NP-MRD: Showing NP-Card for 3-ethenyl-5-methyl-2-methylidenehex-4-en-1-yl acetate (NP0256191)

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Record Information

Version

1.0

Created at

2022-09-07 20:55:49 UTC

Updated at

2022-09-07 20:55:49 UTC

NP-MRD ID

NP0256191

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-ethenyl-5-methyl-2-methylidenehex-4-en-1-yl acetate

Description

(S)-Neolyratyl acetate belongs to the class of organic compounds known as carboxylic acid esters. 3-ethenyl-5-methyl-2-methylidenehex-4-en-1-yl acetate is found in Artemisia vulgaris. These are carboxylic acid derivatives in which the carbon atom from the carbonyl group is attached to an alkyl or an aryl moiety through an oxygen atom (forming an ester group) (S)-Neolyratyl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 32 31  0  0  0  0  0  0  0  0999 V2000
   -0.5868   -0.4262    2.7174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7138   -1.0148    1.5379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5808   -0.3189    0.2317 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8305   -0.6073   -0.5198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6026    0.3330   -1.0505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3372    1.7735   -0.9731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8305   -0.1101   -1.7773 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5455   -0.9881   -0.4837 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3002   -1.5587   -1.6470 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9217   -1.0399    0.0526 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4744    0.2448    0.2485 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7383    0.4448    0.7373 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3473    1.7873    0.9542 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4319   -0.5617    1.0223 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6894   -0.9609    3.6526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3696    0.6408    2.8018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9284   -2.0717    1.5263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3951    0.7666    0.3570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0775   -1.6604   -0.6091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7666    2.2555   -1.8756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8935    2.1954   -0.1033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2662    2.0489   -0.9573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6261   -0.1158   -2.8677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6906    0.5612   -1.5797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1062   -1.1287   -1.4840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6876   -1.5578   -2.0986 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0885   -2.0511   -2.1919 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5731   -1.5926   -0.6493 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8889   -1.6389    0.9885 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2829    1.8039    0.3229 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7161    2.5996    0.5534 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6701    1.9485    1.9909 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0
  5  7  1  0
  5  4  2  3
  4  3  1  0
  3  2  1  0
  2  1  2  3
  3  8  1  0
  8  9  2  3
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
  6 20  1  0
  6 21  1  0
  6 22  1  0
  7 23  1  0
  7 24  1  0
  7 25  1  0
  4 19  1  0
  3 18  1  1
  2 17  1  0
  1 15  1  0
  1 16  1  0
  9 26  1  0
  9 27  1  0
 10 28  1  0
 10 29  1  0
 13 30  1  0
 13 31  1  0
 13 32  1  0
M  END


  Mrv0541 05061312422D          

 14 13  0  0  0  0            999 V2000
   -2.3645   -2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0789    0.2211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    0.2211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355   -0.1914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9224   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3645   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2211   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3645   -0.1914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2079   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2079   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4934   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  2  0  0  0  0
  9  2  1  0  0  0  0
  9  3  1  0  0  0  0
  9  7  2  0  0  0  0
 10  4  2  0  0  0  0
 10  8  1  0  0  0  0
 11  5  1  0  0  0  0
 12  6  1  0  0  0  0
 12  7  1  0  0  0  0
 12 10  1  0  0  0  0
 13 11  2  0  0  0  0
 14  8  1  0  0  0  0
 14 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0256191

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CC(C=C)C(=C)COC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C12H18O2/c1-6-12(7-9(2)3)10(4)8-14-11(5)13/h6-7,12H,1,4,8H2,2-3,5H3

> <INCHI_KEY>
OMXMXPLKVRQEIQ-UHFFFAOYSA-N

> <FORMULA>
C12H18O2

> <MOLECULAR_WEIGHT>
194.2701

> <EXACT_MASS>
194.13067982

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
22.415339298071107

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-ethenyl-5-methyl-2-methylidenehex-4-en-1-yl acetate

