NP-MRD: Showing NP-Card for (1r)-1-[6-methoxy-3-oxo-2-(propan-2-ylidene)-1-benzofuran-5-yl]ethyl propanoate (NP0222176)

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Record Information

Version

2.0

Created at

2022-09-05 23:56:35 UTC

Updated at

2022-09-05 23:56:35 UTC

NP-MRD ID

NP0222176

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r)-1-[6-methoxy-3-oxo-2-(propan-2-ylidene)-1-benzofuran-5-yl]ethyl propanoate

Description

(1R)-1-[6-methoxy-3-oxo-2-(propan-2-ylidene)-2,3-dihydro-1-benzofuran-5-yl]ethyl propanoate belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. (1r)-1-[6-methoxy-3-oxo-2-(propan-2-ylidene)-1-benzofuran-5-yl]ethyl propanoate is found in Enceliopsis argophylla. Based on a literature review very few articles have been published on (1R)-1-[6-methoxy-3-oxo-2-(propan-2-ylidene)-2,3-dihydro-1-benzofuran-5-yl]ethyl propanoate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062201562D          

 22 23  0  0  1  0            999 V2000
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  2  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   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7859   -3.9674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2708   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0958   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5083   -2.5855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5083   -4.0145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7859   -2.6326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0409   -1.8479    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
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 11 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 17 21  1  0  0  0  0
 10 21  1  0  0  0  0
 21 22  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0222176

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(=O)O[C@H](C)C1=CC2=C(OC(=C(C)C)C2=O)C=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C17H20O5/c1-6-15(18)21-10(4)11-7-12-14(8-13(11)20-5)22-17(9(2)3)16(12)19/h7-8,10H,6H2,1-5H3/t10-/m1/s1

> <INCHI_KEY>
YURTZOPWAWAXDX-SNVBAGLBSA-N

> <FORMULA>
C17H20O5

> <MOLECULAR_WEIGHT>
304.342

> <EXACT_MASS>
304.131073744

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
32.734608623647354

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R)-1-[6-methoxy-3-oxo-2-(propan-2-ylidene)-2,3-dihydro-1-benzofuran-5-yl]ethyl propanoate

> <JCHEM_LOGP>
2.8623468643333325

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.770259774041414

> <JCHEM_POLAR_SURFACE_AREA>
61.830000000000005

> <JCHEM_REFRACTIVITY>
82.70960000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R)-1-[6-methoxy-3-oxo-2-(propan-2-ylidene)-1-benzofuran-5-yl]ethyl propanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       4.001  -5.390   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      10.800  -7.406   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      11.706  -6.160   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.246  -6.160   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      14.016  -4.826   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      14.016  -7.494   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.800  -4.914   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      11.276  -3.449   0.000  0.00  0.00           O+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                                                  
CONECT    7    6                                                            
CONECT    8    6    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   21                                                  
CONECT   11   10   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12    8   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16   11   17                                                       
CONECT   17   16   18   21                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   17   10   22                                                  
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

View in JSmol

Synonyms

Value	Source
(1R)-1-[6-Methoxy-3-oxo-2-(propan-2-ylidene)-2,3-dihydro-1-benzofuran-5-yl]ethyl propanoic acid	Generator

Chemical Formula

C₁₇H₂₀O₅

Average Mass

304.3420 Da

Monoisotopic Mass

304.13107 Da

IUPAC Name

(1R)-1-[6-methoxy-3-oxo-2-(propan-2-ylidene)-2,3-dihydro-1-benzofuran-5-yl]ethyl propanoate

Traditional Name

(1R)-1-[6-methoxy-3-oxo-2-(propan-2-ylidene)-1-benzofuran-5-yl]ethyl propanoate

CAS Registry Number

Not Available

SMILES

CCC(=O)O[C@H](C)C1=CC2=C(OC(=C(C)C)C2=O)C=C1OC

InChI Identifier

InChI=1S/C17H20O5/c1-6-15(18)21-10(4)11-7-12-14(8-13(11)20-5)22-17(9(2)3)16(12)19/h7-8,10H,6H2,1-5H3/t10-/m1/s1

InChI Key

YURTZOPWAWAXDX-SNVBAGLBSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Enceliopsis argophylla	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzofurans

Sub Class

Not Available

Direct Parent

Benzofurans

Alternative Parents

Substituents

Coumaran
Benzofuran
Anisole
Aryl ketone
Alkyl aryl ether
Benzenoid
Carboxylic acid ester
Ketone
Carboxylic acid derivative
Oxacycle
Ether
Monocarboxylic acid or derivatives
Organic oxygen compound
Carbonyl group
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	2.86	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	61.83 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	82.71 m³·mol⁻¹	ChemAxon
Polarizability	32.73 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

162917101

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r)-1-[6-methoxy-3-oxo-2-(propan-2-ylidene)-1-benzofuran-5-yl]ethyl propanoate (NP0222176)

MOL for NP0222176 ((1r)-1-[6-methoxy-3-oxo-2-(propan-2-ylidene)-1-benzofuran-5-yl]ethyl propanoate)

3D MOL for NP0222176 ((1r)-1-[6-methoxy-3-oxo-2-(propan-2-ylidene)-1-benzofuran-5-yl]ethyl propanoate)

3D SDF for NP0222176 ((1r)-1-[6-methoxy-3-oxo-2-(propan-2-ylidene)-1-benzofuran-5-yl]ethyl propanoate)

3D-SDF for NP0222176 ((1r)-1-[6-methoxy-3-oxo-2-(propan-2-ylidene)-1-benzofuran-5-yl]ethyl propanoate)

PDB for NP0222176 ((1r)-1-[6-methoxy-3-oxo-2-(propan-2-ylidene)-1-benzofuran-5-yl]ethyl propanoate)

3D PDB for NP0222176 ((1r)-1-[6-methoxy-3-oxo-2-(propan-2-ylidene)-1-benzofuran-5-yl]ethyl propanoate)

SMILES for NP0222176 ((1r)-1-[6-methoxy-3-oxo-2-(propan-2-ylidene)-1-benzofuran-5-yl]ethyl propanoate)

INCHI for NP0222176 ((1r)-1-[6-methoxy-3-oxo-2-(propan-2-ylidene)-1-benzofuran-5-yl]ethyl propanoate)

Structure for NP0222176 ((1r)-1-[6-methoxy-3-oxo-2-(propan-2-ylidene)-1-benzofuran-5-yl]ethyl propanoate)

3D Structure for NP0222176 ((1r)-1-[6-methoxy-3-oxo-2-(propan-2-ylidene)-1-benzofuran-5-yl]ethyl propanoate)