NP-MRD: Showing NP-Card for (1s,4as,5'r,8as)-5'-(2-methoxy-2-oxoethyl)-5,5,5',8a-tetramethyl-4a,6,7,8-tetrahydro-4h-spiro[naphthalene-1,2'-oxolan]-2-ylmethyl 3-methylbutanoate (NP0329913)

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Record Information

Version

2.0

Created at

2022-09-12 14:46:31 UTC

Updated at

2022-09-12 14:46:31 UTC

NP-MRD ID

NP0329913

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,4as,5'r,8as)-5'-(2-methoxy-2-oxoethyl)-5,5,5',8a-tetramethyl-4a,6,7,8-tetrahydro-4h-spiro[naphthalene-1,2'-oxolan]-2-ylmethyl 3-methylbutanoate

Description

[(1S,4aS,5'R,8aS)-5'-(2-methoxy-2-oxoethyl)-5,5,5',8a-tetramethyl-4a,5,6,7,8,8a-hexahydro-4H-spiro[naphthalene-1,2'-oxolane]-2-yl]methyl 3-methylbutanoate belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. (1s,4as,5'r,8as)-5'-(2-methoxy-2-oxoethyl)-5,5,5',8a-tetramethyl-4a,6,7,8-tetrahydro-4h-spiro[naphthalene-1,2'-oxolan]-2-ylmethyl 3-methylbutanoate is found in Grindelia squarrosa. Based on a literature review very few articles have been published on [(1S,4aS,5'R,8aS)-5'-(2-methoxy-2-oxoethyl)-5,5,5',8a-tetramethyl-4a,5,6,7,8,8a-hexahydro-4H-spiro[naphthalene-1,2'-oxolane]-2-yl]methyl 3-methylbutanoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122216462D          

 31 33  0  0  1  0            999 V2000
   -2.0045   -2.3112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2508   -1.9757    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5834   -2.4606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6696   -3.2811    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1703   -2.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8377   -2.6100    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2857   -3.2231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0572   -2.0670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3897   -3.2231    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    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


  Mrv1652309122216462D          

 31 33  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0329913

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C[C@@]1(C)CC[C@@]2(O1)C(COC(=O)CC(C)C)=CC[C@H]1C(C)(C)CCC[C@]21C

> <INCHI_IDENTIFIER>
InChI=1S/C26H42O5/c1-18(2)15-21(27)30-17-19-9-10-20-23(3,4)11-8-12-25(20,6)26(19)14-13-24(5,31-26)16-22(28)29-7/h9,18,20H,8,10-17H2,1-7H3/t20-,24+,25-,26+/m0/s1

> <INCHI_KEY>
ALMXGEAICAOSNG-KBCQWCIPSA-N

> <FORMULA>
C26H42O5

> <MOLECULAR_WEIGHT>
434.617

> <EXACT_MASS>
434.303224452

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
50.422118320518024

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(1S,4aS,5'R,8aS)-5'-(2-methoxy-2-oxoethyl)-5,5,5',8a-tetramethyl-4a,5,6,7,8,8a-hexahydro-4H-spiro[naphthalene-1,2'-oxolane]-2-yl]methyl 3-methylbutanoate

> <JCHEM_LOGP>
5.126915339333332

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.244181852014293

> <JCHEM_POLAR_SURFACE_AREA>
61.830000000000005

> <JCHEM_REFRACTIVITY>
121.10789999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4aS,5'R,8aS)-5'-(2-methoxy-2-oxoethyl)-5,5,5',8a-tetramethyl-4a,6,7,8-tetrahydro-4H-spiro[naphthalene-1,2'-oxolane]-2-ylmethyl 3-methylbutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0      -3.742  -4.314   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.335  -3.688   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.089  -4.593   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -1.250  -6.125   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.318  -3.967   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.564  -4.872   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.533  -6.016   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.334  -3.538   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.840  -3.858   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.594  -6.016   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       8.002  -4.620   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.851  -8.973   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.861 -10.687   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.495  -6.610   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                                                       
CONECT    6    5    7    8   11                                             
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12   30                                             
CONECT   11   10    6                                                       
CONECT   12   10   13   21                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   12   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   30                                                  
CONECT   24   23   25   26   27                                             
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   24   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   23   10   31                                             
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   66    0
END

View in JSmol

Synonyms

Value	Source
[(1S,4AS,5'r,8as)-5'-(2-methoxy-2-oxoethyl)-5,5,5',8a-tetramethyl-4a,5,6,7,8,8a-hexahydro-4H-spiro[naphthalene-1,2'-oxolane]-2-yl]methyl 3-methylbutanoic acid	Generator

Chemical Formula

C₂₆H₄₂O₅

Average Mass

434.6170 Da

Monoisotopic Mass

434.30322 Da

IUPAC Name

[(1S,4aS,5'R,8aS)-5'-(2-methoxy-2-oxoethyl)-5,5,5',8a-tetramethyl-4a,5,6,7,8,8a-hexahydro-4H-spiro[naphthalene-1,2'-oxolane]-2-yl]methyl 3-methylbutanoate

