NP-MRD: Showing NP-Card for 16-methyl-6,14-diazatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2(7),5-dien-5-ol (NP0248060)

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Record Information

Version

2.0

Created at

2022-09-07 10:09:35 UTC

Updated at

2022-09-07 10:09:35 UTC

NP-MRD ID

NP0248060

Secondary Accession Numbers

None

Natural Product Identification

Common Name

16-methyl-6,14-diazatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2(7),5-dien-5-ol

Description

N-Demethyl-alpha-obscurine belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. 16-methyl-6,14-diazatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2(7),5-dien-5-ol is found in Dendrolycopodium obscurum and Lycopodium clavatum. N-Demethyl-alpha-obscurine is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 43 46  0  0  0  0  0  0  0  0999 V2000
    3.1820   -2.0892    1.0686 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9142   -1.6277    0.3321 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3566   -0.9134   -0.8795 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3359    0.0087   -1.4921 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1531   -0.7249   -2.0571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0176   -0.6991   -1.1626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9735   -0.4227    0.1132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1075   -0.7501    0.9949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3991   -0.3151    0.3453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4770   -0.9891   -0.9678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5456   -1.5173   -1.3442 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2937   -0.9951   -1.7467 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2330    0.2235    0.6863 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0872   -0.8682    1.3009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0914    1.1200    1.7511 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6586    2.3608    1.4334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1127    3.0423    0.2082 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0545    2.0354   -0.9398 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9334    0.9645   -0.3988 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7026   -1.1372    1.3609 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8389   -2.5514    2.0063 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8037   -2.7257    0.4350 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4012   -2.5684    0.0293 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6269   -1.6557   -1.6746 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2800   -0.3179   -0.7136 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8372    0.6081   -2.2795 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4148   -1.7940   -2.2428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1423   -0.1973   -2.9977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1891   -1.8699    1.1142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9857   -0.3196    2.0119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2756   -0.5058    0.9791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3669    0.7982    0.1963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3950   -1.2264   -2.7708 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3815   -1.5642    1.8049 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7179   -0.4418    2.1093 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6423    1.1247    2.4723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7637    2.2889    1.3724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4655    3.0690    2.2926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8695    3.7696   -0.1470 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8235    3.5914    0.3834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9471    1.7354   -1.2505 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5266    2.5963   -1.7736 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8301    1.4504    0.0367 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
  7 13  1  0
 13 14  1  0
 13 15  1  1
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 14  2  1  0
 19  4  1  0
 12  6  1  0
 19 13  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  6
  3 24  1  0
  3 25  1  0
  4 26  1  6
  5 27  1  0
  5 28  1  0
  8 29  1  0
  8 30  1  0
  9 31  1  0
  9 32  1  0
 12 33  1  0
 14 34  1  0
 14 35  1  0
 15 36  1  0
 16 37  1  0
 16 38  1  0
 17 39  1  0
 17 40  1  0
 18 41  1  0
 18 42  1  0
 19 43  1  1
M  END


  Mrv1533004201500302D          

 19 22  0  0  0  0            999 V2000
   -1.0983   -0.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4836   -0.0832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1014   -0.7100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8870   -0.9617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6206   -0.5842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8723    0.2015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4948    0.9350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9413    1.6287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7653    1.5889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1429    0.8554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9669    0.8155    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6964    0.1616    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7091    1.1868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0244    0.8092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0708    1.7093    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7010    1.4178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8344    0.6036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1960    0.0810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5758    0.3726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  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
 10 12  1  0  0  0  0
  6 12  1  0  0  0  0
  7 13  1  0  0  0  0
 13 14  1  0  0  0  0
  2 14  1  0  0  0  0
 13 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
  4 19  1  0  0  0  0
 13 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0248060

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CC2CC3=C(CCC(=O)N3)C3(C1)NCCCC23

> <INCHI_IDENTIFIER>
InChI=1S/C16H24N2O/c1-10-7-11-8-14-13(4-5-15(19)18-14)16(9-10)12(11)3-2-6-17-16/h10-12,17H,2-9H2,1H3,(H,18,19)

> <INCHI_KEY>
SODGYLLKKFRBQO-UHFFFAOYSA-N

> <FORMULA>
C16H24N2O

> <MOLECULAR_WEIGHT>
260.381

> <EXACT_MASS>
260.188863401

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
29.69761499729519

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
16-methyl-6,14-diazatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadec-2(7)-en-5-one

