NP-MRD: Showing NP-Card for 1-[(3r,6r,7r)-12-hydroxy-3,6-dimethyl-2,4-dioxatricyclo[7.4.0.0³,⁷]trideca-1(9),10,12-trien-11-yl]ethanone (NP0228592)

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Record Information

Version

2.0

Created at

2022-09-06 08:18:32 UTC

Updated at

2022-09-06 08:18:32 UTC

NP-MRD ID

NP0228592

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-[(3r,6r,7r)-12-hydroxy-3,6-dimethyl-2,4-dioxatricyclo[7.4.0.0³,⁷]trideca-1(9),10,12-trien-11-yl]ethanone

Description

Xyloketal G belongs to the class of organic compounds known as 1-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 1-position. 1-[(3r,6r,7r)-12-hydroxy-3,6-dimethyl-2,4-dioxatricyclo[7.4.0.0³,⁷]trideca-1(9),10,12-trien-11-yl]ethanone was first documented in 2013 (PMID: 23428314). Based on a literature review very few articles have been published on Xyloketal G.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 37 39  0  0  0  0  0  0  0  0999 V2000
    3.6441    2.2539    3.1549 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9686    2.0858    1.8638 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0985    3.0822    1.0502 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1910    0.9364    1.4316 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6112    0.9826    0.1449 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8590   -0.0467   -0.3443 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6216   -1.1920    0.3920 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1695   -1.2565    1.6289 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9607   -0.1939    2.1642 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4410   -0.3920    3.3999 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1585   -2.1704   -0.2069 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3148   -1.7046   -0.9057 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8476   -2.9558   -1.5983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2866   -1.2653   -0.0601 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0442   -0.3403   -0.7282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0719    0.4431   -1.5832 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6894    1.0251   -2.8070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0370   -0.6216   -1.8722 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2911    0.0286   -1.6908 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4412    1.5502    3.3844 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8840    2.2499    3.9590 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0521    3.3209    3.2094 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8017    1.8914   -0.4338 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0032   -2.1481    2.2367 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9618    0.0451    4.0293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1965   -3.2720   -2.4365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9006   -2.8377   -1.8961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8075   -3.7678   -0.8429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5126    0.3285    0.0499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8825   -0.7573   -1.3118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6678    1.2653   -0.9519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6319    0.4727   -3.0673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0345    2.0776   -2.6039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9966    1.1078   -3.6650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1575   -0.9819   -2.9454 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0213   -0.3665   -2.4603 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2163    1.1234   -1.9687 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 16  1  0
 16 15  1  0
 15 14  1  0
 14 12  1  0
 12 13  1  6
 12 11  1  0
 11  7  1  0
  7  6  2  0
  6 19  1  0
 19 18  1  0
  6  5  1  0
  5  4  2  0
  4  2  1  0
  2  1  1  0
  2  3  2  0
  4  9  1  0
  9 10  1  0
  9  8  2  0
 18 16  1  0
 18 12  1  0
  8  7  1  0
 17 32  1  0
 17 33  1  0
 17 34  1  0
 16 31  1  1
 15 29  1  0
 15 30  1  0
 13 26  1  0
 13 27  1  0
 13 28  1  0
 19 36  1  0
 19 37  1  0
 18 35  1  6
  5 23  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
 10 25  1  0
  8 24  1  0
M  END


  Mrv1652309062210182D          

 19 21  0  0  1  0            999 V2000
    6.2102    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8371    0.2900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8838    2.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    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  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
  7 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 12 18  1  0  0  0  0
 18 19  1  1  0  0  0
  6 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0228592

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1CO[C@]2(C)OC3=C(C[C@H]12)C=C(C(C)=O)C(O)=C3

> <INCHI_IDENTIFIER>
InChI=1S/C15H18O4/c1-8-7-18-15(3)12(8)5-10-4-11(9(2)16)13(17)6-14(10)19-15/h4,6,8,12,17H,5,7H2,1-3H3/t8-,12+,15+/m0/s1

> <INCHI_KEY>
BFLZUNPIROUVLO-IBRIGMFSSA-N

> <FORMULA>
C15H18O4

> <MOLECULAR_WEIGHT>
262.305

> <EXACT_MASS>
262.12050906

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
27.831724092041927

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-[(3R,6R,7R)-12-hydroxy-3,6-dimethyl-2,4-dioxatricyclo[7.4.0.0^{3,7}]trideca-1(13),9,11-trien-11-yl]ethan-1-one

> <JCHEM_LOGP>
2.873141243

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.593432334997996

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.347425145952249

> <JCHEM_PKA_STRONGEST_BASIC>
-4.2577588684397565

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
70.88520000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
1-[(3R,6R,7R)-12-hydroxy-3,6-dimethyl-2,4-dioxatricyclo[7.4.0.0^{3,7}]trideca-1(13),9,11-trien-11-yl]ethanone

