NP-MRD: Showing NP-Card for (12br)-3,4,10,11-tetramethoxy-7,8,12b,13-tetrahydro-5h-6-azatetraphen-12-ol (NP0219917)

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Record Information

Version

2.0

Created at

2022-09-05 21:03:58 UTC

Updated at

2022-09-05 21:03:58 UTC

NP-MRD ID

NP0219917

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(12br)-3,4,10,11-tetramethoxy-7,8,12b,13-tetrahydro-5h-6-azatetraphen-12-ol

Description

ZINC4963329 belongs to the class of organic compounds known as protoberberine alkaloids and derivatives. These are alkaloids with a structure based on a protoberberine moiety, which consists of a 5,6-dihydrodibenzene moiety fused to a quinolizinium and forming 5,6-Dihydrodibenzo(a,g)quinolizinium skeleton. (12br)-3,4,10,11-tetramethoxy-7,8,12b,13-tetrahydro-5h-6-azatetraphen-12-ol is found in Corydalis aurea, Corydalis micrantha and Corydalis pallida. Based on a literature review very few articles have been published on ZINC4963329.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309052223032D          

 27 30  0  0  1  0            999 V2000
   -0.4614   -2.2086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1913   -2.9882    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6188   -3.1441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8889   -3.9236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6990   -4.0796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2391   -3.4559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9690   -2.6764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5091   -2.0527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1589   -2.5204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8889   -1.7409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0787   -1.5850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0492   -3.6118    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5893   -2.9882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3994   -3.1441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9395   -2.5204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7497   -2.6764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0197   -3.4559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8298   -3.6118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3699   -2.9882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4796   -4.0796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7497   -4.8591    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2096   -5.4827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6695   -3.9236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1294   -4.5473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3193   -4.3914    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7792   -5.0150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9690   -4.8591    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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  3  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  6 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 20 23  2  0  0  0  0
 14 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 12 25  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
  5 27  1  0  0  0  0
M  END


  Mrv1652309052223032D          

 27 30  0  0  1  0            999 V2000
   -0.4614   -2.2086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1913   -2.9882    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6188   -3.1441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8889   -3.9236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6990   -4.0796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2391   -3.4559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9690   -2.6764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5091   -2.0527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1589   -2.5204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8889   -1.7409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0787   -1.5850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0492   -3.6118    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5893   -2.9882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3994   -3.1441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9395   -2.5204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7497   -2.6764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0197   -3.4559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8298   -3.6118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3699   -2.9882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4796   -4.0796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7497   -4.8591    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2096   -5.4827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6695   -3.9236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1294   -4.5473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3193   -4.3914    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7792   -5.0150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9690   -4.8591    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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  3  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  6 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 20 23  2  0  0  0  0
 14 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 12 25  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
  5 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0219917

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C2C[C@H]3N(CCC4=C3C(O)=C(OC)C(OC)=C4)CC2=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C21H25NO5/c1-24-16-6-5-12-9-15-18-13(10-17(25-2)21(27-4)19(18)23)7-8-22(15)11-14(12)20(16)26-3/h5-6,10,15,23H,7-9,11H2,1-4H3/t15-/m1/s1

> <INCHI_KEY>
GSPIMPLJQOCBFY-OAHLLOKOSA-N

> <FORMULA>
C21H25NO5

> <MOLECULAR_WEIGHT>
371.433

> <EXACT_MASS>
371.173272909

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
40.94794282890922

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(12bR)-3,4,10,11-tetramethoxy-7,8,12b,13-tetrahydro-5H-6-azatetraphen-12-ol

> <JCHEM_LOGP>
2.844409398666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.254781089786764

