NP-MRD: Showing NP-Card for 1-(5-ethenyl-4-{1h,2h,3h,4h,9h-pyrido[3,4-b]indol-1-ylmethyl}-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-yl)ethanone (NP0296810)

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Record Information

Version

2.0

Created at

2022-09-10 06:37:56 UTC

Updated at

2022-09-10 06:37:56 UTC

NP-MRD ID

NP0296810

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-(5-ethenyl-4-{1h,2h,3h,4h,9h-pyrido[3,4-b]indol-1-ylmethyl}-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-yl)ethanone

Description

1-[3-Ethenyl-4-({1H,2H,3H,4H,9H-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-yl]ethan-1-one 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. 1-[3-Ethenyl-4-({1H,2H,3H,4H,9H-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-yl]ethan-1-one is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241509232D          

 37 41  0  0  0  0            999 V2000
    3.3662   -2.5545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  9 10  1  0  0  0  0
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 29 37  1  0  0  0  0
 32 37  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1533004241509232D          

 37 41  0  0  0  0            999 V2000
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  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
  9 18  1  0  0  0  0
 18 19  1  0  0  0  0
  7 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 20 23  1  0  0  0  0
  4 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 25 30  1  0  0  0  0
 30 31  1  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
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 29 37  1  0  0  0  0
 32 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0296810

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)C1=COC(OC2OC(CO)C(O)C(O)C2O)C(C=C)C1CC1NCCC2=C1NC1=CC=CC=C21

> <INCHI_IDENTIFIER>
InChI=1S/C27H34N2O8/c1-3-14-17(10-20-22-16(8-9-28-20)15-6-4-5-7-19(15)29-22)18(13(2)31)12-35-26(14)37-27-25(34)24(33)23(32)21(11-30)36-27/h3-7,12,14,17,20-21,23-30,32-34H,1,8-11H2,2H3

> <INCHI_KEY>
JNFLTBPLJHBVNE-UHFFFAOYSA-N

> <FORMULA>
C27H34N2O8

> <MOLECULAR_WEIGHT>
514.575

> <EXACT_MASS>
514.231516063

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
54.85185262418442

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-[3-ethenyl-4-({1H,2H,3H,4H,9H-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-yl]ethan-1-one

> <ALOGPS_LOGP>
0.47

> <JCHEM_LOGP>
0.47121674166666805

> <ALOGPS_LOGS>
-3.10

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.198483397415501

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.207176222936573

> <JCHEM_PKA_STRONGEST_BASIC>
8.89244850307269

> <JCHEM_POLAR_SURFACE_AREA>
153.5

> <JCHEM_REFRACTIVITY>
133.47979999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.11e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-(5-ethenyl-4-{1H,2H,3H,4H,9H-pyrido[3,4-b]indol-1-ylmethyl}-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4H-pyran-3-yl)ethanone

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       6.284  -4.768   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.790  -5.089   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       8.266  -6.553   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       8.820  -3.944   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.327  -4.264   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      11.357  -3.120   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      10.881  -1.655   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      11.912  -0.511   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      13.418  -0.831   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      14.449   0.314   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      15.955  -0.007   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      16.985   1.138   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      18.492   0.818   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      16.431  -1.471   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      17.937  -1.791   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      15.400  -2.616   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      15.876  -4.080   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      13.894  -2.296   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      12.864  -3.440   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       9.375  -1.335   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.899   0.130   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.930   1.274   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.344  -2.479   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.838  -2.159   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.362  -0.695   0.000  0.00  0.00           C+0
HETATM   26  N   UNK     0       7.393   0.450   0.000  0.00  0.00           N+0
HETATM   27  C   UNK     0       6.917   1.914   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.410   2.235   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.380   1.090   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.856  -0.374   0.000  0.00  0.00           C+0
HETATM   31  N   UNK     0       3.610  -1.280   0.000  0.00  0.00           N+0
HETATM   32  C   UNK     0       2.364  -0.374   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.858  -0.695   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -0.173   0.450   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       0.303   1.914   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       1.810   2.235   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       2.840   1.090   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   23                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   20                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   18                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   11   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16    9   19                                                  
CONECT   19   18                                                            
CONECT   20    7   21   23                                                  
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23   20    4   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   30                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   37                                                  
CONECT   30   29   25   31                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   37                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   29   32                                                  
MASTER        0    0    0    0    0    0    0    0   37    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₄N₂O₈

