NP-MRD: Showing NP-Card for 22-hydroxy-5,8-dimethoxy-24-azapentacyclo[14.7.1.1²,⁶.1⁷,¹¹.0²⁰,²⁴]hexacosa-2,4,6(26),7(25),8,10-hexaen-14-yl acetate (NP0284090)

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Record Information

Version

2.0

Created at

2022-09-09 11:38:52 UTC

Updated at

2022-09-09 11:38:52 UTC

NP-MRD ID

NP0284090

Secondary Accession Numbers

None

Natural Product Identification

Common Name

22-hydroxy-5,8-dimethoxy-24-azapentacyclo[14.7.1.1²,⁶.1⁷,¹¹.0²⁰,²⁴]hexacosa-2,4,6(26),7(25),8,10-hexaen-14-yl acetate

Description

22-Hydroxy-5,8-dimethoxy-24-azapentacyclo[14.7.1.1²,⁶.1⁷,¹¹.0²⁰,²⁴]Hexacosa-2(26),3,5,7,9,11(25)-hexaen-14-yl acetate belongs to the class of organic compounds known as quinolizidines. Quinolizidines are compounds containing a quinolizidine moiety, which is a octahydro-2H-quinolizine derivative. 22-Hydroxy-5,8-dimethoxy-24-azapentacyclo[14.7.1.1²,⁶.1⁷,¹¹.0²⁰,²⁴]Hexacosa-2(26),3,5,7,9,11(25)-hexaen-14-yl acetate is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171515592D          

 35 39  0  0  0  0            999 V2000
    7.3313    4.9129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          2D

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M  END


  Mrv1533004171515592D          

 35 39  0  0  0  0            999 V2000
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  3 30  1  0  0  0  0
 30 31  2  0  0  0  0
  6 31  1  0  0  0  0
  9 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0284090

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C2CCC(CC3CCCC4CC(O)CC(N34)C3=CC=C(OC)C(=C3)C1=C2)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C29H37NO5/c1-18(31)35-24-10-7-19-8-11-28(33-2)25(13-19)26-14-20(9-12-29(26)34-3)27-17-23(32)15-21-5-4-6-22(16-24)30(21)27/h8-9,11-14,21-24,27,32H,4-7,10,15-17H2,1-3H3

> <INCHI_KEY>
PHIFOVBJQMQYRQ-UHFFFAOYSA-N

> <FORMULA>
C29H37NO5

> <MOLECULAR_WEIGHT>
479.617

> <EXACT_MASS>
479.267173295

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
53.618967474284375

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
22-hydroxy-5,8-dimethoxy-24-azapentacyclo[14.7.1.1²,⁶.1⁷,¹¹.0²⁰,²⁴]hexacosa-2,4,6(26),7(25),8,10-hexaen-14-yl acetate

> <ALOGPS_LOGP>
3.88

> <JCHEM_LOGP>
3.9494597266666682

> <ALOGPS_LOGS>
-4.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.148777269300048

> <JCHEM_PKA_STRONGEST_BASIC>
9.140842364871592

> <JCHEM_POLAR_SURFACE_AREA>
68.23000000000002

> <JCHEM_REFRACTIVITY>
135.4302

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.90e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
22-hydroxy-5,8-dimethoxy-24-azapentacyclo[14.7.1.1²,⁶.1⁷,¹¹.0²⁰,²⁴]hexacosa-2,4,6(26),7(25),8,10-hexaen-14-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0      13.685   9.171   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      14.362   7.788   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      13.503   6.510   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      14.181   5.126   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.321   3.848   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.785   3.953   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.665   2.551   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.192   2.104   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.679   2.393   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.474   3.353   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.853   4.762   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.713   3.726   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.247   4.196   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.920   5.701   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.060   6.736   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.733   8.241   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.874   9.277   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       4.547  10.782   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.340   8.807   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.667   7.302   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       5.527   6.267   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0       8.089   8.396   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.379   9.909   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.833  10.414   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.999   9.407   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      12.453   9.913   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      12.743  11.426   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.709   7.895   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       9.255   7.389   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      11.967   6.615   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      11.108   5.336   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       7.036   0.994   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       5.503   0.851   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       4.860  -0.548   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       4.612   2.108   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   30                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   31                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   32                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   21                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   21                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20   11   15                                                  
CONECT   22   20   23   29                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   28                                                  
CONECT   26   25   27                                                       
CONECT   27   26                                                            
CONECT   28   25   29   30                                                  
CONECT   29   28   22                                                       
CONECT   30   28    3   31                                                  
CONECT   31   30    6                                                       
CONECT   32    9   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

View in JSmol

Synonyms

Value	Source
22-Hydroxy-5,8-dimethoxy-24-azapentacyclo[14.7.1.1,.1,.0,]hexacosa-2(26),3,5,7,9,11(25)-hexaen-14-yl acetic acid	Generator
22-Hydroxy-5,8-dimethoxy-24-azapentacyclo[14.7.1.1²,⁶.1⁷,¹¹.0²⁰,²⁴]hexacosa-2(26),3,5,7,9,11(25)-hexaen-14-yl acetic acid	Generator

