NP-MRD: Showing NP-Card for 17-hydroxy-16-methoxy-5,7-dioxa-13λ⁵-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁵,²⁰]henicosa-1(13),2,4(8),9,14,16,18,20-octaen-13-ylium (NP0248032)

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Record Information

Version

2.0

Created at

2022-09-07 10:07:04 UTC

Updated at

2022-09-07 10:07:05 UTC

NP-MRD ID

NP0248032

Secondary Accession Numbers

None

Natural Product Identification

Common Name

17-hydroxy-16-methoxy-5,7-dioxa-13λ⁵-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁵,²⁰]henicosa-1(13),2,4(8),9,14,16,18,20-octaen-13-ylium

Description

Thalifendine 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. 17-hydroxy-16-methoxy-5,7-dioxa-13λ⁵-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁵,²⁰]henicosa-1(13),2,4(8),9,14,16,18,20-octaen-13-ylium is found in Arcangelisia flava, Berberis darwinii, Coptis japonica, Coptis quinquefolia, Fibraurea tinctoria, Glaucium arabicum, Nandina domestica, Papaver dubium, Thalictrum alpinum, Thalictrum cultratum, Thalictrum dioicum, Thalictrum fendleri, Thalictrum foliolosum, Thalictrum javanicum, Thalictrum lankesteri and Thalictrum minus. Thalifendine is possibly neutral.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652310111708352D          

 24 28  0  0  0  0            999 V2000
    2.6587    0.6289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6884   -1.5457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8635   -1.5331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2066    1.2743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3817    1.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9366   -0.8501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4331    0.5410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5864   -0.8752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1335    0.5912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7127   -1.1851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1117   -0.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6082    0.5536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1849   -0.1545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7101   -0.1169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3600   -0.1420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4619   -0.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8347   -0.1796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4113   -0.8877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8852   -0.1043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9584    0.5787    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6370   -0.7999    0.0000 O   0  3  0  0  0  0  0  0  0  0  0  0
    3.4837    0.6163    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6389   -0.3634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9540   -1.5092    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  5  4  1  0  0  0  0
 11  2  1  0  0  0  0
 11  6  2  0  0  0  0
 12  4  1  0  0  0  0
 12  7  2  0  0  0  0
 13  8  2  0  0  0  0
 13 12  1  0  0  0  0
 14  9  1  0  0  0  0
 14 11  1  0  0  0  0
 15  6  1  0  0  0  0
 15 13  1  0  0  0  0
 16  3  1  0  0  0  0
 17  7  1  0  0  0  0
 18  8  1  0  0  0  0
 18 17  2  0  0  0  0
 19 14  2  0  0  0  0
 19 16  1  0  0  0  0
 20  5  1  0  0  0  0
 20  9  2  0  0  0  0
 20 15  2  0  0  0  0
 21 16  2  0  0  0  0
 22  1  1  0  0  0  0
 22 19  1  0  0  0  0
 23 10  1  0  0  0  0
 23 17  1  0  0  0  0
 24 10  1  0  0  0  0
 24 18  1  0  0  0  0
M  CHG  1  21   1
M  END


  Mrv1652310111708352D          

 24 28  0  0  0  0            999 V2000
    2.6587    0.6289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6884   -1.5457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8635   -1.5331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2066    1.2743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3817    1.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9366   -0.8501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4331    0.5410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5864   -0.8752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1335    0.5912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7127   -1.1851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1117   -0.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6082    0.5536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1849   -0.1545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7101   -0.1169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3600   -0.1420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4619   -0.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8347   -0.1796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4113   -0.8877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8852   -0.1043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9584    0.5787    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6370   -0.7999    0.0000 O   0  3  0  0  0  0  0  0  0  0  0  0
    3.4837    0.6163    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6389   -0.3634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9540   -1.5092    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  5  4  1  0  0  0  0
 11  2  1  0  0  0  0
 11  6  2  0  0  0  0
 12  4  1  0  0  0  0
 12  7  2  0  0  0  0
 13  8  2  0  0  0  0
 13 12  1  0  0  0  0
 14  9  1  0  0  0  0
 14 11  1  0  0  0  0
 15  6  1  0  0  0  0
 15 13  1  0  0  0  0
 16  3  1  0  0  0  0
 17  7  1  0  0  0  0
 18  8  1  0  0  0  0
 18 17  2  0  0  0  0
 19 14  2  0  0  0  0
 19 16  1  0  0  0  0
 20  5  1  0  0  0  0
 20  9  2  0  0  0  0
 20 15  2  0  0  0  0
 21 16  2  0  0  0  0
 22  1  1  0  0  0  0
 22 19  1  0  0  0  0
 23 10  1  0  0  0  0
 23 17  1  0  0  0  0
 24 10  1  0  0  0  0
 24 18  1  0  0  0  0
M  CHG  1  21   1
M  END
> <DATABASE_ID>
NP0248032

