NP-MRD: Showing NP-Card for (1r,2s,4s,5r,8s,9r)-5-ethyl-2,8,9-trihydroxy-3,12-dioxatricyclo[6.2.2.0⁴,⁹]dodecan-10-one (NP0325547)

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Record Information

Version

2.0

Created at

2022-09-12 06:22:51 UTC

Updated at

2022-09-12 06:22:51 UTC

NP-MRD ID

NP0325547

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2s,4s,5r,8s,9r)-5-ethyl-2,8,9-trihydroxy-3,12-dioxatricyclo[6.2.2.0⁴,⁹]dodecan-10-one

Description

Mellisol belongs to the class of organic compounds known as oxanes. Oxanes are compounds containing an oxane (tetrahydropyran) ring, which is a six-member saturated aliphatic heterocycle with one oxygen atom and five carbon atoms. (1r,2s,4s,5r,8s,9r)-5-ethyl-2,8,9-trihydroxy-3,12-dioxatricyclo[6.2.2.0⁴,⁹]dodecan-10-one is found in Xylaria mellissii. Based on a literature review very few articles have been published on Mellisol.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 38  0  0  0  0  0  0  0  0999 V2000
   -2.8704    0.0019    1.4764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8052    0.2011    0.0005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5161   -0.2405   -0.6236 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2887   -1.7084   -0.3811 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0583   -2.2319   -0.3240 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2350   -1.3018   -0.2568 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3805   -1.8107   -0.8177 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4396   -0.8616    1.0194 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2524    0.1902    1.2369 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0764    1.4039    0.3799 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9109    0.8860   -1.0235 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6131    1.2408   -1.9180 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7931   -0.0730   -1.0637 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3415   -0.3892   -2.3077 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3142    0.4836   -0.1524 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2385    1.8272   -0.2166 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8221    2.1925    0.6597 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1084    3.5241    0.3450 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2401   -1.0260    1.7582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9595    0.2611    2.0250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6744    0.6921    1.8662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0609    1.2369   -0.2845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6144   -0.4377   -0.4546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6154   -0.0744   -1.7247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8919   -2.2449   -1.1740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8523   -1.9495    0.5697 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1726   -2.9329    0.5577 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2576   -2.9115   -1.2076 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4121   -2.7782   -0.9127 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3133   -0.1395    1.1186 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1568    0.4979    2.2986 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9949    2.0024    0.4112 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3414    0.3979   -2.8743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1797    0.2048    0.9184 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5036    2.1598    1.7045 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9379    3.7076   -0.6286 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  6
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 17  1  0
 17 18  1  0
 17 16  1  0
 16 15  1  0
 15 13  1  0
 13 14  1  6
 13 11  1  0
 11 12  2  0
 15  3  1  0
 13  6  1  0
 11 10  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  3 24  1  6
  4 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  7 29  1  0
  9 30  1  0
  9 31  1  0
 10 32  1  6
 17 35  1  1
 18 36  1  0
 15 34  1  1
 14 33  1  0
M  END


  Mrv1652309122208222D          

 18 20  0  0  1  0            999 V2000
    0.2847    3.9537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3296    3.4030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1600    2.5957    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8165    2.0591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6385    1.2367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1631    0.9330    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3525    0.2890    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6389    0.2108    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5230    0.2686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9930    1.0432    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4094    1.2786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7117    2.0462    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6682    1.5633    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1069    1.8459    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6870    2.3605    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5419    2.5694    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1692    1.9334    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9594    2.1705    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  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  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
  6 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
  3 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  1  0  0  0  0
 10 17  1  0  0  0  0
 17 18  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0325547

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@@H]1CC[C@]2(O)OC[C@@H]3[C@@H](O)O[C@@H]1[C@@]2(O)C3=O

> <INCHI_IDENTIFIER>
InChI=1S/C12H18O6/c1-2-6-3-4-11(15)12(16)8(13)7(5-17-11)10(14)18-9(6)12/h6-7,9-10,14-16H,2-5H2,1H3/t6-,7+,9+,10+,11+,12+/m1/s1

> <INCHI_KEY>
QCQXKQQKNBNWGY-QWNZBCQASA-N

> <FORMULA>
C12H18O6

> <MOLECULAR_WEIGHT>
258.27

> <EXACT_MASS>
258.1103383

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
25.361866603924604

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2S,4S,5R,8S,9R)-5-ethyl-2,8,9-trihydroxy-3,12-dioxatricyclo[6.2.2.0^{4,9}]dodecan-10-one

