NP-MRD: Showing NP-Card for (1r,12r,15s,17s)-1,14,14-trimethyl-3,13-diazapentacyclo[13.2.2.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]nonadeca-2(10),4,6,8-tetraen-19-one (NP0221065)

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Record Information

Version

2.0

Created at

2022-09-05 22:32:49 UTC

Updated at

2022-09-05 22:32:49 UTC

NP-MRD ID

NP0221065

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,12r,15s,17s)-1,14,14-trimethyl-3,13-diazapentacyclo[13.2.2.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]nonadeca-2(10),4,6,8-tetraen-19-one

Description

Aristolasicone belongs to the class of organic compounds known as pyrroloquinolines. Pyrroloquinolines are compounds containing a pyrroloquinoline moiety, which consists of a pyrrole ring fused to a quinoline. (1r,12r,15s,17s)-1,14,14-trimethyl-3,13-diazapentacyclo[13.2.2.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]nonadeca-2(10),4,6,8-tetraen-19-one is found in Aristotelia australasica. Based on a literature review very few articles have been published on Aristolasicone.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062200322D          

 23 27  0  0  1  0            999 V2000
    0.1402    2.0362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5466    1.3183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2378    1.0627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2163    1.8999    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0372    1.6029    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8766    1.7930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4884    1.2115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2655    0.4172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9521   -0.0402    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5993    0.4714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4126    0.3327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9393    0.9677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6527    1.7414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8394    1.8800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3127    1.2450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4427    0.1158    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9177   -0.5588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8805   -0.5587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0102   -0.3990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4981   -1.0458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6498    0.4243    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2699    0.5958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0182    0.7970    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  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  1  0  0  0  0
 10 11  2  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
  7 15  1  0  0  0  0
 10 15  1  0  0  0  0
  8 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
  2 21  1  0  0  0  0
 21 22  1  1  0  0  0
 23 22  1  6  0  0  0
  5 23  1  0  0  0  0
 16 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0221065

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)N[C@@H]2CC3=C(NC4=CC=CC=C34)[C@]3(C)CC(=O)[C@H]1C[C@H]23

> <INCHI_IDENTIFIER>
InChI=1S/C20H24N2O/c1-19(2)14-9-13-16(22-19)8-12-11-6-4-5-7-15(11)21-18(12)20(13,3)10-17(14)23/h4-7,13-14,16,21-22H,8-10H2,1-3H3/t13-,14-,16-,20-/m1/s1

> <INCHI_KEY>
BGFZRKXPCFAWIX-NOAAKOMESA-N

> <FORMULA>
C20H24N2O

> <MOLECULAR_WEIGHT>
308.425

> <EXACT_MASS>
308.188863401

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
35.50936468897429

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,12R,15S,17S)-1,14,14-trimethyl-3,13-diazapentacyclo[13.2.2.0^{2,10}.0^{4,9}.0^{12,17}]nonadeca-2(10),4,6,8-tetraen-19-one

> <JCHEM_LOGP>
3.0594198366666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.584738025948067

> <JCHEM_PKA_STRONGEST_BASIC>
10.008123557357948

> <JCHEM_POLAR_SURFACE_AREA>
44.89

> <JCHEM_REFRACTIVITY>
91.2872

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,12R,15S,17S)-1,14,14-trimethyl-3,13-diazapentacyclo[13.2.2.0^{2,10}.0^{4,9}.0^{12,17}]nonadeca-2(10),4,6,8-tetraen-19-one

> <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       0.262   3.801   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.020   2.461   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.444   1.984   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       2.270   3.546   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       3.803   2.992   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.370   3.347   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.512   2.262   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.096   0.779   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       7.377  -0.075   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       8.585   0.880   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.103   0.621   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.087   1.806   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.552   3.251   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.034   3.509   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.050   2.324   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.560   0.216   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.446  -1.043   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.510  -1.043   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.886  -0.745   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       0.930  -1.952   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.213   0.792   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.370   1.112   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.767   1.488   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4   21                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   23                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   15                                                  
CONECT    8    7    9   16                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14    7   10                                                  
CONECT   16    8   17   18   23                                             
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19    2   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22    5   16                                                  
MASTER        0    0    0    0    0    0    0    0   23    0   54    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₄N₂O

