NP-MRD: Showing NP-Card for Triptregeline I (NP0086124)

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Record Information

Version

2.0

Created at

2022-04-29 06:29:25 UTC

Updated at

2022-04-29 06:29:25 UTC

NP-MRD ID

NP0086124

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Triptregeline I

Description

Triptregeline I is found in Tripterygium regelii. Based on a literature review very few articles have been published on (1S,2S,5S,6S,7S,9R,12R)-7-(benzoyloxy)-5-(furan-3-carbonyloxy)-2-hydroxy-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]Dodecan-12-yl pyridine-3-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292208292D          

 43 48  0  0  1  0            999 V2000
    0.4326   -0.8991    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


  Mrv1652304292208292D          

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    6.2868   -0.5504    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9340   -0.0388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6474    0.7349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8129    2.1500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8099    0.3253    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0894    1.0682    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7749    1.8984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9078    2.2181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6473    3.0009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1609    3.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7086    2.5497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4481    1.7669    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3601    1.6011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0570    2.6681    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7071   -0.6302    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  9 14  1  0  0  0  0
  8 15  2  0  0  0  0
  6 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  6  0  0  0
 19 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 16 24  1  0  0  0  0
 24 25  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 27 31  1  0  0  0  0
 26 32  2  0  0  0  0
 18 33  1  0  0  0  0
  4 33  1  0  0  0  0
 33 34  1  1  0  0  0
 34 35  1  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
 39 40  1  0  0  0  0
 40 41  2  0  0  0  0
 36 41  1  0  0  0  0
 35 42  2  0  0  0  0
 18 43  1  6  0  0  0
  2 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0086124

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)O[C@]23[C@H](OC(=O)C4=CC=CN=C4)[C@H]1C[C@H](OC(=O)C1=CC=CC=C1)[C@]2(C)[C@H](CC[C@]3(C)O)OC(=O)C1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C33H35NO9/c1-30(2)23-17-25(41-27(35)20-9-6-5-7-10-20)32(4)24(40-29(37)22-13-16-39-19-22)12-14-31(3,38)33(32,43-30)26(23)42-28(36)21-11-8-15-34-18-21/h5-11,13,15-16,18-19,23-26,38H,12,14,17H2,1-4H3/t23-,24+,25+,26-,31+,32+,33+/m1/s1

> <INCHI_KEY>
BZAPKFYLGRZYNT-YMLFHJQBSA-N

> <FORMULA>
C33H35NO9

> <MOLECULAR_WEIGHT>
589.641

> <EXACT_MASS>
589.231181711

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
60.5962248367176

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,5S,6S,7S,9R,12R)-7-(benzoyloxy)-5-(furan-3-carbonyloxy)-2-hydroxy-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0^{1,6}]dodecan-12-yl pyridine-3-carboxylate

