NP-MRD: Showing NP-Card for (3r,5r)-3-hydroxy-5-methoxy-1-[(2r)-3-methyl-2,5-dihydrofuran-2-yl]pyrrolidin-2-one (NP0316299)

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Record Information

Version

2.0

Created at

2022-09-11 15:24:01 UTC

Updated at

2022-09-11 15:24:02 UTC

NP-MRD ID

NP0316299

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3r,5r)-3-hydroxy-5-methoxy-1-[(2r)-3-methyl-2,5-dihydrofuran-2-yl]pyrrolidin-2-one

Description

(3R,5R)-3-hydroxy-5-methoxy-1-[(2R)-3-methyl-2,5-dihydrofuran-2-yl]pyrrolidin-2-one belongs to the class of organic compounds known as n-alkylpyrrolidines. N-alkylpyrrolidines are compounds containing a pyrrolidine moiety that is substituted at the N1-position with an alkyl group. Pyrrolidine is a five-membered saturated aliphatic heterocycle with one nitrogen atom and four carbon atoms. (3r,5r)-3-hydroxy-5-methoxy-1-[(2r)-3-methyl-2,5-dihydrofuran-2-yl]pyrrolidin-2-one is found in Hemerocallis fulva. Based on a literature review very few articles have been published on (3R,5R)-3-hydroxy-5-methoxy-1-[(2R)-3-methyl-2,5-dihydrofuran-2-yl]pyrrolidin-2-one.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309112217242D          

 15 16  0  0  1  0            999 V2000
    1.9709    0.2323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2564   -0.1802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2564   -1.0052    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9239   -1.4901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6689   -2.2748    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1538   -2.9422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8439   -2.2748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3590   -2.9422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5890   -1.4901    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1956   -1.2352    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8631   -1.7201    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5305   -1.2352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2756   -0.4506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4506   -0.4506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0343    0.2169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  3  9  1  0  0  0  0
 10  9  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 10 14  1  0  0  0  0
 14 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0316299

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@@H]1C[C@@H](O)C(=O)N1[C@@H]1OCC=C1C

> <INCHI_IDENTIFIER>
InChI=1S/C10H15NO4/c1-6-3-4-15-10(6)11-8(14-2)5-7(12)9(11)13/h3,7-8,10,12H,4-5H2,1-2H3/t7-,8-,10-/m1/s1

> <INCHI_KEY>
WEIIIOYFFMOYSL-NQMVMOMDSA-N

> <FORMULA>
C10H15NO4

> <MOLECULAR_WEIGHT>
213.233

> <EXACT_MASS>
213.100107967

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
21.563932402802266

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R,5R)-3-hydroxy-5-methoxy-1-[(2R)-3-methyl-2,5-dihydrofuran-2-yl]pyrrolidin-2-one

> <JCHEM_LOGP>
0.06740734833333376

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.021053407574755

> <JCHEM_PKA_STRONGEST_BASIC>
-3.664389648122456

> <JCHEM_POLAR_SURFACE_AREA>
59.0

> <JCHEM_REFRACTIVITY>
52.3834

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3R,5R)-3-hydroxy-5-methoxy-1-[(2R)-3-methyl-2,5-dihydrofuran-2-yl]pyrrolidin-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       3.679   0.434   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.345  -0.336   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.345  -1.876   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.591  -2.782   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.115  -4.246   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       4.021  -5.492   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.575  -4.246   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       0.670  -5.492   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0       1.099  -2.782   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      -0.365  -2.306   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.611  -3.211   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -2.857  -2.306   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.381  -0.841   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.841  -0.841   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.064   0.405   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7    3   10                                                  
CONECT   10    9   11   14                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   10   15                                                  
CONECT   15   14                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₀H₁₅NO₄

Average Mass

213.2330 Da

Monoisotopic Mass

213.10011 Da

IUPAC Name

(3R,5R)-3-hydroxy-5-methoxy-1-[(2R)-3-methyl-2,5-dihydrofuran-2-yl]pyrrolidin-2-one

