NP-MRD: Showing NP-Card for (1s,2s,5s,6s,7s,9r,12r)-5-(acetyloxy)-12-(benzoyloxy)-2-(hydroxymethyl)-6,10,10-trimethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl benzoate (NP0324377)

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Record Information

Version

2.0

Created at

2022-09-12 04:25:06 UTC

Updated at

2022-09-12 04:25:06 UTC

NP-MRD ID

NP0324377

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2s,5s,6s,7s,9r,12r)-5-(acetyloxy)-12-(benzoyloxy)-2-(hydroxymethyl)-6,10,10-trimethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl benzoate

Description

CHEMBL454600 belongs to the class of organic compounds known as agarofurans. These are organic compounds containing an agarofuran moiety( a three-ring system, with core fragment oxatricyclo[7.2.1.0^{1,6}]Dodec-2-ene). (1s,2s,5s,6s,7s,9r,12r)-5-(acetyloxy)-12-(benzoyloxy)-2-(hydroxymethyl)-6,10,10-trimethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl benzoate is found in Celastrus orbiculatus. Based on a literature review very few articles have been published on CHEMBL454600.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122206252D          

 39 43  0  0  1  0            999 V2000
    6.0215   -0.7007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3919   -1.2812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309122206252D          

 39 43  0  0  1  0            999 V2000
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    1.8846   -2.8567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8117   -2.3926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5630   -3.1793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2426   -3.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7995   -2.7485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5508   -1.9619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2548   -1.7840    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
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 22 27  1  0  0  0  0
 18 28  1  0  0  0  0
  5 28  1  0  0  0  0
 11 28  1  0  0  0  0
 28 29  1  6  0  0  0
 16 30  1  0  0  0  0
 11 30  1  0  0  0  0
 30 31  1  6  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 34 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0324377

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@H]1CC[C@@H](CO)[C@]23OC(C)(C)[C@H](C[C@H](OC(=O)C4=CC=CC=C4)[C@]12C)[C@H]3OC(=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C31H36O8/c1-19(33)36-24-16-15-22(18-32)31-26(38-28(35)21-13-9-6-10-14-21)23(29(2,3)39-31)17-25(30(24,31)4)37-27(34)20-11-7-5-8-12-20/h5-14,22-26,32H,15-18H2,1-4H3/t22-,23+,24-,25-,26+,30-,31+/m0/s1

> <INCHI_KEY>
PGZSQQPPVDUMHW-VCBFDHLISA-N

> <FORMULA>
C31H36O8

> <MOLECULAR_WEIGHT>
536.621

> <EXACT_MASS>
536.241018119

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
57.35394239538027

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,5S,6S,7S,9R,12R)-5-(acetyloxy)-12-(benzoyloxy)-2-(hydroxymethyl)-6,10,10-trimethyl-11-oxatricyclo[7.2.1.0^{1,6}]dodecan-7-yl benzoate

> <JCHEM_LOGP>
4.501365470333333

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.374478186192864

> <JCHEM_PKA_STRONGEST_BASIC>
-2.635003241359242

> <JCHEM_POLAR_SURFACE_AREA>
108.36000000000001

> <JCHEM_REFRACTIVITY>
141.44409999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,5S,6S,7S,9R,12R)-5-(acetyloxy)-12-(benzoyloxy)-2-(hydroxymethyl)-6,10,10-trimethyl-11-oxatricyclo[7.2.1.0^{1,6}]dodecan-7-yl benzoate

> <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      11.240  -1.308   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.065  -2.392   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      11.015  -3.724   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       8.397  -2.240   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.690  -1.749   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.528  -0.443   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.832   0.943   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.292   1.038   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.270   2.706   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       6.176   4.035   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.358  -0.230   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.086   0.855   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.668   0.065   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.788   1.453   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.029  -0.014   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.976  -1.516   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.664  -2.977   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.264  -3.104   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.661  -4.751   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       3.819  -6.381   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.332  -6.818   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.917  -7.441   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.455  -7.373   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.283  -8.672   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.572 -10.038   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.033 -10.105   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.206  -8.807   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.118  -1.701   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.405  -2.891   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.242  -0.958   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       3.655  -2.378   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       2.994  -3.969   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       3.518  -5.332   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       1.515  -4.466   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       1.051  -5.935   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -0.453  -6.267   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -1.492  -5.131   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -1.028  -3.662   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       0.476  -3.330   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   28                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    8   12   28   30                                             
CONECT   12   11   13                                                       
CONECT   13   12   14   15   16                                             
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   13   17   30                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   28                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   22                                                       
CONECT   28   18    5   11   29                                             
CONECT   29   28                                                            
CONECT   30   16   11   31                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35   39                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   34                                                       
MASTER        0    0    0    0    0    0    0    0   39    0   86    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₁H₃₆O₈

