NP-MRD: Showing NP-Card for 3-hydroxy-7,7a-dimethyl-4'-methylidene-2'-oxo-hexahydro-1h-spiro[indene-2,3'-oxolan]-4-yl 3-methylbutanoate (NP0331046)

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Record Information

Version

1.0

Created at

2022-09-12 17:00:04 UTC

Updated at

2022-09-12 17:00:04 UTC

NP-MRD ID

NP0331046

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-hydroxy-7,7a-dimethyl-4'-methylidene-2'-oxo-hexahydro-1h-spiro[indene-2,3'-oxolan]-4-yl 3-methylbutanoate

Description

3-Hydroxy-7,7a-dimethyl-4'-methylidene-2'-oxo-octahydrospiro[indene-2,3'-oxolane]-4-yl 3-methylbutanoate belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. 3-hydroxy-7,7a-dimethyl-4'-methylidene-2'-oxo-hexahydro-1h-spiro[indene-2,3'-oxolan]-4-yl 3-methylbutanoate is found in Petasites formosanus. 3-Hydroxy-7,7a-dimethyl-4'-methylidene-2'-oxo-octahydrospiro[indene-2,3'-oxolane]-4-yl 3-methylbutanoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004251512222D          

 25 27  0  0  0  0            999 V2000
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3260   -1.7269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1854   -2.6145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8499   -3.3682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0294   -3.2820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4774   -3.8951    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
    4.6704   -3.4544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -2.8413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8419   -4.2614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1274   -4.6739    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5143   -4.1219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7074   -4.2934    0.0000 O   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
  2  4  1  0  0  0  0
  4  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
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  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
  8 19  1  0  0  0  0
 13 19  1  0  0  0  0
 16 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 16 24  1  0  0  0  0
 24 25  2  0  0  0  0
M  END


  Mrv1533004251512222D          

 25 27  0  0  0  0            999 V2000
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3260   -1.7269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1854   -2.6145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8499   -3.3682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0294   -3.2820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4774   -3.8951    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
    4.6704   -3.4544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -2.8413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8419   -4.2614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1274   -4.6739    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5143   -4.1219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7074   -4.2934    0.0000 O   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
  2  4  1  0  0  0  0
  4  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
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  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
  8 19  1  0  0  0  0
 13 19  1  0  0  0  0
 16 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 16 24  1  0  0  0  0
 24 25  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0331046

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)CC(=O)OC1CCC(C)C2(C)CC3(C(O)C12)C(=C)COC3=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O5/c1-11(2)8-15(21)25-14-7-6-12(3)19(5)10-20(17(22)16(14)19)13(4)9-24-18(20)23/h11-12,14,16-17,22H,4,6-10H2,1-3,5H3

> <INCHI_KEY>
YRGARSMVKDFOAY-UHFFFAOYSA-N

> <FORMULA>
C20H30O5

> <MOLECULAR_WEIGHT>
350.455

> <EXACT_MASS>
350.209324066

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
38.62962603401281

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-hydroxy-7,7a-dimethyl-4'-methylidene-2'-oxo-octahydrospiro[indene-2,3'-oxolane]-4-yl 3-methylbutanoate

> <ALOGPS_LOGP>
2.99

> <JCHEM_LOGP>
2.7309897766666658

> <ALOGPS_LOGS>
-3.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.064697582753258

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2079012773037237

> <JCHEM_POLAR_SURFACE_AREA>
72.83000000000001

> <JCHEM_REFRACTIVITY>
92.4134

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.42e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-hydroxy-7,7a-dimethyl-4'-methylidene-2'-oxo-hexahydro-1H-spiro[indene-2,3'-oxolane]-4-yl 3-methylbutanoate

> <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      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -3.850   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.001  -3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335  -1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.002  -1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.075  -3.224   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.813  -4.880   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.186  -6.287   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.655  -6.126   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       4.624  -7.271   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.718  -6.448   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.748  -5.304   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.038  -7.955   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       7.705  -8.725   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       6.560  -7.694   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       5.054  -8.014   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   19                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15   19                                             
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   20   24                                             
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17    8   13                                                  
CONECT   20   16   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   16   25                                                  
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

