NP-MRD: Showing NP-Card for 12-{4-[2-(dimethylamino)ethyl]phenoxymethyl}-5-methyl-7-azahexacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁹,¹⁴.0¹⁴,¹⁸]nonadeca-6,12-dien-9-ol (NP0147346)

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Record Information

Version

2.0

Created at

2022-09-02 02:56:17 UTC

Updated at

2022-09-02 02:56:17 UTC

NP-MRD ID

NP0147346

Secondary Accession Numbers

None

Natural Product Identification

Common Name

12-{4-[2-(dimethylamino)ethyl]phenoxymethyl}-5-methyl-7-azahexacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁹,¹⁴.0¹⁴,¹⁸]nonadeca-6,12-dien-9-ol

Description

12-({4-[2-(Dimethylamino)ethyl]phenoxy}methyl)-5-methyl-7-azahexacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁹,¹⁴.0¹⁴,¹⁸]Nonadeca-6,12-dien-9-ol belongs to the class of organic compounds known as atisane diterpenoids. These are diterpenoids with a structure based on the atisane skeleton, which is a tetracyclic compound containing the [2,2,2]bicyc1ic ring system with the C15-C16 bridge attached at C12. 12-{4-[2-(dimethylamino)ethyl]phenoxymethyl}-5-methyl-7-azahexacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁹,¹⁴.0¹⁴,¹⁸]nonadeca-6,12-dien-9-ol is found in Aconitum naviculare. 12-({4-[2-(Dimethylamino)ethyl]phenoxy}methyl)-5-methyl-7-azahexacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁹,¹⁴.0¹⁴,¹⁸]Nonadeca-6,12-dien-9-ol is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241504222D          

 34 40  0  0  0  0            999 V2000
    0.6136    6.0523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9184    5.2856    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7347    5.1663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4069    4.6383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7117    3.8717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2002    3.2244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5050    2.4578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0065    1.8105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.3343    1.2826    0.0000 O   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


  Mrv1533004241504222D          

 34 40  0  0  0  0            999 V2000
    0.6136    6.0523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  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  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 17 23  1  0  0  0  0
 23 24  1  0  0  0  0
 14 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 12 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 14 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 23 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 18 32  1  0  0  0  0
  9 33  1  0  0  0  0
 33 34  2  0  0  0  0
  6 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0147346

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN(C)CCC1=CC=C(OCC2=CC34CCC5C67CCCC5(C)C=NC6C3(O)CC2CC47)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C30H40N2O2/c1-27-11-4-12-29-24(27)9-13-28-16-22(18-34-23-7-5-20(6-8-23)10-14-32(2)3)21(15-25(28)29)17-30(28,33)26(29)31-19-27/h5-8,16,19,21,24-26,33H,4,9-15,17-18H2,1-3H3

> <INCHI_KEY>
UKUFQEHTYPWMEE-UHFFFAOYSA-N

> <FORMULA>
C30H40N2O2

> <MOLECULAR_WEIGHT>
460.662

> <EXACT_MASS>
460.308978536

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
55.000193100530915

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
12-({4-[2-(dimethylamino)ethyl]phenoxy}methyl)-5-methyl-7-azahexacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁹,¹⁴.0¹⁴,¹⁸]nonadeca-6,12-dien-9-ol

> <ALOGPS_LOGP>
4.85

> <JCHEM_LOGP>
3.9300625403333314

> <ALOGPS_LOGS>
-6.00

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.482370783181409

> <JCHEM_PKA_STRONGEST_BASIC>
9.237930430202807

> <JCHEM_POLAR_SURFACE_AREA>
45.06

> <JCHEM_REFRACTIVITY>
136.41649999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.57e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
12-{4-[2-(dimethylamino)ethyl]phenoxymethyl}-5-methyl-7-azahexacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁹,¹⁴.0¹⁴,¹⁸]nonadeca-6,12-dien-9-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       1.145  11.298   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       1.714   9.867   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       3.238   9.644   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.760   8.658   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.329   7.227   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.374   6.019   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.943   4.588   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.012   3.380   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.536   3.602   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -2.491   2.394   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.922   0.963   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.398   0.740   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.748   1.833   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.278   1.233   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.283   2.519   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.873   2.523   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.781   1.200   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.402  -0.514   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.245  -1.802   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.947  -0.931   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.361   0.558   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.769   0.599   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.059  -0.029   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.492   0.413   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.769   0.125   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.384  -0.629   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.518  -1.711   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.673  -0.584   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       4.126  -0.074   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       4.111  -1.335   0.000  0.00  0.00           C+0
HETATM   31  N   UNK     0       4.765  -2.781   0.000  0.00  0.00           N+0
HETATM   32  C   UNK     0       6.166  -2.105   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -2.105   5.033   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -1.150   6.242   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   34                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   33                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   26                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   24   28                                             
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   23                                                  
CONECT   18   17   19   20   32                                             
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   17   24   30                                             
CONECT   24   23   14   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25   12   27                                                  
CONECT   27   26   28                                                       
CONECT   28   27   14   29   30                                             
CONECT   29   28                                                            
CONECT   30   28   23   31                                                  
CONECT   31   30   32                                                       
CONECT   32   31   18                                                       
CONECT   33    9   34                                                       
CONECT   34   33    6                                                       
MASTER        0    0    0    0    0    0    0    0   34    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₀N₂O₂