> <JCHEM_LOGP>
0.1989612276666661

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.197352793491223

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.119876626141071

> <JCHEM_PKA_STRONGEST_BASIC>
-4.064882613013534

> <JCHEM_POLAR_SURFACE_AREA>
96.22000000000001

> <JCHEM_REFRACTIVITY>
59.08480000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,4S,5R,8S,9R)-5-ethyl-2,8,9-trihydroxy-3,12-dioxatricyclo[6.2.2.0^{4,9}]dodecan-10-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0       0.531   7.380   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.615   6.352   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.299   4.845   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.524   3.844   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.192   2.308   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.304   1.742   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.658   0.540   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       1.193   0.393   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.843   0.501   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.720   1.947   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.631   2.387   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.195   3.820   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.247   2.918   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -0.200   3.446   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.282   4.406   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.878   4.796   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.049   3.609   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.524   4.052   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   15                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8   13                                             
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   17                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11    6   14   15                                             
CONECT   14   13                                                            
CONECT   15   13    3   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   10   18                                                  
CONECT   18   17                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₂H₁₈O₆

Average Mass

258.2700 Da

Monoisotopic Mass

258.11034 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC[C@@H]1CC[C@]2(O)OC[C@@H]3[C@@H](O)O[C@@H]1[C@@]2(O)C3=O

InChI Identifier

InChI=1S/C12H18O6/c1-2-6-3-4-11(15)12(16)8(13)7(5-17-11)10(14)18-9(6)12/h6-7,9-10,14-16H,2-5H2,1H3/t6-,7+,9+,10+,11+,12+/m1/s1

InChI Key

QCQXKQQKNBNWGY-QWNZBCQASA-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
Xylaria mellissii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oxanes. Oxanes are compounds containing an oxane (tetrahydropyran) ring, which is a six-member saturated aliphatic heterocycle with one oxygen atom and five carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Oxanes

Sub Class

Not Available

Direct Parent

Oxanes

Alternative Parents

Substituents

Oxane
Tertiary alcohol
Cyclic alcohol
Ketone
Hemiacetal
Oxacycle
Polyol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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

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

78437073

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101136222

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,2s,4s,5r,8s,9r)-5-ethyl-2,8,9-trihydroxy-3,12-dioxatricyclo[6.2.2.0⁴,⁹]dodecan-10-one (NP0325547)

MOL for NP0325547 ((1r,2s,4s,5r,8s,9r)-5-ethyl-2,8,9-trihydroxy-3,12-dioxatricyclo[6.2.2.0⁴,⁹]dodecan-10-one)

3D MOL for NP0325547 ((1r,2s,4s,5r,8s,9r)-5-ethyl-2,8,9-trihydroxy-3,12-dioxatricyclo[6.2.2.0⁴,⁹]dodecan-10-one)

3D SDF for NP0325547 ((1r,2s,4s,5r,8s,9r)-5-ethyl-2,8,9-trihydroxy-3,12-dioxatricyclo[6.2.2.0⁴,⁹]dodecan-10-one)

3D-SDF for NP0325547 ((1r,2s,4s,5r,8s,9r)-5-ethyl-2,8,9-trihydroxy-3,12-dioxatricyclo[6.2.2.0⁴,⁹]dodecan-10-one)

PDB for NP0325547 ((1r,2s,4s,5r,8s,9r)-5-ethyl-2,8,9-trihydroxy-3,12-dioxatricyclo[6.2.2.0⁴,⁹]dodecan-10-one)

3D PDB for NP0325547 ((1r,2s,4s,5r,8s,9r)-5-ethyl-2,8,9-trihydroxy-3,12-dioxatricyclo[6.2.2.0⁴,⁹]dodecan-10-one)

SMILES for NP0325547 ((1r,2s,4s,5r,8s,9r)-5-ethyl-2,8,9-trihydroxy-3,12-dioxatricyclo[6.2.2.0⁴,⁹]dodecan-10-one)

INCHI for NP0325547 ((1r,2s,4s,5r,8s,9r)-5-ethyl-2,8,9-trihydroxy-3,12-dioxatricyclo[6.2.2.0⁴,⁹]dodecan-10-one)

Structure for NP0325547 ((1r,2s,4s,5r,8s,9r)-5-ethyl-2,8,9-trihydroxy-3,12-dioxatricyclo[6.2.2.0⁴,⁹]dodecan-10-one)

3D Structure for NP0325547 ((1r,2s,4s,5r,8s,9r)-5-ethyl-2,8,9-trihydroxy-3,12-dioxatricyclo[6.2.2.0⁴,⁹]dodecan-10-one)