View in JSmol

Synonyms

Value	Source
3-Hydroxy-7,7a-dimethyl-4'-methylidene-2'-oxo-octahydrospiro[indene-2,3'-oxolane]-4-yl 3-methylbutanoic acid	Generator

Chemical Formula

C₂₀H₃₀O₅

Average Mass

350.4550 Da

Monoisotopic Mass

350.20932 Da

IUPAC Name

3-hydroxy-7,7a-dimethyl-4'-methylidene-2'-oxo-octahydrospiro[indene-2,3'-oxolane]-4-yl 3-methylbutanoate

Traditional Name

3-hydroxy-7,7a-dimethyl-4'-methylidene-2'-oxo-hexahydro-1H-spiro[indene-2,3'-oxolane]-4-yl 3-methylbutanoate

CAS Registry Number

Not Available

SMILES

CC(C)CC(=O)OC1CCC(C)C2(C)CC3(C(O)C12)C(=C)COC3=O

InChI Identifier

InChI=1S/C20H30O5/c1-11(2)8-15(21)25-14-7-6-12(3)19(5)10-20(17(22)16(14)19)13(4)9-24-18(20)23/h11-12,14,16-17,22H,4,6-10H2,1-3,5H3

InChI Key

YRGARSMVKDFOAY-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Petasites formosanus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene lactones

Alternative Parents

Substituents

Terpene lactone
Sesquiterpenoid
Fatty acid ester
Dicarboxylic acid or derivatives
Fatty acyl
Gamma butyrolactone
Cyclic alcohol
Tetrahydrofuran
Carboxylic acid ester
Secondary alcohol
Lactone
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
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	2.99	ALOGPS
logP	2.73	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	14.06	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	92.41 m³·mol⁻¹	ChemAxon
Polarizability	38.63 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	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

85233354

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-hydroxy-7,7a-dimethyl-4'-methylidene-2'-oxo-hexahydro-1h-spiro[indene-2,3'-oxolan]-4-yl 3-methylbutanoate (NP0331046)

MOL for NP0331046 (3-hydroxy-7,7a-dimethyl-4'-methylidene-2'-oxo-hexahydro-1h-spiro[indene-2,3'-oxolan]-4-yl 3-methylbutanoate)

3D MOL for NP0331046 (3-hydroxy-7,7a-dimethyl-4'-methylidene-2'-oxo-hexahydro-1h-spiro[indene-2,3'-oxolan]-4-yl 3-methylbutanoate)

3D SDF for NP0331046 (3-hydroxy-7,7a-dimethyl-4'-methylidene-2'-oxo-hexahydro-1h-spiro[indene-2,3'-oxolan]-4-yl 3-methylbutanoate)

3D-SDF for NP0331046 (3-hydroxy-7,7a-dimethyl-4'-methylidene-2'-oxo-hexahydro-1h-spiro[indene-2,3'-oxolan]-4-yl 3-methylbutanoate)

PDB for NP0331046 (3-hydroxy-7,7a-dimethyl-4'-methylidene-2'-oxo-hexahydro-1h-spiro[indene-2,3'-oxolan]-4-yl 3-methylbutanoate)

3D PDB for NP0331046 (3-hydroxy-7,7a-dimethyl-4'-methylidene-2'-oxo-hexahydro-1h-spiro[indene-2,3'-oxolan]-4-yl 3-methylbutanoate)

SMILES for NP0331046 (3-hydroxy-7,7a-dimethyl-4'-methylidene-2'-oxo-hexahydro-1h-spiro[indene-2,3'-oxolan]-4-yl 3-methylbutanoate)

INCHI for NP0331046 (3-hydroxy-7,7a-dimethyl-4'-methylidene-2'-oxo-hexahydro-1h-spiro[indene-2,3'-oxolan]-4-yl 3-methylbutanoate)

Structure for NP0331046 (3-hydroxy-7,7a-dimethyl-4'-methylidene-2'-oxo-hexahydro-1h-spiro[indene-2,3'-oxolan]-4-yl 3-methylbutanoate)

3D Structure for NP0331046 (3-hydroxy-7,7a-dimethyl-4'-methylidene-2'-oxo-hexahydro-1h-spiro[indene-2,3'-oxolan]-4-yl 3-methylbutanoate)