-{[(3-methylbutanoyl)oxy]methyl}-4a,6,7,8-tetrahydro-4h-spiro[naphthalene-1,2'-oxolan]-5'-ylacetic acid)

PDB for NP0279964 (4-hydroxy-5,5,5',8a-tetramethyl-2-{[(3-methylbutanoyl)oxy]methyl}-4a,6,7,8-tetrahydro-4h-spiro[naphthalene-1,2'-oxolan]-5'-ylacetic acid)

3D PDB for NP0279964 (4-hydroxy-5,5,5',8a-tetramethyl-2-{[(3-methylbutanoyl)oxy]methyl}-4a,6,7,8-tetrahydro-4h-spiro[naphthalene-1,2'-oxolan]-5'-ylacetic acid)

SMILES for NP0279964 (4-hydroxy-5,5,5',8a-tetramethyl-2-{[(3-methylbutanoyl)oxy]methyl}-4a,6,7,8-tetrahydro-4h-spiro[naphthalene-1,2'-oxolan]-5'-ylacetic acid)

INCHI for NP0279964 (4-hydroxy-5,5,5',8a-tetramethyl-2-{[(3-methylbutanoyl)oxy]methyl}-4a,6,7,8-tetrahydro-4h-spiro[naphthalene-1,2'-oxolan]-5'-ylacetic acid)

Structure for NP0279964 (4-hydroxy-5,5,5',8a-tetramethyl-2-{[(3-methylbutanoyl)oxy]methyl}-4a,6,7,8-tetrahydro-4h-spiro[naphthalene-1,2'-oxolan]-5'-ylacetic acid)

3D Structure for NP0279964 (4-hydroxy-5,5,5',8a-tetramethyl-2-{[(3-methylbutanoyl)oxy]methyl}-4a,6,7,8-tetrahydro-4h-spiro[naphthalene-1,2'-oxolan]-5'-ylacetic acid)