NP-MRD: Showing NP-Card for [(1s,2r,5s,6s,7s,8s,9s)-5-(acetyloxy)-7-(benzoyloxy)-8-hydroxy-2,10,10-trimethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-6-yl]methyl pyridine-3-carboxylate (NP0230755)

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Record Information

Version

2.0

Created at

2022-09-06 11:18:43 UTC

Updated at

2022-09-06 11:18:43 UTC

NP-MRD ID

NP0230755

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(1s,2r,5s,6s,7s,8s,9s)-5-(acetyloxy)-7-(benzoyloxy)-8-hydroxy-2,10,10-trimethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-6-yl]methyl pyridine-3-carboxylate

Description

CHEMBL3609881 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,2r,5s,6s,7s,8s,9s)-5-(acetyloxy)-7-(benzoyloxy)-8-hydroxy-2,10,10-trimethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-6-yl]methyl pyridine-3-carboxylate is found in Celastrus angulatus. Based on a literature review very few articles have been published on CHEMBL3609881.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062213182D          

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M  END

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M  END


  Mrv1652309062213182D          

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    3.5964    2.6076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7346    0.0220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5233    0.2640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0578   -0.7370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0253   -0.4007    0.0000 O   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  1  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  1  0  0  0
  8 10  1  0  0  0  0
 10 11  1  1  0  0  0
 12 11  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 19 24  1  0  0  0  0
 15 25  1  0  0  0  0
  5 25  1  0  0  0  0
 10 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 30 35  1  0  0  0  0
 12 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 36 39  1  0  0  0  0
 10 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0230755

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1CC[C@H](OC(C)=O)[C@@]2(COC(=O)C3=CC=CN=C3)[C@H](OC(=O)C3=CC=CC=C3)[C@@H](O)[C@@H]3C[C@]12OC3(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C30H35NO8/c1-18-12-13-23(37-19(2)32)29(17-36-26(34)21-11-8-14-31-16-21)25(38-27(35)20-9-6-5-7-10-20)24(33)22-15-30(18,29)39-28(22,3)4/h5-11,14,16,18,22-25,33H,12-13,15,17H2,1-4H3/t18-,22+,23+,24+,25-,29+,30+/m1/s1

> <INCHI_KEY>
BZILJPGAOXCMJH-IDOIOWBISA-N

> <FORMULA>
C30H35NO8

> <MOLECULAR_WEIGHT>
537.609

> <EXACT_MASS>
537.236267091

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
55.6954214263548

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(1S,2R,5S,6S,7S,8S,9S)-5-(acetyloxy)-7-(benzoyloxy)-8-hydroxy-2,10,10-trimethyl-11-oxatricyclo[7.2.1.0^{1,6}]dodecan-6-yl]methyl pyridine-3-carboxylate

> <JCHEM_LOGP>
3.398043776333332

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.804195745169054

> <JCHEM_PKA_STRONGEST_BASIC>
3.2427432578466977

> <JCHEM_POLAR_SURFACE_AREA>
121.25000000000003

> <JCHEM_REFRACTIVITY>
139.232

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
[(1S,2R,5S,6S,7S,8S,9S)-5-(acetyloxy)-7-(benzoyloxy)-8-hydroxy-2,10,10-trimethyl-11-oxatricyclo[7.2.1.0^{1,6}]dodecan-6-yl]methyl pyridine-3-carboxylate

> <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       7.011   4.351   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.908   3.277   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       6.729   1.974   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       4.369   3.218   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       3.651   1.855   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.490   0.549   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.793  -0.837   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.254  -0.931   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.601  -2.326   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.320   0.337   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.203   1.065   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.063   1.623   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.375   3.084   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.251   4.350   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.226   3.210   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.926   4.582   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.089   5.874   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.449   5.795   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       1.790   7.245   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.952   8.538   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.653   9.909   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.191   9.988   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.028   8.696   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.328   7.324   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.080   1.808   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.359   3.322   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       3.811   3.837   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       4.090   5.352   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       2.919   6.351   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       5.542   5.867   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.821   7.381   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       7.273   7.896   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.444   6.897   0.000  0.00  0.00           C+0
HETATM   34  N   UNK     0       8.165   5.383   0.000  0.00  0.00           N+0
HETATM   35  C   UNK     0       6.713   4.868   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -1.371   0.041   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -2.843   0.493   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -1.975  -1.376   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       0.047  -0.748   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   25                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   25   39                                             
CONECT   11   10   12                                                       
CONECT   12   11   13   36                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   25                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   19                                                       
CONECT   25   15    5   10   26                                             
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   35                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   30                                                       
CONECT   36   12   37   38   39                                             
CONECT   37   36                                                            
CONECT   38   36                                                            
CONECT   39   36   10                                                       
MASTER        0    0    0    0    0    0    0    0   39    0   86    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₃₅NO₈