Average Mass

460.6620 Da

Monoisotopic Mass

460.30898 Da

IUPAC Name

12-({4-[2-(dimethylamino)ethyl]phenoxy}methyl)-5-methyl-7-azahexacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁹,¹⁴.0¹⁴,¹⁸]nonadeca-6,12-dien-9-ol

Traditional Name

12-{4-[2-(dimethylamino)ethyl]phenoxymethyl}-5-methyl-7-azahexacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁹,¹⁴.0¹⁴,¹⁸]nonadeca-6,12-dien-9-ol

CAS Registry Number

Not Available

SMILES

CN(C)CCC1=CC=C(OCC2=CC34CCC5C67CCCC5(C)C=NC6C3(O)CC2CC47)C=C1

InChI Identifier

InChI=1S/C30H40N2O2/c1-27-11-4-12-29-24(27)9-13-28-16-22(18-34-23-7-5-20(6-8-23)10-14-32(2)3)21(15-25(28)29)17-30(28,33)26(29)31-19-27/h5-8,16,19,21,24-26,33H,4,9-15,17-18H2,1-3H3

InChI Key

UKUFQEHTYPWMEE-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
Aconitum naviculare	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as atisane diterpenoids. These are diterpenoids with a structure based on the atisane skeleton, which is a tetracyclic compound containing the [2,2,2]bicyc1ic ring system with the C15-C16 bridge attached at C12.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Atisane diterpenoids

Alternative Parents

Substituents

Atisane diterpenoid
Phenethylamine
Alkaloid or derivatives
Phenoxy compound
Phenol ether
Alkyl aryl ether
Aralkylamine
Tetrahydropyridine
Monocyclic benzene moiety
Benzenoid
Cyclic alcohol
Tertiary alcohol
Tertiary amine
Tertiary aliphatic amine
Organic 1,3-dipolar compound
Organoheterocyclic compound
Azacycle
Ether
Propargyl-type 1,3-dipolar organic compound
Alcohol
Organooxygen compound
Organonitrogen compound
Imine
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Amine
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	4.85	ALOGPS
logP	3.93	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	13.48	ChemAxon
pKa (Strongest Basic)	9.24	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	45.06 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	136.42 m³·mol⁻¹	ChemAxon
Polarizability	55 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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 12-{4-[2-(dimethylamino)ethyl]phenoxymethyl}-5-methyl-7-azahexacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁹,¹⁴.0¹⁴,¹⁸]nonadeca-6,12-dien-9-ol (NP0147346)

MOL for NP0147346 (12-{4-[2-(dimethylamino)ethyl]phenoxymethyl}-5-methyl-7-azahexacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁹,¹⁴.0¹⁴,¹⁸]nonadeca-6,12-dien-9-ol)

3D MOL for NP0147346 (12-{4-[2-(dimethylamino)ethyl]phenoxymethyl}-5-methyl-7-azahexacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁹,¹⁴.0¹⁴,¹⁸]nonadeca-6,12-dien-9-ol)

3D SDF for NP0147346 (12-{4-[2-(dimethylamino)ethyl]phenoxymethyl}-5-methyl-7-azahexacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁹,¹⁴.0¹⁴,¹⁸]nonadeca-6,12-dien-9-ol)

3D-SDF for NP0147346 (12-{4-[2-(dimethylamino)ethyl]phenoxymethyl}-5-methyl-7-azahexacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁹,¹⁴.0¹⁴,¹⁸]nonadeca-6,12-dien-9-ol)

PDB for NP0147346 (12-{4-[2-(dimethylamino)ethyl]phenoxymethyl}-5-methyl-7-azahexacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁹,¹⁴.0¹⁴,¹⁸]nonadeca-6,12-dien-9-ol)

3D PDB for NP0147346 (12-{4-[2-(dimethylamino)ethyl]phenoxymethyl}-5-methyl-7-azahexacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁹,¹⁴.0¹⁴,¹⁸]nonadeca-6,12-dien-9-ol)

SMILES for NP0147346 (12-{4-[2-(dimethylamino)ethyl]phenoxymethyl}-5-methyl-7-azahexacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁹,¹⁴.0¹⁴,¹⁸]nonadeca-6,12-dien-9-ol)

INCHI for NP0147346 (12-{4-[2-(dimethylamino)ethyl]phenoxymethyl}-5-methyl-7-azahexacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁹,¹⁴.0¹⁴,¹⁸]nonadeca-6,12-dien-9-ol)

Structure for NP0147346 (12-{4-[2-(dimethylamino)ethyl]phenoxymethyl}-5-methyl-7-azahexacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁹,¹⁴.0¹⁴,¹⁸]nonadeca-6,12-dien-9-ol)

3D Structure for NP0147346 (12-{4-[2-(dimethylamino)ethyl]phenoxymethyl}-5-methyl-7-azahexacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁹,¹⁴.0¹⁴,¹⁸]nonadeca-6,12-dien-9-ol)