NP-MRD: Showing NP-Card for 5-ethenyl-4-({2-methylpyrido[3,4-b]indol-1-yl}methyl)-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylic acid (NP0307513)

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Record Information

Version

2.0

Created at

2022-09-11 00:41:00 UTC

Updated at

2022-09-11 00:41:00 UTC

NP-MRD ID

NP0307513

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-ethenyl-4-({2-methylpyrido[3,4-b]indol-1-yl}methyl)-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylic acid

Description

3-Ethenyl-4-({2-methyl-2H-pyrido[3,4-b]indol-1-yl}methyl)-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylic acid belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone. 5-ethenyl-4-({2-methylpyrido[3,4-b]indol-1-yl}methyl)-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylic acid is found in Strychnos mellodora. Based on a literature review very few articles have been published on 3-ethenyl-4-({2-methyl-2H-pyrido[3,4-b]indol-1-yl}methyl)-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112202412D          

 38 42  0  0  0  0            999 V2000
    1.5200    2.8444    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


  Mrv1652309112202412D          

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  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
  6 15  1  0  0  0  0
 15 16  1  0  0  0  0
  4 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 19 23  1  0  0  0  0
  3 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  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  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 28 33  1  0  0  0  0
 33 34  2  0  0  0  0
 26 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 25 37  1  0  0  0  0
 37 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0307513

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C=CC2=C3C=CC=CC3=NC2=C1CC1C(C=C)C(OC2OC(CO)C(O)C(O)C2O)OC=C1C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H30N2O9/c1-3-13-16(10-19-21-15(8-9-29(19)2)14-6-4-5-7-18(14)28-21)17(25(34)35)12-36-26(13)38-27-24(33)23(32)22(31)20(11-30)37-27/h3-9,12-13,16,20,22-24,26-27,30-33H,1,10-11H2,2H3,(H,34,35)

> <INCHI_KEY>
XNROSPYMQOEREU-UHFFFAOYSA-N

> <FORMULA>
C27H30N2O9

> <MOLECULAR_WEIGHT>
526.542

> <EXACT_MASS>
526.195130554

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
54.021722276295215

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-ethenyl-4-({2-methyl-2H-pyrido[3,4-b]indol-1-yl}methyl)-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylic acid

> <JCHEM_LOGP>
0.9380908549873849

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.207016212039482

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.618240298458329

> <JCHEM_PKA_STRONGEST_BASIC>
3.3800192122642625

> <JCHEM_POLAR_SURFACE_AREA>
163.73000000000002

> <JCHEM_REFRACTIVITY>
132.79299999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
5-ethenyl-4-({2-methylpyrido[3,4-b]indol-1-yl}methyl)-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4H-pyran-3-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       2.837   5.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.801   3.730   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.783   2.438   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.277   2.758   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -0.206   4.258   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -1.706   4.543   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.711   3.376   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -4.224   3.663   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.229   2.497   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -6.742   2.784   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -4.732   5.117   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -6.245   5.404   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -3.726   6.284   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -4.234   7.738   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -2.213   5.997   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.208   7.163   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -0.754   1.613   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -0.278   0.149   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.228  -0.171   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.297  -1.629   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       1.818  -2.148   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -0.905  -2.763   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       2.259   0.973   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.839   0.791   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.241  -0.812   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.747  -1.132   0.000  0.00  0.00           C+0
HETATM   27  N   UNK     0       6.993  -0.227   0.000  0.00  0.00           N+0
HETATM   28  C   UNK     0       8.239  -1.132   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       9.746  -0.812   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      10.776  -1.956   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      10.300  -3.421   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       8.794  -3.741   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       7.763  -2.597   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       6.223  -2.597   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       5.193  -3.741   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       3.687  -3.421   0.000  0.00  0.00           C+0
HETATM   37  N   UNK     0       3.211  -1.956   0.000  0.00  0.00           N+0
HETATM   38  C   UNK     0       1.984  -3.242   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   23                                                  
CONECT    4    3    5   17                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   15                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    8   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    6   16                                                  
CONECT   16   15                                                            
CONECT   17    4   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   23                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   19    3   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   37                                                  
CONECT   26   25   27   34                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   33                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   28   34                                                  
CONECT   34   33   26   35                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   25   38                                                  
CONECT   38   37                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   84    0
END

View in JSmol

Synonyms

Value	Source
3-Ethenyl-4-({2-methyl-2H-pyrido[3,4-b]indol-1-yl}methyl)-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylate	Generator

Chemical Formula

C₂₇H₃₀N₂O₉

Average Mass

526.5420 Da

Monoisotopic Mass

526.19513 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CN1C=CC2=C3C=CC=CC3=NC2=C1CC1C(C=C)C(OC2OC(CO)C(O)C(O)C2O)OC=C1C(O)=O

InChI Identifier

InChI=1S/C27H30N2O9/c1-3-13-16(10-19-21-15(8-9-29(19)2)14-6-4-5-7-18(14)28-21)17(25(34)35)12-36-26(13)38-27-24(33)23(32)22(31)20(11-30)37-27/h3-9,12-13,16,20,22-24,26-27,30-33H,1,10-11H2,2H3,(H,34,35)

InChI Key

XNROSPYMQOEREU-UHFFFAOYSA-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
Strychnos mellodora	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Terpene glycosides

Alternative Parents

Substituents

Terpene glycoside
Harman
Beta-carboline
Pyridoindole
Glycosyl compound
Secoiridoid-skeleton
O-glycosyl compound
Aromatic monoterpenoid
Monoterpenoid
Indole
Indole or derivatives
Alkaloid or derivatives
Sugar acid
Pyridine
Benzenoid
Oxane
Monosaccharide
Heteroaromatic compound
Pyrrole
Vinylogous ester
Secondary alcohol
Acetal
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Azacycle
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Polyol
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic nitrogen compound
Organic oxygen compound
Carbonyl group
Alcohol
Primary alcohol
Organonitrogen compound
Organooxygen compound
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

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

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

163195772

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5-ethenyl-4-({2-methylpyrido[3,4-b]indol-1-yl}methyl)-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylic acid (NP0307513)

MOL for NP0307513 (5-ethenyl-4-({2-methylpyrido[3,4-b]indol-1-yl}methyl)-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylic acid)

3D MOL for NP0307513 (5-ethenyl-4-({2-methylpyrido[3,4-b]indol-1-yl}methyl)-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylic acid)

3D SDF for NP0307513 (5-ethenyl-4-({2-methylpyrido[3,4-b]indol-1-yl}methyl)-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylic acid)

3D-SDF for NP0307513 (5-ethenyl-4-({2-methylpyrido[3,4-b]indol-1-yl}methyl)-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylic acid)

PDB for NP0307513 (5-ethenyl-4-({2-methylpyrido[3,4-b]indol-1-yl}methyl)-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylic acid)

3D PDB for NP0307513 (5-ethenyl-4-({2-methylpyrido[3,4-b]indol-1-yl}methyl)-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylic acid)

SMILES for NP0307513 (5-ethenyl-4-({2-methylpyrido[3,4-b]indol-1-yl}methyl)-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylic acid)

INCHI for NP0307513 (5-ethenyl-4-({2-methylpyrido[3,4-b]indol-1-yl}methyl)-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylic acid)

Structure for NP0307513 (5-ethenyl-4-({2-methylpyrido[3,4-b]indol-1-yl}methyl)-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylic acid)

3D Structure for NP0307513 (5-ethenyl-4-({2-methylpyrido[3,4-b]indol-1-yl}methyl)-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylic acid)