NP-MRD: Showing NP-Card for (1r,13s)-17-methoxy-5,7-dioxa-21-azapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3,8,10,14(19),15,17-hexaen-16-ol (NP0224468)

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Record Information

Version

2.0

Created at

2022-09-06 02:49:48 UTC

Updated at

2022-09-06 02:49:48 UTC

NP-MRD ID

NP0224468

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,13s)-17-methoxy-5,7-dioxa-21-azapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3,8,10,14(19),15,17-hexaen-16-ol

Description

(1R,13S)-17-methoxy-5,7-dioxa-21-azapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]Henicosa-3(11),4(8),9,14,16,18-hexaen-16-ol belongs to the class of organic compounds known as phenanthridines and derivatives. These are polycyclic compounds containing a phenanthridine moiety, which is a tricyclic system with two benzene rings joined by a pyridine forming a non-linear skeleton. Hydrogenated derivatives are also included. (1r,13s)-17-methoxy-5,7-dioxa-21-azapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3,8,10,14(19),15,17-hexaen-16-ol is found in Argemone ochroleuca. Based on a literature review very few articles have been published on (1R,13S)-17-methoxy-5,7-dioxa-21-azapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]Henicosa-3(11),4(8),9,14,16,18-hexaen-16-ol.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062204492D          

 24 28  0  0  1  0            999 V2000
   -0.6225   -2.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2209   -3.2749    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6040   -3.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0056   -4.0081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8305   -4.0207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2538   -3.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8523   -2.5919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0274   -2.5793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6258   -1.8587    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0788   -3.3251    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5021   -2.6170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3270   -2.6295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7503   -1.9214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5752   -1.9340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9768   -2.6546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5535   -3.3627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7286   -3.3502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3052   -4.0583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4803   -4.0458    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0570   -4.7539    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2321   -4.7413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0961   -3.9842    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8548   -3.6601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7811   -2.8384    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  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  2  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  6  1  6  0  0  0
 10 11  1  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  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 10 19  1  0  0  0  0
 19 20  1  1  0  0  0
 20 21  1  0  0  0  0
  5 21  1  0  0  0  0
 16 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 15 24  1  0  0  0  0
M  END


  Mrv1652309062204492D          

 24 28  0  0  1  0            999 V2000
   -0.6225   -2.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2209   -3.2749    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6040   -3.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0056   -4.0081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8305   -4.0207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2538   -3.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8523   -2.5919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0274   -2.5793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6258   -1.8587    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0788   -3.3251    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5021   -2.6170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3270   -2.6295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7503   -1.9214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5752   -1.9340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9768   -2.6546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5535   -3.3627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7286   -3.3502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3052   -4.0583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4803   -4.0458    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0570   -4.7539    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2321   -4.7413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0961   -3.9842    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8548   -3.6601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7811   -2.8384    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  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  2  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  6  1  6  0  0  0
 10 11  1  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  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 10 19  1  0  0  0  0
 19 20  1  1  0  0  0
 20 21  1  0  0  0  0
  5 21  1  0  0  0  0
 16 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 15 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0224468

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C=C1O)[C@@H]1CC3=CC=C4OCOC4=C3C[C@H]1NC2

> <INCHI_IDENTIFIER>
InChI=1S/C19H19NO4/c1-22-18-5-11-8-20-15-6-13-10(2-3-17-19(13)24-9-23-17)4-14(15)12(11)7-16(18)21/h2-3,5,7,14-15,20-21H,4,6,8-9H2,1H3/t14-,15+/m0/s1

> <INCHI_KEY>
GXFZPZAWQYQWSW-LSDHHAIUSA-N

> <FORMULA>
C19H19NO4

> <MOLECULAR_WEIGHT>
325.364

> <EXACT_MASS>
325.131408096

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
35.46540866460012

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,13S)-17-methoxy-5,7-dioxa-21-azapentacyclo[11.8.0.0^{3,11}.0^{4,8}.0^{14,19}]henicosa-3,8,10,14(19),15,17-hexaen-16-ol

