NP-MRD: Showing NP-Card for 4-hydroxy-9,11,13,14-tetramethyl-8-oxa-4-azatricyclo[7.4.1.0²,⁷]tetradeca-2(7),5-dien-3-one (NP0196417)

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Record Information

Version

2.0

Created at

2022-09-04 14:30:17 UTC

Updated at

2022-09-04 14:30:17 UTC

NP-MRD ID

NP0196417

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-hydroxy-9,11,13,14-tetramethyl-8-oxa-4-azatricyclo[7.4.1.0²,⁷]tetradeca-2(7),5-dien-3-one

Description

4-Hydroxy-9,11,13,14-tetramethyl-8-oxa-4-azatricyclo[7.4.1.0²,⁷]Tetradeca-2(7),5-dien-3-one belongs to the class of organic compounds known as pyranopyridines. These are polycyclic aromatic compounds containing a pyran ring fused to a pyridine ring. 4-hydroxy-9,11,13,14-tetramethyl-8-oxa-4-azatricyclo[7.4.1.0²,⁷]tetradeca-2(7),5-dien-3-one is found in Hypocrella discoidea. Based on a literature review very few articles have been published on 4-hydroxy-9,11,13,14-tetramethyl-8-oxa-4-azatricyclo[7.4.1.0²,⁷]Tetradeca-2(7),5-dien-3-one.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309042216302D          

 20 22  0  0  0  0            999 V2000
   -0.8058    0.3858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0173    0.3301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2466   -0.4624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9316   -0.9222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7338   -1.7231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7518   -0.8341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3236   -0.2393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3792    0.5838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1199    0.9472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8049    0.4874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7493   -0.3357    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4343   -0.7955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0086   -0.6991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9529   -1.5222    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8928    1.2501    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0918    1.4479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0037    2.2682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3512    1.0845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1366    0.2244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3441   -0.0048    0.0000 C   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
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
  7 13  1  0  0  0  0
 13 14  2  0  0  0  0
  8 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
  2 18  1  0  0  0  0
 16 19  1  0  0  0  0
  6 19  1  0  0  0  0
 19 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0196417

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1C2C(C)CC(C)CC1(C)OC1=C2C(=O)N(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H23NO3/c1-9-7-10(2)13-11(3)16(4,8-9)20-12-5-6-17(19)15(18)14(12)13/h5-6,9-11,13,19H,7-8H2,1-4H3

> <INCHI_KEY>
ABYQDZGVWZQEIE-UHFFFAOYSA-N

> <FORMULA>
C16H23NO3

> <MOLECULAR_WEIGHT>
277.364

> <EXACT_MASS>
277.167793605

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
30.350267940390303

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-hydroxy-9,11,13,14-tetramethyl-8-oxa-4-azatricyclo[7.4.1.0^{2,7}]tetradeca-2(7),5-dien-3-one

> <JCHEM_LOGP>
2.520627234666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.547798137651197

> <JCHEM_PKA_STRONGEST_BASIC>
-4.805503793200422

> <JCHEM_POLAR_SURFACE_AREA>
49.769999999999996

> <JCHEM_REFRACTIVITY>
78.17710000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
4-hydroxy-9,11,13,14-tetramethyl-8-oxa-4-azatricyclo[7.4.1.0^{2,7}]tetradeca-2(7),5-dien-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.504   0.720   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.032   0.616   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.460  -0.863   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.739  -1.721   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.370  -3.217   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.270  -1.557   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.337  -0.447   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.441   1.090   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.824   1.768   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.103   0.910   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       6.999  -0.627   0.000  0.00  0.00           N+0
HETATM   12  O   UNK     0       8.277  -1.485   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       5.616  -1.305   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.512  -2.841   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       3.533   2.334   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.038   2.703   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.874   4.234   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.656   2.024   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.122   0.419   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.642  -0.009   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   18                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   19                                                  
CONECT    7    6    8   13                                                  
CONECT    8    7    9   15                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11    7   14                                                  
CONECT   14   13                                                            
CONECT   15    8   16                                                       
CONECT   16   15   17   18   19                                             
CONECT   17   16                                                            
CONECT   18   16    2                                                       
CONECT   19   16    6   20                                                  
CONECT   20   19                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₂₃NO₃