> <ALOGPS_LOGP>
3.35

> <JCHEM_LOGP>
2.539904821666667

> <ALOGPS_LOGS>
-3.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.005058162590127

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
59.252800000000015

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.18e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-ethenyl-5-methyl-2-methylidenehex-4-en-1-yl acetate

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -4.414  -4.977   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.747   0.413   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.080   0.413   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.746  -0.357   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.588  -1.897   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.080  -4.207   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.414  -1.897   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.413  -2.667   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.414  -0.357   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.746  -1.897   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.255  -2.667   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.080  -2.667   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.255  -4.207   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       0.921  -1.897   0.000  0.00  0.00           O+0
CONECT    1    6                                                            
CONECT    2    9                                                            
CONECT    3    9                                                            
CONECT    4   10                                                            
CONECT    5   11                                                            
CONECT    6    1   12                                                       
CONECT    7    9   12                                                       
CONECT    8   10   14                                                       
CONECT    9    2    3    7                                                  
CONECT   10    4    8   12                                                  
CONECT   11    5   13   14                                                  
CONECT   12    6    7   10                                                  
CONECT   13   11                                                            
CONECT   14    8   11                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   26    0
END

View in JSmol

Synonyms

Value	Source
(S)-Neolyratyl acetic acid	Generator
3-Ethenyl-5-methyl-2-methylidenehex-4-en-1-yl acetic acid	Generator

Chemical Formula

C₁₂H₁₈O₂

Average Mass

194.2701 Da

Monoisotopic Mass

194.13068 Da

IUPAC Name

3-ethenyl-5-methyl-2-methylidenehex-4-en-1-yl acetate

Traditional Name

3-ethenyl-5-methyl-2-methylidenehex-4-en-1-yl acetate

CAS Registry Number

Not Available

SMILES

CC(C)=CC(C=C)C(=C)COC(C)=O

InChI Identifier

InChI=1S/C12H18O2/c1-6-12(7-9(2)3)10(4)8-14-11(5)13/h6-7,12H,1,4,8H2,2-3,5H3

InChI Key

OMXMXPLKVRQEIQ-UHFFFAOYSA-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 vulgaris	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as carboxylic acid esters. These are carboxylic acid derivatives in which the carbon atom from the carbonyl group is attached to an alkyl or an aryl moiety through an oxygen atom (forming an ester group).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Carboxylic acid derivatives

Direct Parent

Carboxylic acid esters

Alternative Parents

Substituents

Carboxylic acid ester
Monocarboxylic acid or derivatives
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic 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	3.35	ALOGPS
logP	2.54	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	59.25 m³·mol⁻¹	ChemAxon
Polarizability	22.42 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0041497

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB021467

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

101413630

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-ethenyl-5-methyl-2-methylidenehex-4-en-1-yl acetate (NP0256191)

MOL for NP0256191 (3-ethenyl-5-methyl-2-methylidenehex-4-en-1-yl acetate)

3D MOL for NP0256191 (3-ethenyl-5-methyl-2-methylidenehex-4-en-1-yl acetate)

3D SDF for NP0256191 (3-ethenyl-5-methyl-2-methylidenehex-4-en-1-yl acetate)

3D-SDF for NP0256191 (3-ethenyl-5-methyl-2-methylidenehex-4-en-1-yl acetate)

PDB for NP0256191 (3-ethenyl-5-methyl-2-methylidenehex-4-en-1-yl acetate)

3D PDB for NP0256191 (3-ethenyl-5-methyl-2-methylidenehex-4-en-1-yl acetate)

SMILES for NP0256191 (3-ethenyl-5-methyl-2-methylidenehex-4-en-1-yl acetate)

INCHI for NP0256191 (3-ethenyl-5-methyl-2-methylidenehex-4-en-1-yl acetate)

Structure for NP0256191 (3-ethenyl-5-methyl-2-methylidenehex-4-en-1-yl acetate)

3D Structure for NP0256191 (3-ethenyl-5-methyl-2-methylidenehex-4-en-1-yl acetate)