> <JCHEM_PKA_STRONGEST_BASIC>
5.885799905305719

> <JCHEM_POLAR_SURFACE_AREA>
60.39000000000001

> <JCHEM_REFRACTIVITY>
103.33639999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(12bR)-3,4,10,11-tetramethoxy-7,8,12b,13-tetrahydro-5H-6-azatetraphen-12-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.861  -4.123   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -0.357  -5.578   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.155  -5.869   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.659  -7.324   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.171  -7.615   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.180  -6.451   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.676  -4.996   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.684  -3.832   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.163  -4.705   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.659  -3.250   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.147  -2.959   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.692  -6.742   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.700  -5.578   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.212  -5.869   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.220  -4.705   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.733  -4.996   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.237  -6.451   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      12.749  -6.742   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      13.757  -5.578   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.229  -7.615   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      10.733  -9.070   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       9.725 -10.234   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.716  -7.324   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.708  -8.488   0.000  0.00  0.00           C+0
HETATM   25  N   UNK     0       6.196  -8.197   0.000  0.00  0.00           N+0
HETATM   26  C   UNK     0       5.188  -9.361   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.676  -9.070   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   27                                                  
CONECT    6    5    7   12                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7    3   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    6   13   25                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   23                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20   17   21   23                                                  
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23   20   14   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24   12   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26    5                                                       
MASTER        0    0    0    0    0    0    0    0   27    0   60    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₅NO₅

Average Mass

371.4330 Da

Monoisotopic Mass

371.17327 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC1=CC=C2C[C@H]3N(CCC4=C3C(O)=C(OC)C(OC)=C4)CC2=C1OC

InChI Identifier

InChI=1S/C21H25NO5/c1-24-16-6-5-12-9-15-18-13(10-17(25-2)21(27-4)19(18)23)7-8-22(15)11-14(12)20(16)26-3/h5-6,10,15,23H,7-9,11H2,1-4H3/t15-/m1/s1

InChI Key

GSPIMPLJQOCBFY-OAHLLOKOSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Corydalis aurea	LOTUS Database	35616633
Corydalis micrantha	LOTUS Database	35616633
Corydalis pallida	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as protoberberine alkaloids and derivatives. These are alkaloids with a structure based on a protoberberine moiety, which consists of a 5,6-dihydrodibenzene moiety fused to a quinolizinium and forming 5,6-Dihydrodibenzo(a,g)quinolizinium skeleton.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Protoberberine alkaloids and derivatives

Sub Class

Not Available

Direct Parent

Protoberberine alkaloids and derivatives

Alternative Parents

Substituents

Protoberberine skeleton
Tetrahydroprotoberberine skeleton
Tetrahydroisoquinoline
Anisole
Phenol ether
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
Phenol
Aralkylamine
Benzenoid
Tertiary amine
Tertiary aliphatic amine
Organoheterocyclic compound
Azacycle
Ether
Hydrocarbon derivative
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Amine
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	2.84	ChemAxon
pKa (Strongest Acidic)	9.25	ChemAxon
pKa (Strongest Basic)	5.89	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	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

12302407

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (12br)-3,4,10,11-tetramethoxy-7,8,12b,13-tetrahydro-5h-6-azatetraphen-12-ol (NP0219917)

MOL for NP0219917 ((12br)-3,4,10,11-tetramethoxy-7,8,12b,13-tetrahydro-5h-6-azatetraphen-12-ol)

3D MOL for NP0219917 ((12br)-3,4,10,11-tetramethoxy-7,8,12b,13-tetrahydro-5h-6-azatetraphen-12-ol)

3D SDF for NP0219917 ((12br)-3,4,10,11-tetramethoxy-7,8,12b,13-tetrahydro-5h-6-azatetraphen-12-ol)

3D-SDF for NP0219917 ((12br)-3,4,10,11-tetramethoxy-7,8,12b,13-tetrahydro-5h-6-azatetraphen-12-ol)

PDB for NP0219917 ((12br)-3,4,10,11-tetramethoxy-7,8,12b,13-tetrahydro-5h-6-azatetraphen-12-ol)

3D PDB for NP0219917 ((12br)-3,4,10,11-tetramethoxy-7,8,12b,13-tetrahydro-5h-6-azatetraphen-12-ol)

SMILES for NP0219917 ((12br)-3,4,10,11-tetramethoxy-7,8,12b,13-tetrahydro-5h-6-azatetraphen-12-ol)

INCHI for NP0219917 ((12br)-3,4,10,11-tetramethoxy-7,8,12b,13-tetrahydro-5h-6-azatetraphen-12-ol)

Structure for NP0219917 ((12br)-3,4,10,11-tetramethoxy-7,8,12b,13-tetrahydro-5h-6-azatetraphen-12-ol)

3D Structure for NP0219917 ((12br)-3,4,10,11-tetramethoxy-7,8,12b,13-tetrahydro-5h-6-azatetraphen-12-ol)