> <ALOGPS_LOGP>
4.21

> <JCHEM_LOGP>
4.713935126666665

> <ALOGPS_LOGS>
-4.41

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.75945735620363

> <JCHEM_PKA_STRONGEST_BASIC>
3.2398486229928833

> <JCHEM_POLAR_SURFACE_AREA>
134.39

> <JCHEM_REFRACTIVITY>
152.1693

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.30e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,5S,6S,7S,9R,12R)-7-(benzoyloxy)-5-(furan-3-carbonyloxy)-2-hydroxy-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0^{1,6}]dodecan-12-yl pyridine-3-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       0.807  -1.678   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.788  -0.337   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.150  -0.250   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.147   1.238   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.906   2.668   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.501   2.741   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.926   4.427   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.050   6.061   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.099   7.201   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.511   8.624   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.450   9.845   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.977   9.643   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.565   8.219   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.626   6.998   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.461   6.476   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       5.277   1.317   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.556   2.513   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.508  -0.140   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.522  -1.366   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.076  -2.948   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       4.586  -2.799   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       7.074  -1.222   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.714   0.187   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.829   1.454   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       8.412   2.277   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      10.018   2.635   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.870   1.309   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.454  -0.173   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      11.735  -1.027   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      12.943  -0.072   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      12.409   1.372   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      10.851   4.013   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       3.378   0.607   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       3.900   1.994   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       3.313   3.544   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       1.695   4.140   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       1.208   5.602   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -0.300   5.911   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -1.323   4.759   0.000  0.00  0.00           C+0
HETATM   40  N   UNK     0      -0.836   3.298   0.000  0.00  0.00           N+0
HETATM   41  C   UNK     0       0.672   2.989   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       3.840   4.981   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0       3.187  -1.176   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4   43                                             
CONECT    3    2                                                            
CONECT    4    2    5   33                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   16                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   15                                                  
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    9                                                       
CONECT   15    8                                                            
CONECT   16    6   17   18   24                                             
CONECT   17   16                                                            
CONECT   18   16   19   33   43                                             
CONECT   19   18   20   21   22                                             
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   19   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   16   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   32                                                  
CONECT   27   26   28   31                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   27                                                       
CONECT   32   26                                                            
CONECT   33   18    4   34                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36   42                                                  
CONECT   36   35   37   41                                                  
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   36                                                       
CONECT   42   35                                                            
CONECT   43   18    2                                                       
MASTER        0    0    0    0    0    0    0    0   43    0   96    0
END

View in JSmol

Synonyms

Value	Source
(1S,2S,5S,6S,7S,9R,12R)-7-(Benzoyloxy)-5-(furan-3-carbonyloxy)-2-hydroxy-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0,]dodecan-12-yl pyridine-3-carboxylic acid	Generator

Chemical Formula

C₃₃H₃₅NO₉

Average Mass

589.6410 Da

Monoisotopic Mass

589.23118 Da

IUPAC Name

(1S,2S,5S,6S,7S,9R,12R)-7-(benzoyloxy)-5-(furan-3-carbonyloxy)-2-hydroxy-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0^{1,6}]dodecan-12-yl pyridine-3-carboxylate

Traditional Name

(1S,2S,5S,6S,7S,9R,12R)-7-(benzoyloxy)-5-(furan-3-carbonyloxy)-2-hydroxy-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0^{1,6}]dodecan-12-yl pyridine-3-carboxylate

CAS Registry Number

Not Available

SMILES

CC1(C)O[C@]23[C@H](OC(=O)C4=CC=CN=C4)[C@H]1C[C@H](OC(=O)C1=CC=CC=C1)[C@]2(C)[C@H](CC[C@]3(C)O)OC(=O)C1=COC=C1

InChI Identifier

InChI=1S/C33H35NO9/c1-30(2)23-17-25(41-27(35)20-9-6-5-7-10-20)32(4)24(40-29(37)22-13-16-39-19-22)12-14-31(3,38)33(32,43-30)26(23)42-28(36)21-11-8-15-34-18-21/h5-11,13,15-16,18-19,23-26,38H,12,14,17H2,1-4H3/t23-,24+,25+,26-,31+,32+,33+/m1/s1

InChI Key

BZAPKFYLGRZYNT-YMLFHJQBSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Tripterygium regelii	Plant	KNApSAcK

Chemical Taxonomy

Classification

Not classified

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	4.21	ALOGPS
logP	4.71	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	13.76	ChemAxon
pKa (Strongest Basic)	3.24	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	134.39 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	152.17 m³·mol⁻¹	ChemAxon
Polarizability	60.6 Å³	ChemAxon
Number of Rings	6	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

C00056262

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

163183971

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Triptregeline I (NP0086124)

MOL for NP0086124 (Triptregeline I)

3D MOL for NP0086124 (Triptregeline I)

3D SDF for NP0086124 (Triptregeline I)

3D-SDF for NP0086124 (Triptregeline I)

PDB for NP0086124 (Triptregeline I)

3D PDB for NP0086124 (Triptregeline I)

SMILES for NP0086124 (Triptregeline I)

INCHI for NP0086124 (Triptregeline I)

Structure for NP0086124 (Triptregeline I)

3D Structure for NP0086124 (Triptregeline I)