NP-MRD: Showing NP-Card for 4'-ethenyl-2-hydroxy-3'-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4',4'a,5',5'a,7',8'-hexahydro-3'h-spiro[indole-3,6'-pyrano[3,4-f]indolizin]-10'-one (NP0287981)

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Record Information

Version

2.0

Created at

2022-09-09 17:29:39 UTC

Updated at

2022-09-09 17:29:39 UTC

NP-MRD ID

NP0287981

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4'-ethenyl-2-hydroxy-3'-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4',4'a,5',5'a,7',8'-hexahydro-3'h-spiro[indole-3,6'-pyrano[3,4-f]indolizin]-10'-one

Description

4'-Ethenyl-2-hydroxy-3'-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3',4',4'a,5',5'a,7',8',10'-octahydrospiro[indole-3,6'-pyrano[3,4-f]indolizine]-10'-one belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond. 4'-ethenyl-2-hydroxy-3'-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4',4'a,5',5'a,7',8'-hexahydro-3'h-spiro[indole-3,6'-pyrano[3,4-f]indolizin]-10'-one is found in Alangium javanicum. 4'-Ethenyl-2-hydroxy-3'-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3',4',4'a,5',5'a,7',8',10'-octahydrospiro[indole-3,6'-pyrano[3,4-f]indolizine]-10'-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004191521022D          

 37 42  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004191521022D          

 37 42  0  0  0  0            999 V2000
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 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 13 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 17 26  1  0  0  0  0
 21 26  1  0  0  0  0
 14 27  1  0  0  0  0
 10 27  1  0  0  0  0
 27 28  2  0  0  0  0
 11 29  1  0  0  0  0
  7 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
  5 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
  3 36  1  0  0  0  0
 36 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0287981

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1OC(OC2OC=C3C(CC4N(CCC44C(=O)NC5=CC=CC=C45)C3=O)C2C=C)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C26H30N2O9/c1-2-12-13-9-18-26(15-5-3-4-6-16(15)27-25(26)34)7-8-28(18)22(33)14(13)11-35-23(12)37-24-21(32)20(31)19(30)17(10-29)36-24/h2-6,11-13,17-21,23-24,29-32H,1,7-10H2,(H,27,34)

> <INCHI_KEY>
UXDQUMNIWFOBFX-UHFFFAOYSA-N

> <FORMULA>
C26H30N2O9

> <MOLECULAR_WEIGHT>
514.531

> <EXACT_MASS>
514.195130554

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
51.56640054921559

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4'-ethenyl-3'-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1,2,3',4',4'a,5',5'a,7',8',10'-decahydrospiro[indole-3,6'-pyrano[3,4-f]indolizine]-2,10'-dione

> <ALOGPS_LOGP>
0.35

> <JCHEM_LOGP>
-0.8729217356666661

> <ALOGPS_LOGS>
-2.00

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.925291201991143

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.161490525155251

> <JCHEM_PKA_STRONGEST_BASIC>
0.12169901315472986

> <JCHEM_POLAR_SURFACE_AREA>
158.02

> <JCHEM_REFRACTIVITY>
128.40690000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.11e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4'-ethenyl-3'-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4',4'a,5',5'a,7',8'-hexahydro-1H,3'H-spiro[indole-3,6'-pyrano[3,4-f]indolizine]-2,10'-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  O   UNK     0      16.550  -2.241   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      15.022  -2.054   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      14.420  -0.636   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      12.892  -0.448   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      12.290   0.969   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      10.761   1.157   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       9.835  -0.073   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      10.436  -1.491   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       9.510  -2.720   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.981  -2.533   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.379  -1.115   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.851  -0.927   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.924  -2.157   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       5.526  -3.575   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       4.363  -4.585   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.043  -3.792   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.390  -2.292   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.856  -2.426   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.063  -3.746   0.000  0.00  0.00           O+0
HETATM   20  N   UNK     0       1.254  -1.008   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0       2.416   0.002   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.443   1.542   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.790   2.289   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.110   1.495   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.083  -0.044   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.736  -0.791   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.054  -3.763   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       7.656  -5.180   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       8.306   0.115   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.704   1.532   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.631   2.762   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      13.217   2.199   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      12.615   3.617   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      14.745   2.011   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      15.672   3.241   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      15.347   0.594   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      16.876   0.406   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   36                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   32                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   29                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   27                                                  
CONECT   11   10   12   29                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   17                                                  
CONECT   14   13   15   27                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   13   18   26                                             
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   17   21                                                  
CONECT   27   14   10   28                                                  
CONECT   28   27                                                            
CONECT   29   11    7   30                                                  
CONECT   30   29   31                                                       
CONECT   31   30                                                            
CONECT   32    5   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34    3   37                                                  
CONECT   37   36                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   84    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₀N₂O₉

