NP-MRD: Showing NP-Card for (5r)-5-methyl-5-(4-methyl-2-oxopent-3-en-1-yl)oxolan-2-one (NP0322123)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-12 00:42:54 UTC

Updated at

2022-09-12 00:42:54 UTC

NP-MRD ID

NP0322123

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(5r)-5-methyl-5-(4-methyl-2-oxopent-3-en-1-yl)oxolan-2-one

Description

(R)-Pinnatolide belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. (5r)-5-methyl-5-(4-methyl-2-oxopent-3-en-1-yl)oxolan-2-one is found in Athanasia crithmifolia. Based on a literature review very few articles have been published on (R)-Pinnatolide.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309122202432D          

 14 14  0  0  1  0            999 V2000
    2.7759    3.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2239    2.9536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4788    2.1689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4169    3.1251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8649    2.5120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0579    2.6835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1198    1.7274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0157    1.7274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3297   -0.8227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    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  2  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
  8  7  1  1  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
  8 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0322123

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CC(=O)C[C@@]1(C)CCC(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C11H16O3/c1-8(2)6-9(12)7-11(3)5-4-10(13)14-11/h6H,4-5,7H2,1-3H3/t11-/m1/s1

> <INCHI_KEY>
MJFNQTVRNUJMHF-LLVKDONJSA-N

> <FORMULA>
C11H16O3

> <MOLECULAR_WEIGHT>
196.246

> <EXACT_MASS>
196.109944375

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
20.748598979130424

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5R)-5-methyl-5-(4-methyl-2-oxopent-3-en-1-yl)oxolan-2-one

> <JCHEM_LOGP>
1.920805884666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.979119465063853

> <JCHEM_PKA_STRONGEST_BASIC>
-4.417507261186208

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
53.55480000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(5R)-5-methyl-5-(4-methyl-2-oxopent-3-en-1-yl)oxolan-2-one

> <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       5.182   6.658   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.151   5.513   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.627   4.049   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.645   5.834   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.614   4.689   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.108   5.009   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       2.090   3.224   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.029   3.224   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.615  -1.536   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -0.186   1.175   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   10   14                                             
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    8                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₁H₁₆O₃

Average Mass

196.2460 Da

Monoisotopic Mass

196.10994 Da

IUPAC Name

(5R)-5-methyl-5-(4-methyl-2-oxopent-3-en-1-yl)oxolan-2-one

Traditional Name

(5R)-5-methyl-5-(4-methyl-2-oxopent-3-en-1-yl)oxolan-2-one

CAS Registry Number

Not Available

SMILES

CC(C)=CC(=O)C[C@@]1(C)CCC(=O)O1

InChI Identifier

InChI=1S/C11H16O3/c1-8(2)6-9(12)7-11(3)5-4-10(13)14-11/h6H,4-5,7H2,1-3H3/t11-/m1/s1

InChI Key

MJFNQTVRNUJMHF-LLVKDONJSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Athanasia crithmifolia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Gamma butyrolactones

Direct Parent

Gamma butyrolactones

Alternative Parents

Substituents

Gamma butyrolactone
Acryloyl-group
Enone
Alpha,beta-unsaturated ketone
Oxolane
Carboxylic acid ester
Ketone
Carboxylic acid derivative
Oxacycle
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	1.92	ChemAxon
pKa (Strongest Acidic)	18.98	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.37 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	53.55 m³·mol⁻¹	ChemAxon
Polarizability	20.75 Å³	ChemAxon
Number of Rings	1	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

66552933

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (5r)-5-methyl-5-(4-methyl-2-oxopent-3-en-1-yl)oxolan-2-one (NP0322123)

MOL for NP0322123 ((5r)-5-methyl-5-(4-methyl-2-oxopent-3-en-1-yl)oxolan-2-one)

3D MOL for NP0322123 ((5r)-5-methyl-5-(4-methyl-2-oxopent-3-en-1-yl)oxolan-2-one)

3D SDF for NP0322123 ((5r)-5-methyl-5-(4-methyl-2-oxopent-3-en-1-yl)oxolan-2-one)

3D-SDF for NP0322123 ((5r)-5-methyl-5-(4-methyl-2-oxopent-3-en-1-yl)oxolan-2-one)

PDB for NP0322123 ((5r)-5-methyl-5-(4-methyl-2-oxopent-3-en-1-yl)oxolan-2-one)

3D PDB for NP0322123 ((5r)-5-methyl-5-(4-methyl-2-oxopent-3-en-1-yl)oxolan-2-one)

SMILES for NP0322123 ((5r)-5-methyl-5-(4-methyl-2-oxopent-3-en-1-yl)oxolan-2-one)

INCHI for NP0322123 ((5r)-5-methyl-5-(4-methyl-2-oxopent-3-en-1-yl)oxolan-2-one)

Structure for NP0322123 ((5r)-5-methyl-5-(4-methyl-2-oxopent-3-en-1-yl)oxolan-2-one)

3D Structure for NP0322123 ((5r)-5-methyl-5-(4-methyl-2-oxopent-3-en-1-yl)oxolan-2-one)