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C2C=[N]3=C(C=C2C=CC1=[OH+])C1=CC2=C(OCO2)C=C1CC3

> <INCHI_IDENTIFIER>
InChI=1S/C19H15NO4/c1-22-19-14-9-20-5-4-12-7-17-18(24-10-23-17)8-13(12)15(20)6-11(14)2-3-16(19)21/h2-3,6-9H,4-5,10H2,1H3/p+1

> <INCHI_KEY>
OEGWOBMNQDATKP-UHFFFAOYSA-O

> <FORMULA>
C19H16NO4

> <MOLECULAR_WEIGHT>
322.339

> <EXACT_MASS>
322.107384419

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
34.61536712670941

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{16-methoxy-5,7-dioxa-13lambda5-azapentacyclo[11.8.0.0^{2,10}.0^{4,8}.0^{15,20}]henicosa-1(13),2,4(8),9,13,15,18,20-octaen-17-ylidene}oxidanium

> <ALOGPS_LOGP>
1.32

> <ALOGPS_LOGS>
-3.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
73.51

> <JCHEM_REFRACTIVITY>
115.1595

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.68e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{16-methoxy-5,7-dioxa-13lambda5-azapentacyclo[11.8.0.0^{2,10}.0^{4,8}.0^{15,20}]henicosa-1(13),2,4(8),9,13,15,18,20-octaen-17-ylidene}oxidanium

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-OCT-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-OCT-17         0                                  
HETATM    1  C   UNK     0       4.963   1.174   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.752  -2.885   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.212  -2.862   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.452   2.379   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.912   2.402   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.082  -1.587   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      15.742   1.010   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      14.161  -1.634   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.582   1.104   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      18.130  -2.212   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.542  -1.563   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.202   1.033   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.412  -0.288   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.792  -0.218   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.872  -0.265   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.462  -1.517   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      16.491  -0.335   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      15.701  -1.657   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.252  -0.195   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0      11.122   1.080   0.000  0.00  0.00           N+0
HETATM   21  O   UNK     0       4.922  -1.493   0.000  0.00  0.00           O+1
HETATM   22  O   UNK     0       6.503   1.150   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      17.993  -0.678   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      16.714  -2.817   0.000  0.00  0.00           O+0
CONECT    1   22                                                            
CONECT    2    3   11                                                       
CONECT    3    2   16                                                       
CONECT    4    5   12                                                       
CONECT    5    4   20                                                       
CONECT    6   11   15                                                       
CONECT    7   12   17                                                       
CONECT    8   13   18                                                       
CONECT    9   14   20                                                       
CONECT   10   23   24                                                       
CONECT   11    2    6   14                                                  
CONECT   12    4    7   13                                                  
CONECT   13    8   12   15                                                  
CONECT   14    9   11   19                                                  
CONECT   15    6   13   20                                                  
CONECT   16    3   19   21                                                  
CONECT   17    7   18   23                                                  
CONECT   18    8   17   24                                                  
CONECT   19   14   16   22                                                  
CONECT   20    5    9   15                                                  
CONECT   21   16                                                            
CONECT   22    1   19                                                       
CONECT   23   10   17                                                       
CONECT   24   10   18                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   56    0
END

View in JSmol

Synonyms

Value	Source
Thalifendine chloride	MeSH

Chemical Formula

C₁₉H₁₆NO₄

Average Mass

322.3390 Da

Monoisotopic Mass

322.10738 Da

IUPAC Name

{16-methoxy-5,7-dioxa-13lambda5-azapentacyclo[11.8.0.0^{2,10}.0^{4,8}.0^{15,20}]henicosa-1(13),2,4(8),9,13,15,18,20-octaen-17-ylidene}oxidanium

Traditional Name

{16-methoxy-5,7-dioxa-13lambda5-azapentacyclo[11.8.0.0^{2,10}.0^{4,8}.0^{15,20}]henicosa-1(13),2,4(8),9,13,15,18,20-octaen-17-ylidene}oxidanium

