NP-MRD: Showing NP-Card for (2r,3r,4r)-4,10-diacetyl-3,11,13-trihydroxy-2,12-dimethyl-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(9),6,10,12-tetraen-5-one (NP0196657)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-04 14:46:59 UTC

Updated at

2022-09-04 14:46:59 UTC

NP-MRD ID

NP0196657

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3r,4r)-4,10-diacetyl-3,11,13-trihydroxy-2,12-dimethyl-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(9),6,10,12-tetraen-5-one

Description

(2R,3R,4R)-4,10-diacetyl-3,11,13-trihydroxy-2,12-dimethyl-8-oxatricyclo[7.4.0.0²,⁷]Trideca-1(13),6,9,11-tetraen-5-one belongs to the class of organic compounds known as acetophenones. These are organic compounds containing the acetophenone structure. (2r,3r,4r)-4,10-diacetyl-3,11,13-trihydroxy-2,12-dimethyl-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(9),6,10,12-tetraen-5-one is found in Ramalina stenospora. Based on a literature review very few articles have been published on (2R,3R,4R)-4,10-diacetyl-3,11,13-trihydroxy-2,12-dimethyl-8-oxatricyclo[7.4.0.0²,⁷]Trideca-1(13),6,9,11-tetraen-5-one.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309042216472D          

 25 27  0  0  1  0            999 V2000
    4.4703   -1.3283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6633   -1.1567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1113   -1.7698    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4084   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9604    0.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7674    0.0694    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7054    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2575    1.6387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8985    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6435    1.9817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3464    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6014   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9339   -0.6855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2665   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4595   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0925    0.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8995    0.0694    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1624    1.0256    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3896    1.6387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1966    1.4672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1347    2.4233    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9694    1.1971    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2243    1.9817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5214    0.5840    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8570    1.3377    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
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
  4 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 18 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 14 24  1  0  0  0  0
 11 24  1  0  0  0  0
 24 25  1  6  0  0  0
M  END


  Mrv1652309042216472D          

 25 27  0  0  1  0            999 V2000
    4.4703   -1.3283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6633   -1.1567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1113   -1.7698    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4084   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9604    0.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7674    0.0694    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7054    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2575    1.6387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8985    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6435    1.9817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3464    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6014   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9339   -0.6855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2665   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4595   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0925    0.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8995    0.0694    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1624    1.0256    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3896    1.6387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1966    1.4672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1347    2.4233    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9694    1.1971    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2243    1.9817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5214    0.5840    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8570    1.3377    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
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
  4 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 18 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 14 24  1  0  0  0  0
 11 24  1  0  0  0  0
 24 25  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0196657

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)[C@H]1[C@@H](O)[C@]2(C)C(OC3=C2C(O)=C(C)C(O)=C3C(C)=O)=CC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H18O7/c1-6-14(22)12(8(3)20)16-13(15(6)23)18(4)10(25-16)5-9(21)11(7(2)19)17(18)24/h5,11,17,22-24H,1-4H3/t11-,17-,18-/m1/s1

> <INCHI_KEY>
WMXSSRCBPAZAEH-HWOJHCLVSA-N

> <FORMULA>
C18H18O7

> <MOLECULAR_WEIGHT>
346.335

> <EXACT_MASS>
346.10525292

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
33.989261656633815

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3R,4R)-4,10-diacetyl-3,11,13-trihydroxy-2,12-dimethyl-8-oxatricyclo[7.4.0.0^{2,7}]trideca-1(9),6,10,12-tetraen-5-one

> <JCHEM_LOGP>
1.4699867906666664

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.62222012580038

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.570954875750379

> <JCHEM_PKA_STRONGEST_BASIC>
-3.319153334957031

> <JCHEM_POLAR_SURFACE_AREA>
121.13000000000001

> <JCHEM_REFRACTIVITY>
89.16370000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R,4R)-4,10-diacetyl-3,11,13-trihydroxy-2,12-dimethyl-8-oxatricyclo[7.4.0.0^{2,7}]trideca-1(9),6,10,12-tetraen-5-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       8.344  -2.479   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.838  -2.159   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       5.808  -3.304   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       6.362  -0.695   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.393   0.450   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       8.899   0.130   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       6.917   1.914   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.947   3.059   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.410   2.235   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.935   3.699   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.380   1.090   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.856  -0.374   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       3.610  -1.280   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.364  -0.374   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.858  -0.695   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.173   0.450   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.679   0.130   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.303   1.914   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.727   3.059   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.234   2.739   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -0.251   4.524   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       1.810   2.235   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.285   3.699   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.840   1.090   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.466   2.497   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   12                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   24                                                  
CONECT   12   11    4   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   24                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   22                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   18   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   14   11   25                                             
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₁₈O₇