> <ALOGPS_LOGP>
2.04

> <JCHEM_LOGP>
1.0403117089999983

> <ALOGPS_LOGS>
-3.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.111535179356093

> <JCHEM_PKA_STRONGEST_BASIC>
10.00943936817542

> <JCHEM_POLAR_SURFACE_AREA>
41.13

> <JCHEM_REFRACTIVITY>
76.1217

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.13e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
16-methyl-6,14-diazatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadec-2(7)-en-5-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-15         0                                  
HETATM    1  C   UNK     0      -2.050  -0.083   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.903  -0.155   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.189  -1.325   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.656  -1.795   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.025  -1.090   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.495   0.376   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.790   1.745   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.624   3.040   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.162   2.966   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.867   1.597   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       7.405   1.522   0.000  0.00  0.00           O+0
HETATM   12  N   UNK     0       5.033   0.302   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       1.324   2.215   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.046   1.511   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       0.132   3.191   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0      -1.309   2.647   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.557   1.127   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.366   0.151   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.075   0.696   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   14                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   19                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   12                                                  
CONECT    7    6    8   13                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    6                                                       
CONECT   13    7   14   15   19                                             
CONECT   14   13    2                                                       
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18    4   13                                                  
MASTER        0    0    0    0    0    0    0    0   19    0   44    0
END

View in JSmol

Synonyms

Value	Source
N-Demethyl-a-obscurine	Generator
N-Demethyl-α-obscurine	Generator

Chemical Formula

C₁₆H₂₄N₂O

Average Mass

260.3810 Da

Monoisotopic Mass

260.18886 Da

IUPAC Name

16-methyl-6,14-diazatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadec-2(7)-en-5-one

Traditional Name

16-methyl-6,14-diazatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadec-2(7)-en-5-one

CAS Registry Number

Not Available

SMILES

CC1CC2CC3=C(CCC(=O)N3)C3(C1)NCCCC23

InChI Identifier

InChI=1S/C16H24N2O/c1-10-7-11-8-14-13(4-5-15(19)18-14)16(9-10)12(11)3-2-6-17-16/h10-12,17H,2-9H2,1H3,(H,18,19)

InChI Key

SODGYLLKKFRBQO-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
Dendrolycopodium obscurum	LOTUS Database	35616633
Lycopodium clavatum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
1,7-phenanthroline
Delta amino acid or derivatives
Quinolidine
Tetrahydropyridine
Piperidine
Amino acid or derivatives
Carboxamide group
Lactam
Secondary carboxylic acid amide
Organoheterocyclic compound
Azacycle
Carboxylic acid derivative
Secondary aliphatic amine
Secondary amine
Organic oxide
Carbonyl group
Organic nitrogen compound
Amine
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	2.04	ALOGPS
logP	1.04	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	13.11	ChemAxon
pKa (Strongest Basic)	10.01	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	41.13 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	76.12 m³·mol⁻¹	ChemAxon
Polarizability	29.7 Å³	ChemAxon
Number of Rings	4	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

14487528

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 16-methyl-6,14-diazatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2(7),5-dien-5-ol (NP0248060)

MOL for NP0248060 (16-methyl-6,14-diazatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2(7),5-dien-5-ol)

3D MOL for NP0248060 (16-methyl-6,14-diazatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2(7),5-dien-5-ol)

3D SDF for NP0248060 (16-methyl-6,14-diazatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2(7),5-dien-5-ol)

3D-SDF for NP0248060 (16-methyl-6,14-diazatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2(7),5-dien-5-ol)

PDB for NP0248060 (16-methyl-6,14-diazatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2(7),5-dien-5-ol)

3D PDB for NP0248060 (16-methyl-6,14-diazatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2(7),5-dien-5-ol)

SMILES for NP0248060 (16-methyl-6,14-diazatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2(7),5-dien-5-ol)

INCHI for NP0248060 (16-methyl-6,14-diazatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2(7),5-dien-5-ol)

Structure for NP0248060 (16-methyl-6,14-diazatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2(7),5-dien-5-ol)

3D Structure for NP0248060 (16-methyl-6,14-diazatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2(7),5-dien-5-ol)