CAS Registry Number

Not Available

SMILES

COC1=C2C=[N]3=C(C=C2C=CC1=[OH+])C1=CC2=C(OCO2)C=C1CC3

InChI Identifier

InChI=1S/C19H15NO4/c1-22-19-14-9-20-5-4-12-7-17-18(24-10-23-17)8-13(12)15(20)6-11(14)2-3-16(19)21/h2-3,6-9H,4-5,10H2,1H3/p+1

InChI Key

OEGWOBMNQDATKP-UHFFFAOYSA-O

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Arcangelisia flava	LOTUS Database	35616633
Berberis darwinii	LOTUS Database	35616633
Coptis japonica	LOTUS Database	35616633
Coptis quinquefolia	LOTUS Database	35616633
Fibraurea tinctoria	LOTUS Database	35616633
Glaucium arabicum	LOTUS Database	35616633
Nandina domestica	LOTUS Database	35616633
Papaver dubium	LOTUS Database	35616633
Thalictrum alpinum	LOTUS Database	35616633
Thalictrum cultratum	LOTUS Database	35616633
Thalictrum dioicum	LOTUS Database	35616633
Thalictrum fendleri	LOTUS Database	35616633
Thalictrum foliolosum	LOTUS Database	35616633
Thalictrum javanicum Blume	LOTUS Database	35616633
Thalictrum lankesteri	LOTUS Database	35616633
Thalictrum minus	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
Isoquinoline
Benzodioxole
Anisole
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Pyridine
Pyridinium
Benzenoid
Heteroaromatic compound
Acetal
Ether
Oxacycle
Azacycle
Organoheterocyclic compound
Organonitrogen compound
Hydrocarbon derivative
Organic nitrogen compound
Organooxygen compound
Organic oxygen compound
Organopnictogen compound
Organic cation
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	1.32	ALOGPS
logS	-3.8	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	73.51 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	115.16 m³·mol⁻¹	ChemAxon
Polarizability	34.62 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0187656

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

3084288

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 17-hydroxy-16-methoxy-5,7-dioxa-13λ⁵-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁵,²⁰]henicosa-1(13),2,4(8),9,14,16,18,20-octaen-13-ylium (NP0248032)

MOL for NP0248032 (17-hydroxy-16-methoxy-5,7-dioxa-13λ⁵-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁵,²⁰]henicosa-1(13),2,4(8),9,14,16,18,20-octaen-13-ylium)

3D MOL for NP0248032 (17-hydroxy-16-methoxy-5,7-dioxa-13λ⁵-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁵,²⁰]henicosa-1(13),2,4(8),9,14,16,18,20-octaen-13-ylium)

3D SDF for NP0248032 (17-hydroxy-16-methoxy-5,7-dioxa-13λ⁵-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁵,²⁰]henicosa-1(13),2,4(8),9,14,16,18,20-octaen-13-ylium)

3D-SDF for NP0248032 (17-hydroxy-16-methoxy-5,7-dioxa-13λ⁵-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁵,²⁰]henicosa-1(13),2,4(8),9,14,16,18,20-octaen-13-ylium)

PDB for NP0248032 (17-hydroxy-16-methoxy-5,7-dioxa-13λ⁵-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁵,²⁰]henicosa-1(13),2,4(8),9,14,16,18,20-octaen-13-ylium)

3D PDB for NP0248032 (17-hydroxy-16-methoxy-5,7-dioxa-13λ⁵-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁵,²⁰]henicosa-1(13),2,4(8),9,14,16,18,20-octaen-13-ylium)

SMILES for NP0248032 (17-hydroxy-16-methoxy-5,7-dioxa-13λ⁵-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁵,²⁰]henicosa-1(13),2,4(8),9,14,16,18,20-octaen-13-ylium)

INCHI for NP0248032 (17-hydroxy-16-methoxy-5,7-dioxa-13λ⁵-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁵,²⁰]henicosa-1(13),2,4(8),9,14,16,18,20-octaen-13-ylium)

Structure for NP0248032 (17-hydroxy-16-methoxy-5,7-dioxa-13λ⁵-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁵,²⁰]henicosa-1(13),2,4(8),9,14,16,18,20-octaen-13-ylium)

3D Structure for NP0248032 (17-hydroxy-16-methoxy-5,7-dioxa-13λ⁵-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁵,²⁰]henicosa-1(13),2,4(8),9,14,16,18,20-octaen-13-ylium)