Average Mass

346.3350 Da

Monoisotopic Mass

346.10525 Da

IUPAC Name

(2R,3R,4R)-4,10-diacetyl-3,11,13-trihydroxy-2,12-dimethyl-8-oxatricyclo[7.4.0.0^{2,7}]trideca-1(9),6,10,12-tetraen-5-one

Traditional Name

(2R,3R,4R)-4,10-diacetyl-3,11,13-trihydroxy-2,12-dimethyl-8-oxatricyclo[7.4.0.0^{2,7}]trideca-1(9),6,10,12-tetraen-5-one

CAS Registry Number

Not Available

SMILES

CC(=O)[C@H]1[C@@H](O)[C@]2(C)C(OC3=C2C(O)=C(C)C(O)=C3C(C)=O)=CC1=O

InChI Identifier

InChI=1S/C18H18O7/c1-6-14(22)12(8(3)20)16-13(15(6)23)18(4)10(25-16)5-9(21)11(7(2)19)17(18)24/h5,11,17,22-24H,1-4H3/t11-,17-,18-/m1/s1

InChI Key

WMXSSRCBPAZAEH-HWOJHCLVSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Ramalina stenospora	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acetophenones. These are organic compounds containing the acetophenone structure.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Acetophenones

Direct Parent

Acetophenones

Alternative Parents

Substituents

Acetophenone
Coumaran
Aryl alkyl ketone
Aryl ketone
Cyclohexenone
1,3-diketone
1,3-dicarbonyl compound
Vinylogous ester
Vinylogous acid
Ketone
Secondary alcohol
Cyclic ketone
Polyol
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Organooxygen compound
Organic oxide
Carbonyl group
Hydrocarbon derivative
Alcohol
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	1.47	ChemAxon
pKa (Strongest Acidic)	7.57	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	121.13 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	89.16 m³·mol⁻¹	ChemAxon
Polarizability	33.99 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

163037446

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r,3r,4r)-4,10-diacetyl-3,11,13-trihydroxy-2,12-dimethyl-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(9),6,10,12-tetraen-5-one (NP0196657)

MOL for NP0196657 ((2r,3r,4r)-4,10-diacetyl-3,11,13-trihydroxy-2,12-dimethyl-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(9),6,10,12-tetraen-5-one)

3D MOL for NP0196657 ((2r,3r,4r)-4,10-diacetyl-3,11,13-trihydroxy-2,12-dimethyl-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(9),6,10,12-tetraen-5-one)

3D SDF for NP0196657 ((2r,3r,4r)-4,10-diacetyl-3,11,13-trihydroxy-2,12-dimethyl-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(9),6,10,12-tetraen-5-one)

3D-SDF for NP0196657 ((2r,3r,4r)-4,10-diacetyl-3,11,13-trihydroxy-2,12-dimethyl-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(9),6,10,12-tetraen-5-one)

PDB for NP0196657 ((2r,3r,4r)-4,10-diacetyl-3,11,13-trihydroxy-2,12-dimethyl-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(9),6,10,12-tetraen-5-one)

3D PDB for NP0196657 ((2r,3r,4r)-4,10-diacetyl-3,11,13-trihydroxy-2,12-dimethyl-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(9),6,10,12-tetraen-5-one)

SMILES for NP0196657 ((2r,3r,4r)-4,10-diacetyl-3,11,13-trihydroxy-2,12-dimethyl-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(9),6,10,12-tetraen-5-one)

INCHI for NP0196657 ((2r,3r,4r)-4,10-diacetyl-3,11,13-trihydroxy-2,12-dimethyl-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(9),6,10,12-tetraen-5-one)

Structure for NP0196657 ((2r,3r,4r)-4,10-diacetyl-3,11,13-trihydroxy-2,12-dimethyl-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(9),6,10,12-tetraen-5-one)

3D Structure for NP0196657 ((2r,3r,4r)-4,10-diacetyl-3,11,13-trihydroxy-2,12-dimethyl-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(9),6,10,12-tetraen-5-one)