NP-MRD: Showing NP-Card for {1,5,9-trimethyl-10-oxatricyclo[6.2.2.0²,⁶]dodecan-9-yl}methyl acetate (NP0211285)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-05 09:30:22 UTC

Updated at

2022-09-05 09:30:22 UTC

NP-MRD ID

NP0211285

Secondary Accession Numbers

None

Natural Product Identification

Common Name

{1,5,9-trimethyl-10-oxatricyclo[6.2.2.0²,⁶]dodecan-9-yl}methyl acetate

Description

Valeracetate, also known as valeracetic acid, belongs to the class of organic compounds known as oxepanes. Oxepanes are compounds containing an oxepane ring, which is a seven-member saturated aliphatic heterocycle with one oxygen and six carbon atoms. Valeracetate is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, valeracetate has been detected, but not quantified in, a few different foods, such as fats and oils, herbs and spices, and tea. {1,5,9-trimethyl-10-oxatricyclo[6.2.2.0²,⁶]dodecan-9-yl}methyl acetate is found in Valeriana officinalis. This could make valeracetate a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 48 50  0  0  0  0  0  0  0  0999 V2000
    4.7913    2.6230    0.9458 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3841    2.1334    0.6571 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5344    2.3332    1.5400 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0374    1.5158   -0.4748 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9861    0.9522   -1.0747 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3727   -0.3352   -0.6195 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4219   -1.4291   -0.7821 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3303   -0.6689   -1.5113 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5958   -1.5413   -0.9919 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0785   -2.4206   -2.1375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0072   -2.4993    0.0466 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4981   -1.7362    1.2137 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8935   -0.3185    0.7741 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2593    0.5883    1.0650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3301    0.5848    0.0255 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6474    1.1049    0.5641 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7923    2.5569    0.0960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7355    0.3209   -0.1521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9650   -0.6363   -1.0713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7273   -0.8572   -0.2825 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0255    2.5524    2.0098 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4983    1.9572    0.3956 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9225    3.6616    0.5839 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1619    1.7626   -1.1280 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2145    0.8301   -2.1994 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4336   -0.9659   -1.0022 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5850   -1.9869    0.1582 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2405   -2.0669   -1.6710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1300   -2.6924   -2.0556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4871   -3.3662   -2.1912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8916   -1.9102   -3.1227 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6447   -3.2604   -0.3770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9126   -3.0782    0.4171 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3217   -2.2569    1.7078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2891   -1.6126    2.0005 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7297   -0.0605    1.4521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7509    0.1679    2.0011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0200    1.6192    1.3197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0930    1.0776   -0.9184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7249    1.0465    1.6564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0620    3.2202    0.5919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8499    2.8439    0.2893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6386    2.5101   -1.0178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2571   -0.3455    0.5920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4281    0.9596   -0.7101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7520   -0.0608   -1.9946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6003   -1.5051   -1.2264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0023   -1.3112    0.6878 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 16  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 15  1  0
 15 14  1  0
 14 13  1  0
 13 12  1  0
 12 11  1  0
 11  9  1  0
  9 10  1  6
  9  8  1  0
  8  6  1  0
  6  7  1  1
  6  5  1  0
  5  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  2  0
 15 16  1  0
  6 13  1  0
  9 20  1  0
 17 41  1  0
 17 42  1  0
 17 43  1  0
 16 40  1  1
 18 44  1  0
 18 45  1  0
 19 46  1  0
 19 47  1  0
 20 48  1  1
 15 39  1  6
 14 37  1  0
 14 38  1  0
 13 36  1  1
 12 34  1  0
 12 35  1  0
 11 32  1  0
 11 33  1  0
 10 29  1  0
 10 30  1  0
 10 31  1  0
  7 26  1  0
  7 27  1  0
  7 28  1  0
  5 24  1  0
  5 25  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
M  END


  Mrv0541 02241210222D          

 20 22  0  0  0  0            999 V2000
   -0.8535   -1.5502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8535   -0.7412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0453   -0.5615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3145    0.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0453    0.9209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8535    1.1006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4829    0.5615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4829   -0.2471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2469   -0.4717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7410    0.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2469    0.8311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6512    1.5502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1234   -0.1123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4942    0.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9434    0.6064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5391   -0.3369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3031   -0.0674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0219   -1.3256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0219   -0.4717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7410   -0.0674    0.0000 C   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
  2  8  1  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
  5 14  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7 11  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
 11 12  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 19  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0211285

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CCC2C1CC1CCC2(C)OC1(C)COC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C17H28O3/c1-11-5-6-15-14(11)9-13-7-8-16(15,3)20-17(13,4)10-19-12(2)18/h11,13-15H,5-10H2,1-4H3

> <INCHI_KEY>
DWBIYQVLFODAMM-UHFFFAOYSA-N

> <FORMULA>
C17H28O3

> <MOLECULAR_WEIGHT>
280.4024

> <EXACT_MASS>
280.203844762

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
32.28455386005038

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
{1,5,9-trimethyl-10-oxatricyclo[6.2.2.0²,⁶]dodecan-9-yl}methyl acetate

