NP-MRD: Showing NP-Card for methyl (2e)-3-[(2s)-2-[(2r)-1-hydroxypropan-2-yl]-2,3-dihydro-1-benzofuran-5-yl]prop-2-enoate (NP0212828)

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Record Information

Version

2.0

Created at

2022-09-05 11:36:40 UTC

Updated at

2022-09-05 11:36:40 UTC

NP-MRD ID

NP0212828

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (2e)-3-[(2s)-2-[(2r)-1-hydroxypropan-2-yl]-2,3-dihydro-1-benzofuran-5-yl]prop-2-enoate

Description

Methyl (2E)-3-[(2S)-2-[(2R)-1-hydroxypropan-2-yl]-2,3-dihydro-1-benzofuran-5-yl]prop-2-enoate belongs to the class of organic compounds known as coumarans. Coumarans are compounds containing the coumaran skeleton, which consists of a benzene ring fused to a 2,3-dihydrofuran ring. methyl (2e)-3-[(2s)-2-[(2r)-1-hydroxypropan-2-yl]-2,3-dihydro-1-benzofuran-5-yl]prop-2-enoate is found in Artemisia monosperma and Artemisia xanthochroa. Based on a literature review very few articles have been published on methyl (2E)-3-[(2S)-2-[(2R)-1-hydroxypropan-2-yl]-2,3-dihydro-1-benzofuran-5-yl]prop-2-enoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 37 38  0  0  0  0  0  0  0  0999 V2000
    7.2370   -1.3105    1.4954 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9778   -0.6799    1.4222 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9643   -1.0826    0.5757 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1593   -2.0622   -0.1762 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7134   -0.3269    0.6148 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6812   -0.6186   -0.1449 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4095    0.0906   -0.1562 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1113    1.1749    0.6358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1206    1.8115    0.5813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1171    1.3800   -0.2821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8293    0.2973   -1.0779 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4055   -0.3294   -1.0133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0358    0.0363   -1.8969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0701    0.9369   -1.3230 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1248    0.2290   -0.5189 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.1122    1.2493    0.0087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5756   -0.5205    0.6544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6611   -1.5056    0.2847 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4075    1.8590   -0.5019 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8088   -0.8459    2.3244 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7440   -1.1249    0.5268 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1152   -2.3836    1.6920 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5884    0.5172    1.2840 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8269   -1.4704   -0.8104 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8602    1.5410    1.3210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3487    2.6636    1.2067 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6233   -1.1896   -1.6508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3080   -1.0164   -1.9730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7675    0.3624   -2.9445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5659    1.4977   -2.1414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6532   -0.4997   -1.1657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0095    0.7907    0.4288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5746    1.8915    0.7600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4224    1.9623   -0.7983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4320   -1.0604    1.1262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1732    0.1442    1.4470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9169   -2.4085    0.5835 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 19  1  0
 19 14  1  0
 14 13  1  0
 13 11  1  0
 11 12  2  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 12  7  1  0
 11 10  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  5 23  1  0
  6 24  1  0
  8 25  1  0
  9 26  1  0
 14 30  1  6
 13 28  1  0
 13 29  1  0
 12 27  1  0
 15 31  1  6
 16 32  1  0
 16 33  1  0
 16 34  1  0
 17 35  1  0
 17 36  1  0
 18 37  1  0
M  END


  Mrv1652309052213362D          

 19 20  0  0  1  0            999 V2000
    6.9246    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102    1.9354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1712    1.5229    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5837    0.8085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837    2.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087    2.2374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    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  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  7 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 14 19  1  0  0  0  0
 10 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0212828

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)\C=C\C1=CC=C2O[C@@H](CC2=C1)[C@H](C)CO

> <INCHI_IDENTIFIER>
InChI=1S/C15H18O4/c1-10(9-16)14-8-12-7-11(3-5-13(12)19-14)4-6-15(17)18-2/h3-7,10,14,16H,8-9H2,1-2H3/b6-4+/t10-,14+/m1/s1

> <INCHI_KEY>
DJDWOGSMWYWDBI-SMRHEOAGSA-N

> <FORMULA>
C15H18O4

> <MOLECULAR_WEIGHT>
262.305

> <EXACT_MASS>
262.12050906

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
29.312700422142104

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (2E)-3-[(2S)-2-[(2R)-1-hydroxypropan-2-yl]-2,3-dihydro-1-benzofuran-5-yl]prop-2-enoate

