NP-MRD: Showing NP-Card for 9,20-dihydroxy-4,5-dimethoxy-16-oxa-24-azapentacyclo[15.7.1.1⁸,¹².0²,⁷.0¹⁹,²⁴]hexacosa-2(7),3,5,8(26),9,11,13-heptaen-15-one (NP0315528)

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Record Information

Version

2.0

Created at

2022-09-11 14:12:06 UTC

Updated at

2022-09-11 14:12:06 UTC

NP-MRD ID

NP0315528

Secondary Accession Numbers

None

Natural Product Identification

Common Name

9,20-dihydroxy-4,5-dimethoxy-16-oxa-24-azapentacyclo[15.7.1.1⁸,¹².0²,⁷.0¹⁹,²⁴]hexacosa-2(7),3,5,8(26),9,11,13-heptaen-15-one

Description

9,20-Dihydroxy-4,5-dimethoxy-16-oxa-24-azapentacyclo[15.7.1.1⁸,¹².0²,⁷.0¹⁹,²⁴]Hexacosa-2,4,6,8,10,12(26),13-heptaen-15-one belongs to the class of organic compounds known as quinolizidines. Quinolizidines are compounds containing a quinolizidine moiety, which is a octahydro-2H-quinolizine derivative. 9,20-dihydroxy-4,5-dimethoxy-16-oxa-24-azapentacyclo[15.7.1.1⁸,¹².0²,⁷.0¹⁹,²⁴]hexacosa-2(7),3,5,8(26),9,11,13-heptaen-15-one is found in Heimia salicifolia. 9,20-Dihydroxy-4,5-dimethoxy-16-oxa-24-azapentacyclo[15.7.1.1⁸,¹².0²,⁷.0¹⁹,²⁴]Hexacosa-2,4,6,8,10,12(26),13-heptaen-15-one is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251509462D          

 33 37  0  0  0  0            999 V2000
    5.9755    2.5378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1939    1.7423    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6141    1.1554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8325    0.3598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2527   -0.2271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8396   -0.8069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4314   -1.5239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8482   -2.2358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6732   -2.2308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0814   -1.5139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9064   -1.5088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.3145   -0.7919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8977   -0.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0727   -0.0849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6645   -0.8019    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1533004251509462D          

 33 37  0  0  0  0            999 V2000
    5.9755    2.5378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0315528

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C=C1OC)C1=CC(=CC=C1O)C=CC(=O)OC1CC3C(O)CCCN3C2C1

> <INCHI_IDENTIFIER>
InChI=1S/C26H29NO6/c1-31-24-13-17-18(14-25(24)32-2)20-11-16(12-21-23(29)4-3-9-27(20)21)33-26(30)8-6-15-5-7-22(28)19(17)10-15/h5-8,10,13-14,16,20-21,23,28-29H,3-4,9,11-12H2,1-2H3

> <INCHI_KEY>
VWCBHUSUACQSIV-UHFFFAOYSA-N

> <FORMULA>
C26H29NO6

> <MOLECULAR_WEIGHT>
451.519

> <EXACT_MASS>
451.199487658

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
47.812380922267245

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
9,20-dihydroxy-4,5-dimethoxy-16-oxa-24-azapentacyclo[15.7.1.1⁸,¹².0²,⁷.0¹⁹,²⁴]hexacosa-2(7),3,5,8(26),9,11,13-heptaen-15-one

> <ALOGPS_LOGP>
2.73

> <JCHEM_LOGP>
2.8872260901753934

> <ALOGPS_LOGS>
-3.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.588631049308926

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.116405560801413

> <JCHEM_PKA_STRONGEST_BASIC>
8.097291544985975

> <JCHEM_POLAR_SURFACE_AREA>
88.46000000000001

> <JCHEM_REFRACTIVITY>
124.72209999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.69e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9,20-dihydroxy-4,5-dimethoxy-16-oxa-24-azapentacyclo[15.7.1.1⁸,¹².0²,⁷.0¹⁹,²⁴]hexacosa-2(7),3,5,8(26),9,11,13-heptaen-15-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0      11.154   4.737   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      11.562   3.252   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      10.480   2.157   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.887   0.672   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.805  -0.424   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.901  -1.506   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.139  -2.845   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.917  -4.174   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.457  -4.164   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.219  -2.826   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.759  -2.816   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      15.537  -4.145   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      15.520  -1.478   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.742  -0.149   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.202  -0.159   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0      12.440  -1.497   0.000  0.00  0.00           N+0
HETATM   17  O   UNK     0       9.836  -5.577   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       8.351  -5.984   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       8.361  -7.524   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       6.861  -5.595   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.766  -4.513   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.358  -3.027   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.020  -2.266   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.010  -0.726   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.339   0.052   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       5.330   1.592   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       6.678  -0.709   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.687  -2.249   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.315  -0.034   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.907   1.451   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.990   2.546   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       8.582   4.031   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       7.092   4.421   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   29                                                  
CONECT    6    5    7   16                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   17                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   16                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15    6   10                                                  
CONECT   17    8   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   28                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27   22                                                       
CONECT   29   27    5   30                                                  
CONECT   30   29   31                                                       
CONECT   31   30    3   32                                                  
CONECT   32   31   33                                                       
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₂₉NO₆

