NP-MRD: Showing NP-Card for (20s,21s)-21-hydroxy-5,10,11-trimethoxy-16-azapentacyclo[12.7.0.0²,⁷.0⁸,¹³.0¹⁶,²⁰]henicosa-1(14),2(7),3,5,8(13),9,11-heptaen-16-ium-16-olate (NP0222838)

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Record Information

Version

2.0

Created at

2022-09-06 00:46:26 UTC

Updated at

2022-09-06 00:46:26 UTC

NP-MRD ID

NP0222838

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(20s,21s)-21-hydroxy-5,10,11-trimethoxy-16-azapentacyclo[12.7.0.0²,⁷.0⁸,¹³.0¹⁶,²⁰]henicosa-1(14),2(7),3,5,8(13),9,11-heptaen-16-ium-16-olate

Description

Tylophorinine N-oxide belongs to the class of organic compounds known as phenanthroindolizidines. These are aromatic polycyclic compounds containing the phenanthroindolizidine skeleton, which is structurally characterized by an indolizidine and a phenanthrene, where the indolizidine is fused to the second benzene ring of a phenanthrene. Based on a literature review very few articles have been published on Tylophorinine N-oxide.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062202462D          

 29 33  0  0  1  0            999 V2000
    5.6202   -4.2393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3399   -3.4634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5278   -3.3182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9960   -3.9489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1838   -3.8037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9035   -3.0277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0914   -2.8825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8111   -2.1066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3429   -1.4759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0626   -0.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5945   -0.0692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3142    0.7067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5021    0.8519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4066   -0.2145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9384    0.4162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7505    0.2710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6869   -0.9904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1551   -1.6211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4354   -2.3970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2475   -2.5422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9990   -1.9614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4672   -2.5921    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    0.1073   -1.8497    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -0.3574   -2.6189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5867   -3.4114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0962   -3.8744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7475   -3.3680    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5596   -3.5132    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8399   -4.2891    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
  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
 12 13  1  0  0  0  0
 11 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  2  0  0  0  0
  9 18  1  0  0  0  0
 18 19  1  0  0  0  0
  6 19  1  0  0  0  0
 19 20  2  0  0  0  0
  3 20  1  0  0  0  0
  8 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 27 26  1  6  0  0  0
 22 27  1  0  0  0  0
 27 28  1  0  0  0  0
  7 28  1  0  0  0  0
 28 29  1  6  0  0  0
M  CHG  2  22   1  23  -1
M  END


  Mrv1652309062202462D          

 29 33  0  0  1  0            999 V2000
    5.6202   -4.2393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3399   -3.4634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5278   -3.3182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9960   -3.9489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1838   -3.8037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9035   -3.0277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0914   -2.8825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8111   -2.1066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3429   -1.4759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0626   -0.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5945   -0.0692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3142    0.7067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5021    0.8519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4066   -0.2145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9384    0.4162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7505    0.2710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6869   -0.9904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1551   -1.6211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4354   -2.3970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2475   -2.5422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9990   -1.9614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4672   -2.5921    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    0.1073   -1.8497    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -0.3574   -2.6189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5867   -3.4114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0962   -3.8744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7475   -3.3680    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5596   -3.5132    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8399   -4.2891    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
  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
 12 13  1  0  0  0  0
 11 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  2  0  0  0  0
  9 18  1  0  0  0  0
 18 19  1  0  0  0  0
  6 19  1  0  0  0  0
 19 20  2  0  0  0  0
  3 20  1  0  0  0  0
  8 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 27 26  1  6  0  0  0
 22 27  1  0  0  0  0
 27 28  1  0  0  0  0
  7 28  1  0  0  0  0
 28 29  1  6  0  0  0
M  CHG  2  22   1  23  -1
M  END
> <DATABASE_ID>
NP0222838

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C2C(=C1)C1=CC(OC)=C(OC)C=C1C1=C2[C@H](O)[C@@H]2CCC[N+]2([O-])C1

> <INCHI_IDENTIFIER>
InChI=1S/C23H25NO5/c1-27-13-6-7-14-15(9-13)16-10-20(28-2)21(29-3)11-17(16)18-12-24(26)8-4-5-19(24)23(25)22(14)18/h6-7,9-11,19,23,25H,4-5,8,12H2,1-3H3/t19-,23+,24?/m0/s1