Traditional Name

(3R,5R)-3-hydroxy-5-methoxy-1-[(2R)-3-methyl-2,5-dihydrofuran-2-yl]pyrrolidin-2-one

CAS Registry Number

Not Available

SMILES

CO[C@@H]1C[C@@H](O)C(=O)N1[C@@H]1OCC=C1C

InChI Identifier

InChI=1S/C10H15NO4/c1-6-3-4-15-10(6)11-8(14-2)5-7(12)9(11)13/h3,7-8,10,12H,4-5H2,1-2H3/t7-,8-,10-/m1/s1

InChI Key

WEIIIOYFFMOYSL-NQMVMOMDSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Hemerocallis fulva	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-alkylpyrrolidines. N-alkylpyrrolidines are compounds containing a pyrrolidine moiety that is substituted at the N1-position with an alkyl group. Pyrrolidine is a five-membered saturated aliphatic heterocycle with one nitrogen atom and four carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrrolidines

Sub Class

N-alkylpyrrolidines

Direct Parent

N-alkylpyrrolidines

Alternative Parents

Substituents

Pyrrolidone
2-pyrrolidone
N-alkylpyrrolidine
Dihydrofuran
Tertiary carboxylic acid amide
Secondary alcohol
Lactam
Carboxamide group
Oxacycle
Azacycle
Carboxylic acid derivative
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
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	0.067	ChemAxon
pKa (Strongest Acidic)	13.02	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	59 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	52.38 m³·mol⁻¹	ChemAxon
Polarizability	21.56 Å³	ChemAxon
Number of Rings	2	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

162915349

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3r,5r)-3-hydroxy-5-methoxy-1-[(2r)-3-methyl-2,5-dihydrofuran-2-yl]pyrrolidin-2-one (NP0316299)

MOL for NP0316299 ((3r,5r)-3-hydroxy-5-methoxy-1-[(2r)-3-methyl-2,5-dihydrofuran-2-yl]pyrrolidin-2-one)

3D MOL for NP0316299 ((3r,5r)-3-hydroxy-5-methoxy-1-[(2r)-3-methyl-2,5-dihydrofuran-2-yl]pyrrolidin-2-one)

3D SDF for NP0316299 ((3r,5r)-3-hydroxy-5-methoxy-1-[(2r)-3-methyl-2,5-dihydrofuran-2-yl]pyrrolidin-2-one)

3D-SDF for NP0316299 ((3r,5r)-3-hydroxy-5-methoxy-1-[(2r)-3-methyl-2,5-dihydrofuran-2-yl]pyrrolidin-2-one)

PDB for NP0316299 ((3r,5r)-3-hydroxy-5-methoxy-1-[(2r)-3-methyl-2,5-dihydrofuran-2-yl]pyrrolidin-2-one)

3D PDB for NP0316299 ((3r,5r)-3-hydroxy-5-methoxy-1-[(2r)-3-methyl-2,5-dihydrofuran-2-yl]pyrrolidin-2-one)

SMILES for NP0316299 ((3r,5r)-3-hydroxy-5-methoxy-1-[(2r)-3-methyl-2,5-dihydrofuran-2-yl]pyrrolidin-2-one)

INCHI for NP0316299 ((3r,5r)-3-hydroxy-5-methoxy-1-[(2r)-3-methyl-2,5-dihydrofuran-2-yl]pyrrolidin-2-one)

Structure for NP0316299 ((3r,5r)-3-hydroxy-5-methoxy-1-[(2r)-3-methyl-2,5-dihydrofuran-2-yl]pyrrolidin-2-one)

3D Structure for NP0316299 ((3r,5r)-3-hydroxy-5-methoxy-1-[(2r)-3-methyl-2,5-dihydrofuran-2-yl]pyrrolidin-2-one)