Average Mass

451.5190 Da

Monoisotopic Mass

451.19949 Da

IUPAC Name

9,20-dihydroxy-4,5-dimethoxy-16-oxa-24-azapentacyclo[15.7.1.1⁸,¹².0²,⁷.0¹⁹,²⁴]hexacosa-2(7),3,5,8(26),9,11,13-heptaen-15-one

Traditional Name

9,20-dihydroxy-4,5-dimethoxy-16-oxa-24-azapentacyclo[15.7.1.1⁸,¹².0²,⁷.0¹⁹,²⁴]hexacosa-2(7),3,5,8(26),9,11,13-heptaen-15-one

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C=C1OC)C1=CC(=CC=C1O)C=CC(=O)OC1CC3C(O)CCCN3C2C1

InChI Identifier

InChI=1S/C26H29NO6/c1-31-24-13-17-18(14-25(24)32-2)20-11-16(12-21-23(29)4-3-9-27(20)21)33-26(30)8-6-15-5-7-22(28)19(17)10-15/h5-8,10,13-14,16,20-21,23,28-29H,3-4,9,11-12H2,1-2H3

InChI Key

VWCBHUSUACQSIV-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

Species Name	Source	Reference
Heimia salicifolia	LOTUS Database	35616633

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
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Aralkylamine
Piperidine
Benzenoid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
1,2-aminoalcohol
Amino acid or derivatives
Carboxylic acid ester
Lactone
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Carboxylic acid derivative
Ether
Oxacycle
Monocarboxylic acid or derivatives
Azacycle
Alcohol
Hydrocarbon derivative
Organic nitrogen compound
Carbonyl group
Organic oxide
Organic oxygen compound
Amine
Organonitrogen compound
Organooxygen 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	2.73	ALOGPS
logP	2.89	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	9.12	ChemAxon
pKa (Strongest Basic)	8.1	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	2	ChemAxon
Refractivity	124.72 m³·mol⁻¹	ChemAxon
Polarizability	47.81 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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 9,20-dihydroxy-4,5-dimethoxy-16-oxa-24-azapentacyclo[15.7.1.1⁸,¹².0²,⁷.0¹⁹,²⁴]hexacosa-2(7),3,5,8(26),9,11,13-heptaen-15-one (NP0315528)

MOL for NP0315528 (9,20-dihydroxy-4,5-dimethoxy-16-oxa-24-azapentacyclo[15.7.1.1⁸,¹².0²,⁷.0¹⁹,²⁴]hexacosa-2(7),3,5,8(26),9,11,13-heptaen-15-one)

3D MOL for NP0315528 (9,20-dihydroxy-4,5-dimethoxy-16-oxa-24-azapentacyclo[15.7.1.1⁸,¹².0²,⁷.0¹⁹,²⁴]hexacosa-2(7),3,5,8(26),9,11,13-heptaen-15-one)

3D SDF for NP0315528 (9,20-dihydroxy-4,5-dimethoxy-16-oxa-24-azapentacyclo[15.7.1.1⁸,¹².0²,⁷.0¹⁹,²⁴]hexacosa-2(7),3,5,8(26),9,11,13-heptaen-15-one)

3D-SDF for NP0315528 (9,20-dihydroxy-4,5-dimethoxy-16-oxa-24-azapentacyclo[15.7.1.1⁸,¹².0²,⁷.0¹⁹,²⁴]hexacosa-2(7),3,5,8(26),9,11,13-heptaen-15-one)

PDB for NP0315528 (9,20-dihydroxy-4,5-dimethoxy-16-oxa-24-azapentacyclo[15.7.1.1⁸,¹².0²,⁷.0¹⁹,²⁴]hexacosa-2(7),3,5,8(26),9,11,13-heptaen-15-one)

3D PDB for NP0315528 (9,20-dihydroxy-4,5-dimethoxy-16-oxa-24-azapentacyclo[15.7.1.1⁸,¹².0²,⁷.0¹⁹,²⁴]hexacosa-2(7),3,5,8(26),9,11,13-heptaen-15-one)

SMILES for NP0315528 (9,20-dihydroxy-4,5-dimethoxy-16-oxa-24-azapentacyclo[15.7.1.1⁸,¹².0²,⁷.0¹⁹,²⁴]hexacosa-2(7),3,5,8(26),9,11,13-heptaen-15-one)

INCHI for NP0315528 (9,20-dihydroxy-4,5-dimethoxy-16-oxa-24-azapentacyclo[15.7.1.1⁸,¹².0²,⁷.0¹⁹,²⁴]hexacosa-2(7),3,5,8(26),9,11,13-heptaen-15-one)

Structure for NP0315528 (9,20-dihydroxy-4,5-dimethoxy-16-oxa-24-azapentacyclo[15.7.1.1⁸,¹².0²,⁷.0¹⁹,²⁴]hexacosa-2(7),3,5,8(26),9,11,13-heptaen-15-one)

3D Structure for NP0315528 (9,20-dihydroxy-4,5-dimethoxy-16-oxa-24-azapentacyclo[15.7.1.1⁸,¹².0²,⁷.0¹⁹,²⁴]hexacosa-2(7),3,5,8(26),9,11,13-heptaen-15-one)