Average Mass

536.6210 Da

Monoisotopic Mass

536.24102 Da

IUPAC Name

(1S,2S,5S,6S,7S,9R,12R)-5-(acetyloxy)-12-(benzoyloxy)-2-(hydroxymethyl)-6,10,10-trimethyl-11-oxatricyclo[7.2.1.0^{1,6}]dodecan-7-yl benzoate

Traditional Name

(1S,2S,5S,6S,7S,9R,12R)-5-(acetyloxy)-12-(benzoyloxy)-2-(hydroxymethyl)-6,10,10-trimethyl-11-oxatricyclo[7.2.1.0^{1,6}]dodecan-7-yl benzoate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@H]1CC[C@@H](CO)[C@]23OC(C)(C)[C@H](C[C@H](OC(=O)C4=CC=CC=C4)[C@]12C)[C@H]3OC(=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C31H36O8/c1-19(33)36-24-16-15-22(18-32)31-26(38-28(35)21-13-9-6-10-14-21)23(29(2,3)39-31)17-25(30(24,31)4)37-27(34)20-11-7-5-8-12-20/h5-14,22-26,32H,15-18H2,1-4H3/t22-,23+,24-,25-,26+,30-,31+/m0/s1

InChI Key

PGZSQQPPVDUMHW-VCBFDHLISA-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
Celastrus orbiculatus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as agarofurans. These are organic compounds containing an agarofuran moiety( a three-ring system, with core fragment oxatricyclo[7.2.1.0^{1,6}]Dodec-2-ene).

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Agarofurans

Alternative Parents

Substituents

Agarofuran
Benzoate ester
Benzoic acid or derivatives
Tricarboxylic acid or derivatives
Benzoyl
Oxepane
Monocyclic benzene moiety
Benzenoid
Tetrahydrofuran
Carboxylic acid ester
Ether
Dialkyl ether
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Alcohol
Organic oxide
Organic oxygen compound
Primary 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	4.5	ChemAxon
pKa (Strongest Acidic)	15.37	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	108.36 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	141.44 m³·mol⁻¹	ChemAxon
Polarizability	57.35 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

23329688

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

24898242

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,5s,6s,7s,9r,12r)-5-(acetyloxy)-12-(benzoyloxy)-2-(hydroxymethyl)-6,10,10-trimethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl benzoate (NP0324377)

MOL for NP0324377 ((1s,2s,5s,6s,7s,9r,12r)-5-(acetyloxy)-12-(benzoyloxy)-2-(hydroxymethyl)-6,10,10-trimethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl benzoate)

3D MOL for NP0324377 ((1s,2s,5s,6s,7s,9r,12r)-5-(acetyloxy)-12-(benzoyloxy)-2-(hydroxymethyl)-6,10,10-trimethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl benzoate)

3D SDF for NP0324377 ((1s,2s,5s,6s,7s,9r,12r)-5-(acetyloxy)-12-(benzoyloxy)-2-(hydroxymethyl)-6,10,10-trimethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl benzoate)

3D-SDF for NP0324377 ((1s,2s,5s,6s,7s,9r,12r)-5-(acetyloxy)-12-(benzoyloxy)-2-(hydroxymethyl)-6,10,10-trimethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl benzoate)

PDB for NP0324377 ((1s,2s,5s,6s,7s,9r,12r)-5-(acetyloxy)-12-(benzoyloxy)-2-(hydroxymethyl)-6,10,10-trimethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl benzoate)

3D PDB for NP0324377 ((1s,2s,5s,6s,7s,9r,12r)-5-(acetyloxy)-12-(benzoyloxy)-2-(hydroxymethyl)-6,10,10-trimethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl benzoate)

SMILES for NP0324377 ((1s,2s,5s,6s,7s,9r,12r)-5-(acetyloxy)-12-(benzoyloxy)-2-(hydroxymethyl)-6,10,10-trimethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl benzoate)

INCHI for NP0324377 ((1s,2s,5s,6s,7s,9r,12r)-5-(acetyloxy)-12-(benzoyloxy)-2-(hydroxymethyl)-6,10,10-trimethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl benzoate)

Structure for NP0324377 ((1s,2s,5s,6s,7s,9r,12r)-5-(acetyloxy)-12-(benzoyloxy)-2-(hydroxymethyl)-6,10,10-trimethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl benzoate)

3D Structure for NP0324377 ((1s,2s,5s,6s,7s,9r,12r)-5-(acetyloxy)-12-(benzoyloxy)-2-(hydroxymethyl)-6,10,10-trimethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl benzoate)