NP-MRD: Showing NP-Card for 2-(hydroxymethyl)-6-{10-oxa-2-azatricyclo[4.3.1.0³,⁹]deca-3(9),4-dien-8-yloxy}oxane-3,4,5-triol (NP0215696)

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Record Information

Version

2.0

Created at

2022-09-05 15:24:05 UTC

Updated at

2022-09-05 15:24:05 UTC

NP-MRD ID

NP0215696

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-(hydroxymethyl)-6-{10-oxa-2-azatricyclo[4.3.1.0³,⁹]deca-3(9),4-dien-8-yloxy}oxane-3,4,5-triol

Description

2-(Hydroxymethyl)-6-{10-oxa-2-azatricyclo[4.3.1.0³,⁹]Deca-3(9),4-dien-8-yloxy}oxane-3,4,5-triol 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. 2-(Hydroxymethyl)-6-{10-oxa-2-azatricyclo[4.3.1.0³,⁹]Deca-3(9),4-dien-8-yloxy}oxane-3,4,5-triol is a moderately basic compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004231523572D          

 22 25  0  0  0  0            999 V2000
    0.2734    4.4804    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0195    4.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0877    3.3061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8338    2.9540    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9019    2.1318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6480    1.7798    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7162    0.9576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4211    0.4928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2229   -0.3353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3723   -0.2114    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4483   -0.0090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9719   -0.6795    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8104   -0.5487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0910    0.3772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2942   -1.2691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1336   -1.1794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2240    1.6617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2921    0.8396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4779    2.0138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2001    1.5437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4097    2.8360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3364    3.1881    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  7 14  1  0  0  0  0
 11 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
  9 16  1  0  0  0  0
  5 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
  3 21  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0215696

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1OC(OC2CC3OC4NC(C=C3)=C24)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C14H19NO7/c16-4-8-10(17)11(18)12(19)14(22-8)21-7-3-5-1-2-6-9(7)13(15-6)20-5/h1-2,5,7-8,10-19H,3-4H2

> <INCHI_KEY>
SHXCRZBGPNESNC-UHFFFAOYSA-N

> <FORMULA>
C14H19NO7

> <MOLECULAR_WEIGHT>
313.306

> <EXACT_MASS>
313.116151956

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
29.753538255009254

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(hydroxymethyl)-6-{10-oxa-2-azatricyclo[4.3.1.0³,⁹]deca-3(9),4-dien-8-yloxy}oxane-3,4,5-triol

> <ALOGPS_LOGP>
-1.72

> <JCHEM_LOGP>
-2.5139150459999997

> <ALOGPS_LOGS>
-0.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.189099128969048

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.208837833516347

> <JCHEM_PKA_STRONGEST_BASIC>
2.5880017012479115

> <JCHEM_POLAR_SURFACE_AREA>
120.64000000000001

> <JCHEM_REFRACTIVITY>
73.48049999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.87e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(hydroxymethyl)-6-{10-oxa-2-azatricyclo[4.3.1.0³,⁹]deca-3(9),4-dien-8-yloxy}oxane-3,4,5-triol

> <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       0.510   8.363   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.903   7.706   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.030   6.171   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       3.423   5.514   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       3.550   3.979   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       4.943   3.322   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       5.070   1.787   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.386   0.920   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.016  -0.626   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.428  -0.395   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.704  -0.017   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       1.814  -1.268   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       3.379  -1.024   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.903   0.704   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.282  -2.369   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.849  -2.202   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.285   3.102   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.412   1.567   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       0.892   3.759   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -0.374   2.882   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       0.765   5.294   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -0.628   5.951   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   21                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   17                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   14                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   16                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13    7   11                                                  
CONECT   15   13   16                                                       
CONECT   16   15    9                                                       
CONECT   17    5   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19    3   22                                                  
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₄H₁₉NO₇

Average Mass

313.3060 Da

Monoisotopic Mass

313.11615 Da

IUPAC Name

2-(hydroxymethyl)-6-{10-oxa-2-azatricyclo[4.3.1.0³,⁹]deca-3(9),4-dien-8-yloxy}oxane-3,4,5-triol