> <JCHEM_LOGP>
2.4654067361683634

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.00717017531442

> <JCHEM_PKA_STRONGEST_BASIC>
8.834298417990617

> <JCHEM_POLAR_SURFACE_AREA>
59.95

> <JCHEM_REFRACTIVITY>
88.974

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,13S)-17-methoxy-5,7-dioxa-21-azapentacyclo[11.8.0.0^{3,11}.0^{4,8}.0^{14,19}]henicosa-3,8,10,14(19),15,17-hexaen-16-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.162  -4.768   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -0.412  -6.113   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.128  -6.137   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.877  -7.482   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.417  -7.505   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.207  -6.183   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.458  -4.838   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.918  -4.815   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.168  -3.470   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       5.747  -6.207   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.537  -4.885   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.077  -4.908   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.867  -3.587   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.407  -3.610   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.157  -4.955   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.366  -6.277   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.827  -6.254   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.036  -7.575   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.497  -7.552   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0       5.706  -8.874   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0       4.167  -8.850   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      11.379  -7.437   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      12.796  -6.832   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      12.658  -5.298   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   21                                                  
CONECT    6    5    7   10                                                  
CONECT    7    6    8                                                       
CONECT    8    7    3    9                                                  
CONECT    9    8                                                            
CONECT   10    6   11   19                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   24                                                  
CONECT   16   15   17   22                                                  
CONECT   17   16   12   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   10   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20    5                                                       
CONECT   22   16   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   15                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₁₉NO₄

Average Mass

325.3640 Da

Monoisotopic Mass

325.13141 Da

IUPAC Name

(1R,13S)-17-methoxy-5,7-dioxa-21-azapentacyclo[11.8.0.0^{3,11}.0^{4,8}.0^{14,19}]henicosa-3,8,10,14(19),15,17-hexaen-16-ol

Traditional Name

(1R,13S)-17-methoxy-5,7-dioxa-21-azapentacyclo[11.8.0.0^{3,11}.0^{4,8}.0^{14,19}]henicosa-3,8,10,14(19),15,17-hexaen-16-ol

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C=C1O)[C@@H]1CC3=CC=C4OCOC4=C3C[C@H]1NC2

InChI Identifier

InChI=1S/C19H19NO4/c1-22-18-5-11-8-20-15-6-13-10(2-3-17-19(13)24-9-23-17)4-14(15)12(11)7-16(18)21/h2-3,5,7,14-15,20-21H,4,6,8-9H2,1H3/t14-,15+/m0/s1

InChI Key

GXFZPZAWQYQWSW-LSDHHAIUSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Argemone ochroleuca	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenanthridines and derivatives. These are polycyclic compounds containing a phenanthridine moiety, which is a tricyclic system with two benzene rings joined by a pyridine forming a non-linear skeleton. Hydrogenated derivatives are also included.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Benzoquinolines

Direct Parent

Phenanthridines and derivatives

Alternative Parents

Substituents

Phenanthridine
Tetrahydroisoquinoline
Tetralin
Benzodioxole
Anisole
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Benzenoid
Acetal
Secondary aliphatic amine
Ether
Secondary amine
Oxacycle
Azacycle
Amine
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Organopnictogen 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	2.47	ChemAxon
pKa (Strongest Acidic)	10.01	ChemAxon
pKa (Strongest Basic)	8.83	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	59.95 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	88.97 m³·mol⁻¹	ChemAxon
Polarizability	35.47 Å³	ChemAxon
Number of Rings	5	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

162918871

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,13s)-17-methoxy-5,7-dioxa-21-azapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3,8,10,14(19),15,17-hexaen-16-ol (NP0224468)

MOL for NP0224468 ((1r,13s)-17-methoxy-5,7-dioxa-21-azapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3,8,10,14(19),15,17-hexaen-16-ol)

3D MOL for NP0224468 ((1r,13s)-17-methoxy-5,7-dioxa-21-azapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3,8,10,14(19),15,17-hexaen-16-ol)

3D SDF for NP0224468 ((1r,13s)-17-methoxy-5,7-dioxa-21-azapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3,8,10,14(19),15,17-hexaen-16-ol)

3D-SDF for NP0224468 ((1r,13s)-17-methoxy-5,7-dioxa-21-azapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3,8,10,14(19),15,17-hexaen-16-ol)

PDB for NP0224468 ((1r,13s)-17-methoxy-5,7-dioxa-21-azapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3,8,10,14(19),15,17-hexaen-16-ol)

3D PDB for NP0224468 ((1r,13s)-17-methoxy-5,7-dioxa-21-azapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3,8,10,14(19),15,17-hexaen-16-ol)

SMILES for NP0224468 ((1r,13s)-17-methoxy-5,7-dioxa-21-azapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3,8,10,14(19),15,17-hexaen-16-ol)

INCHI for NP0224468 ((1r,13s)-17-methoxy-5,7-dioxa-21-azapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3,8,10,14(19),15,17-hexaen-16-ol)

Structure for NP0224468 ((1r,13s)-17-methoxy-5,7-dioxa-21-azapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3,8,10,14(19),15,17-hexaen-16-ol)

3D Structure for NP0224468 ((1r,13s)-17-methoxy-5,7-dioxa-21-azapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3,8,10,14(19),15,17-hexaen-16-ol)