NP-MRD: Showing NP-Card for Trachelosiaside (NP0138563)

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Record Information

Version

2.0

Created at

2022-06-29 17:35:18 UTC

Updated at

2022-06-29 17:35:18 UTC

NP-MRD ID

NP0138563

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Trachelosiaside

Description

Trachelosiaside belongs to the class of organic compounds known as lignan glycosides. These are aromatic polycyclic compounds containing a carbohydrate component glycosidically linked to a lignan moiety. They include 1-aryltetralin lactones. Trachelosiaside is found in Trachelospermum asiaticum. Trachelosiaside was first documented in 2008 (PMID: 18348054). Based on a literature review very few articles have been published on Trachelosiaside.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652306292219352D          

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 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 29 34  1  0  0  0  0
 32 35  1  0  0  0  0
 31 36  1  0  0  0  0
 36 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0138563

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(C[C@@H]2[C@@H](CC3=CC(OC)=C(O)C=C3)COC2=O)=CC([C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C26H32O11/c1-34-18-8-12(3-4-17(18)28)5-14-11-36-26(33)15(14)6-13-7-16(21(29)19(9-13)35-2)25-24(32)23(31)22(30)20(10-27)37-25/h3-4,7-9,14-15,20,22-25,27-32H,5-6,10-11H2,1-2H3/t14-,15+,20+,22+,23-,24+,25-/m0/s1

> <INCHI_KEY>
CZGFAWSPACXBMG-OKUUYLHOSA-N

> <FORMULA>
C26H32O11

> <MOLECULAR_WEIGHT>
520.531

> <EXACT_MASS>
520.19446185

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
52.612147943382425

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R,4R)-3-({4-hydroxy-3-methoxy-5-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]phenyl}methyl)-4-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one

> <ALOGPS_LOGP>
0.81

> <JCHEM_LOGP>
0.5344616060000013

> <ALOGPS_LOGS>
-3.20

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.07698368347905

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.364617406906383

> <JCHEM_PKA_STRONGEST_BASIC>
-2.979191500961651

> <JCHEM_POLAR_SURFACE_AREA>
175.36999999999998

> <JCHEM_REFRACTIVITY>
128.7527

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.27e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R,4R)-3-({4-hydroxy-3-methoxy-5-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]phenyl}methyl)-4-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-JUN-22         0                                  
HETATM    1  C   UNK     0      -0.199   4.505   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.134   3.735   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.134   2.195   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.468   1.425   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.468  -0.115   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.134  -0.885   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.199  -0.115   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.199   1.425   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.533   2.195   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.533  -0.885   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.533  -2.425   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.867  -3.195   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.200  -2.425   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.200  -0.885   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -2.867  -0.115   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -5.534  -0.115   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -6.868  -0.885   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -5.534  -3.195   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -2.867  -4.735   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -0.199  -3.195   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       3.802  -0.885   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.802  -2.425   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.048  -3.330   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.572  -4.795   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       3.032  -4.795   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       2.556  -3.330   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       1.091  -2.854   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       6.512  -2.854   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.657  -3.885   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.121  -3.409   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      10.266  -4.439   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.946  -5.946   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.481  -6.422   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.337  -5.391   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      11.090  -6.976   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      11.731  -3.963   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      12.875  -4.994   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   21                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   10                                                  
CONECT    8    7    3    9                                                  
CONECT    9    8                                                            
CONECT   10    7   11   15                                                  
CONECT   11   10   12   20                                                  
CONECT   12   11   13   19                                                  
CONECT   13   12   14   18                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14   10                                                       
CONECT   16   14   17                                                       
CONECT   17   16                                                            
CONECT   18   13                                                            
CONECT   19   12                                                            
CONECT   20   11                                                            
CONECT   21    5   22                                                       
CONECT   22   21   23   26                                                  
CONECT   23   22   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   22   27                                                  
CONECT   27   26                                                            
CONECT   28   23   29                                                       
CONECT   29   28   30   34                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   36                                                  
CONECT   32   31   33   35                                                  
CONECT   33   32   34                                                       
CONECT   34   33   29                                                       
CONECT   35   32                                                            
CONECT   36   31   37                                                       
CONECT   37   36                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₂O₁₁

Average Mass

520.5310 Da

Monoisotopic Mass

520.19446 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

106647-12-5

SMILES

COC1=CC(C[C@@H]2[C@@H](CC3=CC(OC)=C(O)C=C3)COC2=O)=CC([C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)=C1O

InChI Identifier

InChI=1S/C26H32O11/c1-34-18-8-12(3-4-17(18)28)5-14-11-36-26(33)15(14)6-13-7-16(21(29)19(9-13)35-2)25-24(32)23(31)22(30)20(10-27)37-25/h3-4,7-9,14-15,20,22-25,27-32H,5-6,10-11H2,1-2H3/t14-,15+,20+,22+,23-,24+,25-/m0/s1

InChI Key

CZGFAWSPACXBMG-OKUUYLHOSA-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
Trachelospermum asiaticum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lignan glycosides. These are aromatic polycyclic compounds containing a carbohydrate component glycosidically linked to a lignan moiety. They include 1-aryltetralin lactones.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Lignan glycosides

Sub Class

Not Available

Direct Parent

Lignan glycosides

Alternative Parents

Substituents

Lignan glycoside
Dibenzylbutyrolactone
Tetrahydrofuran lignan
9,9p-epoxylignan
Furanoid lignan
Lignan lactone
Phenolic glycoside
C-glycosyl compound
Glycosyl compound
Methoxyphenol
Methoxybenzene
Phenol ether
Phenoxy compound
Anisole
Phenol
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Monosaccharide
Gamma butyrolactone
Oxane
Oxolane
Lactone
1,2-diol
Secondary alcohol
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Dialkyl ether
Polyol
Ether
Monocarboxylic acid or derivatives
Carbonyl group
Organic oxide
Primary alcohol
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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

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

10270392

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21636140

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kousar F, Noomrio MH, Talpur MM, Ahmad VU, Arfan M: Two new lignan glycosides from Trachelospermum lucidum (D. Don) Schum. J Asian Nat Prod Res. 2008 Mar-Apr;10(3-4):317-22. doi: 10.1080/10286020701782692. [PubMed:18348054 ]

Showing NP-Card for Trachelosiaside (NP0138563)

MOL for NP0138563 (Trachelosiaside)

3D MOL for NP0138563 (Trachelosiaside)

3D SDF for NP0138563 (Trachelosiaside)

3D-SDF for NP0138563 (Trachelosiaside)

PDB for NP0138563 (Trachelosiaside)

3D PDB for NP0138563 (Trachelosiaside)

SMILES for NP0138563 (Trachelosiaside)

INCHI for NP0138563 (Trachelosiaside)

Structure for NP0138563 (Trachelosiaside)

3D Structure for NP0138563 (Trachelosiaside)