Traditional Name

2-(hydroxymethyl)-6-{10-oxa-2-azatricyclo[4.3.1.0³,⁹]deca-3(9),4-dien-8-yloxy}oxane-3,4,5-triol

CAS Registry Number

Not Available

SMILES

OCC1OC(OC2CC3OC4NC(C=C3)=C24)C(O)C(O)C1O

InChI Identifier

InChI=1S/C14H19NO7/c16-4-8-10(17)11(18)12(19)14(22-8)21-7-3-5-1-2-6-9(7)13(15-6)20-5/h1-2,5,7-8,10-19H,3-4H2

InChI Key

SHXCRZBGPNESNC-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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

O-glycosyl compound
Meta-oxazepine
Monosaccharide
Oxane
Secondary alcohol
Acetal
Secondary aliphatic amine
Enamine
Oxacycle
Polyol
Azacycle
Secondary amine
Organoheterocyclic compound
Hydrocarbon derivative
Organonitrogen compound
Amine
Primary alcohol
Organic nitrogen compound
Alcohol
Organopnictogen 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	-1.7	ALOGPS
logP	-2.5	ChemAxon
logS	-0.66	ALOGPS
pKa (Strongest Acidic)	12.21	ChemAxon
pKa (Strongest Basic)	2.59	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	120.64 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	73.48 m³·mol⁻¹	ChemAxon
Polarizability	29.75 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-(hydroxymethyl)-6-{10-oxa-2-azatricyclo[4.3.1.0³,⁹]deca-3(9),4-dien-8-yloxy}oxane-3,4,5-triol (NP0215696)

MOL for NP0215696 (2-(hydroxymethyl)-6-{10-oxa-2-azatricyclo[4.3.1.0³,⁹]deca-3(9),4-dien-8-yloxy}oxane-3,4,5-triol)

3D MOL for NP0215696 (2-(hydroxymethyl)-6-{10-oxa-2-azatricyclo[4.3.1.0³,⁹]deca-3(9),4-dien-8-yloxy}oxane-3,4,5-triol)

3D SDF for NP0215696 (2-(hydroxymethyl)-6-{10-oxa-2-azatricyclo[4.3.1.0³,⁹]deca-3(9),4-dien-8-yloxy}oxane-3,4,5-triol)

3D-SDF for NP0215696 (2-(hydroxymethyl)-6-{10-oxa-2-azatricyclo[4.3.1.0³,⁹]deca-3(9),4-dien-8-yloxy}oxane-3,4,5-triol)

PDB for NP0215696 (2-(hydroxymethyl)-6-{10-oxa-2-azatricyclo[4.3.1.0³,⁹]deca-3(9),4-dien-8-yloxy}oxane-3,4,5-triol)

3D PDB for NP0215696 (2-(hydroxymethyl)-6-{10-oxa-2-azatricyclo[4.3.1.0³,⁹]deca-3(9),4-dien-8-yloxy}oxane-3,4,5-triol)

SMILES for NP0215696 (2-(hydroxymethyl)-6-{10-oxa-2-azatricyclo[4.3.1.0³,⁹]deca-3(9),4-dien-8-yloxy}oxane-3,4,5-triol)

INCHI for NP0215696 (2-(hydroxymethyl)-6-{10-oxa-2-azatricyclo[4.3.1.0³,⁹]deca-3(9),4-dien-8-yloxy}oxane-3,4,5-triol)

Structure for NP0215696 (2-(hydroxymethyl)-6-{10-oxa-2-azatricyclo[4.3.1.0³,⁹]deca-3(9),4-dien-8-yloxy}oxane-3,4,5-triol)

3D Structure for NP0215696 (2-(hydroxymethyl)-6-{10-oxa-2-azatricyclo[4.3.1.0³,⁹]deca-3(9),4-dien-8-yloxy}oxane-3,4,5-triol)