Average Mass

514.5750 Da

Monoisotopic Mass

514.23152 Da

IUPAC Name

1-[3-ethenyl-4-({1H,2H,3H,4H,9H-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-yl]ethan-1-one

Traditional Name

1-(5-ethenyl-4-{1H,2H,3H,4H,9H-pyrido[3,4-b]indol-1-ylmethyl}-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4H-pyran-3-yl)ethanone

CAS Registry Number

Not Available

SMILES

CC(=O)C1=COC(OC2OC(CO)C(O)C(O)C2O)C(C=C)C1CC1NCCC2=C1NC1=CC=CC=C21

InChI Identifier

InChI=1S/C27H34N2O8/c1-3-14-17(10-20-22-16(8-9-28-20)15-6-4-5-7-19(15)29-22)18(13(2)31)12-35-26(14)37-27-25(34)24(33)23(32)21(11-30)36-27/h3-7,12,14,17,20-21,23-30,32-34H,1,8-11H2,2H3

InChI Key

JNFLTBPLJHBVNE-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

Not Available

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
O-glycosyl compound
Secoiridoid-skeleton
Aromatic monoterpenoid
Monoterpenoid
3-alkylindole
Indole
Indole or derivatives
Alkaloid or derivatives
Aralkylamine
Monosaccharide
Benzenoid
Oxane
Pyrrole
Heteroaromatic compound
Vinylogous ester
Secondary alcohol
Ketone
Acetal
Secondary aliphatic amine
Oxacycle
Azacycle
Organoheterocyclic compound
Secondary amine
Polyol
Amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Alcohol
Organic nitrogen compound
Organic oxygen compound
Primary alcohol
Carbonyl group
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
logP	0.47	ALOGPS
logP	0.47	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	12.21	ChemAxon
pKa (Strongest Basic)	8.89	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	153.5 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	133.48 m³·mol⁻¹	ChemAxon
Polarizability	54.85 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	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

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1-(5-ethenyl-4-{1h,2h,3h,4h,9h-pyrido[3,4-b]indol-1-ylmethyl}-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-yl)ethanone (NP0296810)

MOL for NP0296810 (1-(5-ethenyl-4-{1h,2h,3h,4h,9h-pyrido[3,4-b]indol-1-ylmethyl}-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-yl)ethanone)

3D MOL for NP0296810 (1-(5-ethenyl-4-{1h,2h,3h,4h,9h-pyrido[3,4-b]indol-1-ylmethyl}-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-yl)ethanone)

3D SDF for NP0296810 (1-(5-ethenyl-4-{1h,2h,3h,4h,9h-pyrido[3,4-b]indol-1-ylmethyl}-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-yl)ethanone)

3D-SDF for NP0296810 (1-(5-ethenyl-4-{1h,2h,3h,4h,9h-pyrido[3,4-b]indol-1-ylmethyl}-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-yl)ethanone)

PDB for NP0296810 (1-(5-ethenyl-4-{1h,2h,3h,4h,9h-pyrido[3,4-b]indol-1-ylmethyl}-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-yl)ethanone)

3D PDB for NP0296810 (1-(5-ethenyl-4-{1h,2h,3h,4h,9h-pyrido[3,4-b]indol-1-ylmethyl}-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-yl)ethanone)

SMILES for NP0296810 (1-(5-ethenyl-4-{1h,2h,3h,4h,9h-pyrido[3,4-b]indol-1-ylmethyl}-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-yl)ethanone)

INCHI for NP0296810 (1-(5-ethenyl-4-{1h,2h,3h,4h,9h-pyrido[3,4-b]indol-1-ylmethyl}-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-yl)ethanone)

Structure for NP0296810 (1-(5-ethenyl-4-{1h,2h,3h,4h,9h-pyrido[3,4-b]indol-1-ylmethyl}-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-yl)ethanone)

3D Structure for NP0296810 (1-(5-ethenyl-4-{1h,2h,3h,4h,9h-pyrido[3,4-b]indol-1-ylmethyl}-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-yl)ethanone)