Average Mass

537.6090 Da

Monoisotopic Mass

537.23627 Da

IUPAC Name

[(1S,2R,5S,6S,7S,8S,9S)-5-(acetyloxy)-7-(benzoyloxy)-8-hydroxy-2,10,10-trimethyl-11-oxatricyclo[7.2.1.0^{1,6}]dodecan-6-yl]methyl pyridine-3-carboxylate

Traditional Name

[(1S,2R,5S,6S,7S,8S,9S)-5-(acetyloxy)-7-(benzoyloxy)-8-hydroxy-2,10,10-trimethyl-11-oxatricyclo[7.2.1.0^{1,6}]dodecan-6-yl]methyl pyridine-3-carboxylate

CAS Registry Number

Not Available

SMILES

C[C@@H]1CC[C@H](OC(C)=O)[C@@]2(COC(=O)C3=CC=CN=C3)[C@H](OC(=O)C3=CC=CC=C3)[C@@H](O)[C@@H]3C[C@]12OC3(C)C

InChI Identifier

InChI=1S/C30H35NO8/c1-18-12-13-23(37-19(2)32)29(17-36-26(34)21-11-8-14-31-16-21)25(38-27(35)20-9-6-5-7-10-20)24(33)22-15-30(18,29)39-28(22,3)4/h5-11,14,16,18,22-25,33H,12-13,15,17H2,1-4H3/t18-,22+,23+,24+,25-,29+,30+/m1/s1

InChI Key

BZILJPGAOXCMJH-IDOIOWBISA-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 angulatus	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
Pyridine carboxylic acid or derivatives
Pyridine carboxylic acid
Benzoyl
Oxepane
Monocyclic benzene moiety
Benzenoid
Pyridine
Heteroaromatic compound
Cyclic alcohol
Tetrahydrofuran
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Oxacycle
Azacycle
Dialkyl ether
Ether
Organoheterocyclic compound
Alcohol
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Organic oxygen compound
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Organic oxide
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	3.4	ChemAxon
pKa (Strongest Acidic)	13.8	ChemAxon
pKa (Strongest Basic)	3.24	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	121.25 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	139.23 m³·mol⁻¹	ChemAxon
Polarizability	55.7 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

59001218

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

122187908

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(1s,2r,5s,6s,7s,8s,9s)-5-(acetyloxy)-7-(benzoyloxy)-8-hydroxy-2,10,10-trimethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-6-yl]methyl pyridine-3-carboxylate (NP0230755)

MOL for NP0230755 ([(1s,2r,5s,6s,7s,8s,9s)-5-(acetyloxy)-7-(benzoyloxy)-8-hydroxy-2,10,10-trimethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-6-yl]methyl pyridine-3-carboxylate)

3D MOL for NP0230755 ([(1s,2r,5s,6s,7s,8s,9s)-5-(acetyloxy)-7-(benzoyloxy)-8-hydroxy-2,10,10-trimethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-6-yl]methyl pyridine-3-carboxylate)

3D SDF for NP0230755 ([(1s,2r,5s,6s,7s,8s,9s)-5-(acetyloxy)-7-(benzoyloxy)-8-hydroxy-2,10,10-trimethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-6-yl]methyl pyridine-3-carboxylate)

3D-SDF for NP0230755 ([(1s,2r,5s,6s,7s,8s,9s)-5-(acetyloxy)-7-(benzoyloxy)-8-hydroxy-2,10,10-trimethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-6-yl]methyl pyridine-3-carboxylate)

PDB for NP0230755 ([(1s,2r,5s,6s,7s,8s,9s)-5-(acetyloxy)-7-(benzoyloxy)-8-hydroxy-2,10,10-trimethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-6-yl]methyl pyridine-3-carboxylate)

3D PDB for NP0230755 ([(1s,2r,5s,6s,7s,8s,9s)-5-(acetyloxy)-7-(benzoyloxy)-8-hydroxy-2,10,10-trimethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-6-yl]methyl pyridine-3-carboxylate)

SMILES for NP0230755 ([(1s,2r,5s,6s,7s,8s,9s)-5-(acetyloxy)-7-(benzoyloxy)-8-hydroxy-2,10,10-trimethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-6-yl]methyl pyridine-3-carboxylate)

INCHI for NP0230755 ([(1s,2r,5s,6s,7s,8s,9s)-5-(acetyloxy)-7-(benzoyloxy)-8-hydroxy-2,10,10-trimethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-6-yl]methyl pyridine-3-carboxylate)

Structure for NP0230755 ([(1s,2r,5s,6s,7s,8s,9s)-5-(acetyloxy)-7-(benzoyloxy)-8-hydroxy-2,10,10-trimethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-6-yl]methyl pyridine-3-carboxylate)

3D Structure for NP0230755 ([(1s,2r,5s,6s,7s,8s,9s)-5-(acetyloxy)-7-(benzoyloxy)-8-hydroxy-2,10,10-trimethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-6-yl]methyl pyridine-3-carboxylate)