Traditional Name

(1S,4aS,5'R,8aS)-5'-(2-methoxy-2-oxoethyl)-5,5,5',8a-tetramethyl-4a,6,7,8-tetrahydro-4H-spiro[naphthalene-1,2'-oxolane]-2-ylmethyl 3-methylbutanoate

CAS Registry Number

Not Available

SMILES

COC(=O)C[C@@]1(C)CC[C@@]2(O1)C(COC(=O)CC(C)C)=CC[C@H]1C(C)(C)CCC[C@]21C

InChI Identifier

InChI=1S/C26H42O5/c1-18(2)15-21(27)30-17-19-9-10-20-23(3,4)11-8-12-25(20,6)26(19)14-13-24(5,31-26)16-22(28)29-7/h9,18,20H,8,10-17H2,1-7H3/t20-,24+,25-,26+/m0/s1

InChI Key

ALMXGEAICAOSNG-KBCQWCIPSA-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 squarrosa	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
Fatty acid ester
Dicarboxylic acid or derivatives
Fatty acyl
Methyl ester
Tetrahydrofuran
Carboxylic acid ester
Carboxylic acid derivative
Dialkyl ether
Oxacycle
Ether
Organoheterocyclic compound
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
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	5.13	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	61.83 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	121.11 m³·mol⁻¹	ChemAxon
Polarizability	50.42 Å³	ChemAxon
Number of Rings	3	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

162875303

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,4as,5'r,8as)-5'-(2-methoxy-2-oxoethyl)-5,5,5',8a-tetramethyl-4a,6,7,8-tetrahydro-4h-spiro[naphthalene-1,2'-oxolan]-2-ylmethyl 3-methylbutanoate (NP0329913)

MOL for NP0329913 ((1s,4as,5'r,8as)-5'-(2-methoxy-2-oxoethyl)-5,5,5',8a-tetramethyl-4a,6,7,8-tetrahydro-4h-spiro[naphthalene-1,2'-oxolan]-2-ylmethyl 3-methylbutanoate)

3D MOL for NP0329913 ((1s,4as,5'r,8as)-5'-(2-methoxy-2-oxoethyl)-5,5,5',8a-tetramethyl-4a,6,7,8-tetrahydro-4h-spiro[naphthalene-1,2'-oxolan]-2-ylmethyl 3-methylbutanoate)

3D SDF for NP0329913 ((1s,4as,5'r,8as)-5'-(2-methoxy-2-oxoethyl)-5,5,5',8a-tetramethyl-4a,6,7,8-tetrahydro-4h-spiro[naphthalene-1,2'-oxolan]-2-ylmethyl 3-methylbutanoate)

3D-SDF for NP0329913 ((1s,4as,5'r,8as)-5'-(2-methoxy-2-oxoethyl)-5,5,5',8a-tetramethyl-4a,6,7,8-tetrahydro-4h-spiro[naphthalene-1,2'-oxolan]-2-ylmethyl 3-methylbutanoate)

PDB for NP0329913 ((1s,4as,5'r,8as)-5'-(2-methoxy-2-oxoethyl)-5,5,5',8a-tetramethyl-4a,6,7,8-tetrahydro-4h-spiro[naphthalene-1,2'-oxolan]-2-ylmethyl 3-methylbutanoate)

3D PDB for NP0329913 ((1s,4as,5'r,8as)-5'-(2-methoxy-2-oxoethyl)-5,5,5',8a-tetramethyl-4a,6,7,8-tetrahydro-4h-spiro[naphthalene-1,2'-oxolan]-2-ylmethyl 3-methylbutanoate)

SMILES for NP0329913 ((1s,4as,5'r,8as)-5'-(2-methoxy-2-oxoethyl)-5,5,5',8a-tetramethyl-4a,6,7,8-tetrahydro-4h-spiro[naphthalene-1,2'-oxolan]-2-ylmethyl 3-methylbutanoate)

INCHI for NP0329913 ((1s,4as,5'r,8as)-5'-(2-methoxy-2-oxoethyl)-5,5,5',8a-tetramethyl-4a,6,7,8-tetrahydro-4h-spiro[naphthalene-1,2'-oxolan]-2-ylmethyl 3-methylbutanoate)

Structure for NP0329913 ((1s,4as,5'r,8as)-5'-(2-methoxy-2-oxoethyl)-5,5,5',8a-tetramethyl-4a,6,7,8-tetrahydro-4h-spiro[naphthalene-1,2'-oxolan]-2-ylmethyl 3-methylbutanoate)

3D Structure for NP0329913 ((1s,4as,5'r,8as)-5'-(2-methoxy-2-oxoethyl)-5,5,5',8a-tetramethyl-4a,6,7,8-tetrahydro-4h-spiro[naphthalene-1,2'-oxolan]-2-ylmethyl 3-methylbutanoate)