NP-MRD: Showing NP-Card for Demethylisoalangiside (NP0069154)

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Record Information

Version

2.0

Created at

2022-04-28 14:28:24 UTC

Updated at

2022-04-28 14:28:25 UTC

NP-MRD ID

NP0069154

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Demethylisoalangiside

Description

(3S,4S,4aS,5aS)-4-ethenyl-7,8-dihydroxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4,4a,5,5a,10,11,13-octahydro-2-oxa-12-azatetraphen-13-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. Demethylisoalangiside is found in Alangium salviifolium , Cephaelis acuminata, Carapichea ipecacuanha and Psychotria ipecacuanha . Based on a literature review very few articles have been published on (3S,4S,4aS,5aS)-4-ethenyl-7,8-dihydroxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4,4a,5,5a,10,11,13-octahydro-2-oxa-12-azatetraphen-13-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282216282D          

 35 39  0  0  1  0            999 V2000
    3.9550    1.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6850    0.2566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.0352   -0.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3052    0.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7651    1.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0352    1.9716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1154    0.7243    0.0000 O   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


  Mrv1652304282216282D          

 35 39  0  0  1  0            999 V2000
    3.9550    1.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6850    0.2566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 34 35  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0069154

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H](O[C@@H]2OC=C3[C@@H](C[C@@H]4N(CCC5=CC(O)=C(O)C=C45)C3=O)[C@@H]2C=C)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C24H29NO10/c1-2-11-13-6-15-12-7-17(28)16(27)5-10(12)3-4-25(15)22(32)14(13)9-33-23(11)35-24-21(31)20(30)19(29)18(8-26)34-24/h2,5,7,9,11,13,15,18-21,23-24,26-31H,1,3-4,6,8H2/t11-,13-,15-,18+,19+,20-,21+,23-,24-/m0/s1

> <INCHI_KEY>
ODZVWJRTEQQVCO-SGQQQZOWSA-N

> <FORMULA>
C24H29NO10

> <MOLECULAR_WEIGHT>
491.493

> <EXACT_MASS>
491.179146138

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
50.2037026984846

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S,4S,4aS,5aS)-4-ethenyl-7,8-dihydroxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4,4a,5,5a,10,11,13-octahydro-2-oxa-12-azatetraphen-13-one

> <ALOGPS_LOGP>
-0.30

> <JCHEM_LOGP>
-0.6510145516666658

> <ALOGPS_LOGS>
-2.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.068591289261803

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.190008034283913

> <JCHEM_PKA_STRONGEST_BASIC>
0.054293376819616435

> <JCHEM_POLAR_SURFACE_AREA>
169.38

> <JCHEM_REFRACTIVITY>
119.84869999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.35e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S,4S,4aS,5aS)-4-ethenyl-7,8-dihydroxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,4a,5,5a,10,11-hexahydro-3H-2-oxa-12-azatetraphen-13-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       7.383   1.934   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.879   0.479   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.887  -0.685   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.399  -0.394   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.903   1.061   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.895   2.225   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       9.399   3.680   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      11.415   1.352   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       7.383  -2.140   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.870  -2.431   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       4.862  -1.267   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       5.366   0.188   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.358   1.352   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.846   1.061   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.342  -0.394   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.830  -0.685   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -0.179   0.479   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.326   1.934   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.838   2.225   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.342   3.680   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.854   3.971   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -0.683   3.098   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -2.195   2.807   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.699   1.352   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -4.211   1.061   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -5.219   2.225   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -4.715   3.680   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -3.203   3.971   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -5.723   4.844   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -7.236   4.553   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -6.732   1.934   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -4.715  -0.394   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -1.691   0.188   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       3.350  -1.558   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       2.846  -3.013   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   12                                                  
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    5                                                            
CONECT    9    3   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   34                                                  
CONECT   12   11    2   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16   34                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   22                                                  
CONECT   19   18   14   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20                                                            
CONECT   22   18   23                                                       
CONECT   23   22   24   28                                                  
CONECT   24   23   25   33                                                  
CONECT   25   24   26   32                                                  
CONECT   26   25   27   31                                                  
CONECT   27   26   28   29                                                  
CONECT   28   27   23                                                       
CONECT   29   27   30                                                       
CONECT   30   29                                                            
CONECT   31   26                                                            
CONECT   32   25                                                            
CONECT   33   24                                                            
CONECT   34   15   11   35                                                  
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₂₉NO₁₀

Average Mass

491.4930 Da

Monoisotopic Mass

491.17915 Da

IUPAC Name

(3S,4S,4aS,5aS)-4-ethenyl-7,8-dihydroxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4,4a,5,5a,10,11,13-octahydro-2-oxa-12-azatetraphen-13-one

Traditional Name

(3S,4S,4aS,5aS)-4-ethenyl-7,8-dihydroxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,4a,5,5a,10,11-hexahydro-3H-2-oxa-12-azatetraphen-13-one

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@@H](O[C@@H]2OC=C3[C@@H](C[C@@H]4N(CCC5=CC(O)=C(O)C=C45)C3=O)[C@@H]2C=C)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C24H29NO10/c1-2-11-13-6-15-12-7-17(28)16(27)5-10(12)3-4-25(15)22(32)14(13)9-33-23(11)35-24-21(31)20(30)19(29)18(8-26)34-24/h2,5,7,9,11,13,15,18-21,23-24,26-31H,1,3-4,6,8H2/t11-,13-,15-,18+,19+,20-,21+,23-,24-/m0/s1

InChI Key

ODZVWJRTEQQVCO-SGQQQZOWSA-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
Alangium salviifolium	Plant	KNApSAcK
Cephaelis acuminata	Plant	KNApSAcK
Cephaelis ipecacuanha	LOTUS Database	35616633
Psychotria ipecacuanha	Plant	KNApSAcK

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
Tetrahydroisoquinoline
1-hydroxy-2-unsubstituted benzenoid
Piperidinone
Delta-lactam
Benzenoid
Piperidine
Oxane
Monosaccharide
Vinylogous ester
Tertiary carboxylic acid amide
Secondary alcohol
Lactam
Carboxamide group
Oxacycle
Azacycle
Organoheterocyclic compound
Polyol
Carboxylic acid derivative
Acetal
Organic nitrogen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organonitrogen compound
Carbonyl group
Alcohol
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	-0.3	ALOGPS
logP	-0.65	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	9.19	ChemAxon
pKa (Strongest Basic)	0.054	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	169.38 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	119.85 m³·mol⁻¹	ChemAxon
Polarizability	50.2 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

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

162942686

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Demethylisoalangiside (NP0069154)

MOL for NP0069154 (Demethylisoalangiside)

3D MOL for NP0069154 (Demethylisoalangiside)

3D SDF for NP0069154 (Demethylisoalangiside)

3D-SDF for NP0069154 (Demethylisoalangiside)

PDB for NP0069154 (Demethylisoalangiside)

3D PDB for NP0069154 (Demethylisoalangiside)

SMILES for NP0069154 (Demethylisoalangiside)

INCHI for NP0069154 (Demethylisoalangiside)

Structure for NP0069154 (Demethylisoalangiside)

3D Structure for NP0069154 (Demethylisoalangiside)