NP-MRD: Showing NP-Card for (6e)-3,7,11-trimethyldodeca-1,6,10-trien-3-yl acetate (NP0274292)

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Record Information

Version

2.0

Created at

2022-09-08 21:38:01 UTC

Updated at

2022-09-08 21:38:01 UTC

NP-MRD ID

NP0274292

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(6e)-3,7,11-trimethyldodeca-1,6,10-trien-3-yl acetate

Description

Nerolidyl acetate belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Nerolidyl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa). Nerolidyl acetate is a sweet, citrus, and freesia tasting compound. Outside of the human body, Nerolidyl acetate has been detected, but not quantified in, herbs and spices. (6e)-3,7,11-trimethyldodeca-1,6,10-trien-3-yl acetate is found in Artemisia annua. This could make nerolidyl acetate a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241218322D          

 19 18  0  0  0  0            999 V2000
   -3.9317   -1.2796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2169   -0.8678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5020   -1.2796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7871   -0.8678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0722   -1.2796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3574   -0.8678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3574   -1.2796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0722   -0.8678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7872   -1.2796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5020   -0.8678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2169   -1.2796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9317   -0.8678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2169   -0.0413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3574   -0.0413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0888   -0.1515    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9152   -0.1515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5020    0.5647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0874    1.2796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3285    0.5661    0.0000 C   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
  2 13  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6 14  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 15  1  0  0  0  0
 10 16  1  0  0  0  0
 11 12  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0274292

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC\C(C)=C\CCC(C)(OC(C)=O)C=C

> <INCHI_IDENTIFIER>
InChI=1S/C17H28O2/c1-7-17(6,19-16(5)18)13-9-12-15(4)11-8-10-14(2)3/h7,10,12H,1,8-9,11,13H2,2-6H3/b15-12+

> <INCHI_KEY>
PRNJXUQTUSFYLV-NTCAYCPXSA-N

> <FORMULA>
C17H28O2

> <MOLECULAR_WEIGHT>
264.403

> <EXACT_MASS>
264.20893014

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
32.80580436117828

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(6E)-3,7,11-trimethyldodeca-1,6,10-trien-3-yl acetate

> <ALOGPS_LOGP>
5.45

> <JCHEM_LOGP>
4.748332137999999

> <ALOGPS_LOGS>
-5.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.021490575271526

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
83.1607

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.60e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(6E)-3,7,11-trimethyldodeca-1,6,10-trien-3-yl acetate

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -7.339  -2.389   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.005  -1.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.670  -2.389   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.336  -1.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.001  -2.389   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.667  -1.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.667  -2.389   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.001  -1.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.336  -2.389   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.670  -1.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.005  -2.389   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.339  -1.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -6.005  -0.077   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.667  -0.077   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       3.899  -0.283   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       5.442  -0.283   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.670   1.054   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.896   2.389   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.213   1.057   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   14                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   15   16                                             
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13    2                                                            
CONECT   14    6                                                            
CONECT   15   10   17                                                       
CONECT   16   10                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   36    0
END

View in JSmol

Synonyms

Value	Source
Nerolidyl acetic acid	Generator
1,6,10-Dodecatrien-3-ol, 3, 7,11-trimethyl-, acetate	HMDB
1,6,10-Dodecatrien-3-ol, 3,7,11-trimethyl-, acetate	HMDB
3,7,11-Trimethyl-1,6, 10-dodecatrien-3-yl acetate	HMDB
3,7,11-Trimethyl-1,6,10-dodecatrien-3-yl acetate	HMDB
Nerolidol, acetate	HMDB
(6E)-3,7,11-Trimethyldodeca-1,6,10-trien-3-yl acetic acid	Generator
(S)-Nerolidyl acetic acid	Generator

Chemical Formula

C₁₇H₂₈O₂

Average Mass

264.4030 Da

Monoisotopic Mass

264.20893 Da

IUPAC Name

(6E)-3,7,11-trimethyldodeca-1,6,10-trien-3-yl acetate

Traditional Name

(6E)-3,7,11-trimethyldodeca-1,6,10-trien-3-yl acetate

CAS Registry Number

Not Available

SMILES

CC(C)=CCC\C(C)=C\CCC(C)(OC(C)=O)C=C

InChI Identifier

InChI=1S/C17H28O2/c1-7-17(6,19-16(5)18)13-9-12-15(4)11-8-10-14(2)3/h7,10,12H,1,8-9,11,13H2,2-6H3/b15-12+

InChI Key

PRNJXUQTUSFYLV-NTCAYCPXSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Artemisia annua	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Farsesane sesquiterpenoid
Sesquiterpenoid
Fatty alcohol ester
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
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	5.45	ALOGPS
logP	4.75	ChemAxon
logS	-5	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	9	ChemAxon
Refractivity	83.16 m³·mol⁻¹	ChemAxon
Polarizability	32.81 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

HMDB0039630

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB019258

KNApSAcK ID

Not Available

Chemspider ID

4515778

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5363426

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (6e)-3,7,11-trimethyldodeca-1,6,10-trien-3-yl acetate (NP0274292)

MOL for NP0274292 ((6e)-3,7,11-trimethyldodeca-1,6,10-trien-3-yl acetate)

3D MOL for NP0274292 ((6e)-3,7,11-trimethyldodeca-1,6,10-trien-3-yl acetate)

3D SDF for NP0274292 ((6e)-3,7,11-trimethyldodeca-1,6,10-trien-3-yl acetate)

3D-SDF for NP0274292 ((6e)-3,7,11-trimethyldodeca-1,6,10-trien-3-yl acetate)

PDB for NP0274292 ((6e)-3,7,11-trimethyldodeca-1,6,10-trien-3-yl acetate)

3D PDB for NP0274292 ((6e)-3,7,11-trimethyldodeca-1,6,10-trien-3-yl acetate)

SMILES for NP0274292 ((6e)-3,7,11-trimethyldodeca-1,6,10-trien-3-yl acetate)

INCHI for NP0274292 ((6e)-3,7,11-trimethyldodeca-1,6,10-trien-3-yl acetate)

Structure for NP0274292 ((6e)-3,7,11-trimethyldodeca-1,6,10-trien-3-yl acetate)

3D Structure for NP0274292 ((6e)-3,7,11-trimethyldodeca-1,6,10-trien-3-yl acetate)