> <INCHI_KEY>
SHQULSXBVKOENG-MLGOWYMSSA-N

> <FORMULA>
C23H25NO5

> <MOLECULAR_WEIGHT>
395.455

> <EXACT_MASS>
395.173272909

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
43.457347772431724

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(20S,21S)-21-hydroxy-5,10,11-trimethoxy-16-azapentacyclo[12.7.0.0^{2,7}.0^{8,13}.0^{16,20}]henicosa-1(14),2,4,6,8,10,12-heptaen-16-ium-16-olate

> <JCHEM_LOGP>
1.8826640120000002

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.751376382674348

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.515745402922025

> <JCHEM_PKA_STRONGEST_BASIC>
3.072989255360828

> <JCHEM_POLAR_SURFACE_AREA>
70.98

> <JCHEM_REFRACTIVITY>
110.66389999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(20S,21S)-21-hydroxy-5,10,11-trimethoxy-16-azapentacyclo[12.7.0.0^{2,7}.0^{8,13}.0^{16,20}]henicosa-1(14),2,4,6,8,10,12-heptaen-16-ium-16-olate

> <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      10.491  -7.913   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       9.968  -6.465   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       8.452  -6.194   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.459  -7.371   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.943  -7.100   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.420  -5.652   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.904  -5.381   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.381  -3.932   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.374  -2.755   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.850  -1.307   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.843  -0.129   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       4.320   1.319   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.804   1.590   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.359  -0.400   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       7.352   0.777   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       8.868   0.506   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.882  -1.849   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.889  -3.026   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.413  -4.474   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.929  -4.746   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.865  -3.661   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0       0.872  -4.839   0.000  0.00  0.00           N+1
HETATM   23  O   UNK     0       0.200  -3.453   0.000  0.00  0.00           O-1
HETATM   24  C   UNK     0      -0.667  -4.889   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.095  -6.368   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.179  -7.232   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.395  -6.287   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.911  -6.558   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       3.434  -8.006   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   20                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   19                                                  
CONECT    7    6    8   28                                                  
CONECT    8    7    9   21                                                  
CONECT    9    8   10   18                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   11   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15                                                            
CONECT   17   14   18                                                       
CONECT   18   17    9   19                                                  
CONECT   19   18    6   20                                                  
CONECT   20   19    3                                                       
CONECT   21    8   22                                                       
CONECT   22   21   23   24   27                                             
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   22   28                                                  
CONECT   28   27    7   29                                                  
CONECT   29   28                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₂₅NO₅

Average Mass

395.4550 Da

Monoisotopic Mass

395.17327 Da

IUPAC Name

(20S,21S)-21-hydroxy-5,10,11-trimethoxy-16-azapentacyclo[12.7.0.0^{2,7}.0^{8,13}.0^{16,20}]henicosa-1(14),2,4,6,8,10,12-heptaen-16-ium-16-olate

Traditional Name

(20S,21S)-21-hydroxy-5,10,11-trimethoxy-16-azapentacyclo[12.7.0.0^{2,7}.0^{8,13}.0^{16,20}]henicosa-1(14),2,4,6,8,10,12-heptaen-16-ium-16-olate

CAS Registry Number

Not Available

SMILES

COC1=CC=C2C(=C1)C1=CC(OC)=C(OC)C=C1C1=C2[C@H](O)[C@@H]2CCC[N+]2([O-])C1

InChI Identifier

InChI=1S/C23H25NO5/c1-27-13-6-7-14-15(9-13)16-10-20(28-2)21(29-3)11-17(16)18-12-24(26)8-4-5-19(24)23(25)22(14)18/h6-7,9-11,19,23,25H,4-5,8,12H2,1-3H3/t19-,23+,24?/m0/s1

InChI Key

SHQULSXBVKOENG-MLGOWYMSSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenanthroindolizidines. These are aromatic polycyclic compounds containing the phenanthroindolizidine skeleton, which is structurally characterized by an indolizidine and a phenanthrene, where the indolizidine is fused to the second benzene ring of a phenanthrene.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenanthrenes and derivatives

