NP-MRD: Showing NP-Card for (3s,4r,4as,5ar)-4-ethenyl-8-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 (NP0145665)

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Record Information

Version

2.0

Created at

2022-09-02 00:54:44 UTC

Updated at

2022-09-02 00:54:44 UTC

NP-MRD ID

NP0145665

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3s,4r,4as,5ar)-4-ethenyl-8-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

Description

3-O-Demethyl-2-O-methylalangiside 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. (3s,4r,4as,5ar)-4-ethenyl-8-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 is found in Alangium salviifolium and Carapichea ipecacuanha. Based on a literature review very few articles have been published on 3-O-Demethyl-2-O-methylalangiside.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022202542D          

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     RDKit          3D

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M  END


  Mrv1652309022202542D          

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 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 29 32  1  0  0  0  0
 32 33  2  0  0  0  0
 25 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 22  1  1  0  0  0
 34 35  1  0  0  0  0
 36 35  1  1  0  0  0
 19 36  1  0  0  0  0
  3 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0145665

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=C2CCN3[C@H](C[C@H]4[C@@H](C=C)[C@H](O[C@@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O)OC=C4C3=O)C2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C25H31NO10/c1-3-12-14-7-16-13-8-18(33-2)17(28)6-11(13)4-5-26(16)23(32)15(14)10-34-24(12)36-25-22(31)21(30)20(29)19(9-27)35-25/h3,6,8,10,12,14,16,19-22,24-25,27-31H,1,4-5,7,9H2,2H3/t12-,14+,16-,19-,20-,21+,22-,24+,25+/m1/s1

> <INCHI_KEY>
UMQSGTQSQZGJOG-MDXCLUIBSA-N

> <FORMULA>
C25H31NO10

> <MOLECULAR_WEIGHT>
505.52

> <EXACT_MASS>
505.194796202

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
51.91153731590723

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S,4R,4aS,5aR)-4-ethenyl-8-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>
-0.12

> <JCHEM_LOGP>
-0.5051204956666661

> <ALOGPS_LOGS>
-2.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.20871680624362

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.845676493555713

> <JCHEM_PKA_STRONGEST_BASIC>
0.05430447600123378

> <JCHEM_POLAR_SURFACE_AREA>
158.38

> <JCHEM_REFRACTIVITY>
124.33099999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.35e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S,4R,4aS,5aR)-4-ethenyl-8-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                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      10.522  -4.741   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.010  -4.450   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.506  -2.995   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.994  -2.704   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       5.986  -3.868   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       4.473  -3.577   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       3.465  -4.741   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.953  -4.450   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.945  -5.614   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.567  -5.323   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.449  -2.995   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.063  -2.704   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.457  -1.831   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.953  -0.376   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       3.969  -2.122   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       4.978  -0.958   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       6.490  -1.249   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       7.498  -0.085   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.010  -0.376   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.018   0.788   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       9.514   2.243   0.000  0.00  0.00           O+0
HETATM   22  N   UNK     0      11.531   0.497   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0      12.539   1.661   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      14.051   1.370   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      14.555  -0.085   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      16.067  -0.376   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      16.571  -1.831   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      18.084  -2.122   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      15.563  -2.995   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      16.067  -4.450   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      15.059  -5.614   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      14.051  -2.704   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      13.547  -1.249   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      12.035  -0.958   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      11.027  -2.122   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       9.514  -1.831   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   36                                                  
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   36                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   34                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   33                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   32                                                  
CONECT   30   29   31                                                       
CONECT   31   30                                                            
CONECT   32   29   33                                                       
CONECT   33   32   25   34                                                  
CONECT   34   33   22   35                                                  
CONECT   35   34   36                                                       
CONECT   36   35   19    3                                                  
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,4R,4aS,5aR)-4-ethenyl-8-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,4R,4aS,5aR)-4-ethenyl-8-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)C=C2CCN3[C@H](C[C@H]4[C@@H](C=C)[C@H](O[C@@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O)OC=C4C3=O)C2=C1

InChI Identifier

InChI=1S/C25H31NO10/c1-3-12-14-7-16-13-8-18(33-2)17(28)6-11(13)4-5-26(16)23(32)15(14)10-34-24(12)36-25-22(31)21(30)20(29)19(9-27)35-25/h3,6,8,10,12,14,16,19-22,24-25,27-31H,1,4-5,7,9H2,2H3/t12-,14+,16-,19-,20-,21+,22-,24+,25+/m1/s1

InChI Key

UMQSGTQSQZGJOG-MDXCLUIBSA-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 salviifolium	LOTUS Database	35616633
Cephaelis ipecacuanha	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
Tetrahydroisoquinoline
Anisole
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Delta-lactam
Piperidinone
Monosaccharide
Oxane
Piperidine
Benzenoid
Vinylogous ester
Tertiary carboxylic acid amide
Secondary alcohol
Carboxamide group
Lactam
Polyol
Azacycle
Organoheterocyclic compound
Oxacycle
Acetal
Carboxylic acid derivative
Ether
Primary alcohol
Organic oxide
Hydrocarbon derivative
Organonitrogen compound
Carbonyl group
Alcohol
Organic nitrogen compound
Organopnictogen 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	-0.12	ALOGPS
logP	-0.51	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	9.85	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	51.91 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

C00051865

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

56589461

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3s,4r,4as,5ar)-4-ethenyl-8-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 (NP0145665)

MOL for NP0145665 ((3s,4r,4as,5ar)-4-ethenyl-8-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)

3D MOL for NP0145665 ((3s,4r,4as,5ar)-4-ethenyl-8-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)

3D SDF for NP0145665 ((3s,4r,4as,5ar)-4-ethenyl-8-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)

3D-SDF for NP0145665 ((3s,4r,4as,5ar)-4-ethenyl-8-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)

PDB for NP0145665 ((3s,4r,4as,5ar)-4-ethenyl-8-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)

3D PDB for NP0145665 ((3s,4r,4as,5ar)-4-ethenyl-8-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)

SMILES for NP0145665 ((3s,4r,4as,5ar)-4-ethenyl-8-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)

INCHI for NP0145665 ((3s,4r,4as,5ar)-4-ethenyl-8-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)

Structure for NP0145665 ((3s,4r,4as,5ar)-4-ethenyl-8-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)

3D Structure for NP0145665 ((3s,4r,4as,5ar)-4-ethenyl-8-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)