NP-MRD: Showing NP-Card for 2-[(2s)-2-(hydroxymethyl)oxiran-2-yl]-5-methylphenyl (2z)-2-methylbut-2-enoate (NP0313636)

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Record Information

Version

2.0

Created at

2022-09-11 11:19:24 UTC

Updated at

2022-09-11 11:19:25 UTC

NP-MRD ID

NP0313636

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-[(2s)-2-(hydroxymethyl)oxiran-2-yl]-5-methylphenyl (2z)-2-methylbut-2-enoate

Description

2-[(2S)-2-(hydroxymethyl)oxiran-2-yl]-5-methylphenyl (2Z)-2-methylbut-2-enoate belongs to the class of organic compounds known as phenol esters. These are aromatic compounds containing a benzene ring substituted by a hydroxyl group and an ester group. 2-[(2s)-2-(hydroxymethyl)oxiran-2-yl]-5-methylphenyl (2z)-2-methylbut-2-enoate is found in Hofmeisteria schaffneri. Based on a literature review very few articles have been published on 2-[(2S)-2-(hydroxymethyl)oxiran-2-yl]-5-methylphenyl (2Z)-2-methylbut-2-enoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 37 38  0  0  0  0  0  0  0  0999 V2000
    2.7001   -0.5261    1.9033 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4158   -1.0094    0.7302 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9111   -0.8702   -0.4821 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6759   -1.3787   -1.6570 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6233   -0.2276   -0.6467 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1732   -0.1100   -1.8175 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8394    0.2695    0.3538 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3890    0.8815    0.1723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4097    2.2623   -0.0383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6146    2.9077   -0.2229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6987    4.3814   -0.4521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7601    2.1493   -0.1906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7458    0.7713    0.0191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5361    0.1332    0.2030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4034   -1.3248    0.4331 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5996   -2.2312   -0.7558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3697   -2.7242   -1.1903 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2021   -1.7637    1.6673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8278   -1.8111    1.5776 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7778   -1.1142    2.0867 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3475   -0.7350    2.8068 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5382    0.5673    1.9276 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3886   -1.5017    0.8015 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2009   -2.3724   -1.9074 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5009   -0.7413   -2.5567 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7270   -1.5540   -1.4366 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4990    2.8488   -0.0616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9432    4.9025    0.1745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6922    4.7682   -0.1226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6036    4.6334   -1.5287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7058    2.6654   -0.3369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6520    0.1901    0.0419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1885   -3.1154   -0.4548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1664   -1.7441   -1.5691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4055   -3.6890   -1.4008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7118   -1.0311    2.2866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6933   -2.7564    1.6432 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  6
 16 17  1  0
 15 18  1  0
 18 19  1  0
 14  8  1  0
 19 15  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  4 24  1  0
  4 25  1  0
  4 26  1  0
  9 27  1  0
 11 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 13 32  1  0
 16 33  1  0
 16 34  1  0
 17 35  1  0
 18 36  1  0
 18 37  1  0
M  END


  Mrv1652309112213192D          

 19 20  0  0  1  0            999 V2000
    1.8747    4.2891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2427    3.7588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3860    2.9463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7540    2.4160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1612    2.6641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7932    3.1944    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3045    1.8517    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0797    1.5695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7117    2.0998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4870    1.8176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1189    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6302    1.0052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9982    0.4749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2230    0.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5910    0.2267    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9590    0.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1838    0.4749    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0035   -0.4877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1785   -0.4877    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  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  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  8 14  1  0  0  0  0
 15 14  1  6  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  1  0  0  0  0
 15 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0313636

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C(\C)C(=O)OC1=CC(C)=CC=C1[C@]1(CO)CO1

> <INCHI_IDENTIFIER>
InChI=1S/C15H18O4/c1-4-11(3)14(17)19-13-7-10(2)5-6-12(13)15(8-16)9-18-15/h4-7,16H,8-9H2,1-3H3/b11-4-/t15-/m0/s1

> <INCHI_KEY>
CQXZARCGOSILEP-WQTJRACASA-N

> <FORMULA>
C15H18O4

> <MOLECULAR_WEIGHT>
262.305

> <EXACT_MASS>
262.12050906

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
27.554174837848837

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(2S)-2-(hydroxymethyl)oxiran-2-yl]-5-methylphenyl (2Z)-2-methylbut-2-enoate