Sub Class

Phenanthroindolizidines

Direct Parent

Phenanthroindolizidines

Alternative Parents

Substituents

Phenanthroindolizidine
Tetrahydroisoquinoline
Naphthalene
Indolizidine
Anisole
Alkyl aryl ether
N-alkylpyrrolidine
Trialkyl amine oxide
Pyrrolidine
Secondary alcohol
Azacycle
Organoheterocyclic compound
Trisubstituted n-oxide
Ether
N-oxide
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organic zwitterion
Organooxygen compound
Organonitrogen compound
Alcohol
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	1.88	ChemAxon
pKa (Strongest Acidic)	12.52	ChemAxon
pKa (Strongest Basic)	3.07	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	70.98 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	110.66 m³·mol⁻¹	ChemAxon
Polarizability	43.46 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

15768068

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (20s,21s)-21-hydroxy-5,10,11-trimethoxy-16-azapentacyclo[12.7.0.0²,⁷.0⁸,¹³.0¹⁶,²⁰]henicosa-1(14),2(7),3,5,8(13),9,11-heptaen-16-ium-16-olate (NP0222838)

MOL for NP0222838 ((20s,21s)-21-hydroxy-5,10,11-trimethoxy-16-azapentacyclo[12.7.0.0²,⁷.0⁸,¹³.0¹⁶,²⁰]henicosa-1(14),2(7),3,5,8(13),9,11-heptaen-16-ium-16-olate)

3D MOL for NP0222838 ((20s,21s)-21-hydroxy-5,10,11-trimethoxy-16-azapentacyclo[12.7.0.0²,⁷.0⁸,¹³.0¹⁶,²⁰]henicosa-1(14),2(7),3,5,8(13),9,11-heptaen-16-ium-16-olate)

3D SDF for NP0222838 ((20s,21s)-21-hydroxy-5,10,11-trimethoxy-16-azapentacyclo[12.7.0.0²,⁷.0⁸,¹³.0¹⁶,²⁰]henicosa-1(14),2(7),3,5,8(13),9,11-heptaen-16-ium-16-olate)

3D-SDF for NP0222838 ((20s,21s)-21-hydroxy-5,10,11-trimethoxy-16-azapentacyclo[12.7.0.0²,⁷.0⁸,¹³.0¹⁶,²⁰]henicosa-1(14),2(7),3,5,8(13),9,11-heptaen-16-ium-16-olate)

PDB for NP0222838 ((20s,21s)-21-hydroxy-5,10,11-trimethoxy-16-azapentacyclo[12.7.0.0²,⁷.0⁸,¹³.0¹⁶,²⁰]henicosa-1(14),2(7),3,5,8(13),9,11-heptaen-16-ium-16-olate)

3D PDB for NP0222838 ((20s,21s)-21-hydroxy-5,10,11-trimethoxy-16-azapentacyclo[12.7.0.0²,⁷.0⁸,¹³.0¹⁶,²⁰]henicosa-1(14),2(7),3,5,8(13),9,11-heptaen-16-ium-16-olate)

SMILES for NP0222838 ((20s,21s)-21-hydroxy-5,10,11-trimethoxy-16-azapentacyclo[12.7.0.0²,⁷.0⁸,¹³.0¹⁶,²⁰]henicosa-1(14),2(7),3,5,8(13),9,11-heptaen-16-ium-16-olate)

INCHI for NP0222838 ((20s,21s)-21-hydroxy-5,10,11-trimethoxy-16-azapentacyclo[12.7.0.0²,⁷.0⁸,¹³.0¹⁶,²⁰]henicosa-1(14),2(7),3,5,8(13),9,11-heptaen-16-ium-16-olate)

Structure for NP0222838 ((20s,21s)-21-hydroxy-5,10,11-trimethoxy-16-azapentacyclo[12.7.0.0²,⁷.0⁸,¹³.0¹⁶,²⁰]henicosa-1(14),2(7),3,5,8(13),9,11-heptaen-16-ium-16-olate)

3D Structure for NP0222838 ((20s,21s)-21-hydroxy-5,10,11-trimethoxy-16-azapentacyclo[12.7.0.0²,⁷.0⁸,¹³.0¹⁶,²⁰]henicosa-1(14),2(7),3,5,8(13),9,11-heptaen-16-ium-16-olate)