NP-MRD: Showing NP-Card for 2-hydroxy-n-[6-(hydroxymethyl)-8-methoxy-7,7-dimethyl-hexahydropyrano[3,2-d][1,3]dioxin-4-yl]-2-(2-methoxy-5,6-dimethyl-4-methylideneoxan-2-yl)ethanimidic acid (NP0161736)

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Record Information

Version

2.0

Created at

2022-09-02 19:59:20 UTC

Updated at

2022-09-02 19:59:21 UTC

NP-MRD ID

NP0161736

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-hydroxy-n-[6-(hydroxymethyl)-8-methoxy-7,7-dimethyl-hexahydropyrano[3,2-d][1,3]dioxin-4-yl]-2-(2-methoxy-5,6-dimethyl-4-methylideneoxan-2-yl)ethanimidic acid

Description

2-Hydroxy-N-[6-(hydroxymethyl)-8-methoxy-7,7-dimethyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-4-yl]-2-(2-methoxy-5,6-dimethyl-4-methylideneoxan-2-yl)ethanimidic acid belongs to the class of organic compounds known as pyranodioxins. These are polycyclic compounds containing a pyranodioxin moiety, which consists of a pyran ring fused to a dioxin ring. 2-hydroxy-n-[6-(hydroxymethyl)-8-methoxy-7,7-dimethyl-hexahydropyrano[3,2-d][1,3]dioxin-4-yl]-2-(2-methoxy-5,6-dimethyl-4-methylideneoxan-2-yl)ethanimidic acid is found in Theonella swinhoei. 2-Hydroxy-N-[6-(hydroxymethyl)-8-methoxy-7,7-dimethyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-4-yl]-2-(2-methoxy-5,6-dimethyl-4-methylideneoxan-2-yl)ethanimidic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004151518332D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004151518332D          

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M  END
> <DATABASE_ID>
NP0161736

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1C2OCOC(NC(=O)C(O)C3(CC(=C)C(C)C(C)O3)OC)C2OC(CO)C1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C22H37NO9/c1-11-8-22(28-7,32-13(3)12(11)2)17(25)19(26)23-20-16-15(29-10-30-20)18(27-6)21(4,5)14(9-24)31-16/h12-18,20,24-25H,1,8-10H2,2-7H3,(H,23,26)

> <INCHI_KEY>
OBDAALQFQJRDKI-UHFFFAOYSA-N

> <FORMULA>
C22H37NO9

> <MOLECULAR_WEIGHT>
459.536

> <EXACT_MASS>
459.246831775

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
48.57992137927626

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-hydroxy-N-[6-(hydroxymethyl)-8-methoxy-7,7-dimethyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-4-yl]-2-(2-methoxy-5,6-dimethyl-4-methylideneoxan-2-yl)acetamide

> <ALOGPS_LOGP>
0.87

> <JCHEM_LOGP>
0.8825440469999994

> <ALOGPS_LOGS>
-2.08

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.039413596321692

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.093964759249031

> <JCHEM_PKA_STRONGEST_BASIC>
-2.949900199081404

> <JCHEM_POLAR_SURFACE_AREA>
124.94000000000001

> <JCHEM_REFRACTIVITY>
111.59209999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.82e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-hydroxy-N-[6-(hydroxymethyl)-8-methoxy-7,7-dimethyl-hexahydropyrano[3,2-d][1,3]dioxin-4-yl]-2-(2-methoxy-5,6-dimethyl-4-methylideneoxan-2-yl)acetamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-APR-15         0                                  
HETATM    1  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       5.335  -4.620   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       8.002  -4.620   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.519  -7.967   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.045  -9.415   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.562  -9.682   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.055 -10.594   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.582 -12.041   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.539 -10.327   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.549 -11.507   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       7.012  -8.880   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       8.529  -6.253   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      10.045  -5.985   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.205  -0.716   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.518   0.536   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   30                                                  
CONECT    4    3    5   25                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   25                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   22   23                                             
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   14                                                       
CONECT   23   14   24                                                       
CONECT   24   23                                                            
CONECT   25    8    4   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   30                                                  
CONECT   28   27   29                                                       
CONECT   29   28                                                            
CONECT   30   27    3   31   32                                             
CONECT   31   30                                                            
CONECT   32   30                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   68    0
END

View in JSmol

Synonyms

Value	Source
2-Hydroxy-N-[6-(hydroxymethyl)-8-methoxy-7,7-dimethyl-hexahydro-2H-pyrano[3,2-D][1,3]dioxin-4-yl]-2-(2-methoxy-5,6-dimethyl-4-methylideneoxan-2-yl)ethanimidate	Generator

Chemical Formula

C₂₂H₃₇NO₉

Average Mass

459.5360 Da

Monoisotopic Mass

459.24683 Da

IUPAC Name

2-hydroxy-N-[6-(hydroxymethyl)-8-methoxy-7,7-dimethyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-4-yl]-2-(2-methoxy-5,6-dimethyl-4-methylideneoxan-2-yl)acetamide