> <JCHEM_LOGP>
2.3064792463333337

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.397102154822903

> <JCHEM_PKA_STRONGEST_BASIC>
-2.625107517480461

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
72.8461

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2E)-3-[(2S)-2-[(2R)-1-hydroxypropan-2-yl]-2,3-dihydro-1-benzofuran-5-yl]prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      12.926   4.383   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      11.592   3.613   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      10.259   4.383   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      10.259   5.923   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       8.925   3.613   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.591   4.383   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.126   4.089   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.320   2.843   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.090   1.509   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.090   4.177   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -2.630   4.177   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.126   1.597   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                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   19                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11    7                                                       
CONECT   13   11   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17                                                            
CONECT   19   14   10                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

View in JSmol

Synonyms

Value	Source
Methyl (2E)-3-[(2S)-2-[(2R)-1-hydroxypropan-2-yl]-2,3-dihydro-1-benzofuran-5-yl]prop-2-enoic acid	Generator

Chemical Formula

C₁₅H₁₈O₄

Average Mass

262.3050 Da

Monoisotopic Mass

262.12051 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC(=O)\C=C\C1=CC=C2O[C@@H](CC2=C1)[C@H](C)CO

InChI Identifier

InChI=1S/C15H18O4/c1-10(9-16)14-8-12-7-11(3-5-13(12)19-14)4-6-15(17)18-2/h3-7,10,14,16H,8-9H2,1-2H3/b6-4+/t10-,14+/m1/s1

InChI Key

DJDWOGSMWYWDBI-SMRHEOAGSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Artemisia monosperma	LOTUS Database	35616633
Artemisia xanthochroa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumarans. Coumarans are compounds containing the coumaran skeleton, which consists of a benzene ring fused to a 2,3-dihydrofuran ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Coumarans

Sub Class

Not Available

Direct Parent

Coumarans

Alternative Parents

Substituents

Coumaran
Styrene
Alkyl aryl ether
Fatty acid ester
Benzenoid
Fatty acyl
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Carboxylic acid ester
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Oxacycle
Alcohol
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Organic oxide
Carbonyl group
Organic oxygen compound
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

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

14730822

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (2e)-3-[(2s)-2-[(2r)-1-hydroxypropan-2-yl]-2,3-dihydro-1-benzofuran-5-yl]prop-2-enoate (NP0212828)

MOL for NP0212828 (methyl (2e)-3-[(2s)-2-[(2r)-1-hydroxypropan-2-yl]-2,3-dihydro-1-benzofuran-5-yl]prop-2-enoate)

3D MOL for NP0212828 (methyl (2e)-3-[(2s)-2-[(2r)-1-hydroxypropan-2-yl]-2,3-dihydro-1-benzofuran-5-yl]prop-2-enoate)

3D SDF for NP0212828 (methyl (2e)-3-[(2s)-2-[(2r)-1-hydroxypropan-2-yl]-2,3-dihydro-1-benzofuran-5-yl]prop-2-enoate)

3D-SDF for NP0212828 (methyl (2e)-3-[(2s)-2-[(2r)-1-hydroxypropan-2-yl]-2,3-dihydro-1-benzofuran-5-yl]prop-2-enoate)

PDB for NP0212828 (methyl (2e)-3-[(2s)-2-[(2r)-1-hydroxypropan-2-yl]-2,3-dihydro-1-benzofuran-5-yl]prop-2-enoate)

3D PDB for NP0212828 (methyl (2e)-3-[(2s)-2-[(2r)-1-hydroxypropan-2-yl]-2,3-dihydro-1-benzofuran-5-yl]prop-2-enoate)

SMILES for NP0212828 (methyl (2e)-3-[(2s)-2-[(2r)-1-hydroxypropan-2-yl]-2,3-dihydro-1-benzofuran-5-yl]prop-2-enoate)

INCHI for NP0212828 (methyl (2e)-3-[(2s)-2-[(2r)-1-hydroxypropan-2-yl]-2,3-dihydro-1-benzofuran-5-yl]prop-2-enoate)

Structure for NP0212828 (methyl (2e)-3-[(2s)-2-[(2r)-1-hydroxypropan-2-yl]-2,3-dihydro-1-benzofuran-5-yl]prop-2-enoate)

3D Structure for NP0212828 (methyl (2e)-3-[(2s)-2-[(2r)-1-hydroxypropan-2-yl]-2,3-dihydro-1-benzofuran-5-yl]prop-2-enoate)