NP-MRD: Showing NP-Card for methyl 2-{5,5,5',8a-tetramethyl-2-methylidene-4a,6,7,8-tetrahydrospiro[naphthalene-1,2'-oxolan]-5'-yl}acetate (NP0263508)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-08 06:42:50 UTC

Updated at

2022-09-08 06:42:50 UTC

NP-MRD ID

NP0263508

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 2-{5,5,5',8a-tetramethyl-2-methylidene-4a,6,7,8-tetrahydrospiro[naphthalene-1,2'-oxolan]-5'-yl}acetate

Description

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

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004251504432D          

 24 26  0  0  0  0            999 V2000
    4.0502    3.7344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1522    2.9157    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4942    2.4180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7342    2.7390    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5963    1.5993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9383    1.1016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5121    1.8080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5020    0.4993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1034   -0.2230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2932   -0.0670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1912    0.7516    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4803   -0.8706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2697   -1.1103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8779   -1.4343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0886   -1.1945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9015   -0.3910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1121   -0.1512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7117   -0.1959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0131   -0.9703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0749    0.6523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5274    1.2160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3168    0.9762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5039    0.1727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9025    0.8950    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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  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
  6 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 10 23  1  0  0  0  0
 16 23  1  0  0  0  0
 23 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0263508

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)CC1(C)CCC2(O1)C(=C)C=CC1C(C)(C)CCCC21C

> <INCHI_IDENTIFIER>
InChI=1S/C21H32O3/c1-15-8-9-16-18(2,3)10-7-11-20(16,5)21(15)13-12-19(4,24-21)14-17(22)23-6/h8-9,16H,1,7,10-14H2,2-6H3

> <INCHI_KEY>
BQKUQSCJPKVGNA-UHFFFAOYSA-N

> <FORMULA>
C21H32O3

> <MOLECULAR_WEIGHT>
332.484

> <EXACT_MASS>
332.23514489

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
38.36049247420847

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 2-{5,5,5',8a-tetramethyl-2-methylidene-4a,5,6,7,8,8a-hexahydro-2H-spiro[naphthalene-1,2'-oxolane]-5'-yl}acetate

> <ALOGPS_LOGP>
4.74

> <JCHEM_LOGP>
4.230449491000001

> <ALOGPS_LOGS>
-6.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.246505138248624

> <JCHEM_POLAR_SURFACE_AREA>
35.53

> <JCHEM_REFRACTIVITY>
96.44930000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.40e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 2-{5,5,5',8a-tetramethyl-2-methylidene-4a,6,7,8-tetrahydrospiro[naphthalene-1,2'-oxolane]-5'-yl}acetate

> <JCHEM_VEBER_RULE>
1

$$$$

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       7.560   6.971   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       7.751   5.443   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       6.523   4.514   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       5.104   5.113   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.713   2.985   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.485   2.056   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.689   3.375   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.537   0.932   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.793  -0.416   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.281  -0.125   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.090   1.403   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.630  -1.625   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.103  -2.073   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.505  -2.677   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.032  -2.230   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.683  -0.730   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.209  -0.282   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.328  -0.366   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.024  -1.811   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.140   1.218   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.985   2.270   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.458   1.822   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.807   0.322   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.551   1.671   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   23                                             
CONECT   11   10    6                                                       
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   23                                                  
CONECT   17   16   18   19   20                                             
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   17   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   10   16   24                                             
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Value	Source
Methyl 2-{5,5,5',8a-tetramethyl-2-methylidene-4a,5,6,7,8,8a-hexahydro-2H-spiro[naphthalene-1,2'-oxolane]-5'-yl}acetic acid	Generator

Chemical Formula

C₂₁H₃₂O₃

Average Mass

332.4840 Da

Monoisotopic Mass

332.23514 Da

IUPAC Name

methyl 2-{5,5,5',8a-tetramethyl-2-methylidene-4a,5,6,7,8,8a-hexahydro-2H-spiro[naphthalene-1,2'-oxolane]-5'-yl}acetate

Traditional Name

methyl 2-{5,5,5',8a-tetramethyl-2-methylidene-4a,6,7,8-tetrahydrospiro[naphthalene-1,2'-oxolane]-5'-yl}acetate

CAS Registry Number

Not Available

SMILES

COC(=O)CC1(C)CCC2(O1)C(=C)C=CC1C(C)(C)CCCC21C

InChI Identifier

InChI=1S/C21H32O3/c1-15-8-9-16-18(2,3)10-7-11-20(16,5)21(15)13-12-19(4,24-21)14-17(22)23-6/h8-9,16H,1,7,10-14H2,2-6H3

InChI Key

BQKUQSCJPKVGNA-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

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
Fatty acid ester
Fatty acyl
Tetrahydrofuran
Methyl ester
Carboxylic acid ester
Carboxylic acid derivative
Dialkyl ether
Ether
Oxacycle
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organooxygen compound
Organic oxide
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	4.74	ALOGPS
logP	4.23	ChemAxon
logS	-6.1	ALOGPS
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	35.53 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	96.45 m³·mol⁻¹	ChemAxon
Polarizability	38.36 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	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

13918356

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 2-{5,5,5',8a-tetramethyl-2-methylidene-4a,6,7,8-tetrahydrospiro[naphthalene-1,2'-oxolan]-5'-yl}acetate (NP0263508)

MOL for NP0263508 (methyl 2-{5,5,5',8a-tetramethyl-2-methylidene-4a,6,7,8-tetrahydrospiro[naphthalene-1,2'-oxolan]-5'-yl}acetate)

3D MOL for NP0263508 (methyl 2-{5,5,5',8a-tetramethyl-2-methylidene-4a,6,7,8-tetrahydrospiro[naphthalene-1,2'-oxolan]-5'-yl}acetate)

3D SDF for NP0263508 (methyl 2-{5,5,5',8a-tetramethyl-2-methylidene-4a,6,7,8-tetrahydrospiro[naphthalene-1,2'-oxolan]-5'-yl}acetate)

3D-SDF for NP0263508 (methyl 2-{5,5,5',8a-tetramethyl-2-methylidene-4a,6,7,8-tetrahydrospiro[naphthalene-1,2'-oxolan]-5'-yl}acetate)

PDB for NP0263508 (methyl 2-{5,5,5',8a-tetramethyl-2-methylidene-4a,6,7,8-tetrahydrospiro[naphthalene-1,2'-oxolan]-5'-yl}acetate)

3D PDB for NP0263508 (methyl 2-{5,5,5',8a-tetramethyl-2-methylidene-4a,6,7,8-tetrahydrospiro[naphthalene-1,2'-oxolan]-5'-yl}acetate)

SMILES for NP0263508 (methyl 2-{5,5,5',8a-tetramethyl-2-methylidene-4a,6,7,8-tetrahydrospiro[naphthalene-1,2'-oxolan]-5'-yl}acetate)

INCHI for NP0263508 (methyl 2-{5,5,5',8a-tetramethyl-2-methylidene-4a,6,7,8-tetrahydrospiro[naphthalene-1,2'-oxolan]-5'-yl}acetate)

Structure for NP0263508 (methyl 2-{5,5,5',8a-tetramethyl-2-methylidene-4a,6,7,8-tetrahydrospiro[naphthalene-1,2'-oxolan]-5'-yl}acetate)

3D Structure for NP0263508 (methyl 2-{5,5,5',8a-tetramethyl-2-methylidene-4a,6,7,8-tetrahydrospiro[naphthalene-1,2'-oxolan]-5'-yl}acetate)