NP-MRD: Showing NP-Card for 4-ethenyl-7,8-dihydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,4a,5,5a,10,11-hexahydro-3h-2-oxa-12-azatetraphen-13-one (NP0229992)

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Record Information

Version

2.0

Created at

2022-09-06 10:17:33 UTC

Updated at

2022-09-06 10:17:33 UTC

NP-MRD ID

NP0229992

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-ethenyl-7,8-dihydroxy-3-{[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

4-Ethenyl-7,8-dihydroxy-3-{[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. 4-ethenyl-7,8-dihydroxy-3-{[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 kurzii, Alangium longiflorum, Alangium platanifolium, Alangium salviifolium and Carapichea ipecacuanha. 4-Ethenyl-7,8-dihydroxy-3-{[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 is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004231521042D          

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M  END

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  Mrv1533004231521042D          

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M  END
> <DATABASE_ID>
NP0229992

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1OC(OC2OC=C3C(CC4N(CCC5=CC(O)=C(O)C=C45)C3=O)C2C=C)C(O)C(O)C1O

> <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

> <INCHI_KEY>
ODZVWJRTEQQVCO-UHFFFAOYSA-N

> <FORMULA>
C24H29NO10

> <MOLECULAR_WEIGHT>
491.493

> <EXACT_MASS>
491.179146138

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
49.15559480819725

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-ethenyl-7,8-dihydroxy-3-{[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>
169.37999999999997

> <JCHEM_REFRACTIVITY>
119.8487

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.35e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-ethenyl-7,8-dihydroxy-3-{[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                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  O   UNK     0      15.952  -0.685   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      14.440  -0.394   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.936   1.061   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      12.424   1.352   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      11.919   2.807   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      10.407   3.098   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       9.399   1.934   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       9.903   0.479   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       8.895  -0.685   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.383  -0.394   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.879   1.061   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.366   1.352   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.358   0.188   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       4.862  -1.267   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       3.854  -2.431   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.342  -2.140   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.838  -0.685   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.326  -0.394   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.179   1.061   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -1.691   1.352   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       0.830   2.225   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.326   3.680   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       2.342   1.934   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.846   0.479   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.375  -1.558   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       6.879  -3.013   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       7.887   2.225   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.383   3.680   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.391   4.844   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      12.928   3.971   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      12.424   5.427   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      14.440   3.680   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      15.448   4.844   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      14.944   2.225   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      16.456   1.934   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   34                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   30                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   27                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   25                                                  
CONECT   11   10   12   27                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   24                                                  
CONECT   14   13   15   25                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   24                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   13   17                                                  
CONECT   25   14   10   26                                                  
CONECT   26   25                                                            
CONECT   27   11    7   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28                                                            
CONECT   30    5   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32    3   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

4-ethenyl-7,8-dihydroxy-3-{[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

4-ethenyl-7,8-dihydroxy-3-{[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

OCC1OC(OC2OC=C3C(CC4N(CCC5=CC(O)=C(O)C=C45)C3=O)C2C=C)C(O)C(O)C1O

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

InChI Key

ODZVWJRTEQQVCO-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 kurzii	LOTUS Database	35616633
Alangium longiflorum	LOTUS Database	35616633
Alangium platanifolium	LOTUS Database	35616633
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
1-hydroxy-2-unsubstituted benzenoid
Delta-lactam
Piperidinone
Monosaccharide
Oxane
Benzenoid
Piperidine
Vinylogous ester
Tertiary carboxylic acid amide
Carboxamide group
Lactam
Secondary alcohol
Acetal
Carboxylic acid derivative
Oxacycle
Azacycle
Organoheterocyclic compound
Polyol
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Carbonyl group
Organonitrogen compound
Organic nitrogen compound
Primary alcohol
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	49.16 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

4491372

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-7,8-dihydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,4a,5,5a,10,11-hexahydro-3h-2-oxa-12-azatetraphen-13-one (NP0229992)

MOL for NP0229992 (4-ethenyl-7,8-dihydroxy-3-{[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 NP0229992 (4-ethenyl-7,8-dihydroxy-3-{[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 NP0229992 (4-ethenyl-7,8-dihydroxy-3-{[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 NP0229992 (4-ethenyl-7,8-dihydroxy-3-{[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 NP0229992 (4-ethenyl-7,8-dihydroxy-3-{[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 NP0229992 (4-ethenyl-7,8-dihydroxy-3-{[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 NP0229992 (4-ethenyl-7,8-dihydroxy-3-{[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 NP0229992 (4-ethenyl-7,8-dihydroxy-3-{[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 NP0229992 (4-ethenyl-7,8-dihydroxy-3-{[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 NP0229992 (4-ethenyl-7,8-dihydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,4a,5,5a,10,11-hexahydro-3h-2-oxa-12-azatetraphen-13-one)