Average Mass

277.3640 Da

Monoisotopic Mass

277.16779 Da

IUPAC Name

4-hydroxy-9,11,13,14-tetramethyl-8-oxa-4-azatricyclo[7.4.1.0^{2,7}]tetradeca-2(7),5-dien-3-one

Traditional Name

4-hydroxy-9,11,13,14-tetramethyl-8-oxa-4-azatricyclo[7.4.1.0^{2,7}]tetradeca-2(7),5-dien-3-one

CAS Registry Number

Not Available

SMILES

CC1C2C(C)CC(C)CC1(C)OC1=C2C(=O)N(O)C=C1

InChI Identifier

InChI=1S/C16H23NO3/c1-9-7-10(2)13-11(3)16(4,8-9)20-12-5-6-17(19)15(18)14(12)13/h5-6,9-11,13,19H,7-8H2,1-4H3

InChI Key

ABYQDZGVWZQEIE-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Hypocrella discoidea	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyranopyridines. These are polycyclic aromatic compounds containing a pyran ring fused to a pyridine ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyranopyridines

Sub Class

Not Available

Direct Parent

Pyranopyridines

Alternative Parents

Substituents

Pyranopyridine
Pyridinone
Alkyl aryl ether
Pyridine
Heteroaromatic compound
Vinylogous ester
Lactam
Oxacycle
Azacycle
Ether
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen 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	2.52	ChemAxon
pKa (Strongest Acidic)	6.55	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	49.77 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	78.18 m³·mol⁻¹	ChemAxon
Polarizability	30.35 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	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

162814807

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-hydroxy-9,11,13,14-tetramethyl-8-oxa-4-azatricyclo[7.4.1.0²,⁷]tetradeca-2(7),5-dien-3-one (NP0196417)

MOL for NP0196417 (4-hydroxy-9,11,13,14-tetramethyl-8-oxa-4-azatricyclo[7.4.1.0²,⁷]tetradeca-2(7),5-dien-3-one)

3D MOL for NP0196417 (4-hydroxy-9,11,13,14-tetramethyl-8-oxa-4-azatricyclo[7.4.1.0²,⁷]tetradeca-2(7),5-dien-3-one)

3D SDF for NP0196417 (4-hydroxy-9,11,13,14-tetramethyl-8-oxa-4-azatricyclo[7.4.1.0²,⁷]tetradeca-2(7),5-dien-3-one)

3D-SDF for NP0196417 (4-hydroxy-9,11,13,14-tetramethyl-8-oxa-4-azatricyclo[7.4.1.0²,⁷]tetradeca-2(7),5-dien-3-one)

PDB for NP0196417 (4-hydroxy-9,11,13,14-tetramethyl-8-oxa-4-azatricyclo[7.4.1.0²,⁷]tetradeca-2(7),5-dien-3-one)

3D PDB for NP0196417 (4-hydroxy-9,11,13,14-tetramethyl-8-oxa-4-azatricyclo[7.4.1.0²,⁷]tetradeca-2(7),5-dien-3-one)

SMILES for NP0196417 (4-hydroxy-9,11,13,14-tetramethyl-8-oxa-4-azatricyclo[7.4.1.0²,⁷]tetradeca-2(7),5-dien-3-one)

INCHI for NP0196417 (4-hydroxy-9,11,13,14-tetramethyl-8-oxa-4-azatricyclo[7.4.1.0²,⁷]tetradeca-2(7),5-dien-3-one)

Structure for NP0196417 (4-hydroxy-9,11,13,14-tetramethyl-8-oxa-4-azatricyclo[7.4.1.0²,⁷]tetradeca-2(7),5-dien-3-one)

3D Structure for NP0196417 (4-hydroxy-9,11,13,14-tetramethyl-8-oxa-4-azatricyclo[7.4.1.0²,⁷]tetradeca-2(7),5-dien-3-one)