Traditional Name

2-hydroxy-N-[6-(hydroxymethyl)-8-methoxy-7,7-dimethyl-hexahydropyrano[3,2-d][1,3]dioxin-4-yl]-2-(2-methoxy-5,6-dimethyl-4-methylideneoxan-2-yl)acetamide

CAS Registry Number

Not Available

SMILES

COC1C2OCOC(NC(=O)C(O)C3(CC(=C)C(C)C(C)O3)OC)C2OC(CO)C1(C)C

InChI Identifier

InChI=1S/C22H37NO9/c1-11-8-22(28-7,32-13(3)12(11)2)17(25)19(26)23-20-16-15(29-10-30-20)18(27-6)21(4,5)14(9-24)31-16/h12-18,20,24-25H,1,8-10H2,2-7H3,(H,23,26)

InChI Key

OBDAALQFQJRDKI-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
Theonella swinhoei	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyranodioxins. These are polycyclic compounds containing a pyranodioxin moiety, which consists of a pyran ring fused to a dioxin ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyranodioxins

Sub Class

Not Available

Direct Parent

Pyranodioxins

Alternative Parents

Substituents

Pyranodioxin
Ketal
Meta-dioxane
Monosaccharide
Oxane
Secondary alcohol
Acetal
Carboximidic acid
Carboximidic acid derivative
Dialkyl ether
Ether
Oxacycle
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Organopnictogen compound
Primary alcohol
Hydrocarbon derivative
Alcohol
Organic nitrogen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	0.87	ALOGPS
logP	0.88	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	11.09	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	124.94 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	111.59 m³·mol⁻¹	ChemAxon
Polarizability	48.58 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

74382354

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-hydroxy-n-[6-(hydroxymethyl)-8-methoxy-7,7-dimethyl-hexahydropyrano[3,2-d][1,3]dioxin-4-yl]-2-(2-methoxy-5,6-dimethyl-4-methylideneoxan-2-yl)ethanimidic acid (NP0161736)

MOL for NP0161736 (2-hydroxy-n-[6-(hydroxymethyl)-8-methoxy-7,7-dimethyl-hexahydropyrano[3,2-d][1,3]dioxin-4-yl]-2-(2-methoxy-5,6-dimethyl-4-methylideneoxan-2-yl)ethanimidic acid)

3D MOL for NP0161736 (2-hydroxy-n-[6-(hydroxymethyl)-8-methoxy-7,7-dimethyl-hexahydropyrano[3,2-d][1,3]dioxin-4-yl]-2-(2-methoxy-5,6-dimethyl-4-methylideneoxan-2-yl)ethanimidic acid)

3D SDF for NP0161736 (2-hydroxy-n-[6-(hydroxymethyl)-8-methoxy-7,7-dimethyl-hexahydropyrano[3,2-d][1,3]dioxin-4-yl]-2-(2-methoxy-5,6-dimethyl-4-methylideneoxan-2-yl)ethanimidic acid)

3D-SDF for NP0161736 (2-hydroxy-n-[6-(hydroxymethyl)-8-methoxy-7,7-dimethyl-hexahydropyrano[3,2-d][1,3]dioxin-4-yl]-2-(2-methoxy-5,6-dimethyl-4-methylideneoxan-2-yl)ethanimidic acid)

PDB for NP0161736 (2-hydroxy-n-[6-(hydroxymethyl)-8-methoxy-7,7-dimethyl-hexahydropyrano[3,2-d][1,3]dioxin-4-yl]-2-(2-methoxy-5,6-dimethyl-4-methylideneoxan-2-yl)ethanimidic acid)

3D PDB for NP0161736 (2-hydroxy-n-[6-(hydroxymethyl)-8-methoxy-7,7-dimethyl-hexahydropyrano[3,2-d][1,3]dioxin-4-yl]-2-(2-methoxy-5,6-dimethyl-4-methylideneoxan-2-yl)ethanimidic acid)

SMILES for NP0161736 (2-hydroxy-n-[6-(hydroxymethyl)-8-methoxy-7,7-dimethyl-hexahydropyrano[3,2-d][1,3]dioxin-4-yl]-2-(2-methoxy-5,6-dimethyl-4-methylideneoxan-2-yl)ethanimidic acid)

INCHI for NP0161736 (2-hydroxy-n-[6-(hydroxymethyl)-8-methoxy-7,7-dimethyl-hexahydropyrano[3,2-d][1,3]dioxin-4-yl]-2-(2-methoxy-5,6-dimethyl-4-methylideneoxan-2-yl)ethanimidic acid)

Structure for NP0161736 (2-hydroxy-n-[6-(hydroxymethyl)-8-methoxy-7,7-dimethyl-hexahydropyrano[3,2-d][1,3]dioxin-4-yl]-2-(2-methoxy-5,6-dimethyl-4-methylideneoxan-2-yl)ethanimidic acid)

3D Structure for NP0161736 (2-hydroxy-n-[6-(hydroxymethyl)-8-methoxy-7,7-dimethyl-hexahydropyrano[3,2-d][1,3]dioxin-4-yl]-2-(2-methoxy-5,6-dimethyl-4-methylideneoxan-2-yl)ethanimidic acid)