Average Mass

308.4250 Da

Monoisotopic Mass

308.18886 Da

IUPAC Name

(1R,12R,15S,17S)-1,14,14-trimethyl-3,13-diazapentacyclo[13.2.2.0^{2,10}.0^{4,9}.0^{12,17}]nonadeca-2(10),4,6,8-tetraen-19-one

Traditional Name

(1R,12R,15S,17S)-1,14,14-trimethyl-3,13-diazapentacyclo[13.2.2.0^{2,10}.0^{4,9}.0^{12,17}]nonadeca-2(10),4,6,8-tetraen-19-one

CAS Registry Number

Not Available

SMILES

CC1(C)N[C@@H]2CC3=C(NC4=CC=CC=C34)[C@]3(C)CC(=O)[C@H]1C[C@H]23

InChI Identifier

InChI=1S/C20H24N2O/c1-19(2)14-9-13-16(22-19)8-12-11-6-4-5-7-15(11)21-18(12)20(13,3)10-17(14)23/h4-7,13-14,16,21-22H,8-10H2,1-3H3/t13-,14-,16-,20-/m1/s1

InChI Key

BGFZRKXPCFAWIX-NOAAKOMESA-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
Aristotelia australasica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrroloquinolines. Pyrroloquinolines are compounds containing a pyrroloquinoline moiety, which consists of a pyrrole ring fused to a quinoline.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Pyrroloquinolines

Direct Parent

Pyrroloquinolines

Alternative Parents

Substituents

Carbazole
Pyrroloquinoline
3-alkylindole
Indole
Indole or derivatives
Aralkylamine
Benzenoid
Piperidine
Heteroaromatic compound
Pyrrole
Ketone
Azacycle
Secondary amine
Secondary aliphatic amine
Amine
Organonitrogen compound
Organooxygen compound
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organic nitrogen 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	3.06	ChemAxon
pKa (Strongest Acidic)	16.58	ChemAxon
pKa (Strongest Basic)	10.01	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	44.89 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	91.29 m³·mol⁻¹	ChemAxon
Polarizability	35.51 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

10238932

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21604798

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,12r,15s,17s)-1,14,14-trimethyl-3,13-diazapentacyclo[13.2.2.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]nonadeca-2(10),4,6,8-tetraen-19-one (NP0221065)

MOL for NP0221065 ((1r,12r,15s,17s)-1,14,14-trimethyl-3,13-diazapentacyclo[13.2.2.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]nonadeca-2(10),4,6,8-tetraen-19-one)

3D MOL for NP0221065 ((1r,12r,15s,17s)-1,14,14-trimethyl-3,13-diazapentacyclo[13.2.2.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]nonadeca-2(10),4,6,8-tetraen-19-one)

3D SDF for NP0221065 ((1r,12r,15s,17s)-1,14,14-trimethyl-3,13-diazapentacyclo[13.2.2.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]nonadeca-2(10),4,6,8-tetraen-19-one)

3D-SDF for NP0221065 ((1r,12r,15s,17s)-1,14,14-trimethyl-3,13-diazapentacyclo[13.2.2.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]nonadeca-2(10),4,6,8-tetraen-19-one)

PDB for NP0221065 ((1r,12r,15s,17s)-1,14,14-trimethyl-3,13-diazapentacyclo[13.2.2.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]nonadeca-2(10),4,6,8-tetraen-19-one)

3D PDB for NP0221065 ((1r,12r,15s,17s)-1,14,14-trimethyl-3,13-diazapentacyclo[13.2.2.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]nonadeca-2(10),4,6,8-tetraen-19-one)

SMILES for NP0221065 ((1r,12r,15s,17s)-1,14,14-trimethyl-3,13-diazapentacyclo[13.2.2.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]nonadeca-2(10),4,6,8-tetraen-19-one)

INCHI for NP0221065 ((1r,12r,15s,17s)-1,14,14-trimethyl-3,13-diazapentacyclo[13.2.2.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]nonadeca-2(10),4,6,8-tetraen-19-one)

Structure for NP0221065 ((1r,12r,15s,17s)-1,14,14-trimethyl-3,13-diazapentacyclo[13.2.2.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]nonadeca-2(10),4,6,8-tetraen-19-one)

3D Structure for NP0221065 ((1r,12r,15s,17s)-1,14,14-trimethyl-3,13-diazapentacyclo[13.2.2.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]nonadeca-2(10),4,6,8-tetraen-19-one)