Chemical Formula

C₂₉H₃₇NO₅

Average Mass

479.6170 Da

Monoisotopic Mass

479.26717 Da

IUPAC Name

22-hydroxy-5,8-dimethoxy-24-azapentacyclo[14.7.1.1²,⁶.1⁷,¹¹.0²⁰,²⁴]hexacosa-2,4,6(26),7(25),8,10-hexaen-14-yl acetate

Traditional Name

22-hydroxy-5,8-dimethoxy-24-azapentacyclo[14.7.1.1²,⁶.1⁷,¹¹.0²⁰,²⁴]hexacosa-2,4,6(26),7(25),8,10-hexaen-14-yl acetate

CAS Registry Number

Not Available

SMILES

COC1=CC=C2CCC(CC3CCCC4CC(O)CC(N34)C3=CC=C(OC)C(=C3)C1=C2)OC(C)=O

InChI Identifier

InChI=1S/C29H37NO5/c1-18(31)35-24-10-7-19-8-11-28(33-2)25(13-19)26-14-20(9-12-29(26)34-3)27-17-23(32)15-21-5-4-6-22(16-24)30(21)27/h8-9,11-14,21-24,27,32H,4-7,10,15-17H2,1-3H3

InChI Key

PHIFOVBJQMQYRQ-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as quinolizidines. Quinolizidines are compounds containing a quinolizidine moiety, which is a octahydro-2H-quinolizine derivative.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolizidines

Sub Class

Not Available

Direct Parent

Quinolizidines

Alternative Parents

Substituents

Quinolizidine
Anisole
Alkyl aryl ether
Aralkylamine
Piperidine
Benzenoid
Amino acid or derivatives
Carboxylic acid ester
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Azacycle
Carboxylic acid derivative
Ether
Monocarboxylic acid or derivatives
Organic oxide
Amine
Organic nitrogen compound
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Alcohol
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	3.88	ALOGPS
logP	3.95	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	15.15	ChemAxon
pKa (Strongest Basic)	9.14	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	68.23 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	135.43 m³·mol⁻¹	ChemAxon
Polarizability	53.62 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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

5319139

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 22-hydroxy-5,8-dimethoxy-24-azapentacyclo[14.7.1.1²,⁶.1⁷,¹¹.0²⁰,²⁴]hexacosa-2,4,6(26),7(25),8,10-hexaen-14-yl acetate (NP0284090)

MOL for NP0284090 (22-hydroxy-5,8-dimethoxy-24-azapentacyclo[14.7.1.1²,⁶.1⁷,¹¹.0²⁰,²⁴]hexacosa-2,4,6(26),7(25),8,10-hexaen-14-yl acetate)

3D MOL for NP0284090 (22-hydroxy-5,8-dimethoxy-24-azapentacyclo[14.7.1.1²,⁶.1⁷,¹¹.0²⁰,²⁴]hexacosa-2,4,6(26),7(25),8,10-hexaen-14-yl acetate)

3D SDF for NP0284090 (22-hydroxy-5,8-dimethoxy-24-azapentacyclo[14.7.1.1²,⁶.1⁷,¹¹.0²⁰,²⁴]hexacosa-2,4,6(26),7(25),8,10-hexaen-14-yl acetate)

3D-SDF for NP0284090 (22-hydroxy-5,8-dimethoxy-24-azapentacyclo[14.7.1.1²,⁶.1⁷,¹¹.0²⁰,²⁴]hexacosa-2,4,6(26),7(25),8,10-hexaen-14-yl acetate)

PDB for NP0284090 (22-hydroxy-5,8-dimethoxy-24-azapentacyclo[14.7.1.1²,⁶.1⁷,¹¹.0²⁰,²⁴]hexacosa-2,4,6(26),7(25),8,10-hexaen-14-yl acetate)

3D PDB for NP0284090 (22-hydroxy-5,8-dimethoxy-24-azapentacyclo[14.7.1.1²,⁶.1⁷,¹¹.0²⁰,²⁴]hexacosa-2,4,6(26),7(25),8,10-hexaen-14-yl acetate)

SMILES for NP0284090 (22-hydroxy-5,8-dimethoxy-24-azapentacyclo[14.7.1.1²,⁶.1⁷,¹¹.0²⁰,²⁴]hexacosa-2,4,6(26),7(25),8,10-hexaen-14-yl acetate)

INCHI for NP0284090 (22-hydroxy-5,8-dimethoxy-24-azapentacyclo[14.7.1.1²,⁶.1⁷,¹¹.0²⁰,²⁴]hexacosa-2,4,6(26),7(25),8,10-hexaen-14-yl acetate)

Structure for NP0284090 (22-hydroxy-5,8-dimethoxy-24-azapentacyclo[14.7.1.1²,⁶.1⁷,¹¹.0²⁰,²⁴]hexacosa-2,4,6(26),7(25),8,10-hexaen-14-yl acetate)

3D Structure for NP0284090 (22-hydroxy-5,8-dimethoxy-24-azapentacyclo[14.7.1.1²,⁶.1⁷,¹¹.0²⁰,²⁴]hexacosa-2,4,6(26),7(25),8,10-hexaen-14-yl acetate)