NP-MRD: Showing NP-Card for Neoalangiside (NP0069332)

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Record Information

Version

2.0

Created at

2022-04-28 14:41:36 UTC

Updated at

2022-04-28 14:41:37 UTC

NP-MRD ID

NP0069332

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Neoalangiside

Description

(3S,4S,4aS,5aR)-4-ethenyl-6-hydroxy-7-methoxy-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. Neoalangiside is found in Alangium lamarckii. Based on a literature review very few articles have been published on (3S,4S,4aS,5aR)-4-ethenyl-6-hydroxy-7-methoxy-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


  Mrv1652304282216412D          

 36 40  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652304282216412D          

 36 40  0  0  1  0            999 V2000
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 30 33  1  1  0  0  0
 29 34  1  6  0  0  0
 28 35  1  1  0  0  0
 35 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0069332

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C2=C(CCN3[C@@H]2C[C@H]2[C@H](C=C)[C@H](O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)OC=C2C3=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C25H31NO10/c1-3-12-13-8-15-18-11(4-5-16(33-2)19(18)28)6-7-26(15)23(32)14(13)10-34-24(12)36-25-22(31)21(30)20(29)17(9-27)35-25/h3-5,10,12-13,15,17,20-22,24-25,27-31H,1,6-9H2,2H3/t12-,13-,15+,17+,20+,21-,22+,24-,25-/m0/s1

> <INCHI_KEY>
CAPTWSBFXVCIAY-ABPMVTQRSA-N

> <FORMULA>
C25H31NO10

> <MOLECULAR_WEIGHT>
505.52

> <EXACT_MASS>
505.194796202

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
51.70199956909335

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S,4S,4aS,5aR)-4-ethenyl-6-hydroxy-7-methoxy-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>
-0.21

> <JCHEM_LOGP>
-0.5051204956666661

> <ALOGPS_LOGS>
-2.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.207937583710669

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.57990403263438

> <JCHEM_PKA_STRONGEST_BASIC>
0.05389402842149971

> <JCHEM_POLAR_SURFACE_AREA>
158.38

> <JCHEM_REFRACTIVITY>
124.33099999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.47e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S,4S,4aS,5aR)-4-ethenyl-6-hydroxy-7-methoxy-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       9.399  -0.394   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       9.903   1.061   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       8.895   2.225   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.383   1.934   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.879   0.479   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.887  -0.685   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.383  -2.140   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.391  -3.304   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.366   0.188   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.358   1.352   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       4.862   2.807   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       6.375   3.098   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       6.879   4.553   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       3.854   3.971   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.342   3.680   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.838   2.225   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.846   1.061   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.342  -0.394   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.830  -0.685   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.179   0.479   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.326   1.934   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.326  -2.140   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -1.187  -2.431   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       3.350  -1.558   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      10.407  -1.558   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      11.919  -1.267   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      12.928  -2.431   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      14.440  -2.140   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      14.944  -0.685   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      13.936   0.479   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      12.424   0.188   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      11.415   1.352   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      14.440   1.934   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      16.456  -0.394   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      15.448  -3.304   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      16.960  -3.013   0.000  0.00  0.00           O+0
CONECT    1    2    6   25                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   12                                                  
CONECT    5    4    6    9                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    5   10                                                       
CONECT   10    9   11   17                                                  
CONECT   11   10   12   14                                                  
CONECT   12   11    4   13                                                  
CONECT   13   12                                                            
CONECT   14   11   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   21                                                  
CONECT   17   16   10   18                                                  
CONECT   18   17   19   24                                                  
CONECT   19   18   20   22                                                  
CONECT   20   19   21                                                       
CONECT   21   20   16                                                       
CONECT   22   19   23                                                       
CONECT   23   22                                                            
CONECT   24   18                                                            
CONECT   25    1   26                                                       
CONECT   26   25   27   31                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   35                                                  
CONECT   29   28   30   34                                                  
CONECT   30   29   31   33                                                  
CONECT   31   30   26   32                                                  
CONECT   32   31                                                            
CONECT   33   30                                                            
CONECT   34   29                                                            
CONECT   35   28   36                                                       
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₁NO₁₀

Average Mass

505.5200 Da

Monoisotopic Mass

505.19480 Da

IUPAC Name

(3S,4S,4aS,5aR)-4-ethenyl-6-hydroxy-7-methoxy-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,5aR)-4-ethenyl-6-hydroxy-7-methoxy-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

COC1=C(O)C2=C(CCN3[C@@H]2C[C@H]2[C@H](C=C)[C@H](O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)OC=C2C3=O)C=C1

InChI Identifier

InChI=1S/C25H31NO10/c1-3-12-13-8-15-18-11(4-5-16(33-2)19(18)28)6-7-26(15)23(32)14(13)10-34-24(12)36-25-22(31)21(30)20(29)17(9-27)35-25/h3-5,10,12-13,15,17,20-22,24-25,27-31H,1,6-9H2,2H3/t12-,13-,15+,17+,20+,21-,22+,24-,25-/m0/s1

InChI Key

CAPTWSBFXVCIAY-ABPMVTQRSA-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 lamarckii	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
Anisole
1-hydroxy-4-unsubstituted benzenoid
Piperidinone
Delta-lactam
Alkyl aryl ether
Benzenoid
Piperidine
Oxane
Monosaccharide
Vinylogous ester
Tertiary carboxylic acid amide
Secondary alcohol
Lactam
Carboxamide group
Oxacycle
Azacycle
Organoheterocyclic compound
Polyol
Ether
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	-0.21	ALOGPS
logP	-0.51	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	9.58	ChemAxon
pKa (Strongest Basic)	0.054	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	158.38 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	124.33 m³·mol⁻¹	ChemAxon
Polarizability	51.7 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

163103628

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Neoalangiside (NP0069332)

MOL for NP0069332 (Neoalangiside)

3D MOL for NP0069332 (Neoalangiside)

3D SDF for NP0069332 (Neoalangiside)

3D-SDF for NP0069332 (Neoalangiside)

PDB for NP0069332 (Neoalangiside)

3D PDB for NP0069332 (Neoalangiside)

SMILES for NP0069332 (Neoalangiside)

INCHI for NP0069332 (Neoalangiside)

Structure for NP0069332 (Neoalangiside)

3D Structure for NP0069332 (Neoalangiside)