> <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      11.592   3.613   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.259   4.383   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      10.259   5.923   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       8.925   3.613   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.591   4.383   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.591   1.303   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.925   2.073   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      10.259   1.303   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       4.924   1.303   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.429   0.541   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.126   1.597   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.126   4.089   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.650   5.553   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   19                                                  
CONECT    7    6    8   11                                                  
CONECT    8    7    9                                                       
CONECT    9    8    4   10                                                  
CONECT   10    9                                                            
CONECT   11    7   12                                                       
CONECT   12   11   13   14   18                                             
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   12   19                                                  
CONECT   19   18    6                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₈O₄

Average Mass

262.3050 Da

Monoisotopic Mass

262.12051 Da

IUPAC Name

1-[(3R,6R,7R)-12-hydroxy-3,6-dimethyl-2,4-dioxatricyclo[7.4.0.0^{3,7}]trideca-1(13),9,11-trien-11-yl]ethan-1-one

Traditional Name

1-[(3R,6R,7R)-12-hydroxy-3,6-dimethyl-2,4-dioxatricyclo[7.4.0.0^{3,7}]trideca-1(13),9,11-trien-11-yl]ethanone

CAS Registry Number

Not Available

SMILES

C[C@H]1CO[C@]2(C)OC3=C(C[C@H]12)C=C(C(C)=O)C(O)=C3

InChI Identifier

InChI=1S/C15H18O4/c1-8-7-18-15(3)12(8)5-10-4-11(9(2)16)13(17)6-14(10)19-15/h4,6,8,12,17H,5,7H2,1-3H3/t8-,12+,15+/m0/s1

InChI Key

BFLZUNPIROUVLO-IBRIGMFSSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 1-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

1-benzopyrans

Alternative Parents

Substituents

1-benzopyran
Acetophenone
Furopyran
Aryl ketone
Aryl alkyl ketone
Ketal
1-hydroxy-2-unsubstituted benzenoid
Pyran
Benzenoid
Oxolane
Furan
Vinylogous acid
Ketone
Acetal
Oxacycle
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Aldehyde
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	2.87	ChemAxon
pKa (Strongest Acidic)	9.35	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	70.89 m³·mol⁻¹	ChemAxon
Polarizability	27.83 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

10480801

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21778202

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Panda B, Sarkar TK: Gold catalysis: regio- and stereoselective total synthesis of xyloketals D and G and the related natural product alboatrin. J Org Chem. 2013 Mar 15;78(6):2413-21. doi: 10.1021/jo302545n. Epub 2013 Mar 6. [PubMed:23428314 ]
LOTUS database [Link]

Showing NP-Card for 1-[(3r,6r,7r)-12-hydroxy-3,6-dimethyl-2,4-dioxatricyclo[7.4.0.0³,⁷]trideca-1(9),10,12-trien-11-yl]ethanone (NP0228592)

MOL for NP0228592 (1-[(3r,6r,7r)-12-hydroxy-3,6-dimethyl-2,4-dioxatricyclo[7.4.0.0³,⁷]trideca-1(9),10,12-trien-11-yl]ethanone)

3D MOL for NP0228592 (1-[(3r,6r,7r)-12-hydroxy-3,6-dimethyl-2,4-dioxatricyclo[7.4.0.0³,⁷]trideca-1(9),10,12-trien-11-yl]ethanone)

3D SDF for NP0228592 (1-[(3r,6r,7r)-12-hydroxy-3,6-dimethyl-2,4-dioxatricyclo[7.4.0.0³,⁷]trideca-1(9),10,12-trien-11-yl]ethanone)

3D-SDF for NP0228592 (1-[(3r,6r,7r)-12-hydroxy-3,6-dimethyl-2,4-dioxatricyclo[7.4.0.0³,⁷]trideca-1(9),10,12-trien-11-yl]ethanone)

PDB for NP0228592 (1-[(3r,6r,7r)-12-hydroxy-3,6-dimethyl-2,4-dioxatricyclo[7.4.0.0³,⁷]trideca-1(9),10,12-trien-11-yl]ethanone)

3D PDB for NP0228592 (1-[(3r,6r,7r)-12-hydroxy-3,6-dimethyl-2,4-dioxatricyclo[7.4.0.0³,⁷]trideca-1(9),10,12-trien-11-yl]ethanone)

SMILES for NP0228592 (1-[(3r,6r,7r)-12-hydroxy-3,6-dimethyl-2,4-dioxatricyclo[7.4.0.0³,⁷]trideca-1(9),10,12-trien-11-yl]ethanone)

INCHI for NP0228592 (1-[(3r,6r,7r)-12-hydroxy-3,6-dimethyl-2,4-dioxatricyclo[7.4.0.0³,⁷]trideca-1(9),10,12-trien-11-yl]ethanone)

Structure for NP0228592 (1-[(3r,6r,7r)-12-hydroxy-3,6-dimethyl-2,4-dioxatricyclo[7.4.0.0³,⁷]trideca-1(9),10,12-trien-11-yl]ethanone)

3D Structure for NP0228592 (1-[(3r,6r,7r)-12-hydroxy-3,6-dimethyl-2,4-dioxatricyclo[7.4.0.0³,⁷]trideca-1(9),10,12-trien-11-yl]ethanone)