> <JCHEM_LOGP>
2.863425568666668

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.127118089989903

> <JCHEM_PKA_STRONGEST_BASIC>
-3.180598547438416

> <JCHEM_POLAR_SURFACE_AREA>
59.06

> <JCHEM_REFRACTIVITY>
72.3601

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
2-[(2S)-2-(hydroxymethyl)oxiran-2-yl]-5-methylphenyl (2Z)-2-methylbut-2-enoate

> <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       3.499   8.006   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.320   7.016   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.587   5.500   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.407   4.510   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.034   4.973   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       5.214   5.963   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       4.302   3.456   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       5.749   2.930   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.929   3.920   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.376   3.393   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.555   4.383   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.643   1.876   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.463   0.886   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.016   1.413   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.837   0.423   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.657   1.413   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.210   0.886   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       5.607  -0.910   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.067  -0.910   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    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    8   15                                                  
CONECT   15   14   16   18   19                                             
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18   15   19                                                       
CONECT   19   18   15                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

View in JSmol

Synonyms

Value	Source
2-[(2S)-2-(Hydroxymethyl)oxiran-2-yl]-5-methylphenyl (2Z)-2-methylbut-2-enoic acid	Generator

Chemical Formula

C₁₅H₁₈O₄

Average Mass

262.3050 Da

Monoisotopic Mass

262.12051 Da

IUPAC Name

2-[(2S)-2-(hydroxymethyl)oxiran-2-yl]-5-methylphenyl (2Z)-2-methylbut-2-enoate

Traditional Name

2-[(2S)-2-(hydroxymethyl)oxiran-2-yl]-5-methylphenyl (2Z)-2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

C\C=C(\C)C(=O)OC1=CC(C)=CC=C1[C@]1(CO)CO1

InChI Identifier

InChI=1S/C15H18O4/c1-4-11(3)14(17)19-13-7-10(2)5-6-12(13)15(8-16)9-18-15/h4-7,16H,8-9H2,1-3H3/b11-4-/t15-/m0/s1

InChI Key

CQXZARCGOSILEP-WQTJRACASA-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
Hofmeisteria schaffneri	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenol esters. These are aromatic compounds containing a benzene ring substituted by a hydroxyl group and an ester group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenol esters

Sub Class

Not Available

Direct Parent

Phenol esters

Alternative Parents

Substituents

Phenol ester
Phenoxy compound
Fatty acid ester
Toluene
Monocyclic benzene moiety
Fatty acyl
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Dialkyl ether
Monocarboxylic acid or derivatives
Oxirane
Ether
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Organic oxide
Primary alcohol
Carbonyl group
Alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic 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	2.86	ChemAxon
pKa (Strongest Acidic)	14.13	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	59.06 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	72.36 m³·mol⁻¹	ChemAxon
Polarizability	27.55 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

163187515

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-[(2s)-2-(hydroxymethyl)oxiran-2-yl]-5-methylphenyl (2z)-2-methylbut-2-enoate (NP0313636)

MOL for NP0313636 (2-[(2s)-2-(hydroxymethyl)oxiran-2-yl]-5-methylphenyl (2z)-2-methylbut-2-enoate)

3D MOL for NP0313636 (2-[(2s)-2-(hydroxymethyl)oxiran-2-yl]-5-methylphenyl (2z)-2-methylbut-2-enoate)

3D SDF for NP0313636 (2-[(2s)-2-(hydroxymethyl)oxiran-2-yl]-5-methylphenyl (2z)-2-methylbut-2-enoate)

3D-SDF for NP0313636 (2-[(2s)-2-(hydroxymethyl)oxiran-2-yl]-5-methylphenyl (2z)-2-methylbut-2-enoate)

PDB for NP0313636 (2-[(2s)-2-(hydroxymethyl)oxiran-2-yl]-5-methylphenyl (2z)-2-methylbut-2-enoate)

3D PDB for NP0313636 (2-[(2s)-2-(hydroxymethyl)oxiran-2-yl]-5-methylphenyl (2z)-2-methylbut-2-enoate)

SMILES for NP0313636 (2-[(2s)-2-(hydroxymethyl)oxiran-2-yl]-5-methylphenyl (2z)-2-methylbut-2-enoate)

INCHI for NP0313636 (2-[(2s)-2-(hydroxymethyl)oxiran-2-yl]-5-methylphenyl (2z)-2-methylbut-2-enoate)

Structure for NP0313636 (2-[(2s)-2-(hydroxymethyl)oxiran-2-yl]-5-methylphenyl (2z)-2-methylbut-2-enoate)

3D Structure for NP0313636 (2-[(2s)-2-(hydroxymethyl)oxiran-2-yl]-5-methylphenyl (2z)-2-methylbut-2-enoate)