NP-MRD: Showing NP-Card for (1s,2s,3r,5r,6r,8s,12s)-12-hydroxy-1,5,9,9-tetramethyl-10-oxatricyclo[6.2.2.0²,⁶]dodecan-3-yl acetate (NP0224958)

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Record Information

Version

2.0

Created at

2022-09-06 03:32:34 UTC

Updated at

2022-09-06 03:32:34 UTC

NP-MRD ID

NP0224958

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2s,3r,5r,6r,8s,12s)-12-hydroxy-1,5,9,9-tetramethyl-10-oxatricyclo[6.2.2.0²,⁶]dodecan-3-yl acetate

Description

Kessyl glycol 2-acetate 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. (1s,2s,3r,5r,6r,8s,12s)-12-hydroxy-1,5,9,9-tetramethyl-10-oxatricyclo[6.2.2.0²,⁶]dodecan-3-yl acetate is found in Valeriana fauriei. Based on a literature review very few articles have been published on Kessyl glycol 2-acetate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062205322D          

 21 23  0  0  1  0            999 V2000
   -1.3373   -3.2401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1555   -2.4354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7616   -1.8756    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3678   -2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1861   -1.3856    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7303   -0.7656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3088   -0.0564    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6348    0.7014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4959   -0.2381    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0909    0.3334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9087    0.2245    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3335   -0.4827    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1550   -0.4068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0454   -1.2558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2614   -1.5125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1525   -2.3303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3324   -0.8795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5482   -0.3005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7449   -0.4887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8493    0.1378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5718   -1.0596    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  1  0  0  0
 11 10  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 11 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 15 21  1  0  0  0  0
 21  5  1  6  0  0  0
  9 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0224958

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1C[C@@H](OC(C)=O)[C@@H]2[C@@H]1C[C@H]1[C@@H](O)C[C@]2(C)OC1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C17H28O4/c1-9-6-14(20-10(2)18)15-11(9)7-12-13(19)8-17(15,5)21-16(12,3)4/h9,11-15,19H,6-8H2,1-5H3/t9-,11-,12+,13+,14-,15+,17+/m1/s1

> <INCHI_KEY>
KSJYGLBFXLTFDO-VQOJOYJTSA-N

> <FORMULA>
C17H28O4

> <MOLECULAR_WEIGHT>
296.407

> <EXACT_MASS>
296.198759382

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
32.95444430188541

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,3R,5R,6R,8S,12S)-12-hydroxy-1,5,9,9-tetramethyl-10-oxatricyclo[6.2.2.0^{2,6}]dodecan-3-yl acetate

> <JCHEM_LOGP>
1.3908498569999987

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.766877738537907

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9007676771635182

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
79.07880000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,3R,5R,6R,8S,12S)-12-hydroxy-1,5,9,9-tetramethyl-10-oxatricyclo[6.2.2.0^{2,6}]dodecan-3-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.496  -6.048   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.157  -4.546   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -3.288  -3.501   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -0.686  -4.089   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -0.347  -2.587   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.363  -1.429   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.576  -0.105   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.185   1.309   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.926  -0.444   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.036   0.622   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.563   0.419   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.356  -0.901   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.889  -0.759   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       3.818  -2.344   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.355  -2.823   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.151  -4.350   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.487  -1.642   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.890  -0.561   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.390  -0.912   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.585   0.257   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.067  -1.978   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   21                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   21                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   18                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   17   21                                             
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   11   19   20                                             
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   15    5    9                                                  
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

View in JSmol

Synonyms

Value	Source
Kessyl glycol 2-acetic acid	Generator

Chemical Formula

C₁₇H₂₈O₄

Average Mass

296.4070 Da

Monoisotopic Mass

296.19876 Da

IUPAC Name

(1S,2S,3R,5R,6R,8S,12S)-12-hydroxy-1,5,9,9-tetramethyl-10-oxatricyclo[6.2.2.0^{2,6}]dodecan-3-yl acetate

