NP-MRD: Showing NP-Card for methyl (R)-2-((3R,6R)-6-(2-(2-(hydroxymethyl)-6,6-dimethylcyclohex-1-en-1-yl)ethyl)-6-methyl-1,2-dioxan-3-yl)propanoate (NP0332483)

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Record Information

Version

2.0

Created at

2024-02-13 00:14:54 UTC

Updated at

2024-09-03 04:19:23 UTC

NP-MRD ID

NP0332483

Natural Product DOI

https://doi.org/10.57994/1736

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (R)-2-((3R,6R)-6-(2-(2-(hydroxymethyl)-6,6-dimethylcyclohex-1-en-1-yl)ethyl)-6-methyl-1,2-dioxan-3-yl)propanoate

Description

Methyl (R)-2-((3R,6R)-6-(2-(2-(hydroxymethyl)-6,6-dimethylcyclohex-1-en-1-yl)ethyl)-6-methyl-1,2-dioxan-3-yl)propanoate belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Based on a literature review very few articles have been published on methyl (R)-2-((3R,6R)-6-(2-(2-(hydroxymethyl)-6,6-dimethylcyclohex-1-en-1-yl)ethyl)-6-methyl-1,2-dioxan-3-yl)propanoate.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 02132400142D          

 25 26  0  0  1  0            999 V2000
    0.1842   -5.1695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8986   -4.7570    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8986   -3.9320    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1842   -3.5195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1842   -2.6945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8986   -2.2820    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3683   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4441   -1.7933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9744   -1.1613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7869   -1.3045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0691   -2.0798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8815   -2.2230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3172   -0.6725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0350    0.1027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2226    0.2460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6923   -0.3860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0421    0.1219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0924   -0.6410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6131   -2.6945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6131   -3.5195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6131   -5.1695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6131   -5.9945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3276   -6.4070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3276   -4.7570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  6  0  0  0
  4  5  1  0  0  0  0
  6  5  1  0  0  0  0
  6  7  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  9 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
  6 19  1  1  0  0  0
  6 20  1  0  0  0  0
 20 21  1  0  0  0  0
  3 21  1  0  0  0  0
  2 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 22 25  2  0  0  0  0
M  END


  Mrv2104 02132400142D          

 25 26  0  0  1  0            999 V2000
    0.1842   -5.1695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8986   -4.7570    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8986   -3.9320    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1842   -3.5195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1842   -2.6945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8986   -2.2820    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3683   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4441   -1.7933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9744   -1.1613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7869   -1.3045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0691   -2.0798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8815   -2.2230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3172   -0.6725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0350    0.1027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2226    0.2460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6923   -0.3860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0421    0.1219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0924   -0.6410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6131   -2.6945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6131   -3.5195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6131   -5.1695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6131   -5.9945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3276   -6.4070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3276   -4.7570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  6  0  0  0
  4  5  1  0  0  0  0
  6  5  1  0  0  0  0
  6  7  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  9 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
  6 19  1  1  0  0  0
  6 20  1  0  0  0  0
 20 21  1  0  0  0  0
  3 21  1  0  0  0  0
  2 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 22 25  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0332483

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@H](C)[C@H]1CC[C@@](C)(CCC2=C(CO)CCCC2(C)C)OO1

> <INCHI_IDENTIFIER>
InChI=1S/C20H34O5/c1-14(18(22)23-5)17-9-12-20(4,25-24-17)11-8-16-15(13-21)7-6-10-19(16,2)3/h14,17,21H,6-13H2,1-5H3/t14-,17-,20-/m1/s1

> <INCHI_KEY>
YTUZEORERBJLPX-WIBUTAKZSA-N

> <FORMULA>
C20H34O5

> <MOLECULAR_WEIGHT>
354.487

> <EXACT_MASS>
354.240624195

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
40.21949134374469

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (2R)-2-[(3R,6R)-6-{2-[2-(hydroxymethyl)-6,6-dimethylcyclohex-1-en-1-yl]ethyl}-6-methyl-1,2-dioxan-3-yl]propanoate

> <JCHEM_LOGP>
3.588047403666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.18300252021299

> <JCHEM_PKA_STRONGEST_BASIC>
-1.8435129366870977

> <JCHEM_POLAR_SURFACE_AREA>
64.99000000000001

> <JCHEM_REFRACTIVITY>
96.69539999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2R)-2-[(3R,6R)-6-{2-[2-(hydroxymethyl)-6,6-dimethylcyclohex-1-en-1-yl]ethyl}-6-methyl-1,2-dioxan-3-yl]propanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 13-FEB-24   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-FEB-24         0                                  
HETATM    1  C   UNK     0       0.344  -9.650   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.677  -8.880   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.677  -7.340   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.344  -6.570   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       0.344  -5.030   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.677  -4.260   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.688  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.829  -3.347   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.819  -2.168   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.336  -2.435   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.862  -3.882   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -5.379  -4.150   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -4.325  -1.255   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.799   0.192   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.282   0.459   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.292  -0.721   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.079   0.228   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.172  -1.196   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.011  -5.030   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.011  -6.570   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.011  -9.650   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       3.011 -11.190   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       4.345 -11.960   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       4.345  -8.880   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   22                                                  
CONECT    3    2    4   21                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   19   20                                             
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   16                                                  
CONECT   10    9   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13   10   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15    9   17   18                                             
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19    6                                                            
CONECT   20    6   21                                                       
CONECT   21   20    3                                                       
CONECT   22    2   23   25                                                  
CONECT   23   22   24                                                       
CONECT   24   23                                                            
CONECT   25   22                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   52    0
END

