NP-MRD: Showing NP-Card for 21,22-dihydroxy-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 (NP0257479)

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Record Information

Version

2.0

Created at

2022-09-07 22:36:56 UTC

Updated at

2022-09-07 22:36:56 UTC

NP-MRD ID

NP0257479

Secondary Accession Numbers

None

Natural Product Identification

Common Name

21,22-dihydroxy-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

21,22-Dihydroxy-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. 21,22-Dihydroxy-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


  Mrv1533004161507052D          

 36 40  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


  Mrv1533004161507052D          

 36 40  0  0  0  0            999 V2000
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 15 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 26 29  1  0  0  0  0
 29 30  2  0  0  0  0
 23 30  1  0  0  0  0
 29 31  1  0  0  0  0
  3 31  1  0  0  0  0
 31 32  2  0  0  0  0
  6 32  1  0  0  0  0
  9 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0257479

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C2CCC(CC3CCCC4C(O)C(O)CC(N34)C3=CC=C(OC)C(=C3)C1=C2)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C29H37NO6/c1-17(31)36-21-10-7-18-8-11-27(34-2)22(13-18)23-14-19(9-12-28(23)35-3)25-16-26(32)29(33)24-6-4-5-20(15-21)30(24)25/h8-9,11-14,20-21,24-26,29,32-33H,4-7,10,15-16H2,1-3H3

> <INCHI_KEY>
PHZITYJHCYPBFZ-UHFFFAOYSA-N

> <FORMULA>
C29H37NO6

> <MOLECULAR_WEIGHT>
495.616

> <EXACT_MASS>
495.262087915

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
54.79031627590935

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
21,22-dihydroxy-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>
3.29

> <JCHEM_LOGP>
3.2591650456666663

> <ALOGPS_LOGS>
-4.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
15.05688173338351

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.487678137715793

> <JCHEM_PKA_STRONGEST_BASIC>
8.759189498663993

> <JCHEM_POLAR_SURFACE_AREA>
88.46000000000001

> <JCHEM_REFRACTIVITY>
136.52730000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.30e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
21,22-dihydroxy-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                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-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  O   UNK     0       2.267   8.711   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.874   9.277   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.547  10.782   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       6.340   8.807   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.667   7.302   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0       5.527   6.267   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0       8.089   8.396   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.379   9.909   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.833  10.414   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.999   9.407   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      12.453   9.913   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      12.743  11.426   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      10.709   7.895   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.255   7.389   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      11.967   6.615   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      11.108   5.336   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       7.036   0.994   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       5.503   0.851   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       4.860  -0.548   0.000  0.00  0.00           O+0
HETATM   36  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   31                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   32                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   33                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   22                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   22                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21   11   15                                                  
CONECT   23   21   24   30                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   29                                                  
CONECT   27   26   28                                                       
CONECT   28   27                                                            
CONECT   29   26   30   31                                                  
CONECT   30   29   23                                                       
CONECT   31   29    3   32                                                  
CONECT   32   31    6                                                       
CONECT   33    9   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

View in JSmol

Synonyms

Value	Source
21,22-Dihydroxy-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
21,22-Dihydroxy-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

C₂₉H₃₇NO₆

Average Mass

495.6160 Da

Monoisotopic Mass

495.26209 Da

IUPAC Name

21,22-dihydroxy-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

21,22-dihydroxy-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(CC3CCCC4C(O)C(O)CC(N34)C3=CC=C(OC)C(=C3)C1=C2)OC(C)=O

InChI Identifier

InChI=1S/C29H37NO6/c1-17(31)36-21-10-7-18-8-11-27(34-2)22(13-18)23-14-19(9-12-28(23)35-3)25-16-26(32)29(33)24-6-4-5-20(15-21)30(24)25/h8-9,11-14,20-21,24-26,29,32-33H,4-7,10,15-16H2,1-3H3

InChI Key

PHZITYJHCYPBFZ-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
Aralkylamine
Alkyl aryl ether
Piperidine
Benzenoid
1,2-diol
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
1,2-aminoalcohol
Carboxylic acid ester
Amino acid or derivatives
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Azacycle
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Amine
Organopnictogen compound
Alcohol
Organic oxygen 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	3.29	ALOGPS
logP	3.26	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	13.49	ChemAxon
pKa (Strongest Basic)	8.76	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	88.46 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	136.53 m³·mol⁻¹	ChemAxon
Polarizability	54.79 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

5319142

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 21,22-dihydroxy-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 (NP0257479)

MOL for NP0257479 (21,22-dihydroxy-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 NP0257479 (21,22-dihydroxy-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 NP0257479 (21,22-dihydroxy-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 NP0257479 (21,22-dihydroxy-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 NP0257479 (21,22-dihydroxy-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 NP0257479 (21,22-dihydroxy-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 NP0257479 (21,22-dihydroxy-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 NP0257479 (21,22-dihydroxy-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 NP0257479 (21,22-dihydroxy-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 NP0257479 (21,22-dihydroxy-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)