> <ALOGPS_LOGP>
3.40

> <JCHEM_LOGP>
3.107057496333333

> <ALOGPS_LOGS>
-5.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.225425843788927

> <JCHEM_POLAR_SURFACE_AREA>
35.53

> <JCHEM_REFRACTIVITY>
77.5247

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.21e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{1,5,9-trimethyl-10-oxatricyclo[6.2.2.0²,⁶]dodecan-9-yl}methyl 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      -1.593  -2.894   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.593  -1.384   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.085  -1.048   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.587   0.293   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.085   1.719   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.593   2.054   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.768   1.048   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.768  -0.461   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.194  -0.881   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.117   0.293   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.194   1.551   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.949   2.894   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -2.097  -0.210   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -0.923   0.293   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.761   1.132   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.006  -0.629   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.432  -0.126   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       3.774  -2.474   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       3.774  -0.881   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.117  -0.126   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    8   13                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   14                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   11                                                  
CONECT    8    2    7    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11    7   10   12                                                  
CONECT   12   11                                                            
CONECT   13    2   14                                                       
CONECT   14    5   13   15   16                                             
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   19                                                       
CONECT   18   19                                                            
CONECT   19   17   18   20                                                  
CONECT   20   19                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

View in JSmol

Synonyms

Value	Source
Valeracetic acid	Generator
{1,5,9-trimethyl-10-oxatricyclo[6.2.2.0²,⁶]dodecan-9-yl}methyl acetic acid	Generator

Chemical Formula

C₁₇H₂₈O₃

Average Mass

280.4024 Da

Monoisotopic Mass

280.20384 Da

IUPAC Name

{1,5,9-trimethyl-10-oxatricyclo[6.2.2.0²,⁶]dodecan-9-yl}methyl acetate

Traditional Name

{1,5,9-trimethyl-10-oxatricyclo[6.2.2.0²,⁶]dodecan-9-yl}methyl acetate

CAS Registry Number

Not Available

SMILES

CC1CCC2C1CC1CCC2(C)OC1(C)COC(C)=O

InChI Identifier

InChI=1S/C17H28O3/c1-11-5-6-15-14(11)9-13-7-8-16(15,3)20-17(13,4)10-19-12(2)18/h11,13-15H,5-10H2,1-4H3

InChI Key

DWBIYQVLFODAMM-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
Valeriana officinalis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oxepanes. Oxepanes are compounds containing an oxepane ring, which is a seven-member saturated aliphatic heterocycle with one oxygen and six carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Oxepanes

Sub Class

Not Available

Direct Parent

Oxepanes

Alternative Parents

Not Available

Substituents

Not Available

Molecular Framework

Aliphatic 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	3.4	ALOGPS
logP	3.11	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	35.53 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	77.52 m³·mol⁻¹	ChemAxon
Polarizability	32.28 Å³	ChemAxon
Number of Rings	3	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

HMDB0041388

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB021320

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

131753132

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for {1,5,9-trimethyl-10-oxatricyclo[6.2.2.0²,⁶]dodecan-9-yl}methyl acetate (NP0211285)

MOL for NP0211285 ({1,5,9-trimethyl-10-oxatricyclo[6.2.2.0²,⁶]dodecan-9-yl}methyl acetate)

3D MOL for NP0211285 ({1,5,9-trimethyl-10-oxatricyclo[6.2.2.0²,⁶]dodecan-9-yl}methyl acetate)

3D SDF for NP0211285 ({1,5,9-trimethyl-10-oxatricyclo[6.2.2.0²,⁶]dodecan-9-yl}methyl acetate)

3D-SDF for NP0211285 ({1,5,9-trimethyl-10-oxatricyclo[6.2.2.0²,⁶]dodecan-9-yl}methyl acetate)

PDB for NP0211285 ({1,5,9-trimethyl-10-oxatricyclo[6.2.2.0²,⁶]dodecan-9-yl}methyl acetate)

3D PDB for NP0211285 ({1,5,9-trimethyl-10-oxatricyclo[6.2.2.0²,⁶]dodecan-9-yl}methyl acetate)

SMILES for NP0211285 ({1,5,9-trimethyl-10-oxatricyclo[6.2.2.0²,⁶]dodecan-9-yl}methyl acetate)

INCHI for NP0211285 ({1,5,9-trimethyl-10-oxatricyclo[6.2.2.0²,⁶]dodecan-9-yl}methyl acetate)

Structure for NP0211285 ({1,5,9-trimethyl-10-oxatricyclo[6.2.2.0²,⁶]dodecan-9-yl}methyl acetate)

3D Structure for NP0211285 ({1,5,9-trimethyl-10-oxatricyclo[6.2.2.0²,⁶]dodecan-9-yl}methyl acetate)