Average Mass

514.5310 Da

Monoisotopic Mass

514.19513 Da

IUPAC Name

4'-ethenyl-3'-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1,2,3',4',4'a,5',5'a,7',8',10'-decahydrospiro[indole-3,6'-pyrano[3,4-f]indolizine]-2,10'-dione

Traditional Name

4'-ethenyl-3'-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4',4'a,5',5'a,7',8'-hexahydro-1H,3'H-spiro[indole-3,6'-pyrano[3,4-f]indolizine]-2,10'-dione

CAS Registry Number

Not Available

SMILES

OCC1OC(OC2OC=C3C(CC4N(CCC44C(=O)NC5=CC=CC=C45)C3=O)C2C=C)C(O)C(O)C1O

InChI Identifier

InChI=1S/C26H30N2O9/c1-2-12-13-9-18-26(15-5-3-4-6-16(15)27-25(26)34)7-8-28(18)22(33)14(13)11-35-23(12)37-24-21(32)20(31)19(30)17(10-29)36-24/h2-6,11-13,17-21,23-24,29-32H,1,7-10H2,(H,27,34)

InChI Key

UXDQUMNIWFOBFX-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
Alangium javanicum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

O-glycosyl compounds

Alternative Parents

Substituents

Hexose monosaccharide
O-glycosyl compound
3-alkylindole
Indole or derivatives
Indolizidine
Piperidinone
Delta-lactam
Piperidine
Monosaccharide
Benzenoid
Oxane
Pyrrolidine
Tertiary carboxylic acid amide
Vinylogous ester
Cyclic carboximidic acid
Lactam
Carboxamide group
Secondary alcohol
Acetal
Carboxylic acid derivative
Oxacycle
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Polyol
Hydrocarbon derivative
Carbonyl group
Organic nitrogen compound
Alcohol
Organonitrogen compound
Organopnictogen compound
Primary alcohol
Organic oxide
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	0.35	ALOGPS
logP	-0.87	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	12.16	ChemAxon
pKa (Strongest Basic)	0.12	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	158.02 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	128.41 m³·mol⁻¹	ChemAxon
Polarizability	51.57 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	No	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

73068172

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4'-ethenyl-2-hydroxy-3'-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4',4'a,5',5'a,7',8'-hexahydro-3'h-spiro[indole-3,6'-pyrano[3,4-f]indolizin]-10'-one (NP0287981)

MOL for NP0287981 (4'-ethenyl-2-hydroxy-3'-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4',4'a,5',5'a,7',8'-hexahydro-3'h-spiro[indole-3,6'-pyrano[3,4-f]indolizin]-10'-one)

3D MOL for NP0287981 (4'-ethenyl-2-hydroxy-3'-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4',4'a,5',5'a,7',8'-hexahydro-3'h-spiro[indole-3,6'-pyrano[3,4-f]indolizin]-10'-one)

3D SDF for NP0287981 (4'-ethenyl-2-hydroxy-3'-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4',4'a,5',5'a,7',8'-hexahydro-3'h-spiro[indole-3,6'-pyrano[3,4-f]indolizin]-10'-one)

3D-SDF for NP0287981 (4'-ethenyl-2-hydroxy-3'-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4',4'a,5',5'a,7',8'-hexahydro-3'h-spiro[indole-3,6'-pyrano[3,4-f]indolizin]-10'-one)

PDB for NP0287981 (4'-ethenyl-2-hydroxy-3'-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4',4'a,5',5'a,7',8'-hexahydro-3'h-spiro[indole-3,6'-pyrano[3,4-f]indolizin]-10'-one)

3D PDB for NP0287981 (4'-ethenyl-2-hydroxy-3'-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4',4'a,5',5'a,7',8'-hexahydro-3'h-spiro[indole-3,6'-pyrano[3,4-f]indolizin]-10'-one)

SMILES for NP0287981 (4'-ethenyl-2-hydroxy-3'-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4',4'a,5',5'a,7',8'-hexahydro-3'h-spiro[indole-3,6'-pyrano[3,4-f]indolizin]-10'-one)

INCHI for NP0287981 (4'-ethenyl-2-hydroxy-3'-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4',4'a,5',5'a,7',8'-hexahydro-3'h-spiro[indole-3,6'-pyrano[3,4-f]indolizin]-10'-one)

Structure for NP0287981 (4'-ethenyl-2-hydroxy-3'-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4',4'a,5',5'a,7',8'-hexahydro-3'h-spiro[indole-3,6'-pyrano[3,4-f]indolizin]-10'-one)

3D Structure for NP0287981 (4'-ethenyl-2-hydroxy-3'-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4',4'a,5',5'a,7',8'-hexahydro-3'h-spiro[indole-3,6'-pyrano[3,4-f]indolizin]-10'-one)