NP-MRD: Showing NP-Card for 7,8-dimethoxy-2-azatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-1(16),2,4,6,8,10,12,14-octaen-11-ol (NP0305935)

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Record Information

Version

2.0

Created at

2022-09-10 22:06:50 UTC

Updated at

2022-09-10 22:06:50 UTC

NP-MRD ID

NP0305935

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7,8-dimethoxy-2-azatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-1(16),2,4,6,8,10,12,14-octaen-11-ol

Description

7,8-Dimethoxy-2-azatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]Hexadeca-1,3,5,7,9(16),10(15),11,13-octaen-11-ol belongs to the class of organic compounds known as isoquinolines and derivatives. These are aromatic polycyclic compounds containing an isoquinoline moiety, which consists of a benzene ring fused to a pyridine ring and forming benzo[c]pyridine. 7,8-dimethoxy-2-azatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-1(16),2,4,6,8,10,12,14-octaen-11-ol is found in Acorus calamus. 7,8-Dimethoxy-2-azatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]Hexadeca-1,3,5,7,9(16),10(15),11,13-octaen-11-ol is a very strong basic compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004261513022D          

 21 24  0  0  0  0            999 V2000
   -0.3059    0.1115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5010   -0.0600    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0531    0.5531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7981    1.3377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3502    1.9508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3172    2.9353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9847    3.4202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7383    3.0847    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8246    2.2642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4920    1.7793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2990    1.9508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8510    1.3377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5961    0.5531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7891    0.3816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5342   -0.4031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2371    0.9946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4121    0.9946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8600    0.3816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1150   -0.4031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5629   -1.0162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1571    1.7793    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  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 10 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
  3 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 17 21  2  0  0  0  0
  5 21  1  0  0  0  0
  9 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0305935

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(OC)C2=C3C(=NC=CC3=C1)C1=CC=CC(O)=C21

> <INCHI_IDENTIFIER>
InChI=1S/C17H13NO3/c1-20-12-8-9-6-7-18-16-10-4-3-5-11(19)14(10)15(13(9)16)17(12)21-2/h3-8,19H,1-2H3

> <INCHI_KEY>
HDOMTHXTTHGHAB-UHFFFAOYSA-N

> <FORMULA>
C17H13NO3

> <MOLECULAR_WEIGHT>
279.295

> <EXACT_MASS>
279.089543283

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
29.367673139545012

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7,8-dimethoxy-2-azatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-1,3,5,7,9(16),10,12,14-octaen-11-ol

> <ALOGPS_LOGP>
3.46

> <JCHEM_LOGP>
2.8331975263333327

> <ALOGPS_LOGS>
-3.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.034334433434491

> <JCHEM_PKA_STRONGEST_BASIC>
5.296016656956355

> <JCHEM_POLAR_SURFACE_AREA>
51.58

> <JCHEM_REFRACTIVITY>
79.10099999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.98e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7,8-dimethoxy-2-azatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-1,3,5,7,9(16),10,12,14-octaen-11-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-15         0                                  
HETATM    1  C   UNK     0      -0.571   0.208   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.935  -0.112   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.966   1.032   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.490   2.497   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.520   3.641   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.459   5.479   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.705   6.384   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       5.112   5.758   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       5.273   4.226   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.518   3.321   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.025   3.641   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.055   2.497   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.579   1.032   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.073   0.712   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       6.597  -0.752   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       6.043   1.857   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.503   1.857   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.472   0.712   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.948  -0.752   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.918  -1.897   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.027   3.321   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   18                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   21                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   21                                                  
CONECT   10    9   11   16                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   10   17                                                  
CONECT   17   16   18   21                                                  
CONECT   18   17    3   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   17    5    9                                                  
MASTER        0    0    0    0    0    0    0    0   21    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₁₃NO₃

Average Mass

279.2950 Da

Monoisotopic Mass

279.08954 Da

IUPAC Name

7,8-dimethoxy-2-azatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-1,3,5,7,9(16),10,12,14-octaen-11-ol

Traditional Name

7,8-dimethoxy-2-azatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-1,3,5,7,9(16),10,12,14-octaen-11-ol

CAS Registry Number

Not Available

SMILES

COC1=C(OC)C2=C3C(=NC=CC3=C1)C1=CC=CC(O)=C21

InChI Identifier

InChI=1S/C17H13NO3/c1-20-12-8-9-6-7-18-16-10-4-3-5-11(19)14(10)15(13(9)16)17(12)21-2/h3-8,19H,1-2H3

InChI Key

HDOMTHXTTHGHAB-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Acorus calamus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoquinolines and derivatives. These are aromatic polycyclic compounds containing an isoquinoline moiety, which consists of a benzene ring fused to a pyridine ring and forming benzo[c]pyridine.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Isoquinolines and derivatives

Sub Class

Not Available

Direct Parent

Isoquinolines and derivatives

Alternative Parents

Substituents

Isoquinoline
Anisole
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Pyridine
Benzenoid
Heteroaromatic compound
Azacycle
Ether
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Hydrocarbon derivative
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	3.46	ALOGPS
logP	2.83	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	9.03	ChemAxon
pKa (Strongest Basic)	5.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	51.58 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	79.1 m³·mol⁻¹	ChemAxon
Polarizability	29.37 Å³	ChemAxon
Number of Rings	4	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

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 7,8-dimethoxy-2-azatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-1(16),2,4,6,8,10,12,14-octaen-11-ol (NP0305935)

MOL for NP0305935 (7,8-dimethoxy-2-azatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-1(16),2,4,6,8,10,12,14-octaen-11-ol)

3D MOL for NP0305935 (7,8-dimethoxy-2-azatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-1(16),2,4,6,8,10,12,14-octaen-11-ol)

3D SDF for NP0305935 (7,8-dimethoxy-2-azatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-1(16),2,4,6,8,10,12,14-octaen-11-ol)

3D-SDF for NP0305935 (7,8-dimethoxy-2-azatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-1(16),2,4,6,8,10,12,14-octaen-11-ol)

PDB for NP0305935 (7,8-dimethoxy-2-azatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-1(16),2,4,6,8,10,12,14-octaen-11-ol)

3D PDB for NP0305935 (7,8-dimethoxy-2-azatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-1(16),2,4,6,8,10,12,14-octaen-11-ol)

SMILES for NP0305935 (7,8-dimethoxy-2-azatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-1(16),2,4,6,8,10,12,14-octaen-11-ol)

INCHI for NP0305935 (7,8-dimethoxy-2-azatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-1(16),2,4,6,8,10,12,14-octaen-11-ol)

Structure for NP0305935 (7,8-dimethoxy-2-azatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-1(16),2,4,6,8,10,12,14-octaen-11-ol)

3D Structure for NP0305935 (7,8-dimethoxy-2-azatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-1(16),2,4,6,8,10,12,14-octaen-11-ol)