View in JSmol

Synonyms

Value	Source
Methyl (R)-2-((3R,6R)-6-(2-(2-(hydroxymethyl)-6,6-dimethylcyclohex-1-en-1-yl)ethyl)-6-methyl-1,2-dioxan-3-yl)propanoic acid	Generator

Chemical Formula

C₂₀H₃₄O₅

Average Mass

354.4870 Da

Monoisotopic Mass

354.24062 Da

IUPAC Name

methyl (2R)-2-[(3R,6R)-6-{2-[2-(hydroxymethyl)-6,6-dimethylcyclohex-1-en-1-yl]ethyl}-6-methyl-1,2-dioxan-3-yl]propanoate

Traditional Name

methyl (2R)-2-[(3R,6R)-6-{2-[2-(hydroxymethyl)-6,6-dimethylcyclohex-1-en-1-yl]ethyl}-6-methyl-1,2-dioxan-3-yl]propanoate

CAS Registry Number

Not Available

SMILES

COC(=O)[C@H](C)[C@H]1CC[C@@](C)(CCC2=C(CO)CCCC2(C)C)OO1

InChI Identifier

InChI=1S/C20H34O5/c1-14(18(22)23-5)17-9-12-20(4,25-24-17)11-8-16-15(13-21)7-6-10-19(16,2)3/h14,17,21H,6-13H2,1-5H3/t14-,17-,20-/m1/s1

InChI Key

YTUZEORERBJLPX-WIBUTAKZSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)	yjlee@kiost.ac.kr	Not Available	Not Available	2024-02-13	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, CDCl3, experimental)	yjlee@kiost.ac.kr	Not Available	Not Available	2024-02-13	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

This compound 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
Cyclofarsesane sesquiterpenoid
Megastigmane sesquiterpenoid
Sesquiterpenoid
Long chain fatty alcohol
Fatty alcohol
Fatty acid ester
Fatty acyl
Ortho-dioxane
Methyl ester
Dialkyl peroxide
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic 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	3.59	ChemAxon
pKa (Strongest Acidic)	17.18	ChemAxon
pKa (Strongest Basic)	-1.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	64.99 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	96.7 m³·mol⁻¹	ChemAxon
Polarizability	40.22 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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

DOI: 10.1021/acs.jnatprod.3c01104

Showing NP-Card for methyl (R)-2-((3R,6R)-6-(2-(2-(hydroxymethyl)-6,6-dimethylcyclohex-1-en-1-yl)ethyl)-6-methyl-1,2-dioxan-3-yl)propanoate (NP0332483)

MOL for NP0332483 (methyl (R)-2-((3R,6R)-6-(2-(2-(hydroxymethyl)-6,6-dimethylcyclohex-1-en-1-yl)ethyl)-6-methyl-1,2-dioxan-3-yl)propanoate)

3D MOL for NP0332483 (methyl (R)-2-((3R,6R)-6-(2-(2-(hydroxymethyl)-6,6-dimethylcyclohex-1-en-1-yl)ethyl)-6-methyl-1,2-dioxan-3-yl)propanoate)

3D SDF for NP0332483 (methyl (R)-2-((3R,6R)-6-(2-(2-(hydroxymethyl)-6,6-dimethylcyclohex-1-en-1-yl)ethyl)-6-methyl-1,2-dioxan-3-yl)propanoate)

3D-SDF for NP0332483 (methyl (R)-2-((3R,6R)-6-(2-(2-(hydroxymethyl)-6,6-dimethylcyclohex-1-en-1-yl)ethyl)-6-methyl-1,2-dioxan-3-yl)propanoate)

PDB for NP0332483 (methyl (R)-2-((3R,6R)-6-(2-(2-(hydroxymethyl)-6,6-dimethylcyclohex-1-en-1-yl)ethyl)-6-methyl-1,2-dioxan-3-yl)propanoate)

3D PDB for NP0332483 (methyl (R)-2-((3R,6R)-6-(2-(2-(hydroxymethyl)-6,6-dimethylcyclohex-1-en-1-yl)ethyl)-6-methyl-1,2-dioxan-3-yl)propanoate)

SMILES for NP0332483 (methyl (R)-2-((3R,6R)-6-(2-(2-(hydroxymethyl)-6,6-dimethylcyclohex-1-en-1-yl)ethyl)-6-methyl-1,2-dioxan-3-yl)propanoate)

INCHI for NP0332483 (methyl (R)-2-((3R,6R)-6-(2-(2-(hydroxymethyl)-6,6-dimethylcyclohex-1-en-1-yl)ethyl)-6-methyl-1,2-dioxan-3-yl)propanoate)

Structure for NP0332483 (methyl (R)-2-((3R,6R)-6-(2-(2-(hydroxymethyl)-6,6-dimethylcyclohex-1-en-1-yl)ethyl)-6-methyl-1,2-dioxan-3-yl)propanoate)

3D Structure for NP0332483 (methyl (R)-2-((3R,6R)-6-(2-(2-(hydroxymethyl)-6,6-dimethylcyclohex-1-en-1-yl)ethyl)-6-methyl-1,2-dioxan-3-yl)propanoate)