Traditional Name

(1S,2S,3R,5R,6R,8S,12S)-12-hydroxy-1,5,9,9-tetramethyl-10-oxatricyclo[6.2.2.0^{2,6}]dodecan-3-yl acetate

CAS Registry Number

Not Available

SMILES

C[C@@H]1C[C@@H](OC(C)=O)[C@@H]2[C@@H]1C[C@H]1[C@@H](O)C[C@]2(C)OC1(C)C

InChI Identifier

InChI=1S/C17H28O4/c1-9-6-14(20-10(2)18)15-11(9)7-12-13(19)8-17(15,5)21-16(12,3)4/h9,11-15,19H,6-8H2,1-5H3/t9-,11-,12+,13+,14-,15+,17+/m1/s1

InChI Key

KSJYGLBFXLTFDO-VQOJOYJTSA-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 fauriei	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

Substituents

Oxepane
Oxane
Cyclic alcohol
Carboxylic acid ester
Secondary alcohol
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid derivative
Oxacycle
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Alcohol
Carbonyl group
Aliphatic heteropolycyclic compound

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	1.39	ChemAxon
pKa (Strongest Acidic)	14.77	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	79.08 m³·mol⁻¹	ChemAxon
Polarizability	32.95 Å³	ChemAxon
Number of Rings	3	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

101635457

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,2s,3r,5r,6r,8s,12s)-12-hydroxy-1,5,9,9-tetramethyl-10-oxatricyclo[6.2.2.0²,⁶]dodecan-3-yl acetate (NP0224958)

MOL for NP0224958 ((1s,2s,3r,5r,6r,8s,12s)-12-hydroxy-1,5,9,9-tetramethyl-10-oxatricyclo[6.2.2.0²,⁶]dodecan-3-yl acetate)

3D MOL for NP0224958 ((1s,2s,3r,5r,6r,8s,12s)-12-hydroxy-1,5,9,9-tetramethyl-10-oxatricyclo[6.2.2.0²,⁶]dodecan-3-yl acetate)

3D SDF for NP0224958 ((1s,2s,3r,5r,6r,8s,12s)-12-hydroxy-1,5,9,9-tetramethyl-10-oxatricyclo[6.2.2.0²,⁶]dodecan-3-yl acetate)

3D-SDF for NP0224958 ((1s,2s,3r,5r,6r,8s,12s)-12-hydroxy-1,5,9,9-tetramethyl-10-oxatricyclo[6.2.2.0²,⁶]dodecan-3-yl acetate)

PDB for NP0224958 ((1s,2s,3r,5r,6r,8s,12s)-12-hydroxy-1,5,9,9-tetramethyl-10-oxatricyclo[6.2.2.0²,⁶]dodecan-3-yl acetate)

3D PDB for NP0224958 ((1s,2s,3r,5r,6r,8s,12s)-12-hydroxy-1,5,9,9-tetramethyl-10-oxatricyclo[6.2.2.0²,⁶]dodecan-3-yl acetate)

SMILES for NP0224958 ((1s,2s,3r,5r,6r,8s,12s)-12-hydroxy-1,5,9,9-tetramethyl-10-oxatricyclo[6.2.2.0²,⁶]dodecan-3-yl acetate)

INCHI for NP0224958 ((1s,2s,3r,5r,6r,8s,12s)-12-hydroxy-1,5,9,9-tetramethyl-10-oxatricyclo[6.2.2.0²,⁶]dodecan-3-yl acetate)

Structure for NP0224958 ((1s,2s,3r,5r,6r,8s,12s)-12-hydroxy-1,5,9,9-tetramethyl-10-oxatricyclo[6.2.2.0²,⁶]dodecan-3-yl acetate)

3D Structure for NP0224958 ((1s,2s,3r,5r,6r,8s,12s)-12-hydroxy-1,5,9,9-tetramethyl-10-oxatricyclo[6.2.2.0²,⁶]dodecan-3-yl acetate)