NP-MRD: Showing NP-Card for Triregelolide B (NP0086130)

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Record Information

Version

2.0

Created at

2022-04-29 06:29:44 UTC

Updated at

2022-04-29 06:29:44 UTC

NP-MRD ID

NP0086130

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Triregelolide B

Description

Triregelolide B is found in Tripterygium regelii. Based on a literature review very few articles have been published on (1S,6R,11R,14S,15S,17R,20S)-6-methoxy-1,6,11,14,17,20-hexamethyl-8-oxo-7-oxapentacyclo[12.8.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²⁰]Docosa-2,4,9-triene-17-carboxylic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292208292D          

 35 39  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652304292208292D          

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  7 25  1  0  0  0  0
 25 26  2  0  0  0  0
  2 26  1  0  0  0  0
 24 27  1  6  0  0  0
 21 28  1  1  0  0  0
 20 29  1  1  0  0  0
 17 30  1  1  0  0  0
 30 31  1  0  0  0  0
 30 32  2  0  0  0  0
 14 33  1  6  0  0  0
 11 34  1  6  0  0  0
  4 35  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0086130

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12C[C@@](C)(CC[C@]1(C)CC[C@]1(C)C3=CC=C4C(=CC(=O)O[C@@]4(C)OC)[C@]3(C)CC[C@@]21C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C29H40O5/c1-24-10-11-25(2,23(31)32)17-21(24)28(5)15-13-26(3)19-16-22(30)34-29(6,33-7)18(19)8-9-20(26)27(28,4)14-12-24/h8-9,16,21H,10-15,17H2,1-7H3,(H,31,32)/t21-,24+,25+,26-,27+,28-,29+/m0/s1

> <INCHI_KEY>
BGMOCXGUWVRVLW-XFCFWDGBSA-N

> <FORMULA>
C29H40O5

> <MOLECULAR_WEIGHT>
468.634

> <EXACT_MASS>
468.287574388

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
52.726372851444786

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,6R,11R,14S,15S,17R,20S)-6-methoxy-1,6,11,14,17,20-hexamethyl-8-oxo-7-oxapentacyclo[12.8.0.0^{2,11}.0^{5,10}.0^{15,20}]docosa-2,4,9-triene-17-carboxylic acid

> <ALOGPS_LOGP>
6.25

> <JCHEM_LOGP>
5.630078529333334

> <ALOGPS_LOGS>
-5.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.776643233250618

> <JCHEM_PKA_STRONGEST_BASIC>
-4.340527838916741

> <JCHEM_POLAR_SURFACE_AREA>
72.83000000000001

> <JCHEM_REFRACTIVITY>
132.71399999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.69e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,6R,11R,14S,15S,17R,20S)-6-methoxy-1,6,11,14,17,20-hexamethyl-8-oxo-7-oxapentacyclo[12.8.0.0^{2,11}.0^{5,10}.0^{15,20}]docosa-2,4,9-triene-17-carboxylic acid

> <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  O   UNK     0       7.796  -6.517   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       8.566  -5.184   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       7.796  -3.850   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       8.566  -2.516   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       7.119  -1.990   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       5.939  -2.980   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.106  -2.516   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.876  -1.183   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.416  -1.183   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.186  -2.516   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.726  -2.516   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      15.496  -1.183   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      17.036  -1.183   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      17.806  -2.516   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      19.346  -2.516   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      20.116  -3.850   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      19.346  -5.184   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      20.793  -5.710   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      17.806  -5.184   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      17.036  -3.850   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      15.496  -3.850   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      14.726  -5.184   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      13.186  -5.184   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      12.416  -3.850   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.876  -3.850   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.106  -5.184   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      11.646  -5.184   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      16.266  -5.184   0.000  0.00  0.00           C+0
HETATM   29  H   UNK     0      16.266  -2.516   0.000  0.00  0.00           H+0
HETATM   30  C   UNK     0      19.078  -6.700   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      20.258  -7.690   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      17.631  -7.227   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      18.576  -1.183   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      13.956  -1.183   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       8.833  -1.000   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   26                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7   35                                             
CONECT    5    4    6                                                       
CONECT    6    5                                                            
CONECT    7    4    8   25                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   24                                                  
CONECT   11   10   12   21   34                                             
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   20   33                                             
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19   30                                             
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   14   21   29                                             
CONECT   21   20   11   22   28                                             
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   10   25   27                                             
CONECT   25   24    7   26                                                  
CONECT   26   25    2                                                       
CONECT   27   24                                                            
CONECT   28   21                                                            
CONECT   29   20                                                            
CONECT   30   17   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   14                                                            
CONECT   34   11                                                            
CONECT   35    4                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

View in JSmol

Synonyms

Value	Source
(1S,6R,11R,14S,15S,17R,20S)-6-Methoxy-1,6,11,14,17,20-hexamethyl-8-oxo-7-oxapentacyclo[12.8.0.0,.0,.0,]docosa-2,4,9-triene-17-carboxylate	Generator

Chemical Formula

C₂₉H₄₀O₅

Average Mass

468.6340 Da

Monoisotopic Mass

468.28757 Da

IUPAC Name

(1S,6R,11R,14S,15S,17R,20S)-6-methoxy-1,6,11,14,17,20-hexamethyl-8-oxo-7-oxapentacyclo[12.8.0.0^{2,11}.0^{5,10}.0^{15,20}]docosa-2,4,9-triene-17-carboxylic acid

Traditional Name

(1S,6R,11R,14S,15S,17R,20S)-6-methoxy-1,6,11,14,17,20-hexamethyl-8-oxo-7-oxapentacyclo[12.8.0.0^{2,11}.0^{5,10}.0^{15,20}]docosa-2,4,9-triene-17-carboxylic acid

CAS Registry Number

Not Available

SMILES

[H][C@]12C[C@@](C)(CC[C@]1(C)CC[C@]1(C)C3=CC=C4C(=CC(=O)O[C@@]4(C)OC)[C@]3(C)CC[C@@]21C)C(O)=O

InChI Identifier

InChI=1S/C29H40O5/c1-24-10-11-25(2,23(31)32)17-21(24)28(5)15-13-26(3)19-16-22(30)34-29(6,33-7)18(19)8-9-20(26)27(28,4)14-12-24/h8-9,16,21H,10-15,17H2,1-7H3,(H,31,32)/t21-,24+,25+,26-,27+,28-,29+/m0/s1

InChI Key

BGMOCXGUWVRVLW-XFCFWDGBSA-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	6.25	ALOGPS
logP	5.63	ChemAxon
logS	-5.7	ALOGPS
pKa (Strongest Acidic)	4.78	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	132.71 m³·mol⁻¹	ChemAxon
Polarizability	52.73 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	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00056268

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

163183965

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Triregelolide B (NP0086130)

MOL for NP0086130 (Triregelolide B)

3D MOL for NP0086130 (Triregelolide B)

3D SDF for NP0086130 (Triregelolide B)

3D-SDF for NP0086130 (Triregelolide B)

PDB for NP0086130 (Triregelolide B)

3D PDB for NP0086130 (Triregelolide B)

SMILES for NP0086130 (Triregelolide B)

INCHI for NP0086130 (Triregelolide B)

Structure for NP0086130 (Triregelolide B)

3D Structure for NP0086130 (Triregelolide B)